How to Spend a Romantic Weekend in Key West


Just a short plane ride from most major airports in the continental U.S., Key West is an ideal tropical spot for a quick winter getaway. It’s known for its relaxed and laid-back atmosphere. Travelers can just go where the day and their mood takes them. Or they can book excursions and tours to fill their days from sun-up to sun-down. Here’s a quick overview of the best Key West has to offer.

Things to do in Key West

See the City

The city of Key West has a public transit system of buses, although bicycling is an extremely popular way to get around this small island. Local tour companies offer biking and walking tours. There’s also the Conch Tour Train, a hop on/hop off guided tour. 2018 marks the 60th anniversary of Conch Tour Train. Passengers hear all about the legends and lore of Old Town Key West. Looking for something different? Consider booking a relaxing sunset cruise on the Schooner Spirit of Independence. It includes light fare and music, with highly acclaimed local commentary by Capt. Rick.

Cultural and Outdoor Adventures

There are multiple places to take in the uniqueness of Key West’s flora and fauna, cultural landmarks, and historical attractions. It’s only natural in a place where the sea, sun, and sand are so intertwined with the history of the area that many local attractions reflect that same overlap.

Botanicals, Wildlife, and Museums

For nature lovers, the Key West Aquarium, Key West Butterfly and Nature Conservatory, Key West Tropical Forest and Botanical Garden, Audubon House and Gardens, and Nancy’s Secret Garden are can’t-miss destinations. Folks interested in local history and culture will enjoy the exhibits at Key West Shipwreck Treasure Museum, Flagler Station, Cayo Hueso y Habana Historeum, Mel Fisher’s Maritime Heritage Society, and Harry S Truman Little White House Museum, as well as the ever-popular Hemingway House and Museum. Watch for special exhibits and events planned throughout the year; admission tickets for some of these attractions are cash only, and a few require reservations if you’d like to join a tour.


Put it all together at the Fort Zachary Taylor State Park, where the Civil War-era fort is the centerpiece; explore the park with guided tours or relax at the picnic areas before swimming and snorkeling. Dry Tortugas National Park — about 70 miles from Key West and accessible only by boat or seaplane — is one of the area’s most popular places for snorkeling. Outdoorsy types may be interested in booking a campsite, otherwise, there’s daily ferry service to and from Key West. In addition to snorkeling, diving, and swimming, park tours include living history walks of Fort Jefferson and stargazing events. Some permit fees may be required for camping and fishing; it’s also a good idea to book ferry passage in advance.

Charter fishing trips are popular past times, too. Many trips can be customized to suit visitors’ skill and interest. Local captains know the best places for reef, wreck, and deep sea fishing, as well as the weather, current, and other conditions that have a role in where and when the fish are biting. Charters typically take care of all necessary fishing permits and gear, leaving guests free to enjoy the fishing and the scenery. If you’re lucky, you’ll find a cook-your-catch restaurant to enjoy your fish afterward!

Shopping and Nightlife

Duval Street and Mallory Square cater to locals and visitors alike. Take a leisurely walk along these sunny streets. View local art in small galleries, drop into cafes for light bites, and stop by souvenir shops for a keepsake of your trip. After dinner, enjoy live music and drinks at one of the jazz clubs in the area.

Key West is known for local stage productions — former residents include Tennessee Williams — and there’s always something going on at the Tennessee Williams Theatre, for example. Year-round, Key West puts on numerous festivals and events. These are especially popular during the winter months when the rest of the U.S. is chilly! In December, there’s an annual lighted boat parade, Key West House and Garden Tour, and New Year’s Eve conch shell drop. Then, start the year off right in January with an annual folk art exhibit, Waterfront Playhouse performances, food and wine festivals, the Key West Literary Seminar, Island Boat show and festival, Celtic festival, and several fishing tournaments.

Local Dining

Key West is foodie’s dream, with an abundance of local seafood and reflecting the influence of international cuisine. While the choices are many, here are just a few. Little Pearl has a romantic setting and serves local seafood dishes with Asian flair (reservations recommended). Don’t miss the tapas and sangria at Santiago’s Bodega. For lunch, dinner, and late night American, Asian, and Caribbean fare, try Garbo’s Grill. Feeling like pizza? Duetto’s has limited seating but great pizza by the pie and slice. Kim’s Kuban is known for breakfasts and lunches, especially the Cuban sandwiches and the tacos. Frita’s Cuban Burger Cafe serves pork tacos, fresh salads, freitas, empanadas, plus burgers. Prime Steakhouse and Latitudes are among the many fine dining restaurants.

Make the most of your time in Key West, whether you’re visiting for a weekend or a week. It’s as relaxing or energizing as you’d like it to be, making it a great destination for many travelers.

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1 Comment

  1. Agness

    I love night walks and exploring night markets with my boyfriend whenever we go. It’s a great way to get to know the area, try some food and spend some quality time talking. Awesome post, saved it for Key West visit. 😉


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