Key West

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.

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.