While it’s possible to hit the high points of Key West in a day, it makes far more sense to arrive, settle in, and spend the next day enjoying the sights — and a few drinks in one of the most bar-packed towns in Florida — before heading out the following day. Whether you come in by car along US 1 or by ferryboat from Fort Myers or Marco Island, plan two nights and a full day to experience the best of Key West. Weekdays are less busy than weekends, of course, and you’ll want to book your hotel in advance.
Arriving after lunch, you have a couple hours to spend before checking into your hotel. Consider a stop at one of the less-heralded but truly beautiful attractions on the island, the Key West Tropical Forest and Botanical Garden. It’s both a tropical forest of native trees and a planted garden of colorful tropical greenery, accented with thematic art from local artists. Pathways wind through the complex, leading to a historic collection of Cuban chugs, boats built by refugees to escape to Florida’s shores.
Check-ins are usually after 3. There are hundreds of small inns, historic lodges, resorts, and brand-name hotels to choose from, but my husband and I have our favorite romantic spot, the Key Lime Inn. The complex is centered around the historic Maloney House, built in 1834 and thoroughly renovated to provide comfortable spaces with a touch of luxury. A lodge and historic cottages also hide among the tropical forest greenery. Once you’re parked, kick back and cool down and enjoy the pool.
After 5, it’s time to stroll out into this very walkable city for dinner. Now, there’s one generality you shoud know about Key West: the east end (sunrise) is the quiet end of downtown, and the west end (sunset) is the noisy end. If you’re here for a party, go west down Duval Street. You’ll find one. For a quiet first night, take Duval Street east to South Street. While it’s still light, walk around the corner for the line for your selfie at the Southernmost Point. Everybody must. Afterwards, go back to Duval Street to take it to its end at the Southernmost Beach Cafe. This lovely spot introduces you to South Beach – your first opportunity to dip a toe in the Atlantic Ocean – and has a variety of fresh local catch for dinner. Afterwards, you can relax with drinks as the sun fades across the ocean, or wander back along Duval to catch the Cabaret or Piano Bar at La Te Da.
Key West doesn’t rise early, and neither should you. A nice continental breakfast comes with your stay at the Key Lime Inn, poolside at 9. If you’d rather get going sooner, walk east on Simonton Street to Ana’s Cuban Cafe for excellent Cafe con Leche, breakfast sandwiches, and omelets. One block south, catch Duval and take it west to start your day with the magic of the Key West Butterfly & Nature Conservancy. Window-shop Duval as you continue west, as some of the better galleries are at this end of the street. When you reach Truman, go one block south to Whitehead Street, where some of the most interesting must-see attractions are located, such as the Hemingway Home. Climb to the top of the Key West Lighthouse across the street for a birds’-eye view of town before gravitating to the Six-Toed Cat for lunch.
After lunch, grab your selfie with the Mile Marker 0 sign in front of the Key West Courthouse. Then it’s on to a visit to the Aububon House & Tropical Gardens. Take the opportunity to chill down inside the air-conditioned house museum, or on a cooler day, relax in the gardens after your tour. There are several other museums nearby — the Mel Fisher Maritime Museum, the Old Custom House, and Harry Truman’s Little White House — should you find one of those more your taste.
Depending on when sunset happens today, you may have time for a circuit up to the waterfront at Key West Bight. Follow Greene Street north to reach the waterfront, but don’t be surprised if the vibe at Captain Tony’s or Sloppy Joe’s draws you in, and so ends your walk for now. But if you do make it to the Bight, walk west and stop in at Alonzo’s Oyster Bar, a must for fresh seafood.
From the Bight, follow Front Street back south to Mallory Square. It’s here that sunset is the big celebration of the day in Key West, so expect a crowd — of gawkers and performance artists. Time your circuit to arrive sometime after 6 and before the sun has settled into the sea.
Your walk back should be along Duval Street. You’ll find many temptations for libations and live music along the way — in fact, a pub crawl is possible! — and a stop at Margaritaville is a must to pay homage to the island’s adopted son, Jimmy Buffet. If the wee hours come too soon and you can’t walk the rest of the way back, hail one of the pink cabs you’ll see hovering around Duval.
After breakfast at the hotel, get ready for a morning on the shore. There are two fabulous options, and one is better if you have a car — Fort Zachary Taylor Historic State Park. Not only does it boast a beach where you can sun and snorkel, but the historic fort is fun to wander through and atop. Watersports rentals are available on sight.
Without a car or as an alternative option, Higgs Beach is a nice sunning and swimming spot along Atlantic Boulevard near White Street. You’ll find a cluster of other attractions here near the White Street Pier, most notably the West Martello Gardens, a historic fortress stuffed full of tropical trees and flowers. Atlantic Avenue is also FL A1A, so follow it north for a scenic exit from Key West.