11/26/2026 to 12/31/2026

Key West Hanukkah and Christmas Holidays 2026

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

Thursday, December 31, 2026

New Year’s Eve Welcoming 2026 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 2027 in island style! 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

January 27th - 31st 2027

Key West Food and Wine Festival 2027

Discover the ultimate food and wine experience at the Key West Food & Wine Festival, January 27th through January 31st. The festival includes over 20 unique events taking place across the southernmost island city, including waterfront wine tastings, winemaker/chef collaborations, local events that present an authentic taste of Key West, and an amazing grand tasting event. Read More

February 2027

KEY WEST ART AND CRAFT FESTIVAL FEBRUARY 2027

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

March 17th, 2027

St. Patrick’s Day in Key West 2027

On this colorful isle, where basically everyday can be a boozy holiday with pagan origins, islanders and visitors celebrate the holiday with a myriad of feasts and festivities. Of course, some opt for staying by their pools or boating to nearby sandbars for secluded fun in the sun! Read More