When you drive along the Overseas Highway through The Florida Keys on a clear day, there’s a moment when it becomes tough to separate blue from blue. There’s the sky, arching overhead, Florida Bay and the Gulf of Mexico stretching out below. In the shallow channels between The Keys the water gets so teal, it’s hard to tell where the sky ends and the liquid begins.
It’s an immensely inviting tableau, one that attracts thousands of visitors each year. They come for some 44 islands connected by the Overseas Highway, plus around 1700 islands and islets scattered around the main archipelago – exact numbers are hard to come by, as it depends on what gets classified as an ‘island.’
Whatever you call a slice of mangrove coast and palm forest surrounded by crystal waters, it’s always special. And that description continues, and grows, in the outdoor spaces and activities The Keys are so justifiably famous for.
Go boating among the islands
For those who live in The Florida Keys, getting a boat is kind of like getting a car when you’re 16 – it opens a world of exploration and freedom that was previously nonexistent. This is an archipelago, after all, and the Overseas Highway notwithstanding, going by boat is the most natural way to get around.
It’s easy to rent a boat in The Keys, with locations in all the major districts of the archipelago (North to south: Key Largo, Islamorada, Marathon, The Lower Keys, and Key West). The bigger question may be: where should you take the boat?
Dry Tortugas National Park is the most obvious answer. Located about 70 miles west of Key West, this 70-island archipelago includes the incomplete 19th-century Fort Jefferson, the largest brick masonry structure in the Americas, and a long list of isolated, excellent snorkeling spots. In the Upper Keys, the most varied island landscapes can be found around Islamorada, while Boot Key Harbor in Marathon boasts one of the best-resourced marinas in the islands.
If you’re into sailing, The Keys are practically paradise, with fair winds, calm waters, leaping dolphins and islands awaiting discovery the norm. Monohull sailors will find plenty of rentals down here, but excellent weather and shallow flats make The Keys especially inviting to multihull sailors. Even if you’ve never sailed, consider taking some lessons down here. Sailing schools dot the islands, and there are few more enjoyable, or forgiving, places to learn.
Whether you go by motor or wind power, talk to locals and your rental company about where to chart your course. By boating standards The Keys are not hard to navigate, but the channels between islands can get shallow, and grounding your vessel is a surefire way to ruin a vacation.
Go paddling & kayaking in the mangroves
Between the calm waters and more than a thousand islands, you could spend a lifetime paddling around The Florida Keys and Key West. Assuming you don’t have that kind of time, consider some quick excursions around John Pennekamp Coral Reef State Park, and bring some snorkeling gear – this is one of the best preserved coral reefs in the Lower 48.
There’s 170 acres of dry parkland here and more than 48,000 acres (75 sq miles) of wet: the vast majority of the protected area is the ocean. The park's most famous attraction is the coral-fringed Christ of the Abyss, an 8.5ft, 4000lb bronze sculpture of Jesus – a copy of a similar sculpture off the Portofino Peninsula in northern Italy.
For another great paddling excursion, head to Islamorada to rent a kayak and cruise out to Indian Key, once a busy little settlement of a few dozen souls, now a place of quiet, moldering ruins and still, natural beauty.
Walk and hike the flat terrain
The simplest way to get outdoors is also the best way to explore The Keys’ most urban environment: Key West. The town’s historic center, on the west side of the island, is not just good for walking; in many ways it’s optimized for it. The narrow streets, dearth of parking and small distances makes having a car pointless as a sightseeing vehicle. Better to walk up Duval Street, take a left or a right, and then get pleasantly lost amid the historical homes shaded by palm fronds and sprays of bougainvillea. If you need a destination in mind, consider heading to the Key West Cemetery, a gothic slice of land where the ancestors of the islands rest in peace, and paradise.
The Keys are not known for hiking – it’s not like there’s any elevation here – but plenty of nice nature walks abound. You can lose yourself in the sweaty shade of the tropical hardwood forest at Curry Hammock State Park in Marathon, or say hello to the alligators that swim around the Blue Hole, on Big Pine Key. The Hole is a limestone sinkhole, surrounded by a platform trail a few hundred feet long; access it by turning onto Key Deer Blvd from the Overseas Highway and following that road until you see signs for the Blue Hole.
Dive and snorkel in the crystal waters
There’s no lack of excellent diving and snorkeling spots in the Keys, but the most well-known spots are John Pennekamp Coral Reef State Park and the Dry Tortugas. Visit Pennekamp because it is one of the few dedicated underwater coral reef parks in the country (and the only one on the Eastern seaboard). Snorkeling and diving tours can be reserved online and – especially for snorkeling – are suitable for newcomers to the sport. The appeal of the Dry Tortugas is the isolation from the rest of the islands and the unique experience of swimming around the old moat of Fort Jefferson.
With all that said, there is some excellent, underrated diving and snorkeling in the middle of The Keys at Islamorada, Marathon, and Big Pine Key. From Islamorada, access patch reefs (small, isolated reefs) like Cheeca Rocks; offshore from Marathon is the wonderful Sombrero Reef; at Big Pine is the ocean-adjacent Looe Key barrier reef. There’s a rainbow of marine life – including sea turtles – at all of these spots, but they must all be accessed via a boat tour.
Bike a chain of keys
Biking around Key West is easy and pleasant, with easy access to Mallory Square, Mile Marker Zero, Ernest Hemingway's home, the southernmost point in the continental U.S., and more. But if you want to pedal a larger swath of the archipelago, consider the Florida Keys Overseas Heritage Trail. The trail connects Key Largo to Key West, and as such, it is the slowest, most scenic means of getting across the islands.
The flat elevation and ocean breezes are perfect for cycling, and gorgeous vantage points are prevalent along the way, but take caution – parts of the trail cross from the ocean side of the road to the bay side, sometimes unexpectedly. Additionally, parts of the trail share a 3-foot shoulder with the busy Overseas Hwy. For all that, cycling around the islands can be utter magic – just check with local outfitters before you get on two wheels.