“Barefoot Elegance”: Must-See Sites and Eats on Captiva Island in Southwest Florida 


Florida, Captiva Island, Roosevelt Channel, Buck Key Preserve and coastline. Photo: Jeff Greenberg/Getty Images; Inset: Key Lime pie from 'Kiel Lime Bistro', Captiva Island Florida. Photo: Joseph Logozzo/Getty Images

Miami, Orlando, Tampa, Fort Lauderdale are the common Floridian cities one might pick for a sunny getaway, but many snowbirds prefer the “barefoot elegance,” as they call it, of Fort Myers on the southwest Gulf Coast and its neighbouring beaches and islands.

One such wonder is the pristine, magical part of the state called Captiva Island, a true paradise where dolphins frolic close to shore, manatee amble in the marinas, key lime pie and seafood are menu staples and a tchotchke-covered Christmas-themed restaurant (The Bubble Room) serves complimentary sticky buns alongside a trademark cheesy deliciousness known as “Bubble” bread. 

As a music journalist, I was there last September for the annual Island Hopper Songwriter Fest, featuring professional songwriters whose songs have been covered by everyone from Garth Brooks to George Strait, Kygo to All-4-One (“I Swear”). The intimate 10-day festival starts off in Captiva Island and Sanibel Island, then moves on to downtown Fort Myers and wraps up at Fort Myers Beach. 

I only took in the Captiva Island portion of the trip but made sure to experience as much of the area as possible and not just sit on patios listening to acoustic music while drinking rum punch.

I didn’t even have to go far. From my balcony at the 330-acre, four-star South Seas Island Resort I could dolphin-watch all day; the smiley mammals come up for air every few minutes, it seemed, and it never gets old seeing a fin come out of the ocean, even for a split second. Even better when they swim in pairs or triplets.


Captiva Island
Manatees on Captiva Island. Photo: Courtesy of the author


At mealtime, I set out on a mandatory taste-testing of key lime pie in every single restaurant I visited — for research purposes, I assure you — from the beachfront Mucky Duck and The Green Flash to Doc Ford’s Rum Bar & Grille. The tangy dessert purportedly originated due south in Key West in the late 1800s, invented by a cook known as Aunt Sally.

In 2006, the state’s legislature declared it Florida’s official dessert, but, alas, a year ago Florida Gov. Ron DeSantis passed a bill in the Florida Senate to designate “strawberry shortcake with natural Florida dairy topping” as the official Florida state dessert; people were not happy (Florida always has the best headlines). Had I known this important detail while I was there, I might have foregone a slice of key lime for shortcake.


Captiva Island
Key lime pie is a menu staple on Captiva Island. Photo: Courtesy of the author


On a more health-conscious note, most of the bars and restaurants — often doubling as venues for the songwriter festival — offered a goodly amount of seafood options. I always chose lobster if they had it; shrimp if they didn’t. 

South Seas Resort — so big it’s half the island — is also a wildlife nature preserve with two-and-a-half miles of beautiful white sand beaches. There is everything on-site from a golf course and fitness centre to a Starbucks and Scoops and Slices shop. My preferred activity, in addition to the odd toe-dipping, was absolutely nothing, just securing a lounge chair on the beach or by one of the pools and staring out at the Gulf of Mexico, marvelling at the view and usually mistaking the sea foam for a dolphin. 

I squeezed in a day trip by boat (the only way to get there) to Cabbage Key, a 100-acre island with no cars or roads, simply for a mandatory visit to the iconic floor-to-ceiling, dollar-bill-plastered, eponymously named restaurant. That in itself is worth the trip, but as someone who has been in the music business for three decades, I had to go to the spot that apparently inspired Jimmy Buffet to write his hit song “Cheeseburger In Paradise.” Of course, I tried the “Heaven on Earth with an onion slice,” as his lyric describes it, and it did not disappoint. I taped up a dollar bill which said so, writing “A Billion Dollar Burger,” and signed my name to the declaration.


The iconic floor-to-ceiling, dollar-bill-plastered, eponymously named restaurant Cabbage Key. Photo: courtesy of the author


Outside, I encountered a sizable tortoise on my way to climb the historic water tower whose sign read (in part): “Our tower is the only water tower not to be destroyed by hurricanes.”

After seeing caution signs about manatee in the area, with illustrations that looked like a seal, I was on a personal head-down mission back at South Seas Island Resort to see one of these creatures, lovingly referred to as a “sea cow.” I truly did not know what one looked like before I got there but on the morning before my return flight I asked a few local boat owners for guidance, which paid off when I was given a “show” by three manatee, who dutifully came out of the water to say hello with their tails (this piece could be subtitled “How Three Manatee Made My Trip”).

Three days after Island Hopper Songwriter Fest ended — less than two weeks since I’d spend a glorious five days there — Hurricane Ian, a Category 4 storm — made landfall at the end of September, causing immense devastation to the entire area, especially along the shores, as well as to the crucial Sanibel Causeway, the only way to and from the islands Sanibel and Captiva, but fortunately didn’t do a ton of damage to Cabbage Key. The Historical Cabbage Key Water Tower is still standing and the legendary restaurant reopened by late October.

Now that five months have passed, according to the Lee County Visitor & Convention Bureau, “As rebuilding continues, the latest figures indicate that 68.4% of Lee County accommodations are now open, with 9,801 rooms.” (A list of reopenings can be found here.)

“Hurricane Ian has had far-reaching effects throughout the greater Fort Myers area,” it reads on the main page. “Parts of the landscape may look different right now, but the way our area makes people feel hasn’t changed. With resilience and optimism, our community is working hard to rebuild. Many businesses are reopening their doors each day.”

The Island Hopper Songwriter Fest has been slated for Sept. 22 to Oct. 1.and South Seas Island Resort plans to be open by then. 

Meanwhile, the fabulous Bubble Room, the fairy tale place for all generations, covered with thousands upon thousands of interesting memorabilia, antiques, and toys from the 1930s, ’40s, and ’50s — including a working toy train track that circulated near the ceiling — is still undergoing repairs. Until it reopens, visitors can drop by Taste of the Bubble Room, a pop-up shop with Broadway Palm Dinner Theatre, to try their famous orange crunch cake or white Christmas cake. 

And, for baseball fans, spring training has already started in Fort Myers for the Boston Red Sox and the Minnesota Twins, which brings a lot of traffic to the area. 


Captiva Island
Bubble Room is the fairy tale place for all generations, covered with thousands upon thousands of interesting memorabilia, antiques, and toys from the 1930s, ’40s, and ’50s. Photo: Courtesy of the author



Places To Stay


Opening Later This Year:

South Seas Island Resort on Captiva Island, plans to open in September 2023.

Margaritaville Beach Resort on Fort Myers Beach, plans a fall 2023 opening.

Visit  www.visitfortmyers.com for up-to-date information on re-openings and rebuilds.


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