Live out Jimmy Buffett’s songs at these 10 best Florida places

Fort Myers Beach, site of a new Margaritaville Resort — Photo courtesy of Chelle Koster Walton

It’s almost as though Jimmy Buffett spent his life writing the soundtrack to Florida. Before he succumbed to a rare skin cancer on September 1, 2023, the American singer-songwriter certainly spent a lot of time in the Sunshine State. Buffett’s lyrics often bring to mind Florida locales deeply loved by Parrot Heads and beachcombers alike.

So, when it’s time to “go where it’s warm,” follow this Buffett-inspired map to live out his songs and keep the memory of this legendary musician alive.

“Stranded on a sandbar” — Cayo Costa

Cayo Costa, an island unconnected to the mainlandCayo Costa, an island unconnected to the mainland — Photo courtesy of Visit Fort Myers

Buffett sang it like it’s a bad thing. If being stuck on a sandbar sounds like your fantasy getaway, Florida has more sandbars than you can shake a kayak paddle at. One of the best for whiling away a Jimmy Buffett kind of day is Cayo Costa Island State Park, off the shores of Fort Myers. It requires boat transportation, which is readily available from water taxis and tours at nearby island marinas.

Its nine miles of beaches are considered some of the best shelling destinations in Florida and even offer overnighting for campers or those who reserve a rustic cabin in advance. Bonus: Just an island hop away, Cabbage Key is considered by many as inspiration for one of Buffett’s most famous ballads, “Cheeseburger in Paradise.”

“But there’s this one particular harbor” — Apalachicola

Apalachicola's working waterfrontApalachicola’s working waterfront — Photo courtesy of Chelle Koster Walton

There is one particular harbor that brings out the romantic wayfarer in me, and that is Apalachicola in the Florida Panhandle. The town is a throwback to the pre-Civil War era and is known for its seafood and working waterfront. Once the third busiest port in Florida, it retains its historic buildings, now home to inns, shops, and seafood restaurants where local shrimp rules.

Here, the Apalachicola River meets the Gulf of Mexico, so you can easily find a waterfront spot to lose yourself. Sit for a spell, let the bobbing boats lull away the present tense, and dream of sailing away for a day. Or the rest of your life.

“I’ve got to fly to Saint Somewhere” — St. Augustine

St. Augustine for history and watersportsSt. Augustine for history and watersports — Photo courtesy of

Most interpret this as a yearning for a Caribbean island, such as St. Croix or St. Kitts. But Buffett’s cure for cabin fever could very well have been St. Augustine, where he lived for a brief period in the early 1970s. Start your Jimmy pilgrimage with a visit to Tradewinds Lounge, “The Oldest Lounge in the Oldest City,” where the young artist performed.

Originally modeled after island sailor bars, it sits at the doorstep to St. Augustine’s Old City, famous for its colonial fort and other structures along cobbled streets. Bars, restaurants, historic attractions, and B&Bs still make it a dream destination for travelers. On the flipside, gorgeous beaches and a surfer’s vibe add to the Parrot Head flavor.

“Got to stop wishing, got to go fishing” — Destin

Destin's gem-like emerald seas and the promise of trophy catchesDestin’s gem-like emerald seas and the promise of trophy catches — Photo courtesy of Destin-Fort Walton Beach

Destin has earned its reputation as the “World’s Luckiest Fishing Village,” thanks to its close proximity to deep, emerald waters, where you can pull in snapper, grouper, marlin, and sailfish. Fishing charter boats dock at the ready to ferry you out for the catch of a lifetime, followed by a seafood dinner fitting its reputation. On par fame-wise with its fishing, Destin’s white powder sand drifts into heavenly visions that transcend the definition of “beach.”

“It’s five o’clock somewhere” — Jupiter

Jupiter's casual, real sideJupiter’s casual, real side — Photo courtesy of Discover The Palm Beaches

This Buffett-Alan Jackson collaboration drew crowds to the Square Grouper Tiki Bar at Jupiter Inlet, where its music video was filmed in 2006. Well, to be truthful, the bar draws crowds on a regular basis to party in the sand and hear live tunes with a magnificent view of the water and Jupiter Inlet Lighthouse.

But you don’t have to wait until 5 p.m. to start your party; Square Grouper opens at 11 a.m. Despite Jupiter’s reputation as a magnate-magnet, its good-time bars and restaurants keep it real. I’d also suggest Guanabanas Restaurant and Dune Dog Café for good-time “slumming” in Jupiter.

“Wastin’ away again in Margaritaville” — Fort Myers Beach

Margaritaville Fort Myers Beach coming soonMargaritaville Fort Myers Beach coming soon — Photo courtesy of Morris Depew & Associates

Some of the first Margaritaville Resorts in Jimmy’s accommodations portfolio went up in Florida, and they continue to populate beach scenes. Coming soon and now accepting reservations for early 2024 is Margaritaville Fort Myers Beach. Some of its signature amenities will be inspired by Buffett songs — License to Chill Bar, Coconut Telegraph Coffee Bar, and Fins Up! Beach Club, to name a few.

“There’s a woman goin’ crazy on Caroline Street” — Key West

B.O.'s Fish Wagon, a food truck that never left Caroline StreetB.O.’s Fish Wagon, a food truck that never left Caroline Street — Photo courtesy of Chelle Koster Walton

Key West is Parrot Head Central and also one of the state’s quirkiest destinations. You haven’t really been to Florida until you’ve done the Duval Crawl through the bars of its main drag, but Buffett sang about a different street. Personally, I’d rather hang out on this side street that intersects with Duval and runs close to the waterfront at its north end.

Here, you will find a couple of my favorite KW eateries: funky B.O.’s Fish Wagon, known for its grouper sandwiches, and Pepe’s Café, dubbed the “oldest eating house in Key West.” Fun shops stream along Caroline Street, and Waterfront Brewery is only a block away.

“You got fins to the left, fins to the right” — Orlando

Sharks at Discovery CoveSharks at Discovery Cove — Photo courtesy of Discovery Cove

Theme parks are not usually my scene, but Discovery Cove, a SeaWorld sidekick, upgrades the experience with limited admissions and so much sea life to love. You want to see fins? The park’s Shark Swim manages it in a safe, controlled way that begins with a training session and ends with a snorkel among 20-some blacktip, reef, nurse, zebra, and bonnethead sharks. A portion of the proceeds supports the research of these beautiful, misunderstood creatures.

“Strollin’ down the avenue that’s known as A1A” — Vero Beach

Very VeroVery Vero — Photo courtesy of Chelle Koster Walton

Buffett named one of his bestselling albums after a road whose alphanumeric name has become code for romance. State Road A1A wriggles through slim barrier islands and delightfully backtracks to intriguing eras in the state’s history. Personally, my favorite segment of the 330-mile route through East Coast Florida takes in Vero Beach and environs.

I suggest a drive, rather than a stroll, from Fort Pierce Inlet to Sebastian Inlet, bookended by beachy state parks known for their gnarly surfing. Between the two inlets, glimpses of Atlantic blue and old-growth oak trees make this “a lovely cruise,” with offshoot roads leading to surf-washed beaches that keep less crowded than the metro shoreline to the south.

“Hey Mr. Spaceman, won’t you please take me along. I won’t do anything wrong.” — Space Coast

Spacing out at Kennedy Space CenterSpacing out at Kennedy Space Center — Photo courtesy of Florida Space Coast Office of Tourism

It’s likely that few will recognize these lyrics or know that Buffett sang them in a duet with Gonzo. Yes, Gonzo of The Muppets fame. It appeared on a 1994 compilation album with other artists, titled “Kermit Unpigged.” When it comes to Florida, any extraplanetary reference automatically lands you on the Space Coast in the northeast, home to Kennedy Space Center.

That’s the main attraction, but the stretch of shoreline from Titusville to Melbourne has so much more going on. Thanks to KSC, the federal government has protected thousands of acres around it. That means Canaveral National Seashore keeps beaches in the most pristine condition, while Merritt Island National Wildlife Refuge is a haven for manatees, birds, alligators, and other creatures of the sky, land, and sea — from the tubbiest to the tiniest. The latter includes dinoflagellates, microscopic organisms that light up the waters during summer like topsy-turvy fireworks.

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