With just a short plane ride from nearly anywhere in the continental U.S., the Florida city of Key West offers a wide range of culinary delights, welcoming accommodations, and enjoyable activities. Whether you’re the kind of person who wants to relax or do as much as you can when you’re on vacation, you’ll find it here, and you can do it all in a weekend.

Arrive and Settle In: From Luxury Resorts to Cozy B&Bs

One of the great things about Key West is that it’s compact. Nearly every kind of place you could want to stay is close to the airport, so once you land, it’s a short drive to your accommodations. It’s easy to find the right lodging for your personal style and budget.

From upscale resorts with full spa amenities to exclusive bed-and-breakfasts, courtyard hotels, and even camping facilities, you can find it all here.

Among the stand-out choices is the Marquesa in Old Key West, known for its delightful interior courtyard and pool, and its cozy wrap-around porches and full gardens. It’s a convenient choice, too, as there’s a cafe on-site serving a high-end Contemporary American menu that includes butter-poached lobster.

Once you’ve checked in, head back out and make Mallory Square your first stop. It sits at the end of Duval Street, which is one of the main–and best-known–streets in Key West. It’s lined with restaurants, shops, bars, jazz clubs, galleries, and more.

If you feel like taking it easy, stick around Mallory Square for the Sunset Celebration, a nightly party that kicks off as the sun goes down. Enjoy live music and street performances, food and drink vendors, and arts and crafts vendors, too. 

As a relaxing yet exciting alternative, book a sunset schooner or sailboat ride. It’s a cruise to nowhere but you’ll get amazing views and the chance to unwind with a cocktail, wine or beer, and light music.

The friendly and experienced crew ensures everyone has a great time, and you’ll often get to hear amazing stories of local history and culture from those who know it best. Be sure to pack your camera and binoculars for a unique perspective on highly recognizable features like Fort Zachary Taylor and the Key West Lighthouse.

Sunshine, Fun Times, and Food

Start your second day in Key West by booking an early ferry to Dry Tortugas National Park. The reservations sell out quickly so you’ll want to do this well in advance of your trip.

It’s about a one-hour trip and when you arrive, you’ll be taken aback by the natural beauty of this mostly-underwater park. Dry Tortugas includes seven small islands, one of which–Garden Key– is home to Fort Jefferson, a Civil War-era installation.

Enjoy tours and historic reenactments and walk the seawall. You can also enjoy the picnic and beach areas of Garden Key. Rent a kayak for birdwatching as you glide around the additional keys or try snorkeling. There are multiple coral reefs and shipwrecks to explore, and because the water is so clear and calm, even beginners will have a rewarding experience. As an alternative, book a fishing charter trip with All In Fishing Charters for an exciting day of wreck, flats or reef fishing for snapper, grouper, and more.

All that physical activity will probably leave you quite hungry upon your return to Key West, so make your first stop Eaton Street Seafood Market. The fish tacos, fried conch strips, crab cakes, and lobster roll are amazing, and it’s clear that every dish is made with the freshest catch around. Dine outdoors or take your order to go. Among the other popular restaurants in Key West are Blue Heaven (get the key lime pie!), Garbo’s Grill, and Caroline’s Cafe. If you want more familiar flavors, check out Duetto’s, where the hand-tossed pizza and the house-made gelato are famous.

Give yourself time to revisit your hotel and rest a bit before heading back out to visit some of the best art galleries in Key West. Key West Pottery, Art on Duval Key West, Collections Key West, and Wild Side Gallery offer pottery, sculpture, ceramics, paintings, glass, objets d’art, jewelry, and more. Then enjoy an intimate dinner at Little Pearl, a small restaurant with a neighborhood feel and internationally inspired menu. Don’t miss the jumbo lump crab tamago and the extensive wine list with a perfectly matched glass for every dish.

Fond Farewells

Make your last day special with breakfast at Cuban Coffee Queen, Moondog Cafe & Bakery or Keys Coffee Co. Then visit Prana Spa for a soothing massage and facial to return home truly refreshed. It’s a quick trip back to the airport, but chances are you’ll already be planning your return trip!

In Key West, you’ll find everything you need for an amazing vacation. Whether you’re more interested in being active or relaxing, you can do it here. You’ll find a wide range of excursions, tours, and activities to suit your every vacation wish.

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