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Utrip’s advanced artificial intelligence algorithms aggregate the most unique and exciting travel experiences including activities, restaurants, and nightlife. Each one of these destinations has been curated and validated by the Utrip Team to bring you a unique set of hourly and daily recommendations personalized to fit your interests and budget. We are still working on refining and enhancing these destinations. Learn more about the Utrip process.

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Ernest Hemingway, Tennessee Williams, Robert Frost, Harry Truman, Shel Silverstein - either this is one wild party of "Who's Who" in the 20th century, or we're talking about the illustrious history of one of Florida's most popular destinations, Key West. As soon as you step foot on thriving and historic Duval street, however, it's easy to see why there's such a storied past. Palm trees mix with gingerbread Victorian houses, the temperature hovers around perfect all year long, and the bars are practically on the beaches themselves. Not to mention that the culture here is welcoming to one and all, not surprising when you look at the mix of Caribbean, American, African, and Indigenous heritage on the island. They call it, "One Human Family" down here, and how could anyone argue with their neighbor when the sun is shining and fish practically jump onto your plate from the ocean? 

With its strategic position between the Gulf of Mexico and the Atlantic ocean, money originally poured into the town from shipping traffic...but not in the expected way. Men called "wreckers" were responsible for salvage operations on the countless ships that ran aground on the shallow reefs surrounding Key West. This income attracted the attention of folks from far and near, including Henry Flagler, a renowned Florida industrialist, who built a railway across the ocean to connect the keys and the mainland. The ease of access set off a century of unstoppable tourism, fed by the tropical appeal of the keys and the accessibility brought by infrastructure improvements. Key West's popularity for honeymooners, partiers, and the rich and famous was set in stone. Where else can you drive in the contiguous United States that features such a unique mix of tropical reefs, historic architecture, bars open until 4 AM, and nightly sunset festivities? It's like the residents and visitors alike are there for one purpose - to celebrate life. And that invitation is extended to you, too. Will you join the party? 


The Ernest Hemingway Home and Museum

The Legend, and Cats

Audubon House and Tropical Gardens

Residence to Restoration

Duval Street

As Sung By the Village People

Mallory Square

Party at Sundown

Dry Tortugas National Park

Snorkeling at the Fort

Key West Butterfly and Nature Conservatory

Relax and Be the Butterfly

Higgs Beach

A Pocket-Sized Paradise

Mel Fisher Maritime Heritage Museum

History of Treasure and Slavery