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.
This immensely inviting tableau 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. 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 akin to getting a car when you’re 16 – it opens up a world of exploration and freedom that was previously nonexistent. This is an archipelago, after all, and although the Overseas Highway connects it, going by boat is the most natural way to get around.
Renting a boat in The Keys is easy, with locations in all the major districts of the archipelago (from north to south: Key Largo, Islamorada, Marathon, The Lower Keys, and Key West). However, the more pertinent question might 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 features the incomplete 19th-century Fort Jefferson, the largest brick masonry structure in the Americas, and numerous isolated, excellent snorkeling spots. In the Upper Keys, the most varied island landscapes can be found around Islamorada. Notably, 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 ripe for exploration. Monohull sailors will find plenty of rentals down here, but excellent weather and shallow flats also make The Keys especially inviting to multihull sailors. Even if you’ve never sailed before, consider taking some lessons; sailing schools dot the islands, providing some of the most enjoyable and forgiving places to learn.
Whether you choose to go by motor or wind power, it’s beneficial to talk to locals and your rental company about potential routes. While navigating The Keys is not overwhelmingly difficult, 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. For those with limited time, consider quick excursions around John Pennekamp Coral Reef State Park and bring snorkeling gear – this is among the best-preserved coral reefs in the contiguous United States.
With 170 acres of dry parkland and more than 48,000 acres (75 square miles) of protected wetland, the majority of the park’s area is ocean. The park’s most famous attraction is the coral-fringed Christ of the Abyss, an 8.5ft, 4000lb bronze sculpture of Jesus – a replica of a similar sculpture off the Portofino Peninsula in northern Italy.
For another great paddling excursion, go to Islamorada to rent a kayak and cruise out to Indian Key, once a bustling settlement, now a place of quiet ruins and 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 designed for it. The narrow streets, lack of parking, and small distances render having a car pointless for sightseeing. 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, consider heading to the Key West Cemetery, a gothic slice of land where the ancestors of the islands rest in peace.
While the Keys are not known for hiking due to their flat terrain, plenty of 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, found 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 renowned sites include John Pennekamp Coral Reef State Park and the Dry Tortugas. Visit Pennekamp as it is one of the few dedicated underwater coral reef parks in the nation (and the only one along the Eastern seaboard). Snorkeling and diving tours can be reserved online and especially for snorkeling, are suitable for newcomers to the sport. The allure of the Dry Tortugas lies in their isolation from the rest of the islands and the unique experience of swimming around the old moat of Fort Jefferson.
Moreover, there is some excellent, underrated diving and snorkeling in central The Keys at Islamorada, Marathon, and Big Pine Key. From Islamorada, you can access patch reefs (small, isolated reefs) like Cheeca Rocks; offshore from Marathon is the splendid Sombrero Reef; at Big Pine is the ocean-adjacent Looe Key barrier reef. You’ll find a vibrant selection of marine life – including sea turtles – at these spots, though they must all be accessed via boat tour.
Bike a Chain of Keys
Biking around Key West is easy and pleasant, providing access toMallory Square, Mile Marker Zero, Ernest Hemingway’s home, the southernmost point in the continental U.S., and more. If you want to pedal across a larger swath of the archipelago, consider the Florida Keys Overseas Heritage Trail. This scenic trail connects Key Largo to Key West, serving as a beautiful way to traverse the islands.
The flat elevation and ocean breezes are perfect for cycling, and stunning vantage points are prevalent along the way. However, take caution – parts of the trail cross unexpectedly from the ocean side of the road to the bay side. Additionally, some sections of the trail share a 3-foot shoulder with the busy Overseas Highway. Despite these considerations, cycling around the islands can be truly magical; just check with local outfitters before you embark.
