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10 Things to Love About Key West, Florida

While Key West, Florida is famously known for its vibrant nightlife, soft-sand beaches, iconic conch-style architecture, and of course, Ernest Hemingway, there is so much more to explore on this tropical archipelago. We’re taking you beyond Duval Street and sharing ten of our favorite things to love about Key West.


1. National Sovereignty

Nearly 40 years ago, in 1982, in protest of a U.S. Border Patrol roadblock that shut down tourism, the mayor at the time “seceded” Key West from the United States to become the Conch Republic. Although a tongue-in-cheek demonstration, the “fifth world nation” stuck – today, complete with its own flag, passports, and their April 23rd “Independence” celebration.

2. The Clucking Locals

Yes, most prefer their fowl battered and fried, but here, some 2,000 feral chickens – descendants of nineteenth-century roosters bred to cockfight – are protected and roam the streets freely.

3. Salty Sweets

Find candies that honor the sea at Duval Street’s sweet shop, Kilwins: chocolate caramels topped with a choice of six sea salts from around the world, including the Himalayas, Bali, the Mediterranean, and Hawaii. While visiting Kilwin’s southernmost location, visitors can watch treats like fudge, caramel, chocolate confections, and nut brittle be made from start to finish on the shop’s marble-topped tables.

4. Morning Mixers

Sipping 8 a.m. happy hour cocktails while listening to “Kokomo” is not only approved but encouraged on the dock of the historic Schooner Wharf Bar, still a customary stop for The Beach Boys’ Al Jardine. Nibble on local seafood dishes and listen to sets from the best musicians in the Keys for breakfast or lunch at this quaint, open-air bar along the iconic Seaport harbor walk.

5. Presidential Approval

Front Street is home to the “Little White House,” the presidential winter retreat for Harry S. Truman. Guests can take a guided tour of the former president’s home and learn how the 33rd U.S. president spent 175 days out of his year here. Additionally, this island home has served as a retreat for several other presidents, including Dwight D. Eisenhower, John F. Kennedy, Jimmy Carter, and Bill Clinton.

6. Traditional Cigars

Cuba’s world-class cigars may be a stone’s throw away, but Duval Street is rolling with just as high-quality smokes – from Island Cigar Factory, a casual cigar bar with an open-air patio, to Rodriguez Cigar Factory, the oldest cigar company in Key West. Here, guests can take a 1 hour and 15 minute-long tour to learn about the history and process of making authentic cigars. The experience wraps up with a complimentary award-winning cigar and a Cuban espresso.

7. Will Soto

You haven’t seen the 70-something-year-old juggling tightrope walker enthralling the crowds at Mallory Square’s Sunset Celebration? The undisputed symbol of the evening event, he has been practicing his high-wire act here for over 40 years – ask the busker how a few cocktails first landed him in Key West. 

8. The Underwater Film Set

Before the 523-foot-long Gen. Hoyt S. Vandenberg was scuttled, it played a Russian science ship in the 1999 Jamie Lee Curtis film Virus. It was intentionally sunk to create an artificial reef, the second largest of its kind across the globe. Now sitting just 145 feet below Key West’s waterline, its current cast includes both deep-sea and shallow-water fish, coral, and sponges, making it a prime diving location. 

9. Lobsterfest

Honoring the beloved clawless sweet Key lobsters, locals and visitors kick off the beginning of lobster season with a four-day-long celebration. The festival features a Lobsterfest pool party, Duval Pub Crawl, Lobster Brunch, and plenty of creative takes on classic seafood dishes. 

10. West Martello Tower

This 1864 Civil War fort, now a horticultural oasis, sits on the island’s southern shore and offers a view of the endless stretch of the Straits of Florida. Dripping with orchids, lonesome cacti, and fragrant lilies, this retreat is quiet and, best of all, free.

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