Explore Hidden Gems in sarasota. Discover sarasota’s secrets: Find of the beaten path gems, cafes, parks, and more.

Sarasota, Florida, a jewel on the Gulf Coast, promises an enchanting week-long escape filled with vibrant cultural experiences, sun-drenched beaches, and diverse culinary delights. Nestled between the azure waters of the Gulf of Mexico and the lush landscapes of Southwest Florida, Sarasota beckons with its unique blend of coastal charm and urban sophistication. Whether you’re exploring the artistic treasures of The Ringling Museum, lounging on the powdery sands of Siesta Key, or savoring fresh seafood at a waterfront restaurant, each day in Sarasota offers a new adventure and a chance to discover the heart of this captivating city. Get ready to immerse yourself in “7 Unforgettable Days in Sarasota,” where every moment is a cherished memory in the making.

Day 1: Siesta Key Adventures

Morning:

•Breakfast: Start your day at Another Broken Egg in Siesta Village. This charming eatery offers a variety of delicious breakfast options, perfect for fueling up for the day.

•Beach Time: Head to Siesta Public Beach or (even better!) Sunset Point at North Siesta Beach, a quieter spot ideal for relaxing and only steps from my recommended, Tropical Breeze Resorts, boasting classic bungalows and steps to the beach & Siesta Village. The soft, white sand and turquoise waters are perfect for building sandcastles or simply soaking in the sun.

Afternoon:

•Lunch: Swing back to Siesta Key Village and choose from Gilligan’s, The Old Salty Dog, or Flavio’s Brick Oven Pizza & Bar for a delightful meal.

•Explore the Village: Spend some time exploring the local shops for unique souvenirs.

•Electric Beach Bike Ride: Rent electric bikes from Robin Hood Rentals and cruise along Siesta Beach. Make sure to check out Point of Rocks, a popular snorkeling spot at the south end where you’ll think you were transported to a different area, featuring massive limestone formations and a rocky shoreline.

Evening:

•Dinner: Enjoy a delicious dinner at Siesta Key Summer House, known for its fresh seafood and tropical ambiance.

•Stroll and Relax: End the day with a relaxed walk along the beach, enjoying the sound of the waves and the cool evening breeze.

Day 2: Discovering Lido Key

Morning:

•Breakfast: Enjoy a hearty breakfast at the Blue Dolphin Cafe on St. Armands Circle. This spot is a favorite for its cozy atmosphere and delicious breakfast fare.

•St. Armands Circle: After breakfast, take a leisurely walk around the Circle to explore the unique shops and beautiful sculptures.

Late Morning:

•Kayak Tour: Head over to South Lido Key for a scheduled kayak tour among the mangrove tunnels with Kayaking SRQ or Lido Key Mangrove Kayak Tours at Ted Sperling Park at South Lido Beach Nature Park. By the way, watch out for those tiny crabs that enjoy falling off the mangroves into your hair. Wear a cap. This is a great way to experience Florida’s unique ecosystem and spot wildlife like manatees and dolphins.

Afternoon:

•Lunch: Have lunch at Tommy Bahama Restaurant & Bar with a view of St. Armands Circle.

•Beach Time: Spend the afternoon at Lido Beach. If you prefer a quieter setting, drive to the south end of Lido Beach for a more serene experience.

Evening:

•Dinner: Choose from Columbia Restaurant, Crab & Fin, or Venezia Restaurant on St. Armands Circle. Each offers a unique dining experience ranging from Spanish cuisine to fresh seafood.

•Night Stroll: Enjoy a stroll around St. Armands Circle taking in the vibrant nightlife and perhaps indulging in some ice cream from Kilwin’s.

Day 3: Sarasota's Hidden Gems

Morning:

•Breakfast: Visit Toasted Mango Cafe in The Rosemary District for a locally beloved breakfast.

•Sarasota Jungle Gardens: Spend the morning exploring Sarasota Jungle Gardens. This family-owned attraction is home to exotic animals and offers interactive experiences like feeding flamingos and holding a parrot.

Afternoon:

•Lunch: Grab lunch at Food+Beer in The Rosemary District or try The Spice Station for a flavorful meal.

•Explore Downtown: Spend the afternoon exploring downtown Sarasota. Visit the art galleries, boutiques, and historic sites.

Evening:

•Dinner: Head to The Westin Rooftop Bar for dinner, drinks, and a stunning sunset view over Sarasota.

•Night Out: Enjoy an evening in downtown Sarasota, perhaps catching a live performance or simply strolling along the picturesque streets.

Day 4: The Ringling & More

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby café before heading out.

•The Ringling: Spend the day at The Ringling. Explore the courtyard art galleries featuring the inimitable Statue of David, the circus museum boasting the world’s largest miniature Barnum & Bailey Big Top circus, the Ca’d’Zan mansion (i.e. John & Mable Ringling’s stunning winter home with amazing stories about its construction, decline, and resurrection. Are you aware this very Ca’ d’Zan had fallen in such disrepair, it was used in the 1998 adaptation of Charles Dickens’ “Great Expectations,” the backdrop for Miss Havisham’s broken castle? Don’t miss the chance to stroll through the finely manicured grounds, enjoying Mable’s rose gardens, banyan trees, ponds with fountains nestled among winding sidewalks, and enjoy the stunning views of Sarasota Bay.

Afternoon:

•Lunch: Have lunch at The Banyan Cafe or The Ringling Grillroom on the grounds of The Ringling.

•Discover Sarasota Tours: After lunch, relax on a sightseeing tour with Discover Sarasota Tours. These tours provide a great overview of the city’s history and hidden gems including their popular City Sightseeing Tour, Haunted Sarasota Tour, or their City Secrets of Sarasota tour.

Evening:

•Dinner: Head back to Siesta Key for a daiquiri at The Daiquiri Deck. For dinner, choose Captain Curt’s Crab & Oyster Bar or Siesta Key Oyster Bar.

•Nightlife: Quickly, catch a sunset at Siesta Beach before experiencing nightlife at Siesta Village, whether you prefer the lively atmosphere at Gilligan’s or the more relaxed vibe at Captain Curt’s Sniki Tiki Bar, located just off the south Siesta bridge.

Day 5: Marine Adventures & More

Morning:

•Breakfast: Start your day with a healthy breakfast at Green Zebra Cafe.

•Mote Marine Laboratory & Aquarium: Spend the morning exploring Mote Marine Laboratory & Aquarium. It’s a wonderful place to learn about marine life and conservation efforts.

Afternoon:

•Lunch: Have lunch at Tommy Bahama or ChaCha Coconuts on St. Armands Circle.

•Lido Beach: It’s beach time at Lido Beach! Pitch your umbrella, soak in the lapping waves, and enjoy the ocean breeze. Stroll to the enchanting mermaid wall at Lido’s northern tip. Lido Beach offers a quieter, more serene escape compared to the lively Siesta Beach.

Evening:

•Dinner: Enjoy a casual dinner at Venezia (Italian) and finish the evening with some ice cream from Kilwin’s. Take a leisurely walk around St. Armands Circle to enjoy the ambiance or swing over to South Lido Beach where you park & stroll to the iconic Lido Key Tiki Bar for a nightcap & sunset on the sand with your favorite tropical drink.

Day 6: Bayfront Adventures

Morning:

•Breakfast: Grab coffee from Project Coffee and head to Bayfront Park. Enjoy a morning stroll, taking in the beautiful bay views and lush greenery, surrounded by boats, banyan trees, and beautiful Sarasota Bay.

•Pontoon Boat Adventure: Rent a Starcraft 19 SVX Deck Boat or an Aloha 26 Double Decker w/ Slide from Suntex Boat Club & Rentals, located at Bayfront Park, and spend a few hours exploring Sarasota Bay for mandatory stops for water fun. It’s a great way to see the local wildlife and enjoy the water.

Afternoon:

•Lunch: Enjoy lunch at Marina Jack, with a stunning view of the bay and Island Park.

•LeBarge Sightseeing Cruise: After lunch, enjoy a sightseeing cruise with LeBarge. These cruises offer a chance to see dolphins and manatees in their natural habitat while the boat captain handles the driving.

Evening:

•Dinner: Head to Owen’s Fish Camp in Burns Court for a fantastic seafood dinner. The rustic, laid-back atmosphere is perfect for ending the day on a high note.

Day 7: Myakka River State Park

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby Myakka River State Park: Spend the day exploring Myakka River State Park.

•Hike the trails, take a guided airboat tour, and enjoy the park’s natural beauty and wildlife. The park offers a glimpse into “Old Florida” with its lush landscapes and abundant wildlife.

Afternoon:

•Lunch: Pack a picnic or grab lunch at the park’s café, Pink Gator Café. If you choose the park’s cafe, enjoy lunch, dessert or a craft beer, all while immersed in the beautiful Upper Myakka Lake from the cafe’s elevated dining room. The cafe’s menu includes a fresh homemade menu, including alligator stew and seafood gumbo, sandwiches, wraps, grilled hamburgers and hotdogs, and popular sides such as onion rings, jalapeno poppers and more. The cafe also offers a dessert bar with Swamp Gator Sundaes, ice cream, cakes and pies.

•Explore More: Spend the afternoon exploring more of the park. Consider renting bikes: single bicycles, tandem bicycles, and children’s bicycles are available to rent. Myakka’s 37,000-plus acres provide a wonderful habitat for wading birds, raptors, songbirds, migratory birds, and ducks. Whether you are a professional or amateur birder, you won’t be disappointed.

•Hike to Myakka State Park’s Deep Hole, where (when the weather is dry and cool) you are guaranteed to observe hundreds, perhaps thousands of alligators (in the wild, not fenced in) crowding around the shoreline and/or gators’ beady eyes poking through the river’s waterline.

•Stop by the canopy walkway for stunning views or rent a canoe for a peaceful paddle on the river. Kids enjoy the park’s geo-caching: Geocaching is an outdoor game using hand-held global positioning systems (GPS) devices. What kid or parent doesn’t have a mobile device today? It’s an inexpensive, interactive high-tech treasure hunt that’s a great way to learn geography. Last, consider guided horseback trail ride. Myakka has 12 miles of designated horse trails.

Evening:

•Dinner: Head back to Sarasota for your final dinner. Choose a restaurant downtown Sarasota that offers a special farewell meal, perhaps Mattison’s City Grille, Duval’s (for fresh, local seafood), or Patrick’s 1481 (to list a few or many) for a lively atmosphere and delicious food.

•Final Night Stroll: End your trip with a sunset stroll Downtown, at Bayfront Park, across the Ringling Causeway, or along Lido Beach, reflecting on the wonderful memories you’ve made during your week in Sarasota.

The Magic Doesn’t End Here… 🌴

Your week in Sarasota may be coming to a close, but the memories — the fiery Gulf sunsets, the taste of fresh seafood, the laughter echoing down Siesta Village — will linger long after your flip-flops are packed away. Whether you kayaked with crabs, danced in the sand, or stood in awe beneath The Ringling’s banyan trees, you’ve only scratched the surface of what Sarasota offers.

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Sarasota is waiting. Will you return — or stay for good? 🐚
#SarasotaLifestyle #VisitSarasota #7DaysInSarasota #PlanYourEscape #GulfCoastDreaming

Best Tropical Drink Recipes…Even when you’re not in sarasota – Mix up sarasota’s favorite tropical drinks and enjoy island vibes wherever you are.

Day 1: Siesta Key Adventures

Morning:

•Breakfast: Start your day at Another Broken Egg in Siesta Village. This charming eatery offers a variety of delicious breakfast options, perfect for fueling up for the day.

Afternoon:

•Lunch: Swing back to Siesta Key Village and choose from Gilligan’s, The Old Salty Dog, or Flavio’s Brick Oven Pizza & Bar for a delightful meal.

•Explore the Village: Spend some time exploring the local shops for unique souvenirs.

Evening:

•Dinner: Enjoy a delicious dinner at Siesta Key Summer House, known for its fresh seafood and tropical ambiance.

•Stroll and Relax: End the day with a relaxed walk along the beach, enjoying the sound of the waves and the cool evening breeze.

Day 2: Discovering Lido Key

Morning:

•Breakfast: Enjoy a hearty breakfast at the Blue Dolphin Cafe on St. Armands Circle. This spot is a favorite for its cozy atmosphere and delicious breakfast fare.

•St. Armands Circle: After breakfast, take a leisurely walk around the Circle to explore the unique shops and beautiful sculptures.

Late Morning:

Afternoon:

•Lunch: Have lunch at Tommy Bahama Restaurant & Bar with a view of St. Armands Circle.

•Beach Time: Spend the afternoon at Lido Beach. If you prefer a quieter setting, drive to the south end of Lido Beach for a more serene experience.

Evening:

•Night Stroll: Enjoy a stroll around St. Armands Circle taking in the vibrant nightlife and perhaps indulging in some ice cream from Kilwin’s.

Day 3: Sarasota's Hidden Gems

Morning:

•Breakfast: Visit Toasted Mango Cafe in The Rosemary District for a locally beloved breakfast.

Afternoon:

•Lunch: Grab lunch at Food+Beer in The Rosemary District or try The Spice Station for a flavorful meal.

•Explore Downtown: Spend the afternoon exploring downtown Sarasota. Visit the art galleries, boutiques, and historic sites.

Evening:

•Dinner: Head to The Westin Rooftop Bar for dinner, drinks, and a stunning sunset view over Sarasota.

•Night Out: Enjoy an evening in downtown Sarasota, perhaps catching a live performance or simply strolling along the picturesque streets.

Day 4: The Ringling & More

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby café before heading out.

Afternoon:

•Lunch: Have lunch at The Banyan Cafe or The Ringling Grillroom on the grounds of The Ringling.

Evening:

•Dinner: Head back to Siesta Key for a daiquiri at The Daiquiri Deck. For dinner, choose Captain Curt’s Crab & Oyster Bar or Siesta Key Oyster Bar.

Day 5: Marine Adventures & More

Morning:

•Breakfast: Start your day with a healthy breakfast at Green Zebra Cafe.

•Mote Marine Laboratory & Aquarium: Spend the morning exploring Mote Marine Laboratory & Aquarium. It’s a wonderful place to learn about marine life and conservation efforts.

Afternoon:

•Lunch: Have lunch at Tommy Bahama or ChaCha Coconuts on St. Armands Circle.

Evening:

Day 6: Bayfront Adventures

Morning:

Afternoon:

•Lunch: Enjoy lunch at Marina Jack, with a stunning view of the bay and Island Park.

Evening:

•Dinner: Head to Owen’s Fish Camp in Burns Court for a fantastic seafood dinner. The rustic, laid-back atmosphere is perfect for ending the day on a high note.

Day 7: Myakka River State Park

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby Myakka River State Park: Spend the day exploring Myakka River State Park.

•Hike the trails, take a guided airboat tour, and enjoy the park’s natural beauty and wildlife. The park offers a glimpse into “Old Florida” with its lush landscapes and abundant wildlife.

Afternoon:

Evening:

The Magic Doesn’t End Here… 🌴

Sarasota is waiting. Will you return — or stay for good? 🐚
#SarasotaLifestyle #VisitSarasota #7DaysInSarasota #PlanYourEscape #GulfCoastDreaming

Sea Turtie Time: from May to October, watch sea turties nest on sarasota beaches and learn how to protect them.

Day 1: Siesta Key Adventures

Morning:

•Breakfast: Start your day at Another Broken Egg in Siesta Village. This charming eatery offers a variety of delicious breakfast options, perfect for fueling up for the day.

Afternoon:

•Lunch: Swing back to Siesta Key Village and choose from Gilligan’s, The Old Salty Dog, or Flavio’s Brick Oven Pizza & Bar for a delightful meal.

•Explore the Village: Spend some time exploring the local shops for unique souvenirs.

Evening:

•Dinner: Enjoy a delicious dinner at Siesta Key Summer House, known for its fresh seafood and tropical ambiance.

•Stroll and Relax: End the day with a relaxed walk along the beach, enjoying the sound of the waves and the cool evening breeze.

Day 2: Discovering Lido Key

Morning:

•Breakfast: Enjoy a hearty breakfast at the Blue Dolphin Cafe on St. Armands Circle. This spot is a favorite for its cozy atmosphere and delicious breakfast fare.

•St. Armands Circle: After breakfast, take a leisurely walk around the Circle to explore the unique shops and beautiful sculptures.

Late Morning:

Afternoon:

•Lunch: Have lunch at Tommy Bahama Restaurant & Bar with a view of St. Armands Circle.

•Beach Time: Spend the afternoon at Lido Beach. If you prefer a quieter setting, drive to the south end of Lido Beach for a more serene experience.

Evening:

•Night Stroll: Enjoy a stroll around St. Armands Circle taking in the vibrant nightlife and perhaps indulging in some ice cream from Kilwin’s.

Day 3: Sarasota's Hidden Gems

Morning:

•Breakfast: Visit Toasted Mango Cafe in The Rosemary District for a locally beloved breakfast.

Afternoon:

•Lunch: Grab lunch at Food+Beer in The Rosemary District or try The Spice Station for a flavorful meal.

•Explore Downtown: Spend the afternoon exploring downtown Sarasota. Visit the art galleries, boutiques, and historic sites.

Evening:

•Dinner: Head to The Westin Rooftop Bar for dinner, drinks, and a stunning sunset view over Sarasota.

•Night Out: Enjoy an evening in downtown Sarasota, perhaps catching a live performance or simply strolling along the picturesque streets.

Day 4: The Ringling & More

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby café before heading out.

Afternoon:

•Lunch: Have lunch at The Banyan Cafe or The Ringling Grillroom on the grounds of The Ringling.

Evening:

•Dinner: Head back to Siesta Key for a daiquiri at The Daiquiri Deck. For dinner, choose Captain Curt’s Crab & Oyster Bar or Siesta Key Oyster Bar.

Day 5: Marine Adventures & More

Morning:

•Breakfast: Start your day with a healthy breakfast at Green Zebra Cafe.

•Mote Marine Laboratory & Aquarium: Spend the morning exploring Mote Marine Laboratory & Aquarium. It’s a wonderful place to learn about marine life and conservation efforts.

Afternoon:

•Lunch: Have lunch at Tommy Bahama or ChaCha Coconuts on St. Armands Circle.

Evening:

Day 6: Bayfront Adventures

Morning:

Afternoon:

•Lunch: Enjoy lunch at Marina Jack, with a stunning view of the bay and Island Park.

Evening:

•Dinner: Head to Owen’s Fish Camp in Burns Court for a fantastic seafood dinner. The rustic, laid-back atmosphere is perfect for ending the day on a high note.

Day 7: Myakka River State Park

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby Myakka River State Park: Spend the day exploring Myakka River State Park.

•Hike the trails, take a guided airboat tour, and enjoy the park’s natural beauty and wildlife. The park offers a glimpse into “Old Florida” with its lush landscapes and abundant wildlife.

Afternoon:

Evening:

The Magic Doesn’t End Here… 🌴

Sarasota is waiting. Will you return — or stay for good? 🐚
#SarasotaLifestyle #VisitSarasota #7DaysInSarasota #PlanYourEscape #GulfCoastDreaming

Beach yoga in sarasota – Find your zen: Practice yoga on Siesta Key’s sandy shores at sunrises or sunset for a serence, scenic experience.

Day 1: Siesta Key Adventures

Morning:

•Breakfast: Start your day at Another Broken Egg in Siesta Village. This charming eatery offers a variety of delicious breakfast options, perfect for fueling up for the day.

Afternoon:

•Lunch: Swing back to Siesta Key Village and choose from Gilligan’s, The Old Salty Dog, or Flavio’s Brick Oven Pizza & Bar for a delightful meal.

•Explore the Village: Spend some time exploring the local shops for unique souvenirs.

Evening:

•Dinner: Enjoy a delicious dinner at Siesta Key Summer House, known for its fresh seafood and tropical ambiance.

•Stroll and Relax: End the day with a relaxed walk along the beach, enjoying the sound of the waves and the cool evening breeze.

Day 2: Discovering Lido Key

Morning:

•Breakfast: Enjoy a hearty breakfast at the Blue Dolphin Cafe on St. Armands Circle. This spot is a favorite for its cozy atmosphere and delicious breakfast fare.

•St. Armands Circle: After breakfast, take a leisurely walk around the Circle to explore the unique shops and beautiful sculptures.

Late Morning:

Afternoon:

•Lunch: Have lunch at Tommy Bahama Restaurant & Bar with a view of St. Armands Circle.

•Beach Time: Spend the afternoon at Lido Beach. If you prefer a quieter setting, drive to the south end of Lido Beach for a more serene experience.

Evening:

•Night Stroll: Enjoy a stroll around St. Armands Circle taking in the vibrant nightlife and perhaps indulging in some ice cream from Kilwin’s.

Day 3: Sarasota's Hidden Gems

Morning:

•Breakfast: Visit Toasted Mango Cafe in The Rosemary District for a locally beloved breakfast.

Afternoon:

•Lunch: Grab lunch at Food+Beer in The Rosemary District or try The Spice Station for a flavorful meal.

•Explore Downtown: Spend the afternoon exploring downtown Sarasota. Visit the art galleries, boutiques, and historic sites.

Evening:

•Dinner: Head to The Westin Rooftop Bar for dinner, drinks, and a stunning sunset view over Sarasota.

•Night Out: Enjoy an evening in downtown Sarasota, perhaps catching a live performance or simply strolling along the picturesque streets.

Day 4: The Ringling & More

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby café before heading out.

Afternoon:

•Lunch: Have lunch at The Banyan Cafe or The Ringling Grillroom on the grounds of The Ringling.

Evening:

•Dinner: Head back to Siesta Key for a daiquiri at The Daiquiri Deck. For dinner, choose Captain Curt’s Crab & Oyster Bar or Siesta Key Oyster Bar.

Day 5: Marine Adventures & More

Morning:

•Breakfast: Start your day with a healthy breakfast at Green Zebra Cafe.

•Mote Marine Laboratory & Aquarium: Spend the morning exploring Mote Marine Laboratory & Aquarium. It’s a wonderful place to learn about marine life and conservation efforts.

Afternoon:

•Lunch: Have lunch at Tommy Bahama or ChaCha Coconuts on St. Armands Circle.

Evening:

Day 6: Bayfront Adventures

Morning:

Afternoon:

•Lunch: Enjoy lunch at Marina Jack, with a stunning view of the bay and Island Park.

Evening:

•Dinner: Head to Owen’s Fish Camp in Burns Court for a fantastic seafood dinner. The rustic, laid-back atmosphere is perfect for ending the day on a high note.

Day 7: Myakka River State Park

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby Myakka River State Park: Spend the day exploring Myakka River State Park.

•Hike the trails, take a guided airboat tour, and enjoy the park’s natural beauty and wildlife. The park offers a glimpse into “Old Florida” with its lush landscapes and abundant wildlife.

Afternoon:

Evening:

The Magic Doesn’t End Here… 🌴

Sarasota is waiting. Will you return — or stay for good? 🐚
#SarasotaLifestyle #VisitSarasota #7DaysInSarasota #PlanYourEscape #GulfCoastDreaming

Sarasota’s Rhythm & Vibes Series

Day 1: Siesta Key Adventures

Morning:

•Breakfast: Start your day at Another Broken Egg in Siesta Village. This charming eatery offers a variety of delicious breakfast options, perfect for fueling up for the day.

Afternoon:

•Lunch: Swing back to Siesta Key Village and choose from Gilligan’s, The Old Salty Dog, or Flavio’s Brick Oven Pizza & Bar for a delightful meal.

•Explore the Village: Spend some time exploring the local shops for unique souvenirs.

Evening:

•Dinner: Enjoy a delicious dinner at Siesta Key Summer House, known for its fresh seafood and tropical ambiance.

•Stroll and Relax: End the day with a relaxed walk along the beach, enjoying the sound of the waves and the cool evening breeze.

Day 2: Discovering Lido Key

Morning:

•Breakfast: Enjoy a hearty breakfast at the Blue Dolphin Cafe on St. Armands Circle. This spot is a favorite for its cozy atmosphere and delicious breakfast fare.

•St. Armands Circle: After breakfast, take a leisurely walk around the Circle to explore the unique shops and beautiful sculptures.

Late Morning:

Afternoon:

•Lunch: Have lunch at Tommy Bahama Restaurant & Bar with a view of St. Armands Circle.

•Beach Time: Spend the afternoon at Lido Beach. If you prefer a quieter setting, drive to the south end of Lido Beach for a more serene experience.

Evening:

•Night Stroll: Enjoy a stroll around St. Armands Circle taking in the vibrant nightlife and perhaps indulging in some ice cream from Kilwin’s.

Day 3: Sarasota's Hidden Gems

Morning:

•Breakfast: Visit Toasted Mango Cafe in The Rosemary District for a locally beloved breakfast.

Afternoon:

•Lunch: Grab lunch at Food+Beer in The Rosemary District or try The Spice Station for a flavorful meal.

•Explore Downtown: Spend the afternoon exploring downtown Sarasota. Visit the art galleries, boutiques, and historic sites.

Evening:

•Dinner: Head to The Westin Rooftop Bar for dinner, drinks, and a stunning sunset view over Sarasota.

•Night Out: Enjoy an evening in downtown Sarasota, perhaps catching a live performance or simply strolling along the picturesque streets.

Day 4: The Ringling & More

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby café before heading out.

Afternoon:

•Lunch: Have lunch at The Banyan Cafe or The Ringling Grillroom on the grounds of The Ringling.

Evening:

•Dinner: Head back to Siesta Key for a daiquiri at The Daiquiri Deck. For dinner, choose Captain Curt’s Crab & Oyster Bar or Siesta Key Oyster Bar.

Day 5: Marine Adventures & More

Morning:

•Breakfast: Start your day with a healthy breakfast at Green Zebra Cafe.

•Mote Marine Laboratory & Aquarium: Spend the morning exploring Mote Marine Laboratory & Aquarium. It’s a wonderful place to learn about marine life and conservation efforts.

Afternoon:

•Lunch: Have lunch at Tommy Bahama or ChaCha Coconuts on St. Armands Circle.

Evening:

Day 6: Bayfront Adventures

Morning:

Afternoon:

•Lunch: Enjoy lunch at Marina Jack, with a stunning view of the bay and Island Park.

Evening:

•Dinner: Head to Owen’s Fish Camp in Burns Court for a fantastic seafood dinner. The rustic, laid-back atmosphere is perfect for ending the day on a high note.

Day 7: Myakka River State Park

Morning:

•Breakfast: Enjoy breakfast at your resort or a nearby Myakka River State Park: Spend the day exploring Myakka River State Park.

•Hike the trails, take a guided airboat tour, and enjoy the park’s natural beauty and wildlife. The park offers a glimpse into “Old Florida” with its lush landscapes and abundant wildlife.

Afternoon:

Evening:

The Magic Doesn’t End Here… 🌴

Sarasota is waiting. Will you return — or stay for good? 🐚
#SarasotaLifestyle #VisitSarasota #7DaysInSarasota #PlanYourEscape #GulfCoastDreaming

15 Must-See Icons of Sarasota That Shape the Community

The must see icons of Sarasota aren’t just landmarks or restaurants—they’re touchstones of memory and community. For nearly 40 years, my wife and I have enjoyed these Sarasota icons, raising kids, meeting friends, and making memories we thought would last forever. Some remain, others have disappeared, but all of them helped shape Sarasota’s character.

Patriot’s Pier @ Sunset Point (North Siesta Key Beach)

Patriot’s Pier has always been more than just the remains of an old foundation—it’s one of the must see icons of Sarasota. Back in the ’90s and early 2000s, kids would walk to the end and perform backflips into the Gulf, where the water was once deep enough to welcome them.

I can still picture strolling the mile-and-a-half stretch from Siesta Beach to Sunset Point. The Gulf waves once pounded the rocky shoreline at the Point, a natural barrier between Whispering Sands and Sunset Point. Today, Mother Nature has shifted the sands, softening the north end, but one ritual remains: every night, the flag is lowered to the sound of Taps.

Did You Know?

Locals have been lowering the flag at Patriot’s Pier with the playing of Taps every night for decades, entirely organized by community volunteers.

O’Leary’s Tiki Bar & Grill

For my family, Island Park was always “the backyard we wish we owned.” My kids grew up running along its paths and climbing onto benches and swings. Tucked into one corner is O’Leary’s Tiki Bar & Grill, where live music spills into the salty Bay breeze nearly every night.

We’d grab a sandwich or cold drink, sit back, and let the sounds drift over us. Between O’Leary’s and Marina Jack, the music always carried across the water.

Fun Fact

O’Leary’s is one of the few tiki bars in Sarasota where you can hear live music seven days a week — everything from reggae to acoustic rock.

Lido Key Tiki Bar

Years ago, around Christmas, I took my kids to South Lido Beach. My son skimboarded while my daughter played in the sand. She’d dig in the sand, build trenches, & fill a pail hundreds of times without tiring. Together, we tried shaping a sandman, laughing at the result while knowing the joy was in the attempt.

Later we wandered to the Lido Key Tiki Bar, one of the must see icons of Sarasota for both locals and visitors. I grabbed a drink, sodas for the kids, and we circled the firepit—not because it was cold, but because it was fun. They chattered about Christmas, Disney, and Santa as if Sarasota’s barefoot winter was the most normal thing in the world.

To this day, it remains an off-the-beaten-path treasure, accessible only by staying nearby, walking from the public beach, or parking at South Lido.

Did You Know?

The Lido Key Tiki Bar has no formal street address — it’s tucked behind the Ritz-Carlton condos & Beach Club, making it one of Sarasota’s best “hidden” gems.

Statue of David @ The Ringling

The replica of Michelangelo’s David at The Ringling has always been one of the must see icons of Sarasota. I remember the first time I took high school students there in the 1980s—they were in awe, not just of the size of the statue but of the fact that Sarasota had something so world-class in its backyard.

Today, the David continues to symbolize Sarasota’s love of art, its willingness to dream big, and its roots as a cultural destination.

Fun Fact

The David statue at The Ringling is a replica of Michelangelo’s masterpiece in Florence, Italy, and it has stood as Sarasota’s unofficial art ambassador since 1986.

Owen’s Fish Camp in Burns Court

Owen’s Fish Camp is Sarasota’s definition of quirky charm. Nestled in Burns Court, it feels like Old Florida wrapped in string lights. The first time my wife and I dined there, we felt like we’d stumbled into a secret hideout where Southern comfort food meets Sarasota creativity.

From the funky décor to the outdoor seating, Owen’s is the kind of place that captures Sarasota’s character—laid-back, authentic, and unforgettable.

Did You Know?

Owen’s Fish Camp is named after the original property owner’s son, Owen Burns, who helped shape much of Sarasota’s early development in the 1920s.

The Mermaid Wall at North Lido Beach

Murals always grab my attention, and the Mermaid Wall at North Lido Beach about 1 mile from the public beach parking lot stopped me in my tracks the first time I saw it. Bright, whimsical, and larger-than-life, it turned a blank wall into a community landmark.

The funky, whimsical mermaid wall is enough of a reason to stroll or jog from the public beach parking. You’ll encounter few people past the public beach, creating a zen-like beach experience with this reward at the end of the journey…or at the halfway point.

Fun Fact

The Mermaid Wall at the north end of Lido Beach has been a living canvas for years. What began as a single mermaid sketch has evolved through multiple revisions—adding brighter colors, a second mermaid, even tops to the figures. Each layer tells the story of how locals and beachgoers have left their creative imprint on this quirky Sarasota landmark.

The Stockyard (Gone But Not Forgotten)

Most people – including longtime locals – never stepped foot in the Stockyard off Cattlemen.

Christmastime was my reason each year to stop by for a small bale of hay for our Nativity. I couldn’t help but wander around the store and feel I was whisked back to my grandpa’s horse stable & barn.

No doubt, the Stockyard represented Old Sarasota, farmers and ranchers. Recently, it shut down forever, leaving behind memories for even non farmers and ranchers like me who returned each year.

Did You Know?

Stockyard Feed & Western Wear in Sarasota traced its roots back to 1956, doing business for nearly 70 years before closing its doors.

Siesta Key Beach Rentals “Shack” (Gone But Not Forgotten)

The little shack at Siesta Key Beach Rentals provided chairs & umbrella for decades. Its weathered wood and casual vibe felt like it belonged perfectly in Siesta’s relaxed rhythm.

Every time I walked past, I smiled at how it served as a quiet reminder that the best parts of Siesta aren’t polished—they’re authentic.

Fun Fact

The Shack that's long gone was a beach icon for decades, renting chairs & umbrellas to beachgoers.

The Yellow Lifeguard Stand – Siesta Key Beach

From the first time I visited Siesta Key Beach, the yellow lifeguard stand has been my favorite. Nearly 40 years later, I still head to the south lot just to set up near it.

Yellow dominates my photos because it just works: bold against the white quartz sand, the blue Gulf, and the open sky. For me, that lifeguard stand isn’t just a backdrop—it’s one of the must see icons of Sarasota.

Did You Know?

Each of Siesta Beach’s lifeguard stands is color-coded (red, blue, green, and yellow), but the yellow stand is the most photographed thanks to its southern location and perfect Gulf backdrop.

JR’s Old Packinghouse Café

At JR’s Old Packinghouse Café, food and music blend into one experience. The first time I walked in, it felt like a throwback—a little worn, a little loud, and completely authentic.

Over the years, it’s been the kind of place where strangers share tables, musicians fill the air, and locals walk out with new friends. It’s Sarasota stripped of pretense, and that’s why it’s endured.

Fun Fact

JR’s Old Packinghouse Café is inside a 1920s citrus packinghouse building, preserving Sarasota’s agricultural roots with live music and comfort food.

Hart’s Landing Bait & Tackle

The rustic charm of Hart’s Landing defines the space at Eloise Werlin Park under the Ringling Causeway. When my kids were small, we’d stop for bait, linger to watch pelicans dive, and laugh as they crash-landed into the Bay.

Sometimes we fished, sometimes we just strolled the bridge, circling back for sodas or ice cream. For us, Hart’s wasn’t just about fishing—it was about time together, surrounded by Sarasota’s simplest pleasures.

Did You Know?

Hart’s Landing is Sarasota’s oldest saltwater fishing bait shop, serving locals and visitors for more than 50 years.

Golden Apple Dinner Theatre (Gone But Not Forgotten)

Though it’s gone now, the Golden Apple Dinner Theatre once anchored Sarasota’s nightlife. My wife and I enjoyed comedies, musicals, and dinners there, nights that always felt special.

It wasn’t just about the shows—it was about Sarasota gathering together. Its absence is still felt.

Fun Fact

The Golden Apple Dinner Theatre hosted Broadway actors and touring performers for decades, making it one of the first venues to bring professional theater to Sarasota.

Hob Nob Drive-In Burger Joint (Gone But Not Forgotten)

At the corner of 301 and 17th Street, Hob Nob had been flipping burgers and pouring milkshakes since the 1950s.

I’d taken my kids there countless times, a quaint burger joint that made you feel like you’d stepped back in time. Hob Nob is a Sarasota icon because it didn’t changed much—it was comfort food and nostalgia rolled into one.

Did You Know?

Hob Nob opened in 1957, making it Sarasota’s longest-running drive-in restaurant until it recently flipped its last burger.

New Pass Grill

On the water by New Pass Bridge, the New Pass Grill is as classic as it gets. Grab a grouper sandwich, sit at a picnic table, and let the view remind you why Sarasota’s lifestyle is hard to beat.

What I’ve always loved is how it hasn’t overcomplicated itself. It’s just food, water, and the people you’re with—that’s the Sarasota way.

Did You Know?

The New Pass Grill claims to have served more than 1 million grouper sandwiches since opening in the 1920s.

The Ringling Causeway

The Ringling Causeway is more than a bridge—it’s one of the must see icons of Sarasota, stretching gracefully across the Bay to connect downtown with Lido Key. From Island Park, my favorite vantage point, I often capture a sunset sky above the Bay, the domed Grande Riviera condos on Golden Gate Point, and the bridge arcing across it all.

For my kids, though, the bridge wasn’t just a photo backdrop—it was an adventure. Walking or biking to the top felt like climbing Mount Olympus, surrounded by water at the highest point in Sarasota. Of course, when they were little, I rarely made it across without carrying one of them part of the way. The Causeway has always been more than infrastructure—it’s a symbol of connection, a stage for exercise, and one of Sarasota’s most iconic views.

Fun Fact

The current John Ringling Causeway Bridge opened in 2003, replacing the original 1959 drawbridge — and it won awards for its sleek, artistic design.

Closing Thoughts: Why Sarasota’s Icons Matter

The must see icons of Sarasota aren’t just places—they’re memories. They’re the tiki bars where we warmed ourselves around a fire in December, the bait shops where pelicans stole the show, the lifeguard stands that framed our family photos, the bridges that became family hikes, and the theaters where we laughed late into the night.

They remind us that Sarasota is more than sunshine and real estate—it’s a community shaped by places where people gather.

📌 Keep Exploring Sarasota:

📅 Browse the Sarasota Lifestyle Events Calendar to find today’s local icons. It’s growing each week, as I am determined to make it your go-to “What’s happening in Sarasota?” resource.

🌐 Learn more through Sarasota County Parks & Recreation.

🌴 Dive into our pillar guide: 7 Unforgettable Days in Sarasota.

Sarasota Chalk Festival – Stories from a Local

I still remember walking through Burns Court that first year (I think 2007) the Chalk Festival hit Sarasota. My wife’s parents were visiting. We’d just strolled the Bayfront Park, swinging over to Burns Square for lunch at Owen’s Fish Camp. Imagine my surprise to see the streets blocked off and artists leaning into their section of blacktop. The sun was hot, the pavement was alive with color, and I stopped in my tracks when I realized what I was seeing wasn’t just “chalk drawings.” It was world-class art being created right under my shoes — and watching kids crouch down beside masters from Italy and Mexico, trying to copy their strokes in the dust, made me think: Only in Sarasota could a sidewalk feel like a gallery opening.

What Makes the Sarasota Chalk Festival Special

When the festival first started in Burns Court in Downtown Sarasota (c 2007), it was small, intimate, and personal. That year, my wife’s parents were visiting. We’d just strolled the Bayfront had had swung over to Burns Square & Owen’s Fish Camp for lunch. Imagine my surprise when we stumbled upon a closed South Pineapple & several artists on hands & knees, in various stages of their chalk masterpieces.

In those early years, the atmosphere felt more like a neighborhood block party than an international event. Artists would pause mid-sketch to answer questions, kids crouched at the edges of the drawings with wide eyes, and locals wandered from one creation to the next with coffee cups in hand. There was no rush, no crowds pressing in—just the magic of asphalt being transformed into a gallery of color.

One of my favorite parts was the way the whole street became a stage for Sarasota itself. Live music drifted in from nearby cafés, food aromas from local restaurants hung in the air, and neighbors lingered around chalk squares as if they were gathering in someone’s living room. It wasn’t just an art show; it was Sarasota celebrating creativity in its purest form.

Beyond the dazzling art, the Sarasota Chalk Festival stands out for its atmosphere. Live music often floated through the streets, while nearby restaurants spilled aromas of freshly prepared food into the air. Crowds strolled from one masterpiece to the next, pausing to talk with artists, snap photos, and soak in the creative energy that seemed to rise right out of the pavement.

What makes this festival special isn’t just the art—it’s the way Sarasota itself becomes part of the canvas.

Sarasota Chalk Festival 2011: When Lego Soldiers Took Over

The 2011 Sarasota Chalk Festival, the fourth year of the event, was unforgettable for the buzz it created. That was the year Dutch chalk artist Leon Keer made international headlines with his creativity and flair for spectacle. Before the festival even began, Sarasota was abuzz after a giant Lego-like statue mysteriously “washed ashore” on a local beach. The publicity stunt was connected to the playful work of artist Ego Leonard, and it set the stage for something even bigger at ChalkFest.

On the pavement, Leon Keer unveiled his astonishing 3D anamorphic chalk masterpiece, the Lego Terracotta Army, inspired by the famous clay soldiers buried with Qin Shi Huang, the first Emperor of China. The painting wasn’t just technically brilliant—it carried a deeper message. Designed in honor of Ego Leonard, the piece symbolized support for his “release from protective custody,” blending whimsy with historical gravity.

The illusion of Lego soldiers stretching into the distance left festivalgoers speechless. People crouched, posed, and photographed themselves “standing among the Terracotta Army.” That year, Sarasota felt like the global epicenter of street art, with the world’s top chalk artists gathering downtown to transform ordinary asphalt into extraordinary statements.

Sarasota Chalk Festival 2012 – A Circus Tribute with the Wallendas

If I had to pick one year, 2012 was my favorite ChalkFest. The festival theme celebrated Sarasota’s circus heritage, and the streets came alive with elephants, acrobats, and ringmasters rendered in chalk. For someone who grew up here, with the Ringling legacy woven into the fabric of the city, it felt like the perfect tribute.

One of my favorite parts was the Chalk Grill, a pop-up hub where local musicians played and festivalgoers lounged on oversized chairs that lined the street. The scent of grilled food and nearby restaurant menus spilled into the air, creating this cozy blend of art, music, and food that made the whole festival feel alive. It wasn’t just an art show; it was Sarasota gathering around creativity in its purest form.

That was also the year I witnessed world-renowned 3D artist Kurt Wenner guide the creation of a circus-themed marquee piece featuring an elephant-drawn carriage. The spectacle wasn’t just on the pavement—tightrope walker Nik Wallenda and his wife Erendira wowed the crowd one Saturday night, balancing high above the street while my daughter, too young and nervous, couldn’t even bear to look up. Later, their 73-foot sway pole act left the entire audience holding its breath as the couple performed dazzling stunts that felt almost impossible against the Sarasota night sky.

The Wallendas: Sarasota’s Circus Legacy

The Wallenda family are more than just daredevils—they’re Sarasota natives who have given so much back to this community, both in spirit and through charity. Nik Wallenda, a seventh-generation member of the legendary Flying Wallendas, epitomizes the blend of Sarasota’s fleeting circus past and its living, breathing present.

Nik’s shows have incorporated nearly every daring circus art imaginable—water and diving feats, the Wheel of Death, incline motorcycles, aerial silks, hoops, the globe of death, and of course, his signature tightrope walks. As Nik himself says: “We’ve performed nearly every circus or daredevil skill there is. I like to mix it up. It keeps our family on our toes and gives the public something new to see every year.”

That year, between the chalk tributes on the streets and the Wallendas soaring above them, Sarasota felt like the circus capital of the world once again.

Why the Sarasota Chalk Festival Captures the Spirit of the City

Beyond the dazzling art, the Sarasota Chalk Festival stands out for its atmosphere. Music filled the streets from the Chalk Grill stage, where loungers and food vendors created an outdoor living room feel. Restaurants nearby poured their menus into the air, filling downtown with aromas that mixed with chalk dust and the ocean breeze.

What makes this festival special isn’t just the art—it’s the way Sarasota itself becomes part of the canvas.

FAQs about the Sarasota Chalk Festival

•Who are the well-known chalk artists who’ve created stunning street art at the Chalk Festival in Sarasota?
The Sarasota Chalk Festival has drawn many of the world’s top street painters, thanks to Denise Kowal’s vision and Sarasota’s early embrace of the art form. Some of the most well-known chalk artists who’ve left their mark on Sarasota’s pavement include:

🎨 Internationally Renowned 3D Chalk Artists:

•Kurt Wenner (USA) – Considered the father of modern 3D street painting, Wenner brought his mind-bending illusions to Sarasota, including the famous circus-themed elephant-drawn carriage marquee piece.

•Leon Keer (Netherlands) – Known for playful, thought-provoking anamorphic art, Keer created the unforgettable 3D Lego Terracotta Army (2011), which became one of the most photographed pieces in festival history.

•Eduardo Relero (Spain) – A surrealist chalk artist, Relero’s work often combines humor with social commentary, making his Sarasota pieces both visually stunning and conversation-starting.

•Julian Beever (UK) – Nicknamed “the Pavement Picasso,” Beever is world-famous for optical illusion chalk art. His Sarasota work drew massive crowds.

•Tracy Lee Stum (USA) – A Guinness World Record holder for the largest chalk painting, she’s known for her vivid colors and massive 3D illusions.

🌍 Other Notable Street Artists at Sarasota ChalkFest:

•Eduardo Kobra (Brazil) – International muralist who also created chalk works during Sarasota’s festival years.

•Jennifer Chaparro (USA) – An award-winning Florida-based chalk artist recognized for her whimsical 3D scenes.

•Eduardo Monteiro (Mexico) – Brought large-scale cultural and historic themes to Sarasota streets.

•Ever Galvez (USA) – Known for ultra-realistic portraits and classical style chalk murals.

Why They Came to Sarasota….

By around 2010–2012, Sarasota’s Chalk Festival had become one of the largest and most prestigious street painting festivals in the world, drawing artists from five continents. What started on Pineapple Avenue in Burns Court quickly earned Sarasota an international reputation as a hub for pavement art.

•Who founded the Sarasota Chalk Festival and how long has it run?

Denise Kowal, a Sarasota resident and community organizer, founded and launched the Sarasota Chalk Festival in 2007.

She started it in the Burns Square Historic District (often called Burns Court) in downtown Sarasota. What began as a small, local gathering quickly grew into an internationally recognized street art festival, attracting top chalk artists from around the world within just a few years.

•What makes ChalkFest unique?
Its combination of interactive street and wall art, different theme each year (i.e. circus heritage), and an intimate atmosphere where visitors can talk directly with artists.

💬 Final Thoughts from Mike

The Sarasota Chalk Festival has always been one of my favorite reminders of what makes this community so special: creativity, culture, and people coming together. Whether it’s circus tributes, 3D illusions, or artists from across the world filling our streets, it shows how Sarasota mixes art with everyday life in a way few places can.

And ChalkFest is just one piece of the Sarasota story. If you enjoyed reading about it, you’ll probably love exploring more of what this city offers—whether it’s planning a week-long visit or keeping up with the next great festival.

👉 Start with our 7 Day Sarasota Itinerary: Beaches, Food & Hidden Gems for a perfect balance of beaches, culture, and hidden gems.
👉 Don’t miss the Sarasota Events Calendar to keep track of festivals, concerts, and local happenings.

Because while the chalk may wash away, the creativity and energy of Sarasota never really leave—it just shows up in new colors, new events, and new memories waiting to be made.

Sarasota Medieval Fair: Jousting, Comedy, and Feasting Under the Oaks

I’ll never forget the first time I saw the carillon at the Sarasota Medieval Fair.

A man dressed in all black—his face hidden by the mask of a bird—stood before a massive tower of bronze bells. His arms swooped in and out with exaggerated movements, mimicking the wings of a crow or raven. When he pounded the keys, the music that poured out was jarring at first: tense, booming notes that unsettled the crowd. But as the rhythm carried on, the sound shifted into something trance-like. Hypnotic. The longer he played, the more it felt like the bells themselves were alive, drawing everyone deeper into his strange, captivating performance.

That uneasy mix of laughter, awe, and mystery is exactly what makes Sarasota’s Medieval Fair so memorable.

Hilarity, Rowdiness, and Wholesome Fun at the Sarasota Medieval Fair

The festival doesn’t just rely on music to grab your attention. The stage shows alone are worth the price of admission. Take the Wishing Well Wenches—two women who don corsets, lace, and mischievous grins to deliver one of the most irreverent comedy acts you’ll ever see. Their R-rated banter has a way of filling the stands quickly, as they poke fun at everything from relationships to taboo topics that wouldn’t dare make it onto a polite stage. The laughter is raucous, the humor shameless, and the crowds keep coming back for more.

Other corners of the fairground invite the same spirit of rowdy fun. A line of revelers dressed in Renaissance garb winds its way past artisans’ tents, loud and playful—it’s the fair’s version of a pub crawl, and they throw themselves into character with gusto. Meanwhile, families gather for jousting tournaments, where knights thunder across the field on horseback, splintering lances to the roar of the crowd.

When the Sarasota Medieval Fair Finally Found Its Stride

By 2015, I had already been to the Sarasota Medieval Fair several times. But that year felt different. It wasn’t my first visit—it was the year the fair seemed to finally find its stride. The pieces all clicked into place: the immersive set design, the artisans hard at work, the irreverent stage shows, the musicians filling the air with bagpipes and drums, the vendors offering wares that looked lifted straight from history, and the devoted fans who fully embraced the role-playing.

What once felt like a fun distraction now stopped me in my tracks as a truly authentic medieval experience. I stepped under the faux castle façade, and immediately bagpipes and percussion thundered through the oaks from a stage to my left. The smell of smoke from open-air grills drifted in from the food court. Everywhere, artisans worked at their crafts as though history had folded in on itself—blacksmiths hammering iron, leatherworkers shaping boots, an apothecary hawking oils and herbs. Bright gowns in shades of gold and crimson spilled from “Tickle Ye Fancy.” Tarot readers and palm readers beckoned from shaded tents.

It wasn’t just a fair. It was a living world.

Why the Sarasota Medieval Fair Feels So Real

One of the things that struck me most was how authentic it all felt. This wasn’t a flea market dressed up with plastic swords. The artisans weren’t reselling trinkets from Amazon—they were creating real, working displays of their craft.

The musicians were real.
The camels were real.
The entertainers were real.

And many of them were hilarious—sometimes irreverent, sometimes awe-inspiring, but always committed to the roles they played. From sword fights to human chess to the aerialist spinning through the air on his “wheel of death,” every corner of the fairgrounds hummed with energy.

Food, Drink, and Revelry at the Sarasota Medieval Fair

Of course, no Medieval Fair would be complete without a proper feast. The food court at Sarasota’s fair is as much a stage as any jousting field. Giant turkey legs drip with juice, gyros spin on open-air spits, and ales are poured by “barmaids” who are quick with a joke and a wink. Sit long enough with your plate and you’ll hear the sound of pipes and drums marching past as a band of musicians strikes up a tune.

Everywhere you turn, it’s a feast for the senses: laughter, smoke, music, and merriment layered together into one unforgettable atmosphere.

Sarasota Medieval Fair – Its History and Roots

While the magic of the fair is in the experience, it helps to understand where it all began. The Sarasota Medieval Fair first launched in 2005, originally staged at the Sarasota Fairgrounds. Even in those early years, jousting tournaments, artisans’ booths, and costumed performers were the heart of the event.

But the festival quickly outgrew its downtown space. In 2021, it relocated to its current home at the Woods of Mallaranny, a sprawling 47-acre site east of I-75. Surrounded by oak trees and winding trails, the new location elevated the experience into something more immersive. Instead of concrete and asphalt, visitors now wander shaded pathways that feel far closer to an authentic medieval village.

The fair typically unfolds across multiple weekends each November, drawing locals and visitors alike. Its success lies in the careful blend of history, entertainment, and community—it’s not just about reliving the Middle Ages, but about celebrating the creativity and joy that come from stepping out of the modern world for a while.

Sights and Sounds of the Sarasota Medieval Fair

One of the things that surprised me most was just how much there was to do and see. I had taught high school English for nearly two decades, with the Medieval period as a staple in my classroom, but seeing it brought to life like this was something else entirely:

•Human Chess – A life-sized chessboard where real people served as the pieces, acting out their moves with sword fights and drama.

•Axe Throwing & Swordplay – Guests could test their aim or watch armored combatants battle it out.

•The Joust – Knights in shining armor thundered across the field on horseback, lances at the ready. The roar of the crowd rivaled any sports arena.

•“St. Nikolaus” – Seasonal entertainment reminding everyone of the holidays through a medieval lens.

•Food & Drink Court – Yes, the famous turkey legs were there, but so were gyros, stews, ales, and ciders—served with a wink by costumed “barmaids.”

•Irreverent Stage Shows – From bawdy comedy acts to whip-cracking performers, the humor was sharp, funny, and often R-rated. The Washing Well Wenches, in particular, filled their stage every time.

•Aerial Acts – One year I watched an acrobat spin through the air on his “wheel of death,” a spectacle equal parts terrifying and mesmerizing.

•Cast in Bronze – Perhaps the most unforgettable of all: a carillon performance unlike anything I’d ever seen. Imagine five centuries of music history performed on four tons of bronze bells. The sound shook the air, weaving magic out of metal and rhythm.

•Even the animals were real—camels, horses, and falcons on display, adding to the authenticity.

For me, it’s the mix of the expected and the unexpected that keeps drawing me back. I go for the knights and artisans, but I always leave remembering the strange masked figure pounding out trance-like rhythms on his carillon, or the crowd howling with laughter as two wenches turned taboos into comedy gold.

Final Thoughts on Sarasota’s Medieval Fair

Sarasota has plenty of festivals, but none that match the Medieval Fair’s ability to transport you into another world. From its early days at the Sarasota Fairgrounds to its new life at the Woods of Mallaranny, it has grown into a regional attraction that remains deeply local in spirit.

Whether you come for the history, the food, the comedy, or just the sheer joy of wandering through a recreated medieval village, you’ll walk away with a memory that sticks.

For me, that memory will always begin with the masked bird-man at the carillon—his pounding arms and hypnotic bells reminding me that the Sarasota Medieval Fair is not just a festival. It’s an experience.

Frequently Asked Questions about the Sarasota Medieval Fair

Q: When did the Sarasota Medieval Fair begin?
A: The Sarasota Medieval Fair launched in 2005, originally held at the Sarasota Fairgrounds near downtown Sarasota before moving to the Woods of Mallaranny in 2021.

Q: Where is the Sarasota Medieval Fair held today?
A: The fair is now located at the Woods of Mallaranny, a 47-acre site east of I-75, which offers shaded oak trails, permanent structures, and a more immersive medieval village setting.

Q: What can you see and do at the Sarasota Medieval Fair?
A: Visitors can enjoy jousting tournaments, human chess matches, axe throwing, artisan crafts, costumed performers, stage shows, live music, and unique acts like Cast in Bronze.

Q: What kind of food is served at the Sarasota Medieval Fair?
A: Expect giant turkey legs, gyros, hearty stews, and drinks served by costumed barmaids—all in the lively food court atmosphere that’s as much entertainment as dining.

Q: Is the Sarasota Medieval Fair family-friendly?
A: Yes, the fair is popular with families, offering jousts, interactive games, and historical demonstrations. Some shows, like the Wishing Well Wenches, are adult-oriented, but the festival overall provides entertainment for all ages.

👉 Looking for more upcoming events and festivals? Check out our Sarasota Events Calendar for the latest happenings across the Suncoast.

👉 Want more Sarasota cultural experiences? Don’t miss our coverage of the Sarasota Chalk Festival.

👉 Visit the official Sarasota Medieval Fair website for tickets, maps, themed weekends, and more.

Sarasota Seafood & Music Festival: A Feast by the Bay

The first time I wandered into the Sarasota Seafood & Music Festival, I wasn’t planning to stay long. I had told my wife, “Let’s just check it out for an hour, maybe grab a grouper sandwich, and then head home.” Famous last words.

We parked near Gulfstream Avenue, and the music hit me before I even saw the stage. A horn section was letting loose with a blues riff that felt like it rolled straight in off the Gulf.

Duval’s Fresh. Local Seafood.

Walt’s Fish Market & Seafood Restaurant.

The smell of garlic butter and blackened mahi-mahi floated through the air, and before I knew it, we were pulled in like everyone else—one food booth, one band, one story at a time. Three hours later, we were still there, tapping our feet and licking our fingers clean after a basket of coconut shrimp.

That’s the thing about the Sarasota Seafood & Music Festival: you don’t just go for the food, and you don’t just go for the music. You go for the way it all blends together into one unforgettable weekend by the bay.

Each year, we enjoy the seafood smorgasbord. So much great seafood that’s it’s a little challenging to choose. We enjoy strolling among the booths boasting stunning art with that expected tropical flair. One artist’s colorful & whimsical wood carvings of fish, egrets, sea turtles, flamingoes, & pelicans to name a few that I loved made me wish my budget could afford that $4,800.00 for that stunning fish wall art.

From St Armands Circle to Sarasota Bayfront

What a lot of people don’t realize is that the Seafood & Music Festival didn’t begin downtown. The event originally launched at St. Armands Circle, with booths wrapping around the park in the middle of the Circle. It was a clever idea—the iconic Circle, surrounded by shops and restaurants, seemed like the perfect backdrop.

But as the festival grew, downtown Sarasota became its natural home. JD Hamel Park and Gulfstream Avenue offered more space, better flow, and easier staging for the live bands. It may be a little “out of the way,” tucked near the bayfront instead of Main Street itself, but that works in its favor. Parking is easier, traffic isn’t as snarled, and yet you’re still only a short stroll from downtown’s shops and restaurants.

In many ways, the move downtown has allowed the Seafood & Music Festival to hit its stride, becoming one of Sarasota’s most recognizable annual events.

A Festival That Feels Like Sarasota

Every January, when the weather couldn’t be better, locals and visitors flock to the bayfront. Cooler temperatures, lower humidity, and crisp breezes make it the ideal time for an outdoor block party. The setup is simple but perfect: rows of food vendors cooking everything from lobster rolls to jambalaya, local restaurants showcasing their specialties, and a stage that never seems to take a break.

Rock, jazz, funk, blues—you name it, it pours out over the crowd, mingling with the laughter of families and the clink of plastic cups filled with local craft beer.

It’s Sarasota in a nutshell: sun, seafood, and the soundtrack of a community that knows how to celebrate.

From Fresh Catches to Festival Classics

What impressed me that first year—and every year since—is the quality of the food. We’re not talking about your typical fairground fried everything (though you’ll still find a few guilty pleasures).

Instead, you’ll see chefs grilling grouper cheeks, steaming mussels in wine and garlic, and serving up paella big enough to feed an army. Some of Sarasota’s best restaurants get involved, including Walt’s Fish Market, whose vintage signage always draws a crowd.

And if seafood isn’t your thing? Don’t worry. There are plenty of land-based options, from smoky BBQ to gator bites. My wife usually grabs the coconut shrimp, while I make it a mission to track down the soft-shell crab sandwiches.

One year, I remember running into a couple visiting from Michigan. They told me they had come down for the beach, but it was the Seafood & Music Festival that convinced them Sarasota was more than just sand and sunshine. “This feels like the kind of thing you move for,” the husband said. I couldn’t help but smile—because that’s exactly the kind of moment that defines Sarasota.

Music That Moves with the Tide

Of course, the other half of the festival is the music. Over the years, I’ve heard everything from high-energy rock cover bands to smooth jazz ensembles that had couples swaying side by side.

One name that always draws a crowd is Twinkle and Rock Soul Radio. If you’ve lived here any length of time, you know Twinkle’s powerhouse voice. She’s been a staple of the Sarasota music scene for decades, headlining festivals like this one and keeping a busy schedule at venues such as Stottlemeyer’s Smokehouse. At the Seafood & Music Festival, her sets are always packed shoulder-to-shoulder, the kind of performance that gets locals dancing and visitors wondering how Sarasota produces so much talent.

One of my favorite memories was watching a New Orleans brass band light up the stage just as the sun was setting over Sarasota Bay. The light turned orange across the water, kids were twirling glow sticks, and strangers were dancing together like they’d known each other forever.

That’s the magic of this festival: it breaks down walls. You might show up to eat, but you stay because the music makes you feel like you belong.

Art That Feels Like Florida

Beyond the food and music, the artisan booths add a unique flavor. Coastal-themed art fills the walkways: vibrant fish sculptures, hand-painted pelicans, and nautical treasures that feel right at home by the Gulf.

Tips for Making the Most of It

If you’re planning to go, here are a few lessons I’ve learned the hard way:

•Arrive early. Parking fills up fast, and you’ll want time to wander before the crowds peak.

•Bring a chair. There are places to sit, but nothing beats setting up your own spot near the stage.

•Come hungry. Seriously. Don’t make the rookie mistake of eating lunch before you arrive.

•Plan to stay longer than you think. Trust me—between the food and the music, “just an hour” won’t cut it.

Closing Thoughts on the Annual Sarasota Seafood & Music Festival

The Sarasota Seafood & Music Festival isn’t just another date on the calendar—it’s a celebration of everything that makes this community special. Whether you’re a longtime local like me or just visiting for the weekend, it’s the kind of experience that leaves you full—not just from the food, but from the energy, the music, and the sense of being part of something bigger than yourself.

If you’ve never been, make it a priority. And if you’re already a regular, you know exactly what I mean when I say: see you down by the bay.

For more information about the upcoming Festival, check out its official page – Sarasota’s Seafood & Music Festival

Looking for more Sarasota happenings?

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Sarasota Powerboat Grand Prix: Speed, Tradition & My Ride of a Lifetime

It was the Sarasota Powerboat Grand Prix, and the year was 2015. I had gotten to know Lucy Nicandri, executive director of Suncoast Charities for Children, the organization behind the Sarasota Powerboat Grand Prix. Each year, Lucy asked me and a few friends from Sarasota Lifestyle to help organize volunteers for the beach clean-up that followed the races. It became our tradition—something small we could do to give back to a festival that brought so much excitement to our city.

But that year at the Hyatt Regency, Lucy leaned over and told me with a grin:

“Mike, I’ve got a surprise for you.”

I thought maybe it was extra passes or a chance to meet a driver. Instead, it was the ride of a lifetime.

Minutes later, I found myself climbing aboard a sleek Cigarette boat with three other media guests. The captain waved me into the seat right beside him. Shotgun.

“Stay low. Hold on to the straps. Don’t stand up. You’re going to enjoy the ride,” he said.

We slipped out of the marina, eased past the Ringling Bridge, and glided toward Big Pass. The Gulf was waiting.

Then the throttles went down.

The roar was deafening. A white curtain of spray shot up behind us as the bow lifted. The boat didn’t pound or slam—it sliced through the chop like a blade. My stomach floated as the hull skipped across the water.

“That’s 100!” the captain yelled over the wind.

I gripped the straps tighter, suddenly convinced I’d be launched into the Gulf. No seatbelts. No room for error. Just me, the spray, and a speed I couldn’t fully comprehend. My hair was plastered straight back, my camera clutched like my life depended on it.

We pushed faster—120 mph. It didn’t feel like a boat anymore. It felt like a jet gliding just above the surface of the Gulf.

When the engines finally cut, I couldn’t tell whether Lucy had rewarded me or punished me with that front-row seat. In the end, I decided it was the best reward I’d ever been given.

That ride changed how I saw the Sarasota Powerboat Grand Prix. Suddenly it wasn’t just an event I attended or volunteered at. It was personal.

The Birth of Sarasota Powerboat Grand Prix

The Sarasota Powerboat Grand Prix began in the 1980s, when offshore racing was in its golden age. Sarasota had all the right ingredients: open Gulf waters, a strong boating culture, and a community eager to celebrate the Fourth of July with something bigger than just fireworks.

The idea caught on. By the mid-1990s, the Grand Prix powerboat races had grown into one of the premier events on the offshore racing calendar. The biggest teams came. The fastest boats raced. The world watched.

It wasn’t just about the racing, though. The festival became a community anchor—part sporting event, part fundraiser, part patriotic celebration. Sarasota’s summers became defined by it.

Lido Beach Becomes the Grandstand

If Main Street was the prelude, Lido Beach was the theater.

Fans staked their claim on the sand as soon as the gates opened. They came loaded with coolers, tents, umbrellas, and chairs. These weren’t casual beachgoers—they were seasoned race fans who knew how to set up for a day under the blazing July sun.

Saturday brought the preliminary heats. But Sunday—that was the big show. By 8 a.m., Lido Beach was wall-to-wall people. From the water’s edge back to the sea oats, the sand disappeared under a sea of spectators.

For years, I was fortunate to have a parking pass and credentials for the VIP tent near the Sandcastle Resort. Those were some of the best days—ducking into the shade for a cold drink, talking with racers and sponsors, then stepping right back out to the shoreline for the raw power of the race.

The July 4th Celebration, Sarasota Style

The Sarasota Powerboat Grand Prix quickly became the centerpiece of Sarasota’s Independence Day celebration.

Downtown Sarasota came alive with the Grand Prix Parade along Main Street. Back then, there were no roundabouts, no railings, no ropes to keep people back. Locals crowded the curbs, sometimes just feet from the action. Semi-trucks customized by race teams hauled massive powerboats right through the heart of downtown, their polished hulls gleaming in the sun.

Crew members perched proudly on top of the boats, waving like celebrities as fans cheered. Kids darted forward for high-fives. The atmosphere was electric—half small-town parade, half world-class spectacle.

The Racing Experience | Sarasota Powerboat Grand Prix

If you’ve only watched offshore racing on TV, you haven’t truly experienced it.

On screen, the boats look fast. In person, they are thunder and lightning combined. The sound rattles your chest. The spray creates a haze that sometimes makes it impossible to even see the boats.

Then, just as quickly, a boat bursts through the cloud of white water, flying across the Gulf with engines screaming. The speed is jaw-dropping. Blink and you miss it.

Fans erupted every time a boat surged ahead. Cheers rolled down the beach like waves themselves. You could hear the collective gasp when a boat caught air, or when two roared side by side toward the turn buoy.

It was Sarasota at its loudest, boldest, and most alive.

Meeting Legends of Powerboat Racing Who Built the Sarasota Powerboat Grand Prix

That 2015 pre-race meeting gave me another gift besides my ride: the chance to meet Steve Curtis, one of offshore racing’s legendary throttlemen.

If you don’t know, throttlemen are half of the racing equation. While the driver handles steering, the throttleman controls speed and trim—balancing the boat at insane speeds, making split-second adjustments, and working in perfect sync with the driver.

Meeting Curtis reminded me that offshore racing isn’t just about machines. It’s about people—their courage, their skill, their willingness to push the limits in pursuit of victory.

The Community Impact

The Sarasota Powerboat Grand Prix’s impact on Sarasota has always been twofold:

•Tourism & Economy – The event brought thousands of visitors, filling hotels, restaurants, and shops. It generated millions of dollars in revenue for the local economy and put Sarasota on the map as an international racing destination.

•Charity & Community – Through Suncoast Charities for Children, proceeds went directly to programs supporting children and adults with special needs. Executive director Lucy Nicandri made sure the mission stayed front and center.

That’s why I loved volunteering for the beach cleanup. It wasn’t glamorous, but it mattered. After a weekend of speed and celebration, restoring Lido Beach to its natural beauty felt like closing the loop—giving back to the community that had given so much.

The Best of Times

Looking back, those years when I had a VIP pass and a reserved parking spot feel like the golden days.

I’d walk from the lot, credentials swinging, into the cool shade of the Sandcastle tent. Inside, the hum of conversation mixed with the smell of catered food. Outside, the Gulf roared with horsepower.

It felt like Sarasota was at the center of the world. And in many ways, for that weekend, it was.

Why The Sarasota Powerboat Grand Prix Endures

The Sarasota Offshore Grand Prix endures because it has always been about more than speed. It’s about:

•Tradition – A July 4th celebration that became part of Sarasota’s identity.

•Community – Locals volunteering, businesses sponsoring, families making memories.

•Spectacle – Racing that has to be seen and felt in person to be believed.

•Charity – Giving back through Suncoast Charities for Children. Once you live in Sarasota, you quickly discover the myriad amazing, much-needed charities including All Faiths Food Bank & Suncoast Charities for Children.

When people ask me why it matters, I tell them it’s not just about the boats. It’s about the way Sarasota comes alive—united, proud, and electric.

And for me, it’s also personal.

When Lucy asked me to help get the word out in the community about the annual beach clean-up—a requirement of the permit for the Grand Prix—I was thrilled. I knew our Sarasota Lifestyle community would step up, and sure enough, each year we had more and more volunteers. It was an opportunity to help Lucy, help the beach by removing trash and cigarette butts, and to finally meet people I’d only known through Facebook.

The beach clean-ups became something we all looked forward to—not just a good deed, but a chance to come together. Before long, we added a few more clean-ups beyond the festival itself, because it gave us another excuse to do good and spend time as friends.

And I’ll never forget the generosity of the Daiquiri Deck on St. Armands Circle, who welcomed us after the clean-ups with daiquiris and finger foods. It turned into an afterparty of sorts, where I met even more wonderful people who had joined the Sarasota Lifestyle community.

That’s the heart of why the Grand Prix endures. It’s not only about what happens on the water, but about what happens on the sand, in the community, and in the friendships built around it.

Looking Back, Looking Ahead

Every June and July, when the calendar rolls around to Grand Prix weekend, I think back to that wild ride in 2015. I can still feel the adrenaline, the roar of the engines, the strange calm when I finally surrendered to the speed.

That day gave me more than a story. It gave me a connection to Sarasota’s Grand Prix that will stay with me forever.

Ready to Experience Sarasota?

If you want to experience Sarasota beyond the Sarasota Powerboat Grand Prix and at its most thrilling:

•Check out our Sarasota Events Calendar for the latest happenings.

•Relive the best of summer with 7 Unforgettable Days in Sarasota: Your Perfect Week-Long Escape

•Planning a family trip? Don’t miss Family Fun Things to Do in Sarasota

•Stay updated on the 2026 Sarasota Powerboat Grand Prix from the PowerboatP1 event organizer.

Sarasota is full of stories. Some you watch from the sidelines. Others—like my 120-mph ride across the Gulf—you carry with you forever.