No matter where you stay in the Florida Keys, you’ll feel a bit outside of normal USA time.
Throughout this chain of coral islands drifting south from the tip of Florida, you’ll find incredible things to do: lost-in-time dive bars and weather-worn marinas are interwoven with oceanfront views from five-star resorts and Michelin-star-worthy dining experiences.
While all of the Keys share a relaxed, easy energy – and an appealing blend of beauty and laid-back inelegance – each island maintains its own distinct character, and it’s easy to hop between them. From the scuba paradise of Key Largo to the unapologetic eccentricity of Key West, whatever kind of vacation you’re looking for, you’ll find it here. Here’s a guide to the best islands in the Florida Keys.
1. Key Largo
Best for adventures on land and sea
Key Largo, the biggest island in the Upper Keys, acts as a bridge between the mainland and the rest of the archipelago. Water and land-based thrills here will meet the demands of even the most intrepid explorer; start the adventure at John Pennekamp Coral Reef State Park, a 70-sq-mile tract of protected seaspace, teeming with marine life. Pennekamp is a scuba and snorkeler’s dream, boasting stunning coral reefs that can also be viewed on glass-bottomed boat tours. There’s even an undersea statue of Jesus known as Christ of the Abyss, a 9ft-tall replica of the famous statue in Genoa, Italy.
Take a kayak out along the shores of Blackwater Sound and scan the swampy forests for birdlife and American crocodiles at Crocodile Lake National Wildlife Refuge, a 6600-acre nature preserve in the northern part of Key Largo.
Activities abound on land, too, starting with the Key Largo Hammock Botanical State Park. This patch of wilderness was saved from developers, and now, instead of condominiums, it’s home to one of America’s largest West Indian tropical hardwood hammocks (the local term for areas of forest that form an ecological island, distinct from surrounding types of vegetation). Visitors can walk along nature trails surrounded by land that still feels wild and untamed, and the area is also open to cyclists.
Planning tip: If you want to beat the heat on the trail, March to May might be the best time to visit.
2. Islamorada
Best for a bit of everything
Islamorada is widely known as the sportfishing capital of the world, and with the abundance of marinas and plentiful stocks of billfish and other desirable catches, it’s hard to argue with this moniker. The island has a well-developed scene for both backcountry and deep-sea fishing, but there are plenty of other unique draws, too.
For rest and relaxation, head to the white sands of Anne’s Beach, book a massage at Blu Bamboo Salon Spa or just perch at the poolside in a luxury resort such as Cheeca Lodge or the Moorings Village.
Just offshore, Lignumvitae Key, a haven for native plants, provides a chance to experience the natural beauty of the islands. Bougainvillea, lignum vitae and hardwood hammock forests thrive in this undeveloped landscape, giving a hint at what the whole archipelago might have looked like hundreds of years ago.
Planning tip: Time your visit for the third Thursday of the month, when the Morada Way Arts and Cultural District hosts an evening arts walk (6 to 9pm) with live music over a six-block stretch of downtown studded with studio spaces and galleries.
3. Marathon
Best for beaches
Marathon’s main beach, known to locals as Sombrero Beach, is one of the best in the Keys. Open to the public year-round, it’s sprinkled with some of the archipelago’s finest sand and is also a protected nesting ground for turtles. Sun-worshippers will find more fine sand at Coco Plum Beach, a smaller and more natural beach popular with windsurfers.
Planning tip: As the halfway point of the Keys, Marathon is also a great place to stay for travelers looking to explore more widely. Head north to Long Key State Park – one of the quieter preserves in the Keys – or drive south across the famed Seven Mile Bridge to adventures in Bahia Honda State Park or Key West.
4. Big Pine Key
Best for nature lovers
Nature nuts will not be disappointed by a trip to Big Pine Key. This sparsely populated island is mostly devoid of luxury and nightlife, especially as you move further away from US Route 1. But what Big Pine Key lacks in action, it makes up for in tropical beauty.
The most famous wild space in the Lower Keys is Bahia Honda State Park, just east of Big Pine along the highway. You can swim, snorkel or kayak in the park’s turquoise waters before hiking up to one of the highest points in the Keys. Watch the sky burst into color as the sun sets, then stick around to gawk at the sparkling stars. The best view of all, though, is of the landmark Saddleback Bridge, a rusty remnant of Henry Flagler’s ill-fated Overseas Railway.
Big Pine Key is also home to the rare Key deer, a small, endangered subspecies of white-tailed deer found only in the archipelago. Wander the rambling trails of National Key Deer Refuge and stop at Blue Hole, the only freshwater lake in the entire Florida Keys – an unmatched place to see the diversity of local wildlife.
5. Key West
Best for art, culture and nights out
Key West, perhaps the most famous island in the Keys, is a sun-filled carnival and the closest thing to a proper city in the archipelago. For vacationers seeking parties that spill out into the streets, late-night wining and dining and epic drag shows, Key West is your best bet.
While its wild child reputation is well earned, there are many reasons to visit the southernmost Key beyond the rowdiness of Duval St. Literary pilgrims flock to the Ernest Hemingway Home and Museum, where the famed writer lived from 1931 to 1939 (the cats that wander the grounds are descendants of Papa’s six-toed kitten, Snow White).
Other worthy stops include Audubon House, where ornithologist John James Audubon produced some of his famous bird illustrations in the 1830s, and the Key West Historical Society, showcasing the rich history of the island. Take time for a stop at the Key West Pottery and Key West Island Books, a new and used bookstore with a great assortment of local titles.
This article was first published Oct 19, 2021 and updated Oct 17, 2024.
