If you’re looking for a getaway to channel your inner Jimmy Buffet or vacation like Carrie Underwood, look no further than the beaches of Fort Myers and Sanibel.
While Florida in its entirety is pretty much at full capacity year-round thanks to the luscious beaches and booming atmosphere, there are still some breathtaking spots with lots of wiggle room left to be explored about two hours south of St. Petersburg on the Gulf of Mexico. Everyone already knows about the margarita vibes in Key West, but the vibes found throughout the beaches of Fort Myers and Sanibel (most notably Captiva Island) are much less crowded and equally wanderlust-worthy. Indeed perfectly capable of handling any variation of your margarita request.
There is so much to explore in the area, you’ll want to get a rental car (a cab from the airport to Captiva Island runs more than $70, so save some money by renting a car).
Plenty of room to explore — or do nothing. There's more than 50 miles of white sandy beaches and 590 miles of shoreline, so you’ll have plenty of stuff to see and do — or do nothing at all but lounge around with a cocktail and/or good book. The sunsets here draw quite the crowd, so come early and stay late.
Stay like a celebrity. We all want Carrie Underwood’s legs, but what about her vacation style? The country powerhouse recently paid a visit to Captiva Island, at one of South Seas Island Resort’s luxurious private vacation homes. Guests can feel at home in a variety of accommodations, ranging from hotel rooms to condominiums and cottages to private villas and homes. The property is so large you’ll need a golf cart to navigate it, and there are miles and miles of beaches, not to mention wildlife preserves to keep you occupied.
Picture-worthy. Everywhere is Instagram-worthy, but you’ll definitely want to check out the “preppiest place on earth,” Boca Grande. Boca Grande is the heart of Gasparilla Island nestled off southwest Florida’s Gulf coast, and it is the unique and quaint locale that was Katharine Hepburn’s temporary respite from paparazzi and fans. It’s clustered around the old train depot and serves up a taste of Florida’s yesteryear. Boca Grande has evolved into a playground for discerning travelers and celebrities.
Have a few cold ones with $70,000 scattered around you. Home of the historic Cabbage Key Inn, Cabbage Key is a unique island that was purchased by highly acclaimed author and playwright Mary Roberts Rinehart in the 1930s. The home was later converted into a cozy inn with six guest rooms and an open-air restaurant, which attracts thousands of visitors each year. Cabbage Key is now wallpapered with signed dollar bills (more than $70,000 as of last count). The tradition began when a thirsty fisherman left his autographed bill taped to the wall, ensuring a cold drink the next time he stopped by. Talk about a man with a plan.
Celeb sightings make vacations extra-memorable. The Cabbage Key Inn & Restaurant has been a popular hot spot for celebrity sightings like Julia Roberts, Jimmy Carter, John F. Kennedy Jr. (whose dollar bill is hanging behind the main counter in the restaurant), and Ernest Hemingway, to name a few.
We promised margarita vibes and cheeseburgers in paradise. If you’re a Jimmy Buffett fan, Cabbage Key is rumored to be the spot that inspired his hit song "Cheeseburger in Paradise," transforming the diminutive inn into a world-famous attraction. Plus, the cheeseburgers and atmosphere are exactly as the song says.
The Island Cow Eatery is another great dining option with one of the most diverse menus. The Island Cow will be the place that reminds you to relax — you're on island time. And we wouldn't be surprised if you made more than one visit here during your stay. It's that good.
A place for inspiration. Buffett’s hit song wasn’t the only big hit inspired in the area. When Anne Morrow Lindbergh visited Captiva Island and penned her famous book, Gift from the Sea, she wrote: “The beach was covered with beautiful shells and I couldn’t let one go by unnoticed. I couldn’t even walk head up looking out to sea, for fear of missing something precious at my feet.” There are more than 400 shell varieties of all shapes, sizes, and colors, making it a seashell lover’s paradise.
You have to see it to believe it. One of Captiva Island’s most popular restaurants, The Bubble Room is a three-story venue decked out in nostalgic décor from the '30s, '40s, and '50s, and filled to the brim with outlandish décor featuring unique Christmas items, antiques, and Hollywood glam. The restaurant is nationally recognized for its quirky menu items, such as “Duck Ellington” and “Gone With the Fin,” in addition to its award-winning and incredibly oversized desserts that are bigger than your actual head. It’s the most eclectic place you’ll ever have the pleasure of grabbing a meal — guaranteed.
Pro tip: Grab dinner at one of the many outside patios (opt for any variation of seafood that’s fresh) and then head to The Bubble Room for drinks and dessert after. And you’ll want to share your cake — take our word.
Sanibel lighthouse. The beaches of Fort Myers and Sanibel (most notably Captiva Island) are much less crowded.
Participants at last year's inaugural Yuletide Festival. Photo courtesy of Sherwood Forest Faire 
The CultureMap City Rink will be open through January 5, 2026. Photo by Ashley Gongora 
