Our list of top things to do and reasons to love Key West reach well beyond Duval Street and its reputation as an eclectic, tropical home for legendary writers, pirates, and true free spirits of all types.

Photo © Pola Damonte

1.) National Sovereignty

Some 30 years ago, in protest to a U.S. Border Patrol roadblock that shut down tourism, the then-mayor “seceded” Key West from the United States to become the Conch Republic. Although a totally tongue-in-cheek demonstration, the “fifth world nation” stuck – today, complete with its own flag, passports, and an 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 newest 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.

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 habitual stop for The Beach Boys’s Al Jardine.

5.) Presidential Approval

Front Street is home to the “Little White House,” the presidential winter retreat for Harry S. Truman. Additionally, the island has been a getaway for Dwight D. Eisenhower, John F. Kennedy, Jimmy Carter, and Bill Clinton.

6.) 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 Garcia Cigar’s rickety shack to Cork & Stogie’s front porch seating accompanied with fine wines.

7.) Will Soto

Oh, 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 38 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. Now, just 145 feet below Key West’s waterline, its current cast includes both deep-sea and shallow-water fish, coral, and sponges for prime diving.

9.) Lobsterfest

Ukulele-playing, drag-queen-drag-racing, and history-reenacting festivals are clearly a big draw, but don’t miss the August event that worships the clawless sweet Key lobsters, with three days of all the “bugs” – as locals call them – you can eat.

10.) West Martello Tower

This 1864 Civil War fort, now a horticultural oasis, sits on the southern shore of the island 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.

Where to Stay The Laureate Key West | Sunset Key CottagesOpal Key Resort & Marina| The Capitana Key West