With more than 1,300 miles of shoreline along its Atlantic and Gulf coasts, it’s no wonder Florida offers some of the dreamiest island escapes in the country.
The Florida Keys, strung like a necklace off south Florida’s tip, might be the first to spring to mind. But you’ll find islands in all sizes up and down the Sunshine State, each with its own personality, excursions, and resorts or inns.
I’ve called Florida home for more than 25 years and have hit a fair few islands during road trips with my family, solo vacations, and other adventures. These are some of my favorite islands to consider for your next Florida vacation.
Gasparilla Island
Off Florida’s southwest coast in Charlotte County, roughly at the midway mark between Tampa and Naples, this seven-mile-island delivers true Old Florida vibes—you won’t see any towering condos, strip malls, or chain stores marring the waterfront.
The clear Gulf waters lure amateur and more serious anglers looking to hook tarpon, especially in mid-May, when the “World’s Richest Tarpon Tournament” comes to town with a top prize of more than $100,000. Everyone who visits Gasparilla Island, however, is rewarded with soft white sands and incredible views best enjoyed from the top of Gasparilla Island Lighthouse (worth the climb up 134 spiraling stairs).
Head to the northern community of Boca Grande, where people ditch their cars to get around on golf carts and bicycles. Here, the Temptation Restaurant serves some of the freshest seafood around (try the crab cakes and fried oysters).
Where to stay: Opt for an adorable cottage or the main building at the Gasparilla Inn in Boca Grande, which dates to 1913 and has a gorgeous private beach club fronting powdery sand.
Cabbage Key
This island in southwest Florida was named after cabbage palm trees.
Photo by katherine.muld/Shutterstock (L); photo by glenrichardphoto/Shutterstock (R)
More Old Florida vibes await at this 100-acre, tropical Gulf Coast island near Fort Myers that you can only reach by boat or seaplane. Catch a ride to Cabbage Key from the northern tip of Captiva Island with Captain Brian on the Water, helmed by Floridian Brian Holoway who is certified as a master naturalist. You’ll learn all about the area’s natural history and maybe even spot dolphins and manatees along the way.
Once there, walk along the island’s shaded trails or rent an SUP or kayak to paddle the shallow waters around nearby mangrove islands. The island’s lone restaurant, inside the historic Old House, is popular with day-trippers who arrive in their own boats to dine on platters of stone crab while overlooking the water. The setting is said to have inspired the famous Jimmy Buffett song, “Cheeseburger in Paradise.”
Where to stay: Cabbage Key Inn & Restaurant has six rooms and a collection of fishing cottages, some waterfront and on stilts. The historic inn overlooks a marina that’s far from most light pollution, so the sky fills with a canopy of stars at night.
Amelia Island
You can’t escape history on Amelia Island, with an Old Spanish City, historic African American beach, and Civil War relics.
Photo by MLairamore/Shutterstock
Many visitors tend to beeline through north Florida on their way in or out of the state. But they miss one of the state’s most appealing islands just north of Jacksonville, near the Georgia border. Florida’s northernmost barrier island, Amelia Island, has wide, golden beaches backed by towering dunes home to threatened gopher tortoises and endangered seabirds like least terns.
Fernandina Beach, the last city in the Western Hemisphere designed according to Spain’s official guidelines for colonial cities, has a beautiful historic district filled with boutiques, seafood restaurants selling wild-caught fish and shrimp, and inviting spots for a sip, like Bar Zin. Stroll among Civil War cannons at Fort Clinch State Park or along the wide sands of historic American Beach, listed on the National Register of Historic Places as Florida’s first African American Beach.
Where to stay: For such a large resort, the 446-room Ritz-Carlton, Amelia Island feels surprisingly intimate. Come for incredible ocean views from most suites, a newly renovated spa, and marine biologist-led birding excursions in nearby wetlands.
Related: You’ll Find Seafood Shacks, Surf Spots, and Scenic Hikes in These Charming U.S. Beach Towns
Islamorada
Highway U.S. 1 runs through Islamorada, Florida.
Photo by Gary570/Shutterstock
Don’t miss this island detour along a road trip through the Florida Keys. Located between mile marker 72 and 90, Islamorada is favorite for on-land activities such as gallery-hopping in the Morada Way Arts & Cultural District and visiting rescued sea turtles at the Turtle Hospital. Make time to head out on private eco tours to spot manatees and dolphins in mangrove islands with Allergic To Land Charters. You can do your part to help curtail the invasive lionfish population in the Keys by booking a table at Castaway Waterfront Restaurant & Sushi Bar and feasting on a lionfish sushi roll.
Where to stay: Islands of Islamorada has a collection of 22 villas (each can sleep up to 10 people) with ocean views, as well as luxurious one-bedroom suites. Relax in the oceanfront pools, play pickleball on the property’s courts, or let the resort’s “Coastal Concierge” book a fishing charter for your group.
Related: 4 Days in the Florida Keys: Shipwreck Dives, Teeny-Tiny Deer, and Legendary Key Lime Pie
Manasota Key
Manasota Key Beach is idyllic place to unplug.
Photo by Wirestock Creators/Shutterstock
Drive about an hour south of Sarasota on Florida’s Cultural Coast to reach this 11-mile-long barrier island that feels like stepping back to the Florida of yesteryear, too, as there are no high-rise hotels or big-box chain stores. Along the clear Gulf of Mexico waters, you’ll find chalk-white beaches where shells and shark teeth wash ashore in abundance. The main Manasota Key pastimes involve strolling, sunning, and swimming in the shallow waters, followed by a meal of fresh Florida shrimp and Gulf grouper at a waterfront spot like Magnolias on the Bay. During the winter months, Stump Beach Pass State Park offers quiet beaches for unfurling a towel for the day; stick around for sunset to look for the “green flash,” a rare optical phenomenon that can occur at the moment when the sun sinks below the horizon.
Where to stay: Listed on the National Register of Historic Places, Manasota Beach Club has midcentury and 1920s-era cottages overlooking calm Gulf waters. Enjoy the hotel’s croquet and pickleball courts or kayaks and SUPs available to guests.
