The Florida Keys attract all sorts, but you’ll find a definite concentration of folks who live life to an island beat that’s just a little out of step with the mainland. Indeed, as Florida is to the US – a sunbaked land that's simultaneously part of the nation and a nation apart – the Keys are to Florida.
The 30-some inhabited islands, not to mention the 1000-plus uninhabited islands and islets, that make up the Keys are fascinating, both for their natural beauty – turquoise waters, coral reefs, mangrove coastline and subtropical forests – and for their residents, who have created a community quite unlike anywhere in the United States.
If you’re venturing to this archipelago off Florida’s southern tip in hopes of a less touristy experience, spring is a great time to go – though festivals and holidays keep crowds coming in, there’s a bit more balance between visitors and locals, and humidity levels are manageable. Look further ahead to summer if you’re shopping for a deal; it’s hot and sticky and hurricane season, but there are bargains to be had on flights and accommodations.
No matter the season, there's more than enough to keep you busy here. These are the best things to do in the Florida Keys.
1. Go diving & snorkeling around the Keys
There is arguably more to see in the water around the Keys than on the islands themselves. (If you’re wondering, “Key” comes from the Taino word cairi – “island” – which became the Spanish cayo and the English cay, or Key.)
Some of the best undersea scenery is at Dry Tortugas National Park, which you must access by boat or seaplane. Located about 70 miles west of Key West, the name “Dry Tortugas” is a bit of a misnomer, as only 1% of this 70-island archipelago, now protected by the National Park Service, is dry land. (Again, some nomenclature context: the Tortugas were designated “dry” by sailors because there is no source of fresh water here.)
There’s a great mix of natural and human-made highlights to explore, including the Moat Wall, which surrounds 19th-century Fort Jefferson, and the leftover pilings from coaling piers built by the US Navy in the same century. Note that divers who bring their own tanks cannot bring them onto the Dry Tortugas ferry; you’ll have to charter your own transportation instead.
Dry Tortugas sits at the end of the Keys running east to west. On the other side of the island chain, close to the Florida peninsula on Key Largo, is John Pennekamp Coral Reef State Park, the first underwater park in the country. Pennekamp is certainly the more beginner-friendly reef excursion: you can drive to the state park, and there are glass bottom boat tours for those who don’t want to strap on fins.
To be clear, the shore snorkeling at the park is only OK – you may see some fish, but there’s no reef here. The best underwater sights still require a boat trip that technically leaves the park and enters the Florida Keys National Marine Sanctuary, where barrier reefs make for excellent snorkeling and diving for all levels of experience.
2. Play on the beaches or go kayaking around the islands
When newcomers to the Keys think of outdoor activities, they often ask about the best local beaches. There is some good sand here, but because the Keys are mainly mangrove islands, the natural coast tends more to mudflats and mangroves. That said, don’t pass up the opportunity to relax with the kids at gentle Bahia Honda or poke around sandy Fort Zachary Taylor.
The narrow channels that divide the Keys are generally calm. While their shallows can be difficult for power boats, they – along with networks of unmeasured, ever-shifting mangrove tunnels – are perfect for kayakers. You don’t even need to be a particularly experienced paddler to cut across the waters surrounding the islands, particularly in the Upper and Middle Keys, where you’ll find quiet, abandoned islets like Indian Key.
3. Experience Old Town Key West
The island’s homegrown weirdness is on display every evening at Mallory Square, a plaza that becomes a busker variety show come sunset. One of the top free things to do in the Florida Keys, the quality of the acts here may vary – you might see fire eaters or tightrope walkers or fire-eating tightrope walkers – but the showmanship is invariably top-notch.
Mallory sits at the top of Duval St, which runs through the heart of Key West’s Old Town, a historic district filled block to block with candy-colored tropical homes, ranging from Caribbean-style shotgun shacks to shaded, palm-bedecked mansions.
4. Eat your way across the islands
Seeing as the Keys sit at a tropical crossroads that enfolds the Caribbean and the American South, there is no shortage of good food here. Even the local gas stations are good for island-style quick eats like Jamaican patties or picnic fried chicken.
Cuban emigres can be found on all of the islands, but they manage one of the better Cuban restaurants in South Florida (this is saying something, by the way) at La Nina on Marathon. On the same island, you’ll find Keys Fisheries, where fresh seafood and outdoor dining will inevitably cure your hunger pangs.
Speaking of fresh seafood and fresher ocean breezes, you can find both, along with a (slightly) more formal, romantic vibe, at Lazy Days in Islamorada. If refined, romantic, tropical fine dining is your thing, it’s hard to beat the excellent Square Grouper on Cudjoe Key, one of the most buzzed-about restaurants on the islands.
But save your appetite for Key West, which has a ridiculous concentration of great eats for such a small island – grab a beer and a grouper sandwich at BO’s, soak in the sun and vegetarian cuisine at the Café or watch the roosters wander by while you eat Caribbean-style shrimp and jerk chicken in the rakishly disheveled backyard of Blue Heaven.
5. Get in touch with your artistic side in Key West
The Florida Keys are roughly 125 miles long, but a full third of its residents live on Key West. The westernmost inhabited island in the chain, and the southernmost point in the continental USA, Key West is also the most dynamic island in the Keys, a place that defies easy categorization.
For all that Key West is undoubtedly a tourist destination, it is also a lived-in place, giving it a vitality you don’t often find in resort towns. This sort of energy is on full display at events like Fantasy Fest, a brilliant, bright carnival for adults, replete with some of the most outrageous costumes this side of Mardi Gras.
Key West has long been a haven for artists, authors and the sort of folks who want to live in a creative kettle. Perhaps the island's most famous resident was Ernest Hemingway, whose magnificent home remains open to the public for incisive, humorous tours. For a broader overview of the local arts scene, peek into the galleries that line Duval St and its surrounding blocks, or lose yourself in the Customs House Museum, which includes exhibitions on the history of the archipelago.
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