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How To Spend 48 Perfect Hours In Key West, Florida

How To Spend 48 Perfect Hours In Key West, Florida

Picture of David Lindsey
Updated: 21 October 2016
Key West is established as one of Florida’s most beautiful getaway destinations. There are so many things to do; from water sports and activities to historical points of interest and local attractions, choosing is the hardest part. Make it easy and use our guide to plan the perfect 48 hours in Key West.
Snorkeling in the Dry Tortugas National Park | © David Lindsey
Snorkeling in the Dry Tortugas National Park | © David Lindsey

Where To Stay

To be close to all the action, find a hotel, resort or one of the many bed and breakfasts that are near Duval Street—the main drag of Old Town. There are well-known watering holes in this area, such as Sloppy Joe’s and Margaritaville, Captain Tony’s, and the Smokin Tuna Saloon. In addition to great bars and restaurants, popular attractions such as the Key West Butterfly and Nature Conservatory, the Key West Aquarium, John James Audubon House, and Ernest Hemingway Home are footsteps away. Here are a couple of our favorite retreats.

Marker Waterfront Resort

This brand new luxury resort is making its mark in Key West’s historical seaport. With picturesque views of the Gulf, three beautiful pools, and rich landscaping throughout the grounds, you can’t go wrong at The Marker during a stay in Key West. Be sure to grab a cocktail poolside at the Cero Bodega restaurant and pool bar.

The Marker Key West, 200 William St, Key West, FL, USA, +1 305-501-5193

Saint Hotel Key West

This newly renovated, uber-chic boutique hotel is located right in the heart of Duval Street. It consists of 37 guest rooms and six suites with exquisite décor, an outside oasis with a pool, and a lobby bar with an excellent drink menu. Saint Hotel has a fun, opulent vibe, making it a perfect spot for tourists and travelers.

Saint Hotel, Key West 33040, 417 Eaton St, Key West, FL, USA

View of Key West sunset from Mallory Square | © David Lindsey
View of Key West sunset from Mallory Square | © David Lindsey

Where To Play

Take a tour

Sightseeing tours are a great way to learn about the history of the southernmost city. The Old Town Trolley Tour makes stops at more than 100 different points of interest and is fully narrated by a local historian. Patrons are able to get off, hang out and get back on at any of the stops, which is great because you can spend as much time as you want exploring the sights. Some of the stops include: Mel Fisher’s Maritime Museum, West Martello Fort, Key West Tropical Forest & Botanical Garden, and Truman Little White House.

Old Town Trolley Tour, 1 Whitehead St, Key West, FL, USA, +1 305-296-6688

Be Adventurous

Key West is surrounded by shimmering, aqua waters that offer a myriad of fun and adventure. Fury Water Adventures offers a variety of quick trips (less than three hours), which is perfect for a relatively short stay in Key West. For the experienced thrill seeker choose the Ultimate Express, which includes parasailing and jet skiing. For the novice, try a Dolphin Watch eco-tour.

Fury Water Adventures, 241 Front St, Key West, FL, USA, +1 855-990-0197

Visit the Dry Tortugas National Park

To make a Key West vacation unforgettable, book a seat aboard the Yankee Freedom III, the official ferry of the Dry Tortugas National Park. This incredible eco-treasure is simply breathtaking with its natural beauty, exotic wildlife and massive Civil War fortress. The Yankee Freedom transports visitors to this secluded cluster of islands in comfort and includes a complementary breakfast, lunch, cold beverages and top-of-the-line snorkel gear. After a leisurely sail across the Gulf of Mexico, visitors can explore the pristine beach, snorkel in the warm shallow waters and tour the fort that was once home to soldiers, war prisoners and the famous Samuel Mudd. A day at the Dry Tortugas is unlike any other Key West experience, and one not to be missed.

Dry Tortugas National Park, Key West, FL, USA, +1 305-242-7700

Celebrate the Sunset

You’ve heard about it, seen pictures of it, but until you’ve experienced a Key West sunset yourself, nothing compares. For the perfect view and to celebrate it properly, head to Mallory Square for their nightly sunset celebration. Get there early to sample homemade conch fritters and a refreshing mojito. Check out the arts and crafts by local artists. Then walk along the seawall to witness the many street performances that have made this celebration famous. There are sword swallowers, tightrope walkers, jugglers, magicians, musicians, comedians and more. As the sun begins its dramatic departure off of the horizon, watch in wonder and discover why there’s nothing quite like a Key West sunset.

Mallory Square, 400 Wall St, Key West, FL, USA

El Meson de Pepe | © David Lindsey
El Meson de Pepe | © David Lindsey

Where To Eat

El Meson de Pepe

For truly authentic Cuban cuisine, live music and a world famous Key West sunset, El Meson de Pepe is the place to be. Located right in Mallory Square, this is a fan favorite from locals and tourists alike. Indulge in rabirubia frita entera, a Cuban staple, fried whole yellowtail with fresh key lime, garlic and onions, churrasco – grilled skirt steak with a tangy chimichurri sauce. Enjoy freshly made mojitos and take in the lively atmosphere in the heart of Key West.

El Meson de Pepe, 410 Wall St, Key West, FL, USA, +1 305-295-2620


For those looking for the best pizza on the island, stop by Duetto on Greene Street just steps from the Truman Little White House. You can choose from traditional or stuffed, vegetarian or meat – they have something for everyone. Combine this with their gelato and super friendly staff, and you’ll see why visitors can’t go wrong with Duetto for a quick bite.

Duetto 540 Greene St, Key West, FL, USA, +1 305-848-4981

Where to Drink

Green Parrot Bar

This iconic, century old bar defines what a ‘dive bar’ really is. Whether bar hopping or anchoring down for the night with cold brews, this place is a must-do. There is live music every day, and locals and tourists alike from all over frequent this Key West staple. Green Parrot Bar’s casual atmosphere and excellent drink specials make this the best dive bar in Key West.

Green Parrot Bar, 601 Whitehead St, Key West, FL, USA, +1 305-294-6133

Irish Kevin’s

For an authentic Irish dive and ice cold Guinness, stop in at Irish Kevin’s on Duval Street. Situated right in the heart of all the Key West action, you’re sure to have a fun and engaging time with all the tourists and locals that frequent this place. There is live entertainment every night, served up with delicious Irish pub grub, allowing you to sit-back and enjoy the rustic atmosphere.

Irish Kevin’s, 211 Duval St, Key West, FL, USA, +1 305-292-1262