10-20 to 10-29, 2023

Fantasy Fest 2023, Uniforms & Unicorns

Key West Fantasy Fest is an exciting annual event that takes place in October. Every fall, the streets of Key West come to life for 10 days of unbelievable costumes, parades, and parties. Since its inception in 1979, The Key West Fantasy Fest has become one of the biggest events in Key West. People from all over the world come to Key West to explore their imaginations and celebrate creativity. Live your Fantasy in Key West! Read More

November 5-12th, 2023

Race World Offshore Key West Championships – 2023

The Race World Offshore Key West Championships will be November 5th-12th, 2023. This is an exciting annual event that brings the world’s top offshore boat racers to Key West. Every fall, the beautiful water off of the coast of Key West is a proving ground where professional boat racers push the limits. With three days of racing and seven full days of events, the Key West Offshore Racing World Championships is a fun time to be on our special island. Read More

November 14 - 19, 2023

Key West Film Festival

The Key West Film Festival—where passion meets paradise—is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community. The festival offers multiple screenings and events with a variety of themes and categories, including LGBTQ, Florida Focus, International, Documentaries and Shorts. The Festival includes Opening & Closing, Spotlight and Special Free Events. KWFF showcases the best of Florida filmmaking, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the business. The festival also supports the next generation of local student filmmakers with scholarships and other key awards. The Key West Film Festival has become a vital stop on the awards season’s fall festival circuit. Publications represented in KWFF Critics’ Focus program and Critics’ Prize at the festival include: Los Angeles Times, Vulture.com, Rolling Stone, Indiewire, Vanity Fair, Washington Post, TimeOut NY, Roger Ebert, and others. Read More

Wednesday, November 22 to Sunday, November 26, 2023

Key West Thanksgiving 2023

Thanksgiving is a fantastic Key West holiday. The island remains un-crowded, there’s great energy, and the weather is beautifully moderate. If you want to enjoy a special Thanksgiving, book a trip to Key West. On this page, we highlight Key West Thanksgiving dinner options and the best Key West bars to watch the big game. On Key West, we have a lot to be thankful for, and we’re happy to share this gratitude with our guests. Thanksgiving in Key West will be extra special this year. Read More

12/01/2023 to 07/31/2024

THE KEY WEST FISHING TOURNAMENT 2023-2024

Founded in 1965, the Key West Fishing Tournament is an annual fishing competition that runs from January to August. Throughout 2024, anglers will compete from boats, land, piers, and bridges around Key West. Special attention is paid to the size and species of fish. Fish are tracked by entering weighed and released fish for no charge. Top awards include Outstanding Angling Achievement, Master Angler, and Sportsmanship Award. To support the health of Key West's fisheries, the Key West Fishing Tournament encourages the release of game fish. Read More

11/22/2023 to 12/30/2023

Key West Hanukkah and Christmas Holidays 2023

Key West is a special place to enjoy the holiday season. During the holidays, Key West lights up with fun festivities and offers a unique atmosphere to celebrate this exciting time of year. If you’re looking to escape the cold and enjoy the Hanukkah and Christmas holidays full of sun and artistic events; Key West is the perfect place for you and yours to gather and create very special holiday memories! Read More

Sunday, December 31, 2023 – Countdown to Midnight Celebrations

New Year’s Eve Welcoming 2024 Celebrations!

Key West is a magical place to ring in the New Year! With usually balmy temperatures at midnight, island style countdowns dropping everything and everyone from famous drag queens to slices of key lime pie happen all over the island. Enjoy festive parties, acclaimed street food or fine island dining, and ring in 2024 in island style! Read More

Wednesday, January 24 to Sunday, January 28, 2024

Key West Food and Wine Festival 2024

Experience the 2024 Key West Food & Wine Festival! Held from Wednesday, January 24 through Sunday, January 28, 2024. The Key West Food and Wine Festival is a sequence of wine and food themed events, showcasing a varied range of wines and creative cuisine. Come experience over 20 distinctive events, including waterfront tastings, winemaker and chef collaborations and local events that showcase the authentic taste of the southernmost city. Read More

January 11 - 14, 2024

Key West Literary Seminar

The Key West Literary Seminar is a four-day event that brings readers from all over the world to join with today's best writers for conversations, readings, lectures, parties and more! Read More

February 24-25, 2024

59th Old Island Days Art Festival

This Art Festival is a time-honored tradition dating back to the early 60’s when Old Island Days was a 10-week celebration of special events. The art show has grown to nearly 100 artists from near and far spreading up Whitehead Street and down onto Caroline Street into the beautiful Truman Annex residential gated community. Fine Craftsmen and Artists will be selected to show and sell their original work in beautiful Old Town Key West. Read More