01/01/2025 to 01/25/2025

“2025 A Fresh Start: Unmissable Events This January”

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. Key West is the perfect place for you and yours to gather and create very special holiday memories! Read More

January 9- 12, 2025

Key West Literary Seminar 2025

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 21-25, 2025

Mile 0 Fest Key West, 2025

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

Tuesday, January 21 to Sunday, January 26, 2025

Oaxaca Food and Wine Festival ~Colorful, Diverse & Delicious~Key West ,2025

Discover the ultimate food and wine experience at the Key West Food & Wine Festival, Jan. 21st through Jan. 26. 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 22-23, 2025

60TH KEYWEST ART AND CRAFT FESTIVAL FEBRUARY 22, 23 2025.

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 to April, 2025

“A Spring Escape to Key West’s Tropical Charm”~2025

Spring is a special time of year to visit Key West. The island is great for people who are looking for a different spring break experience, because there's a nice mix of visitors. From anglers to artists, to families and retirees, there's something for everyone on Key West. We have highlighted below just a few of the top reasons to visit Key West during Spring Break 2025. Read More

March 17, 2025

St. Patrick’s Day in Key West 2025

Chicago dyes its river green, NYC, Boston, and practically every American city hosts perpetual parades featuring bagpipers, step dancers and politicians galore. Non-practiced imbibers guzzle pitchers of green beer, and chase shots of Irish Whisky with pints of Guinness, or mugs of said cheap, green beer. The luck of the Irish awaits you at the end of the rainbow in Key West! Read More

April 30-May 4,2025

The Key West Songwriters Festival 2025!

One of the largest songwriting events in the world. Every May, for over 20 years, music fans, performers, and Key West locals have gathered together to enjoy music at many of Key West’s most popular beaches, boats, bars, resorts, and historic theaters. Read More

June 22-29, 2025

Key West Pride Week 2025

Key West Pride 2025 brings downtown Key West to life for eight days in June. In just one week, you will experience fun talent shows, pool parties, plays, a street fair, and a big parade. During this great event, the Key West community comes together to celebrate Pride. Across the entire island, you can feel the collective energy. Read More

June, 2025

9th Annual Mango Fest Key West, 2025

Mango Fest Key West, June,2025 featuring all things Mango. See what the king of fruit offers at Mango Fest. Visitors enter a world of Mangoes. Experience all things Mango through shopping, education and demonstrations. Read More