Brendan O’Connor Is Livin’ the Salt Life In Fort Myers

Edgardo Carmona’s life-size metalworks abound in Fort Myers. Seen here is “The Chess Players.” ©Brendan O’Connor

I had heard of Fort Myers, but I don’t think I really understood what it was all about. Just another waterfront playground for the rich that I’d never see, I assumed. I’d been to Naples and streaked on a few golf courses before, how different could it be? Completely different, y’all. 

I was extended an invitation by Visit Fort Myers to come and see firsthand what made them so special, and I have to say, at the end of the trip, I had drunk the Fort Myers Kool-Aid. 

For the duration of the trip, we had the lovely Margaritaville Beach Resort Fort Myers Beach as our headquarters. The hotel was mercifully mostly untouched by Hurricane Ian in September 2022, when Fort Myers took a direct hit from the storm. It had just started construction when the storm hit and just the pool area needed to be redone, as it was washed away into the ocean. That head start has meant that while most of the other hotel properties on Fort Myers Beach are still rebuilding, Margaritaville is open for business, and has become the defacto downtown of sorts, serving locals and visitors alike. 

JWB Grill at @Margaritaville Beach Resort Fort Myers Beach overlooks the Gulf of Mexico.

We had our first supper at JWB Grill at Margaritaville FMB, overlooking the Gulf of Mexico through massive floor-to-ceiling windows. The Grill offers contemporary takes on gulf-inspired seafood dishes and steaks with live entertainment, but my favorite moment was when a pirate ship cruised by on the horizon, likely carrying sunburned tourists, but in my head, it was looking for booty. I twerked at it, but the Visit Fort Myers folks gave me a look that said, “We’re just starting, Brendan. Reign it in.”

A segment of the McCollum Hall mural in the Dunbar neighborhood. ©Brendan O’connor

The next day started with a mural tour led by our new friends at the Fort Myers Mural Society. The first stop was the historic McCollum Hall on Dr. Martin Luther King Jr. Boulevard in the Dunbar neighborhood, which sported beautiful pieces inspired by local Black history. The Hall was once part of a hotel during Segregation that housed big time Black talent making its way across the country on the Chitlin Circuit. Now it was empty, but the Mural Society rep was sure it was about to become a food hall. 

Lunch was at the dockside Oxbow Fort Myers, with panoramic riverfront views of the Caloosahatchee River. Which made me giggle every time I heard it, so I kept saying it to myself under my breath when I needed a pick-me-up. Which came in handy when we went to the Six Mile Cypress Slough Preserve. It’s a 3,400-acre preserved wetland with a gorgeous boardwalk cutting through the more picturesque parts of the property like a massive cypress dome. We saw snakes, butterflies, fish and gigantic Hobbit-eating spiderwebs. I loved it. These little slices of native Florida are so important, not only for preserving wildlife, but to give visitors the context they need to better appreciate how special Florida really is. And how much impact we have on it. 

Nautical Tiki Cruises ©Brendan O’connor

The highlight of the day was the 90-minute sunset tour with Nautical Tiki Cruises, which was absolutely magical. It was a 90-minute cruise on a catamaran with a thatched tiki roof that cruises out into Matanzas Pass, the channel that separates Fort Myers Beach from the mainland. And it was absolutely filled with wildlife. Cormorants were perched on half-sunk speedboats left behind by Hurricane Ian. Manatees cruised by and mooned us as they crested by the boat. Dolphins jumped in the sunset kissed horizon like we were living in a Lisa Frank coloring book. Our captain, whose name escapes me, but we’ll call him Dan, was a retired tech mogul from out west, who left it all and moved into a houseboat in Fort Myers to live the Jimmy Buffet-inspired escapist good life after just a single visit. A bit of an amateur musician himself, he had helped found a new public plaza music program in places like Bayside Park, which had been newly built before the hurricane and then had to be completely redone. 

It was the perfect way to end the day on the beach and fodder for the weirdest dreams I’ve had in a long time, with cheeseburger-eating porpoises laughing at my jokes a little too hard. 

The Gulf Stone Crab Claw appetizer at Cabbage Key, ©Brendan O’connor

After I washed those dreams out of my hair the next morning, we all hopped on a private boat tour with our guide, Captain Brian on the Water. Brian took us out to the barrier islands, which were beat to hell by the hurricane. These places are only accessible by boat, haunted islands where whole trees had been stripped of foliage and jutted out of the sand like wizard wands or gnarled fingers poking skyward. We cruised by North Captiva Island, where only 36 permanent residents call it home and traverse the island in little golf carts. He knew all the critters that poked their noses out at our boat, from spotted eagle rays and ospreys to manatees, dolphins and permit fish. His enthusiasm was contagious. 

I knew lunch was going to be a treat when I saw the glint of mischief in Capt. Brian’s eye. He shuttled us over to Cabbage Key, the home of the historic Dollar Bill Bar and Restaurant, a beautiful collection of buildings that opened to the public in 1944. The place was packed to the railings with happy and hungry visitors. The walls and ceilings were covered with paper currency from around the world, with names and messages scrawled in Sharpies, and stuck in place with a prayer and a piece of gum. 

It was that afternoon with Capt. Brian that really drove home it was the water and the islands that made Fort Myers so special. The resorts and the restaurants were all top notch and we still had more to see on the mainland, but you could tell that both Capt. Brian and Capt. Dan (if that was his real name) had embraced the Salt Life and weren’t coming back. 

The Dollar Bill Bar and Restaurant. ©Brendan O’connor

It shouldn’t have been a surprise to learn then that one of the area’s largest draws is its annual Island Hopper Songwriter Fest, which was named one of the Top 5 Music Festivals by USA Today’s Reader’s Choice Awards. This year’s festival is coming up on September 20-29 and features award-winning songwriters and performers in smaller venues dotted around the Fort Myers area like Captiva Island, Cape Coral, Fort Myers Beach and downtown Fort Myers. Most of the performances are free, but some of the larger bills are ticketed, so check out the lineup at IslandHopperFest.com and make a weekend out of it. 

Up next was a quick trip to the Bailey-Matthews National Shell Museum and Aquarium on Sanibel Island. It was recently renovated, as they lost a large part of their building in the storm, and now includes a very fancy aquarium, with plenty of facts about shells and shell-hunting history of the area. There’s a long continental shelf on the Gulf, which means waves can’t build up to be too intense (barring a massive storm like Ian) which means more intact shells make their way to the beach then a lot of other areas in Florida. 

Our last day in Fort Myers was spent downtown, seeing the historic buildings and hotels like The Banyan Hotel Fort Myers, Tapestry Collection by Hilton and the new Hampton Inn. All of which are popular with wedding groups—apparently people love getting married in Fort Myers. There’s a Wild West vibe with the architecture and storefronts in downtown, a nod to its history as a major cattle town. Herds used to be, well, herded, through the city from North Florida to Sanibel Island where they were put on boats and sent to Cuba in the 1800s. And post-Ian, there’s a bit of a Gold Rush vibe to be felt, as new development money pours into the downtown core. Everywhere I looked there were construction crews putting up new drywall and the streets were full of shoppers popping into the eclectic collection of stores and restaurants.

Thomas Edison famously made Fort Myers his winter residence for 50 years and conducted botanical research in his River District laboratory and gardens. Fort Myers has had a prosperous past and I couldn’t help but feel like there was an even more prosperous future, on that dolphin-filled pink glitter horizon.