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How to Spend 2 Days In Key West

Only have 2 days in Key West? No problem! You can encounter plenty of fun and excitement in just 48 hours. Stick to Old Town, which is only about one square mile in all, and rent bicycles to get around town with ease just like the locals do.

Day One
Morning – Get the lay of the land
Start your morning aboard Old Town Trolley Tours, departing every half hour from Mallory Square. With 13 stops and more than 100 points of interest throughout Key West, you’ll leave with a wealth of knowledge about this quirky island paradise and get a lay of the land. Our expert conductors are seasoned tour guides and provide fun facts about Key West’s fascinating history. You have the option to hop on/hop off throughout the tour and your ticket is good for two consecutive days of rides throughout the island.

Image of Old Town Trolley Tours in Key West

Afternoon – Cruise Duval Street and hit Bahama Village for lunch
Once you’ve explored Key West by trolley, it’s time to discover it on foot. Duval Street is the heart of Key West, teeming with restaurants, shops, bars and art galleries. A mile long in all, there’s always something to discover. Veer off on Petronia Street for lunch in Bahama Village at La Creperie. This casual French bistro serves made to order crepes and paninis with the freshest ingredients in a lovely open air setting. While you’re there, swing by Blue Heaven for a spiked pink lemonade at the bar and pick up a game of ping pong in the backyard. Besame Mucho is an excellent shop next door for sophisticated souvenirs.

Evening – Sunset sailing & dinner
One of the best ways to enjoy the sunset is cruising offshore aboard a catamaran. Set sail with aboard the Live Music Sunset Sail with a live band, all you can drink beer, wine and margaritas, as well as appetizers galore. The two hour sunset cruise is one of the best parties in town with great views of the spectacular sunset. Afterwards, opt for a laid-back dinner at Pepe’s, a classic dining establishment serving fresh caught fish with a great bar and back patio.

Day Two
Morning – Let’s go snorkeling!
You’re heading back on the water this morning to experience the world’s third largest barrier reef aboard a morning snorkel trip. Fury’s 65-foot sailing catamarans get you to the reef seven miles offshore in about an hour. Once there, you’ll have a full hour in the water to commune with nature and snorkel with amazing tropical fish, like rainbow parrotfish, yellowtail snapper and angelfish. You might even spot a stingray, sea turtle or even a nurse shark. On the sail home, enjoy cold beers and sodas, and beautiful views.

Image of people snorkeling in Key West with Fury Water Adventures

Afternoon – A spin around the Historic Seaport & organic burritos for lunch
Explore the docks along Key West’s charming Historic Seaport. Lined with open air bars and fine dining restaurants, the marina is filled with yachts, sailboats and fishing charters.  Veer off on Elizabeth Street and make a pit stop at Fisherman’s Cafe for a “Bucci Zing” Cuban coffee and then hop on your bikes to Simonton Street. Stop at Bad Boy Burrito for a delicious and nutritious organic burrito with your choice of fixin’s, ranging from kobe beef to grilled chicken to tofu, stuffed with fresh veggies, like avocado, jalapeno and cabbage.

Evening – Sunsets, conch fritters & key lime pie
Wrap up your visit to Key West with the sunset celebration at Mallory Square where you’ll find street performers, magicians and musicians every night performing before a backdrop provided by mother nature. Head to the conch fritter stand near the Margaritaville Hotel for some of the tastiest conch in town and grab a mojito from another cart nearby to savor while the sun makes its nightly descent into the western horizon. If you’ve got a sweet tooth, make your way to Kermit’s for a frozen key lime pie on a stick dipped in chocolate. Of course, your evening doesn’t have to end here. The bars in Key West stay open late. Hit up Sloppy Joe’s, The Porch and the Green Parrot for live music, dancing and cold beers into the wee hours.

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