Changes in latitude
GETAWAYS • Keys
There’s something about the moment you drive past the last traffic light in Florida City — when the mainland recedes into the rearview mirror, the Florida Keys horizon opens up, and only calm and freedom lie ahead.
One of the great American roads, the Overseas Highway stretches from the tip of Florida across dozens of islands for about 100 scenic miles until it ends in Key West. Here, four idyllic stops along the way:
→ Playa Largo (Key Largo, MM 97): As one of the only new-build resorts to go up in Key Largo over the last 20 years, Playa Largo brings an air of luxury to its namesake key, from a landscaped bayfront beach to the lagoon-style swimming pool, four thoughtful restaurants worthy of a Miamian’s discerning tastes, and modern, spacious rooms.
The Ticket: For lunch or sunset cocktails, Sol by the Sea is tucked inside a charming reclaimed boathouse perched on the bay on property.
→ Amara Cay Resort (Islamorada, MM 80): A stylish oceanfront boutique hotel with rattan furniture framed by warm leather and natural wood accents in a neutral color palette. Amara Cay’s dreamy rooms feature floor-to-ceiling windows with views of the lagoon pool and sparkling ocean below. It’s the kind of place you can fall into a trance watching pelicans swoop and dive along the pier.
The Ticket: A mile up the road, Chef Michael’s is a classic white-tablecloth Islamorada institution for fresh hogfish snapper and other locally caught fish prepared half a dozen different ways. And yes, it serves one of the best key lime pies in the Keys.
→ Isla Bella Beach Resort (Marathon, MM 44, above): Just before the iconic Seven Mile Bridge, Isla Bella is tucked away on the edge of Marathon. One of the newest resorts in the Keys (it opened in 2019), it spans 24 acres on village-like grounds with five swimming pools, a cove beach, and spa. Every room features ocean views and outdoor space with one- and two-bedroom suites available.
The Ticket: Less than a mile up the road, Lazy Days South is a laidback go-to in Marathon for fresh seafood and prime sunset views with indoor and outdoor seating.
→ Casa Marina (Key West, MM 0): After making it to Key West, it’s only appropriate to check into the 1920s-era resort conceived by oil tycoon Henry Flagler, who built the Overseas Railroad, which originally connected Key West to mainland Florida (remnants of the railroad can be seen throughout the drive). A bastion of Mediterranean Revival opulence, with a private beach and one of the prettiest poolscapes around, it’s fresh off a $79 million renovation.
The Ticket: The fabled, slightly off-the-beaten-path Louie’s Backyard is about a five-minute walk. For the classic experience, book a table on the tiered oceanfront patio and indulge in sophisticated preparations of local seafood, or walk in at the upstairs cafe for a more casual small plates menu and a glass of wine. After dinner, shuffle down to the salty Afterdeck bar situated directly on the water. Ah, that Keys life. –Shayne Benowitz