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Sunset Key Guest Cottages, A Westin Resort
245 Front Street · Key WestFlorida33040 · United States  • Phone: 305.292.5300 · Hotel Reservations: 866-837-4249
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Local Time: 3:30 AM • Weather: Clear, 64 °F

Key West Events Calendar: Signature Key West Events

Many of Key West’s signature events are as well known to fans of the Conch Republic as the iconic Southernmost Point buoy or the Mile Marker 0 sign. Here’s a selection of annual events that celebrate the island’s history and culture.

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At the Key West Literary Seminar, held at the historic San Carlos Institute, four days of diverse presentations include readings, workshops, panel discussions and lectures by contemporary, award-winning authors.

Key West Race Week is a world-class regatta with more than 100 racing yachts from 12 countries and 24 states competing for class championships. Viewing is available from spectator boats including historic tall ships and excursion catamarans.

Participants in the Key West Half Marathon run 13.1 miles past such historic sites as the Key West Lighthouse, Hemingway Home & Museum and Key West’s iconic waterfront.

At the Key West Food & Wine Festival, top chefs and restaurateurs showcase their most imaginative creations based on Key West’s indigenous cuisine.


Witness history at the Civil War Days Heritage Festival at Fort Zachary Taylor State Park, with roaring cannons and re-enactments by soldiers in uniform at the historic Civil War-era fort.

Old Island Days Art Festival, on lower Whitehead and Caroline streets in historic Old Town, is an acclaimed art show featuring oil paintings, watercolors, sculpture and photography by renowned American artists.Conch


During the Conch Shell Blowing Contest, an Old Island Days tradition, contestants compete to create novel sounds and make music on fluted conch shells.

The Cuban Cultural Exposition & Hot Havana Nights is an annual event to celebrate Key West’s Cuban heritage with authentic Cuban food, original artwork, a live auction and salsa music.


The annual Conch Republic Independence Celebration is a 10-day birthday party commemorating the 1982 mock secession of Key West from the Union, which gave birth to the Conch Republic. Highlights include a wacky bed race and sea battle featuring tall ships.

A prestigious sailfish challenge with a $100,000 top prize, the World Sailfish Championship draws top teams, all competing to benefit the Don Shula Foundation for Breast Cancer Research.


Celebrating its 17th year, the Key West Songwriter’s Festival is one the country’s premier music festivals. It features more than 100 performers and more than 25 free shows over five days and nights, held at intimate island locales and music hotspots.

The Harry S. Truman Legacy Symposium pays homage to Key West’s political history and presidential legacy with panel discussions, a reception and tours of the Little White House.


Key West Pride, a five-day celebration of Key West’s vibrant gay community, includes a film festival, dance parties, drag shows, a parade, street fair and bike tours.


Part of the annual Hemingway Days Festival, the Drambuie Key West Marlin Tournament is a four-day fishing tournament with $50,000 awarded in cash prizes.

Perhaps Key West’s most famous event is Sloppy Joe’s “Papa” Hemingway Look-Alike-Contest. Contestants from around the world, dressed to resemble Ernest Hemingway, converge at the legendary bar to vie for the title of Look-Alike contest winner.




Fantasy Fest – a 10-day celebration with lavish costume competitions, a Pet Masquerade and Parade, a Headdress Ball, promenades, street fairs and a grand parade – is Key West’s most outrageous event.


A weeklong event, the Key West World Championship is considered the Indianapolis 500 of powerboat racing, a high-speed offshore powerboat race held in Key West Harbor and in the surrounding waters.

For the Key West “Bight” Before Christmas, the Historic Seaport is transformed into a holiday wonderland with live holiday music, games for kids and photos with Santa. Through December.

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