Another Side of Only In Florida — Captiva and the Southwest Coast Are Full of a Different Kind of Story

“Legend has it. . .” I heard that phrase often while exploring the islands off of the southwest Florida coast, especially Sanibel and Captiva. Just a breezy causeway jaunt from Fort Myers brings you to this chain of white sand beaches, Caribbean cool blue and green waters, bays, inlets and even more islands. And every one seems like it holds its own wondrous tale.

For my home base on this legendary getaway, I stayed at Captiva’s South Seas Island Resort. The 330 acres private resort has become synonymous with Captiva itself, taking up much of the north end of the island. What began as a key lime planation that opened as a fishing resort in the 1940s, has become a premium resort experience that seems to use the natural diversity of the environment (250 types of seashells, 230 species of birds) as inspiration for its range of luxury accommodations.

Whether staying for a romantic weekend, family vacation or any iteration of a boys/girls getaways or special event, South Seas offers a variety of rooms, condos, villas and even island-style mansions.

The Harbourside Hotel guest rooms give visitors a choice of quiet beach views while the marina rooms provide balcony views of the sailboats and yachts coming and going into the resort’s private harbor. But for those wanting to make themselves really at home in this paradise time zone, the mid-sized to expansive multi-bedroom villas and even two to six bedroom specially cottages and private home rentals may be the ticket.

South Seas Island offers almost as many restaurant options as accommodation choices, from fine, but casual dining at the Harborside Bar & Grill with its speciality seafood focused menu to poolside kid-friendly and healthy eats at The Pointe to a pizza and old fashioned ice cream parlor. The Attitudes Beach Bar & Latitudes Food Shack offers tacos and salads and an extensive margarita menu right on the beach. Attitudes also hosts nightly live music that usually culminates in a decades-long tradition that encourages audience members to throw a shell into the sea at sunset while making a secret wish.

With more than 20 pools (from private villa pools to cabana lined hotel pools) at the resort, tennis, golf, outdoor yoga and boundless water sports — including wave runners, parasailing, kayaking and paddle boarding — plus two and a half miles of beach for some of the best shelling in the United States, it would have been easy to spend a week sampling all the sun and fun activities. Or for those wanting to practice the fine art of doing nothing, there’s always the option of sipping margaritas on the long balcony of an ocean view room, just watching the dolphins go by.

Captiva Adventures

Since I’m a travel lover always on the listen for the stories of a place, I set sail for a wider exploration of Old Florida, another term I heard throughout my trip. I soon realized that “old” can mean anything from ecological time (as various storms have shaped and multiplied the islands) to the area’s Spanish colonial history to its Buccaneer Coast period when pirates ruled the seas and shores.

I also heard romanticized tales of the coast as a haven for 19th and early 20th century leaders, industrialist and celebrities including the likes Teddy Roosevelt, Thomas Edison, Henry Ford and Charles Lindbergh. Then there’s that famed later 20th century good time beach vibe crystalized into song — and likely trademarked — by Jimmy Buffett.

I dove into some of those old Florida legends during a Captiva Cruises boat tour to nearby North Captiva Island, Cabbage Key and Cayo Costa State Park. The knowledgable captains and guides of this fleet of tour boats and catamarans are able to separate all those legends with real human local history. Not to mention their fascinating commentary about the marine life and birds you’re likely to see on a voyage.

We stopped for lunch at Cabbage Key, another of those legendary places filled with stories. The island first began as the winter retreat dream of 1930s mystery writer Mary Roberts Rinehart, mother of The Butler Did It plotting.

Parts of Cabbage Key Island passed through several owners’ hands and along the way the Cabbage Key Bar became a favorite hangout for fishermen. Another story claims those fishermen, fresh from a bountiful day’s catch, began a tradition of writing their names on a dollar bill and taping it to the ceiling for future payment when the fish weren’t as accommodating.

Decades later, every inch of Cabbage Key Restaurant’s ceiling is covered in dollar bills. Whenever gravity prevails, the falling money is donated to local charities.

Another tale tells that a certain Cabbage Key menu item inspired Jimmy Buffet to write his ode to paradisal cheeseburgers. I can’t speak to the veracity of that particular burger muse story, but after an appetizer of the famous stone crab claws and few sips of the Cabbage Creeper, the house piña colada with a coffee liquor twist, I felt inspired to jump on a chair and tape my own dollar to the ceiling while humming a Buffett medley.

After lunch, our Captiva Cruise captain plotted a course for Cayo Costa State Park, where we saw more magnificent osprey nesting than humans. My small group hiked through a mangrove woods to quiet, empty pristine beaches for some of the best shelling on the Gulf.

The next day, I hoisted my sail, literally, for a sailing lesson out of the resort marina from Colgate Offshore Sailing School. The educational adventure made for a glorious morning on the water and the chance to use words like “jib” and “luff” in conversation. I had my fun, but the family owned company is an actual sailing school with everything from beginning three hour clinics to week-long intensive certification courses.

The resort marina was the setting for some of my fondest memories of my stay. One afternoon as I walked from one excursion to another I saw a few people on one of the docks just staring into the water. I wandered over to see a family of manatees having a leisurely feast on seagrass.

My tightly scheduled afternoon activities forgotten, I sat down on the dock to watch my new gentle giant friends have lunch. Later that night, after a beach dinner under the stars, I went headed back to my room via the marina and passed a human family having a multigenerational sing-a-long. Together they crooned that so-familiar song about humanity’s existential search for our lost margarita saltshaker, their voices luffing along the anchored multi-million dollar yachts.

Just another legendary, Only in Florida moment.