First-time Florida Keys: island hopping along the Overseas Highway

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 that don’t necessarily fit anywhere else, a dongle of improbable geography.

The equally improbable Overseas Hwy (US 1) runs through these 113 miles of mangrove islands and fishing villages, its mile markers setting a countdown from the Florida mainland to the idiosyncratic pot of gold at the end of the rainbow: madcap, colorful Key West.

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

Editor's note: Please check the latest travel restrictions before planning any trip and always follow government advice.

Key Largo

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

As the name implies, the Conch House is in Key Largo, the first main island in the Keys archipelago. So close to the mainland and so wide, relative to her sister islands, she almost feels like a chunk of the mainland herself.

A big draw here is John Pennekamp Coral Reef State Park, which hosts the most visitor-accessible coral reef habitat in the continental US. Activities here include glass-bottom boat tours, a mangrove trail, stand-up paddleboarding, kayaking and of course, scuba diving and snorkeling.

Lots of birds use the Keys as a stopover on their yearly migrations, and the islands themselves seem to attract those who are committed to wildlife rehabilitation. These two qualities come together at the Laura Quinn Wild Bird Sanctuary. A small boardwalk leads visitors past healing avian fauna, including some permanent residents who cannot be reintroduced to the wild.

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Islamorada

Islamorada is the next major island (actually, island cluster) you’ll hit as you drive south. You can explore the unique geology of the Keys at Windley Key Fossil Reef Geological State Site, a former quarry where you’ll get a sense of the layers of coral that form the solid ground of these exposed reef islands.

Their geology is fascinating, but due to a lack of topography and relatively thick forest cover in the islands’ interior, you can sometimes miss a sense of being on an island. Not so in Islamorada, where the teal waters of Florida Bay and the Gulf squeeze in on the Overseas Hwy. There aren’t many traditional beaches in the Keys, but locals love Anne’s Beach, which mixes up mudflats with a bit of sand and lovely warm waters for swimming and back paddling.

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

Marathon

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

Sombrero Beach is extremely popular with Keys residents, largely because it is one of the few traditional white-sand beaches in the archipelago. Sea turtle lovers – and anyone with a general sense of wildlife curiosity – may want to pop into the Turtle Hospital, which provides a rehabilitation space for sea turtles who have been laid low by disease, boat propellers, fishing nets and other hazards.

There’s not a ton of walking space in the Keys, but you can get pleasantly lost (well, turned around at least) at the Crane Point Museum, which includes 63 acres and some 1.75 miles of trails that cut through fine examples of native Keys habitats, including rare palm hammocks (forests).

Marathon’s biggest – at least, longest – attraction is accessed as you leave the island and proceed south along the 7-Mile Bridge, which clocks in at, hey, seven miles. It’s an engineering marvel. On sunny days you may see fish jumping up from the water, racing you on your road trip.

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Big Pine & Lower Keys

Big Pine is the quintessential residential Key, mostly populated by the locals who keep the islands running. But as the name implies, Big Pine is largely blanketed in forest, which is also inhabited by the tiny Key Deer. This species is protected within 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 by for a pizza.)

Almost adjacent to Big Pine is Bahia Honda State Park, which is widely recognized as the nicest beach in the Keys. Aside from some lovely sand, you’ll find nature trails, a science center, and the surreal old Bahia Honda Rail Bridge – a literal bridge to nowhere that sits atop the water.

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Key West

As if to underline the themes of escape and eccentricity, Key West feels almost separate from the other Keys. Those 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 Florida’s largest for a significant period), but it is way livelier than any other island in the chain. A longtime magnet for the gay community, artists, authors and anyone else enamored by her Caribbean architecture and leafy streets, Key West has a New Orleans vibe, albeit with a shot of coconut rum.

The Florida Keys boast one of the world’s most unique ecosystems. You can learn about this fascinating natural world at the Eco-Discovery Center (the sanctuary offices and the visitor center are temporarily closed due to COVID-19), which is one of the kid-friendliest attractions in the islands (but also great for adults!). If you want a quiet escape from everything, 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 spookier bit of silence should wander amidst the gothic headstones and crumbling vaults of the island’s fantastically atmospheric main cemetery.

Finally, dispel all of this quiet, peaceful escape with a visit to Mallory Square, Key West’s main plaza, where street performers and touts set the night up for an epic evening of eating and drinking in Key West’s heart-meltingly lovely Old Town.

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