Florida Keys

The tropical waters of Key West are home to some of the most protected living coral reefs in the country. There are tons of outfits offering kayaking, snorkeling, scuba diving, and even glass-bottom boat tours, but we like the in-house folks at John Pennekamp, which is a massive underwater park (statues, sculptures, and the like) that justifies the drive. They’re also nicely attuned to visitors’ wishes and skill levels.

Visiting Key West without making a pilgrimage to the Ernest Hemingway Home and gardens (and its resident family of six-toed cats) is kind of blasphemous. Much of the interior and a smattering of personal possessions from Hemingway’s years on the estate are lovingly salvaged originals. Don’t skimp on the tour as the guides are extremely well-versed in Hemingway trivia.

Not nearly as touristy as other Duval Street spots, this refreshingly theme-free spot serves the kind of elegant dishes (tartines, dumplings, carpaccios) and craft cocktails you can’t really find elsewhere on the island. It’s been around for 25 years, but the clean, modern décor doesn’t show it one bit. The weekend brunch is so good they start serving it on Wednesday. You’ll want to make a reservation.

Seafood is understandably abundant here, and there’s really no better place for conch fritters than Alabama Jack’s in Key Largo. But you should come here just as much for the ambiance as the food as it’s a bit of a haul from Key West. It looks like a standard roadside dive (there are dedicated motorcycle parking spots out front) except that it sits on a floating barge with insane views of the creek and neighboring mangroves. Come on a weekend for live music and dancing.

In a town dominated by novelty t-shirt shops, Besame Mucho’s lovingly packed displays of Astier de Villatte candles, letterpress stationery, Fig & Yarrow skincare, and vintage and new home goods are pretty refreshing. They also carry one of the deepest selections of Santa Maria Novella products we’ve seen outside of Florence.

Look no further for a fittingly kitschy but wonderfully practical Key West souvenir. You can watch your sandals being made, and some of the styles are legitimately cute—plus, they’re sturdy and really reasonably priced ($15).

The Ocean Key resort sits at the very top of Duval Street on one side and the lively Sunset Pier on the other, making it a convenient home base from which to explore. The décor is fittingly perky—with pops of turquoise and rattan accents scattered throughout the rooms; the on-site restaurant, Hot Tin Roof (killer sunset-watching spot); and the rooftop pool—but just enough so as not to be overwhelming.

This is a big, beautiful, Deco-style resort that somehow manages to strike a balance between the glitz of a Waldorf Astoria property and local clout: The structure has been here since the ’20s and is listed on the National Register for Historic Places. The massive, 300-plus-room compound sits on a private beach, so you can retreat to a lounge chair, or your beautifully appointed guest room, or the world-class spa whenever the craziness of Duval Street, which is walking distance from the hotel, gets to be too much.

Lush tropical plants tower over the thatched-roof bungalows on the private white sand beach of this luxury resort on Little Palm Island. No phones, TVs, or kids under sixteen make it a romantic, secluded retreat with not much else to do besides lounge or learn how to deep sea fish or sky dive. The resort’s SpaTerre offers delicious sounding treatments inspired by the area, like coconut sugar scrubs and margarita-infused pedicures. They also offer massages on the beach for optimal relaxation.