The Keys are to Florida what Florida is to the United States: an unexpected appendage, a hybrid space where North America and the Caribbean meet, an escape for those who cannot necessarily find their place elsewhere, a dongle of an improbable geography.

The equally unlikely Overseas Hwy (US 1) traverses these 113 miles of mangrove islands and fishing villages, its mile markers fixing a countdown from mainland Florida to the idiosyncratic pot of gold at the end of the arc. rainbow: the crazy, colorful Key West.

Take the long drive, literally, and use this handy guide to map out the best places to explore. Remember, there is never a need to rush on island time.

Editor’s Note: Please check the latest travel restrictions before planning a trip and always follow government advice.

Discover Key Largo by catamaran

Largo key

But first, as they say, coffee. After leaving the mainland at Homestead, 30 miles south of Miami, continue your trucking until you reach the tropical mansion of Key Largo Conch House, a perfect breakfast spot.

As the name suggests, the Conch House is located in Key Largo, the first main island in the Archipelago of the Keys. So close to the mainland and so wide, compared to its sister islands, it almost feels like a part of the mainland itself.

John Pennekamp Coral Reef State Park, home to the most accessible coral reef habitat for visitors to the continental United States, is a big draw. Activities here include glass-bottom boat trips, a mangrove trail, stand-up paddleboarding, kayaking, and of course, scuba diving and snorkeling.

Many birds use the Keys as a stopover on their annual migrations, and the islands themselves seem to attract those who engage in wildlife rehabilitation. These two qualities come together at the Laura Quinn Wild Bird Sanctuary. A short walk takes visitors past the healing bird life, including some permanent residents who cannot be reintroduced into the wild.

The turquoise waters of Islamorada will have you stopping for a quick dip © Corey Jenkins / Getty Images


Islamorada is the next main island (actually, a group of islands) that you’ll hit as you head south. You can explore the unique geology of the Keys at the Windley Key Reef Geological Status Site, a former quarry where you’ll get a feel for the layers of coral that form the solid soil of these exposed reef islands.

Their geology is fascinating, but due to a lack of topography and relatively thick forest cover inside the islands, you can sometimes miss the feeling of being on an island. This is not the case in Islamorada, where the turquoise waters of Florida Bay and the Gulf crowd over the Overseas Hwy. There aren’t many traditional beaches in the Keys, but locals love Anne’s Beach, which mixes mudflats with a bit of sand and nice warm waters for swimming and paddling.

Some of Islamorada’s coolest attractions can be found a little offshore – places like Indian Key and Lignumvitae Key; tiny, once inhabited, now abandoned, islands best accessed by kayak, which can be hired from Robbie’s Marina (itself a flea market and tourist attraction worth wandering around).

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Features - Turtle Hospital, Sea Center, Wildlife Clinic, Overseas Highway Wildlife, Street, US1 Highway with cars, Florida Keys Parking, Key
Turtle Hospital provides rehabilitation services for sea turtles © ablokhin / Getty


Marathon truly marks the “middle” of the Keys, synchronizing the islands’ ultimately rural character with their undeniable reliance on tourism and fishing.

Sombrero Beach is extremely popular with residents of the Keys, in large part because it is one of the few traditional white sand beaches in the archipelago. Sea turtle lovers – and anyone with a general sense of curiosity about wildlife – might want to stop by the Turtle Hospital, which provides a space for rehabilitation for sea turtles that have been slaughtered by disease, boat propellers, fishing nets and other hazards.

There isn’t a ton of walking space in the Keys, but you can pleasantly get lost (well, turn around at least) at the Crane Point Museum, which includes 63 acres and some 1.75 miles of trails. which cross beautiful examples of native habitats of the Keys. , including rare hammocks of palm trees (forests).

Marathon’s largest – at least the longest – attraction is accessible when you leave the island and head south along the 7-Mile Bridge, which points to, hey, seven miles. It is an engineering marvel. On sunny days, you can see fish leaping out of the water, packing you in on your road trip.

Specifications - Florida Key Deer
In Key Deer, a small deer the size of a dog that inhabits Big Pine Key © John Piekos / Getty

Big Pine & Lower Keys

Big Pine is the quintessential residential key, mostly populated by the locals who operate the islands. But as the name suggests, Big Pine is largely covered in forest, which is also home to the tiny Key Deer. This species is protected in the National Key Deer Refuge, which encompasses much of Big Pine and the adjacent No Name Key. (Yes, that’s the name of the island. Stop for a pizza.)

Almost next to Big Pine is Bahia Honda State Park, which is widely recognized as the most beautiful beach in the Keys. In addition to the gorgeous sand, you’ll find nature trails, a science center, and the surreal old Bahia Honda railway bridge – a bridge to nowhere that sits atop the water.

Features - Duval Street shopping architecture in Mallory Square with no people in Florida, city trip, sunny day, merchant vendors
Shopping in the colorful Mallory Square in Key West © krblokhin / Getty

Key West

As if to emphasize the themes of escape and eccentricity, Key West almost feels apart from the other Keys. These islands are largely rural – small towns afloat on the Gulf of Mexico and Florida Bay. Key West isn’t a big city (although it was the largest in Florida for a long time), but it is way busier than any other island in the chain. A longtime magnet for the gay community, artists, writers, and anyone else enamored of its Caribbean architecture and leafy streets, Key West has a New Orleans vibe, but with a glass of rum at the coconut.

Parasailing in Key West, Florida

The Florida Keys have one of the most unique ecosystems in the world. You can learn more about this fascinating natural world at the Eco-Discovery Center (sanctuary offices and reception center are temporarily closed due to COVID-19), which is one of the most kid-friendly attractions on the islands (but also great for adults!). If you want a leisurely escape from it all, it’s hard to beat a simple stroll through the Key West Butterfly and Nature Conservancy, which has a positively Zen vibe. Those who want a little more spooky silence should stroll among the Gothic tombstones and crumbling vaults of the main cemetery with the fantastic atmosphere of the island.

Finally, dispel all that quiet and peaceful getaway with a visit to Mallory Square, Key West’s main plaza, where street performers and touts prepare the night for an epic evening of eating and drinking in charming Old Town Key. West.

Explore Key West on foot

This article was first published on January 11, 2019 and updated on October 18, 2021


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