September, 2025

Key West BrewFest 2025

This multi-day festival hosted by Southernmost Beach Resort includes beer pairing dinners and pool parties along with other island-wide activities. The festival culminates with the signature tasting event. Each day offers things to do with events taking place at many restaurants, hotels, beaches and bars all over Key West. Read More

10-17 to 10-26, 2025

Fantasy Fest 2025

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 2-9th, 2025

Race World Offshore Key West Championships – 2025

The Race World Offshore Key West Championships will be November 2nd-9th, 2025. 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

Wednesday, November 26 to Sunday, November 30, 2025

Key West Thanksgiving 2025

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

11/26/2025 to 12/30/2025

Key West Hanukkah and Christmas Holidays 2025

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

Tuesday, December 31, 2025 – Countdown to Midnight Celebrations

New Year’s Eve Welcoming 2025 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 2025 in island style! Read More

September 2025

September 3rd-7th 2025, Key West Womenfest!

Womenfest has attracted a diverse group of woman since its inception decades ago. The festival offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party, laugh and dance the night away. Read More

January 9- 12, 2025

Key West Literary Seminar 2026

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

January 27-31, 2026

Mile 0 Fest Key West ~ 2026

Calling all music lovers! Immerse yourself in the laid back island vibes of Mile 0 Fest Key West, a premier boutique music festival. Each year boasts a stellar lineup of established and rising artists performing in beautiful outdoor venues. Experience all Key West has to offer while listening to your favorite bands and making new life-long friends. With only a few thousand passes available, don't wait to book your dream music vacation! Read More

February 21-22, 2026

60TH KEYWEST ART AND CRAFT FESTIVAL FEBRUARY 21 & 22, 2026.

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