Guides

Sit back, relax, and let loose on the island that practically requires you to do all three.

From day trips to weekend getaways, our biweekly Traveler newsletter shows you the best of New England and beyond.

A large, elegant building with white walls and a red-tiled roof, featuring multiple arched doorways and windows illuminated with warm lights. Tall palm trees line a central walkway leading to the entrance, flanked by narrow water features on both sides. The sky is a soft gradient of purple and blue, suggesting dusk.

Sunset at Casa Marina Key West, which recently underwent an extensive renovation. / Photo by Casa Marina Key West, Curio Collection by Hilton

Immediately upon stepping off the plane and into Florida’s southernmost key, it’s clear the vibe has shifted. No longer are you in the land of tight smiles and buttoned-up New Englanders, but somewhere much more laid-back, where everyone wears flip-flops exclusively and wants to know if you’d like another drink. And with a festival-heavy lineup of events, April marks a prime time to party here. Prepare to settle into the island’s relaxing rhythms with the help of a slice (or three) of Key lime pie, azure waters in every direction, and more rum than you ever thought possible.

A tabby cat is lying on a polished wooden table in a room decorated with framed pictures and wall sconces. In front of the cat, there is a sign that reads,

The Ernest Hemingway Home & Museum. / Photo by Mark Hedden, Courtesy of the Florida Keys & Key West

PLAY

The best way to see the Conch Republic is from the seat of a wind-whipped jet ski. Embark on a tour with Barefoot Billy’s; you’ll circle the entirety of Key West in just 90 minutes while cruising over the waves, and in certain areas, you’ll slow down to possibly catch a glimpse of a dolphin or manatee. Come down from your adrenaline rush at Papa’s Pilar, a distillery named for famed resident Ernest Hemingway and his beloved fishing boat (and recent winner of Rum Producer of the Year from the USA Spirits Ratings). Opt for a tour from Bahama Bob, the on-site rum consultant, who’ll tell you about the business’s barrel-blending and bottling processes, plus give you a taste of the distillery’s light and dark rum varieties. It’s a perfect precursor to visiting the Ernest Hemingway Home & Museum, where you’ll see, among other things, his writing studio, his original typewriter, and a gang of six-toed cats. From April 17 through 26, partake in the 44th annual Conch Republic Independence Celebration, which marks the island’s playful “secession” with parades, parties, a pirate ball, and more. Then, stay for the beginning of the Key West Songwriters Festival starting April 29, when live music takes over the island.

Three colorful cocktails are arranged on a dark green marble table. One cocktail is in a coupe glass garnished with a lime wheel and mint leaves, another is a peach-colored drink in a coupe glass with a cherry garnish, and the third is a tall yellow drink garnished with a pineapple leaf and a pineapple wedge. A yellow menu with

Cocktails at Casa Marina Key West’s Canary Room. / Photo by Casa Marina Key West, Curio Collection by Hilton

SHOP

Key West is only 90 miles from Cuba—much closer than the mainland U.S.—so it makes sense that the country’s rich history of cigar-making has made its way to Florida. At the Rodriguez Cigar Company factory, you can watch master cigar rollers in action, then shop its four varieties; the Vintage 1925 Series is the original tobacco blend that the company began with in 1984. You’ll also want to make a stop at Books & Books @ the Studios, author Judy Blume’s nonprofit bookstore, for a wide selection of Key West–themed books. That includes the staff-recommended The Last Train to Key West, a historical fiction novel that tells the story of the infamous 1935 Labor Day hurricane through the lives of three women.

A slice of lemon meringue pie with a thick, toasted meringue topping, a yellow lemon filling, and a graham cracker crust, served on a floral-patterned plate on a multicolored table.

A towering slice of Key lime piece from Blue Heaven. / Photo by Madeline Bilis

EAT

You must start at least one day of your trip at Blue Heaven, the legendary restaurant serving beloved breakfast dishes like pecan pancakes, Key West shrimp Benedict, and a towering slice of the fluffiest Key lime pie on the island—best enjoyed beneath the sweet-smelling shade of the patio’s bougainvillea and palm trees. Later, as you duck in and out of the shops lining Duval Street, stop for lunch at the soon-to-open Fishwife for Bahamian-inspired seafood, a seriously indulgent smash burger, and an inventive vegetarian take on oysters. As the day winds down and you make your way to Mallory Square for its nightly sunset celebration, save time for dinner at Bagatelle. Start with a fresh salad that mixes Costa Rican hearts of palm, roasted cherry tomatoes, maple-glazed pecans, and radicchio, followed by a main course of seared black grouper over coconut rice and grilled asparagus.

A long wooden pier extends over clear turquoise water toward a sandy beach lined with palm trees and white buildings with red-tiled roofs. An American flag flies at the end of the pier, and a few small boats are near the shore. The sky is clear and blue.

The Henry Flagler-built hotel’s private beach is the largest in Key West. / Photo by Casa Marina Key West, Curio Collection by Hilton

STAY

Casa Marina Key West, Curio Collection by Hilton dates to 1920, when the grande dame was built by railroad tycoon Henry Flagler. A recent top-to-bottom renovation plays up the resort’s Old World glamour, along with dazzling updates like the Canary Room, its walls completely handpainted with a tropical mural by local artist Katlin Spain. Outside, the retreat offers the largest stretch of private beach on Key West, in addition to two pools and a new open-air oceanfront restaurant, Dorada.

This article was first published in the print edition of the April 2026 issue, with the headline,“Key West, Florida.”