Things to Do in Sarasota This Weekend: May 28–31, 2026

Mike Payne
Last Modified: May 28

Summer is starting to make itself known in Sarasota.

It is getting hotter. It is getting more humid. The AC is running longer, and those electric bills are probably getting a little less friendly.

But the calendar is still giving us plenty of good reasons to get out of the house.

This weekend brings outdoor movies at The Bay, Laser Light Nights at The Bishop, guided kayaking on the water, live music at Waterside Place, a free workout at UTC, kids’ fun on Anna Maria Island, the Sarasota Margarita Festival, improv comedy at Florida Studio Theatre, a fine art show outside Sarasota Art Museum, and a Sunday farmers’ market at Lakewood Ranch.

So scroll through the top picks, choose what fits your weekend, and make a little room for something fun, local, and worth your time.

See you out there. — Mike Payne

Quick Weekend Snapshot:

🎬 Cinema at The Bay: The Matrix → The Bay, Sarasota — Thursday, 7:30–9:45 p.m.

🌈 Laser Light Nights → The Bishop Museum of Science and Nature, Bradenton — Thursday–Saturday, shows at 7 p.m. and 9 p.m.

🛶 Ride and Paddle at The Bay → The Bay, Sarasota — Friday & Saturday, 9–11 a.m.

👽 Family Movie Night at The Bay: E.T. the Extra-Terrestrial → The Bay, Sarasota — Friday, 7:30–9:30 p.m.

🎸 Live Music at Waterside Place: Zach Pomerleau → Waterside Place, Lakewood Ranch — Friday, 6–9 p.m.

💪 UTC FIT with BODY Hot Pilates → The Green at UTC — Saturday, 9:30–10:30 a.m.

🏴‍☠️ Snook Adams Kids Day → Holmes Beach City Field, Anna Maria Island — Saturday, 11 a.m.–2 p.m.

🍹 Sarasota Margarita Festival → Big Top Brewing Company at Fruitville Commons — Saturday, 12–6 p.m.

🎭 Blockbusted! → Florida Studio Theatre, Sarasota — Saturday, 7:30–9 p.m.

🎨 Sarasota Fine Art Show by Hot Works → Sarasota Art Museum — Saturday & Sunday, 10 a.m.–5 p.m.

🥕 Farmers’ Market at Lakewood Ranch → Waterside Place — Sunday, 10 a.m.–2 p.m.

🎶 Sundays at The Bay: Tasa + Rob → The Bay, Sarasota — Sunday, 6–7 p.m.

🏃‍♀️ Bonus: Kids Summer Beach Runs → Siesta Beach & Brohard Beach — Tuesday & Wednesday, 5:30–7 p.m.

Don’t want to search for this every weekend?

I send this out every Thursday morning so you don’t have to think about it.

If You Only Do One Thing This Weekend…

If you only do one thing this weekend, make it Family Movie Night at The Bay: E.T. the Extra-Terrestrial.

It is free. It is outdoors. It is family-friendly. And it is one of those rare movie nights that works for kids, parents, grandparents, and anyone who still remembers how magical this movie felt the first time around.

Family Movie Night at The Bay: E.T. the Extra-Terrestrial
Friday, May 29 | 7:30 p.m.–9:30 p.m.
The Bay, Sarasota
Free

This is a simple Sarasota weekend win: bring blankets, chairs, friends, and the kids, then settle in for a classic movie under the stars.

The Nest Café will have food, fresh popcorn, and drinks available, so you do not have to overcomplicate the night. Just show up, get comfortable, and enjoy one of the most lovable films ever made in one of Sarasota’s best outdoor public spaces.

Free parking is available around The Bay, including along Blvd of the Arts and near the Van Wezel, Municipal Auditorium, and Blue Pagoda. Just avoid designated Sarasota Orchestra parking areas.

If your weekend needs one easy, all-ages pick, this is it.

Top Picks This Weekend

👽 Family Movie Night at The Bay: E.T. the Extra-Terrestrial

Friday, May 29 | 7:30 p.m.–9:30 p.m.
The Bay, Sarasota
Free

Outdoor movie nights at The Bay are one of the easiest Sarasota weekend plans, and this one is especially family-friendly.

E.T. the Extra-Terrestrial still has that cross-generational pull. Adults get the nostalgia. Kids get the wonder. Everyone gets a relaxed Friday night outside.

Bring blankets, chairs, and friends. Food, popcorn, and drinks will be available from The Nest Café.

🥕 Sarasota Farmers Market

Every Saturday | 7:00 a.m.–1:00 p.m.
Downtown Sarasota off Lemon Avenue
Free admission

Spend Saturday morning at the Sarasota Farmers Market, the original downtown market that has been part of Sarasota since 1979.

This is the “OG” local market — the one every other market around the area tries to emulate. Set in the heart of downtown Sarasota, the market brings together local farmers, growers, artisans, chefs, food vendors, makers, and community organizations every Saturday morning, rain or shine, 52 weeks a year.

You’ll find fresh produce, flowers, prepared foods, baked goods, specialty items, handmade products, and plenty of local flavor. But the real appeal is the atmosphere: people walking Lemon Avenue, running into neighbors, grabbing coffee, browsing vendor tents, and starting the weekend in a way that feels very Sarasota.

If you want the classic Sarasota market experience, this is still the one.

🎭 Blockbusted! at Florida Studio Theatre

Saturday, May 30 | 7:30 p.m.–9:00 p.m.
Florida Studio Theatre, Sarasota
Ticketed event

Florida Studio Theatre is always worth keeping on your radar, especially in the summer.

This is the perfect time of year to find a show, get inside, cool off, and remember how much talent Sarasota has sitting right in the middle of downtown.

Blockbusted! is an improvised comedy show where the audience helps call the shots. The performers take suggestions and turn them into scenes that can become mysteries, rom-coms, dramas, disasters, or something nobody saw coming.

That unpredictability is the point. It is fast, funny, and completely different each time.

If you have not been to FST in a while — or you keep meaning to go and never quite make it happen — summer is a great time to fix that.

🌈 Laser Light Nights at The Bishop

Thursday, May 28 – Saturday, May 30 | Shows at 7:00 p.m. & 9:00 p.m.
The Bishop Museum of Science and Nature, Bradenton
$15

Laser Light Nights are back at The Bishop, turning the planetarium dome into a concert-style experience with music, lights, and visuals from every angle.

The lineup includes classic artists, pop favorites, rock shows, themed nights, and throwback options, so this is not a quiet museum stroll. It is loud, flashy, and built more like a night out.

If you want something different from dinner, drinks, or the usual walk-around plan, this is one of the more eye-catching options of the weekend.

🛶 Ride and Paddle at The Bay: Guided Kayak Tour

Friday, May 29 & Saturday, May 30 | 9:00 a.m.–11:00 a.m.
The Bay, Sarasota
Free

Experience The Bay from the water during this free guided kayak tour through the restored mangroves and bayou area.

Kayaks and life jackets are provided, and the tour is best suited for ages 12 and older. Space is limited, so registration matters — and if it is sold out, it may still be worth checking for cancellations or no-shows.

This is a strong pick if you want something active, outdoors, and more connected to Sarasota’s natural side.

🍹 Sarasota Margarita Festival

Saturday, May 30 | 12:00 p.m.–6:00 p.m.
Big Top Brewing Company at Fruitville Commons, Sarasota
Ticketed event

Margarita lovers get their Saturday moment at the Sarasota Margarita Festival.

This one-day tasting competition brings local bars and restaurants together to compete for the title of best margarita in Sarasota. Attendees sample and vote, with each ticket including ten margarita samples.

There will also be a live DJ, street food vendors, a beer garden, and a chance to win a trip to Mexico. A portion of proceeds supports children’s charities.

This is the adult Saturday afternoon pick if your weekend calls for something social, sunny, and not especially subtle.

🎨 Sarasota Fine Art Show by Hot Works

Saturday, May 30 & Sunday, May 31 | 10:00 a.m.–5:00 p.m. daily
Sarasota Art Museum, Sarasota
Free admission

The Sarasota Fine Art Show brings a juried outdoor art event to Sarasota Art Museum for the weekend.

Expect original handmade work from professional artists across a wide range of mediums, styles, and price points. It is boutique-sized, family-friendly, and easy to pair with lunch, a museum visit, or a slow walk through the area.

This is one of the stronger overall weekend picks because it works for locals, visitors, serious art buyers, and casual browsers.

🏴‍☠️ Snook Adams Kids Day

Saturday, May 30 | 11:00 a.m.–2:00 p.m.
Holmes Beach City Field, Anna Maria Island
Free

Snook Adams Kids Day brings a pirate-themed end-of-school-year celebration to Anna Maria Island.

Families can expect goody bags, a treasure hunt, games, sand art, coloring pages, face painting, pizza, hot dogs, and chips.

This is one of the better family-friendly picks of the weekend if you are closer to Anna Maria Island or want something built specifically for kids.

🆓 Free Things to Do This Weekend

Looking for something to do without spending much? These are some of the best free events happening this weekend:

🎬 Cinema at The Bay: The Matrix — Thursday at The Bay

🛶 Ride and Paddle at The Bay — Friday and Saturday at The Bay

👽 Family Movie Night at The Bay: E.T. the Extra-Terrestrial — Friday at The Bay

🎸 Live Music at Waterside Place: Zach Pomerleau — Friday at Waterside Place

💪 UTC FIT with BODY Hot Pilates — Saturday at The Green at UTC

🏴‍☠️ Snook Adams Kids Day — Saturday at Holmes Beach City Field

🎨 Sarasota Fine Art Show by Hot Works — Saturday and Sunday at Sarasota Art Museum

🥕 Farmers’ Market at Lakewood Ranch — Sunday at Waterside Place

🎶 Sundays at The Bay featuring Tasa + Rob — Sunday at The Bay

🏃‍♀️ Bonus: Kids Summer Beach Runs — Tuesday at Siesta Beach and Wednesday at Brohard Beach

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More Things to Do This Weekend

Cinema at The Bay: The Matrix

Thursday, May 28 | 7:30 p.m.–9:45 p.m.
The Bay, Sarasota
Free

Enjoy a free outdoor movie under the stars at The Bay with The Matrix, the mind-bending sci-fi classic that introduced the world to “bullet time.”

Bring blankets, chairs, and friends. The Nest Café will be serving food, popcorn, and drinks, which makes this a simple Thursday night plan if you want to ease into the weekend early.

Live Music at Waterside Place: Zach Pomerleau

Friday, May 29 | 6:00 p.m.–9:00 p.m.
Waterside Place, Lakewood Ranch
Free

Enjoy live blues music from Zach Pomerleau at The Plaza while taking in the waterfront views of Kingfisher Lake.

This is a relaxed Friday evening option if you want music, dinner nearby, and a casual Lakewood Ranch setting without making the night too formal.

UTC FIT with BODY Hot Pilates

Saturday, May 30 | 9:30 a.m.–10:30 a.m.
The Green at UTC, Sarasota
Free

Start Saturday with a free outdoor workout at UTC FIT, led this week by BODY Hot Pilates.

The class is designed to sculpt and strengthen the full body, and all levels are welcome. Bring a mat, water bottle, and enough motivation to get through a morning workout before the day gets too hot.

Farmers’ Market at Lakewood Ranch

Sunday, May 31 | 10:00 a.m.–2:00 p.m.
Waterside Place, Lakewood Ranch
Free admission

Spend Sunday morning lakeside at the Farmers’ Market at Lakewood Ranch.

The market features 100+ local vendors with produce, flowers, honey, fresh bread, baked goods, prepared foods, pet products, jewelry, and more. There is usually live music, food, and a Kids’ Zone, which makes this an easy Sunday outing for families.

This is one of those reliable local events that works even when you do not want to make a big plan.

Sundays at The Bay featuring Tasa + Rob

Sunday, May 31 | 6:00 p.m.–7:00 p.m.
The Bay, Sarasota
Free

Close out the weekend with a free live performance by Tasa + Rob at The Bay.

Their mix of vocals, guitar, violin, and Cajon gives familiar cover songs a soulful, acoustic feel. This is a nice Sunday evening pick if you want something easy, outdoors, and low-pressure before the week starts again.

St. Armands Fine Art Festival

Saturday, May 23 – Sunday, May 24 | 10:00 a.m.–5:00 p.m.
St. Armands Circle, Sarasota
Free admission

St. Armands Circle turns into an outdoor art gallery for the weekend with fine art and fine crafts from artists throughout Florida and across the country.

Expect sculpture, jewelry, painting, photography, glass, ceramics, mixed media, metalwork, fiber art, woodworking, and more.

If you want something walkable, browseable, and easy to pair with lunch or dinner, this is a strong weekend option.

Sarasota Weekend Picks That Also Show How the Area Really Lives

This weekend has that early-summer Sarasota feel.

There are outdoor movies at The Bay, kayak tours through the mangroves, art outside Sarasota Art Museum, live music by the water, a Saturday farmers’ market inn downtown Sarasota, a Sunday farmers’ market at Lakewood Ranch, and kids getting ready for summer with beach runs on Siesta Key and in Venice.

That mix says a lot about how this area actually lives.

Sarasota is not just the beach photo, the sunset shot, or the real estate listing with the palm tree in the background. It is also the Thursday night movie crowd, the Saturday morning workout group, the families at a kids’ day on Anna Maria Island, the people browsing art under a tent, the locals listening to music at The Bay, and the parents signing kids up for summer beach runs after dinner.

One thing I tell relocation buyers and sellers all the time: Sarasota is not just about what a property looks like online.

It is about how the area lives day to day.

•Where people gather.
•How far things really are.
•What the weekends feel like.
•Which towns match your pace.
•Which places feel fun on vacation but may or may not fit your actual life.

This weekend gives you a little window into that.

If you are already local, use it to enjoy the area you live in. If you are thinking about moving here, pay attention to the rhythm behind the events. And if you are preparing to sell, remember that buyers are not just buying square footage. They are buying a version of life they hope will feel right.

That’s your Sarasota weekend — whether you are watching a movie at The Bay, paddling through the mangroves, browsing art, catching a show at Florida Studio Theatre, sipping margaritas, taking the kids to Anna Maria Island, or keeping it simple with a Sunday market stroll.

That’s your Sarasota weekend—whether you’re going out Friday night, exploring Saturday, or keeping it simple Sunday. Want this sent to you every Thursday? Join Sarasota Weekly here →
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