Point your compass south on U.S. 1, and explore a string of sunbaked islands surrounded by turquoise water.

Hector Manuel Sanchez

A guidebook won't do them justice. Neither will the best posts on Instagram. Nothing can adequately prepare you for your first visit to the Florida Keys. The slips of islands that make up this South Florida chain take most visitors by surprise. From the wild sunset skies to tranquil beaches, bustling shops, and once-in-a-lifetime restaurants, The Keys are filled with hidden gems. These islands are all connected by the Overseas Highway (U.S. 1), a strip of sun-soaked pavement stretching mile after mile into the blue horizon.

There are some classic experiences every Keys traveler must have: the aforementioned overseas drive, a slice of Key lime pie, a visit to the six-toed cats at Hemingway's former home, a sunset in Mallory Square. But there's more to this place than the roads most traveled. Strike up a conversation with any Keys native (they call themselves Conchs), and they'll tell you so.

Hector Manuel Sanchez

The Hideaway: Islamorada

Stay and shop off the beaten path
One place that definitely deserves an extended stop is Islamorada, also known as the Village of Islands. The pace of life in this town is always set to island time—one reason it's beloved by the locals too. "People may move away from Islamorada for job opportunities or school, but the smart ones always come back," says Liz Huddleston, a Keys native with a ready smile and all the inside scoop. "There's more to do and see here than ever before, but it's still such a laid-back place to live."

Huddleston is the co-owner of Miss Monroe Boutique, a charming shop found in the Village Square at The Trading Post. It's a tucked-away courtyard located behind the namesake Trading Post, a long-lived pastel market that has been family owned and operated since 1966. Many know about the store but not the grassy plaza that's behind it, which is easily the best-kept secret in town. It's also home to Boo Kee Sue Botanics, a gorgeous open-air plant bazaar; Bad Boy Burrito, a breezy spot for tacos, burritos, and smoothies; and Café Moka, a Keys-favorite destination for coffee and fresh baked goods.

Step inside, and you'll be tempted to stay all day. Huddleston says it's all part of a recent explosion of shops, restaurants, and breweries that are making Islamorada a must-stop destination for travelers.

WATCH: The South’s Most Under-the-Radar Beaches

The town and its attractions were badly damaged by Hurricane Irma in 2017, but many are flourishing once again. One dreamy Florida Keys hide-away that has come back better than ever is The Moorings Village, an honest-to-goodness paradise. Think delicate epiphytic orchids curling around the knobby trunks of waving palms; white clapboard cottages with shutters in shades of salmon, sunshine, and seafoam; and a stretch of private beach with a lighthouse sentinel on the horizon. (The lighthouse can also forecast the weather: If it disappears from view, you can expect a downpour within the hour.) Rain or shine, after a day spent exploring the hidden treasures of sandy Islamorada, this tranquil resort will be your idyll.

Find your way to Tranquility Bay Beach House Resort in Marathon, where the blue skies and sleepy beaches will entice you to stay awhile.
Hector Manuel Sanchez

The Sanctuary: Marathon

Discover a secluded world of mangrove labyrinths and endless beaches
No drive from Islamorada to Key West is complete without making a stop in Marathon, with its sublime concentration of state parks and beaches. This Middle Keys destination encourages outdoor adventures as well as languid afternoons spent watching mangrove branches sway in the ocean breeze.

One of Marathon's must-visit outdoor attractions is just off the Overseas Highway, and if you blink, you just might miss it. (So be sure to keep your eyes peeled.) Crane Point Museum & Nature Center lies behind a wall of tropical trees along the island's central thoroughfare. It has an incredible history and a landscape to match.

The Keys offer every kind of adventure, including plenty of places to dip a toe or a paddle. Soak up the sun on a leisurely kayak tour through the mangroves.
Hector Manuel Sanchez

The 63-acre preserve is filled with walking trails winding through a wild mangrove forest; rippling tidal lagoons; the Adderley House and other storied structures that have withstood a century of hurricanes; and resident fauna wandering through the coastal scrub. (Just be warned: The center's iguanas have a tendency to drop from the trees overhead.) After Hurricane Irma cut a destructive path through the Middle Keys, Crane Point invited visitors back to the property to see how nature heals itself, with the trees recovering and wildlife returning.

While you'll find many opportunities for adventure in Marathon, you'll also discover places for leisurely seaside sojourns. From Crane Point, you can follow nearby Sombrero Beach Road as it meanders toward its namesake stretch of sand. Or look beyond the town: To the north are Long Key State Park and Curry Hammock State Park. To the south, U.S. 1 meanders through Bahia Honda State Park and Big Pine Key. The latter is famed for its National Key Deer Refuge, which is a haven for a population of now-famous miniature deer. It's also home to No Name Pub, a mythic watering hole that's on the outer reaches of most maps. This establishment's walls are covered in thick, decades-old layers of sea salt-crusted dollar bills. Finding No Name Pub requires some searching, so dust off your map-reading skills, because this fabled spot serves a plate of smoked-fish dip that's well worth your effort.

Hector Manuel Sanchez

The Town: Key West

Ramble the artistic capital of the Conch Republic
Spend years in Key West, and you'll still discover daily surprises. Look for them tucked along island streets—the corners of which are attended by crowing rooster sentries that amble around the place—or hidden behind thick tapestries of tropical trees decked with vibrant blooms drooping in the humid air.

All these wonders are accessible from a room at the exquisite Marquesa Hotel, which is nestled on Fleming Street and painted in an aquamarine echo of the sea. Its facades encircle quiet courtyards and shimmering pools. The hotel is within walking distance of the bustle of busy Duval Street—of everything, really—but it feels miles away.

The lures of Old Town Key West are manifold: They're buoyed by the island's thriving creative spirit and bolstered by the vibrant artistic and literary communities that call it home.

Hector Manuel Sanchez

The intersection of Key West's originality and tropical beauty can be found in the Gallery on Greene, an art hub that's home to works by many makers, including artists Peter Vey, Mario Sanchez, and Wayne Garcia, lauded painters of Key West scenes, whose canvases are filled with the colors and character of the town. "Their work captures the spirit of the island," explains owner Nance Frank, an esteemed art dealer and collector. "It's unlike any other place on Earth."

Frank, a lifelong resident of The Keys, sees the area's appeal reflected in the works hanging in her gallery, paintings with blue skies, waving palms, and the brightly colored landmarks that locals and visitors alike have come to love. It's the town that inspired countless artists and writers to linger and to create. Frank explains the island's allure: "There's so much to discover here. Ask anyone—we'd never dream of leaving."

Advertisement