How to Spend a Weekend in Key West

Key West is a wonderful weekend destination, especially during the winter months. High tourism season runs January through April; however, by planning your weekend away well in advance, it’s possible to make the most of it while avoiding delays and missed opportunities. This is the largest of the islands that trail off the southern coast of Florida and offers attractions you won’t find anywhere else in the U.S.

 

Getting to Key West

 

Flying into the city is relatively easy. There are direct flights from Miami, as well as several other major metropolitan airports across the U.S., so even if you live far away, a connecting flight isn’t hard to find. For folks who’d prefer to drive, the Overseas Highway is a straight run south through the Keys; the trip takes around three hours by car. And of course, being an island, it’s always possible to sail into Key West. There are a few hotels with marinas of their own for guests to book.

 

Friday – Explore the Excitement of Duval Street

 

After your arrival in Key West, head to the Simonton Court Historic Inn and Cottages, located right off Duval Street; Simonton Street is parallel to Duval so guests enjoy a great location but slightly off the beaten path. This bed and breakfast offers cozy and private accommodations ranging from cottage, inn, guesthouse, and townhouse rooms. There are four 24-hour pools and full concierge services available, along with a daily continental breakfast served poolside.

Once settled in your room, join the Conch Tour Train at Front and Duval. It’s brief, only a little more than an hour long, but will give you a good idea of the layout of the city, the location of major landmarks and attractions, as well as an overview of the city’s history and culture. The train makes a total of three stops, and allows passengers to hop on/hop off at any of them: Front and Duval, Truval Village (Duval and Truman), and Flagler Station off Caroline Street.

After your tour, check out Papa’s Pilar Rum Distillery and Hemingway Rum Company at  201 Simonton St. Guests can take a tour and get an insider look at the rum distilling process and the history of the Hemingway family, rum production in the area, and Key West.

For dinner, check out Hot Tin Roof, part of the Ocean Key Resort and Spa. This award-winning restaurant offers indoor and harborside dining on the deck, as well as a well-curated wine selection and attentive service. This puts you in a great spot to catch the Sunset Celebration at Mallory Square, located at the end of Duval. It’s a party every night, with music, craft vendors, food, games, performances, and more, and it’s a great way to kick off your weekend!

 

Saturday – See Key West’s Natural Beauty

 

Get up early and enjoy breakfast at Simonton Court or head out to Date and Thyme, an organic grocery and cafe. In addition to breakfast items, you can also pick up to-go items for lunch, and it’s vegetarian and gluten-free friendly, too. Enjoy breakfast on the patio, and then grab a few things for a picnic lunch later.

The Key West Tropical Forest and Botanical Garden is actually located on Stock Island, on the northwest side of the island. Lush gardens of naturally native plants and trees grow wild here. It’s the only frost-free botanical garden of its kind in the country. Spend a few hours strolling the boardwalks through the gardens, and bring a picnic lunch. Don’t miss the Cuban Palms! Bring a hat and wear comfortable shoes. Some parts of the park are still recouping from damage caused by Hurricane Irma, but still worth the trip from the more commercial areas of Key West.

Travel back towards Duval Street along the northern part of the island, and stop at the Kennedy Cafe for dinner, serving authentic Middle Eastern and Mediterranean dishes. It’s open until midnight. 3 miles from Duval St., and they deliver! This is a popular restaurant among tourists and locals alike. Kabobs, falafel, pitas, pizzas, salads, hot and cold sandwiches, shawarma, gyros are prepared on-site.  

Freshen up and rest at your hotel for a bit, and then head out for drinks, music, and more. Better Than Sex is well-known for its one-of-a-kind dessert menu and intimate seating. Popular bars for live music along Duval include Green Parrot, Blue Heaven, and Irish Kevin’s. Don’t want to wander too far off Duval? Go with Virgilio’s or head back to Duval’s Ocean Key Resort and Spa for live music in the HTR Lounge.

 

Sunday – On the Water

 

Enjoy a light breakfast at your hotel and then spend the morning fishing. The fishing in Key West is legendary. Book with a local captain who can give you a customized excursion, from reef to wreck to deep-sea fishing, or go out for grouper, mahi-mahi, and more. No need to worry about packing fishing tackle or getting the necessary licenses or permits-a local fishing charter company takes care of that for guests.

Upon returning to Key West, visit Garbo’s Grill for lunch or an early dinner on Caroline St. If the name sounds familiar, it might be because it was featured on an episode of “Diners, Drive-ins & Dives”. Enjoy burgers, specialty hot dogs, burritos and tacos, and other food truck favorites.

Head south for Smathers Beach, the largest of Key West’s public beaches. Swim, walk white sandy shores, rent water sports gear or beach chairs from local vendors and just relax. Parking is free, and there are restrooms but other amenities are limited. This is one of the best places to enjoy the sunset.

Head back to Simonton Court to freshen up and then head out for a nice dinner at Nine One Five on Duval before calling it a night. Salads, shareable plates, and homemade pasta alongside choice meat and seafood dishes make for a memorable meal, prepared creatively in this old Victorian-turned-restaurant and bar.

 

Monday – One More for the Road

 

Check out of Simonton Court and visit Banana Cafe for crepes, a great send-off from Key West. This casual French bistro setting serves traditional cafe favorites with Key West flair. Choose from omelets and crepes featuring fresh seafood, vegetables, and more, along with freshly roasted coffee to prepare for your journey home.

A good weekend in Key West goes fast, and there’s no way to see everything; the good news is, that just means you’ll need to book a return trip soon!