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.

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.

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.

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.

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.

Thunder by the Bay Sarasota began in the late 1990s when Downtown was sleepier, Main Street wasn’t yet the bustling nightlife hub it would become, and few could have imagined that a motorcycle festival would grow into one of the city’s signature annual events.

That was when this very different festival (for Sarasota, that is) was born.

It began quite literally by the Bay, as a modest gathering of motorcycle enthusiasts. But it quickly became more than that. Each January or February, thousands of riders descended on Sarasota—some on well-worn Harleys, others on gleaming custom machines that looked like rolling works of art. Main Street filled curb to curb, and in some places even down the middle, with bikes ranging from everyday cruisers to outrageous creations reminiscent of the Tuttle family’s Orange County Choppers.

I’ll never forget the first time I stumbled upon the Siesta Key Crystal Classic at Siesta Key Beach. It was 2010, a Saturday, and the beach looked familiar, yet entirely different. Sculptors crouched over their work, chiseling, carving, shaping.

Back then, the sand sculptures were smaller, simpler. The festival wasn’t a festival or international. Founder Brian Wigelsworth, himself a talented sand artist, had gathered a handful of friends to showcase their craft on our world-famous white quartz sand. None of us could have known that those humble beginnings would evolve into one of Sarasota’s most beloved international festivals.