April 17th-26th, 2026

Conch Republic Independence Celebration 2026

Come to Key West and celebrate the founding of the Conch Republic! The Conch Republic was born on April 23, 1982, in response to a United States Border Patrol Blockade of the Florida Keys. Since the United States insisted on treating the Keys like a foreign country, Mayor Dennis Wardlow seceded from the Union. Today we stand proudly as a community of who have “Sovereign State Of Mind” and as the “People who seceded where others have failed” This celebration includes amazing markets, battle reenactments and the annual "World's Looooongest Parade"! Come see what the Conch Republic is all about this April. Read More

April 29th-May 3rd, 2026

The Key West Songwriters Festival 2026!

One of the largest songwriting events in the world. Every May, for almost 30 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 3rd-7th, 2026

Key West Pride Week 2026

Key West Pride brings downtown Key West to life for five 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

July 2 - 5, 2026

Key West 4th of July 2026

Key West 4th of July offers exciting events for the entire family. Celebrate Independence Day in Key West with a tour of historic Old Town all dolled up in American decorations, indulging in key lime pie, and, of course, watching a spectacular fireworks display. Whether you're interested in viewing from land or water, Key West is one of the best places to celebrate the 4th of July. Read More

July 21st-26th, 2026

Sloppy Joe’s 45th Annual Hemingway® Look-Alike Contest July 21st-26th, 2026

Hemingway Days in Key West celebrates the literary success and lifestyle of Ernest Hemingway, one of America’s most famous writers. Every year, to honor Hemingway’s birthday, Key West comes to life with lively literary events. During Hemingway Days, locals, visitors, and fans celebrate Hemingway with a look-a-like contest, poetry readings, and a three-day marlin tournament. Read More

September 5th, 2026

Key West BrewFest 2026

Key West BrewFest is an island wide festival hosted by the Key West Sunrise Rotary of the Conch Republic and the Southernmost Beach Resort. This is a 100% nonprofit, charitable event, to raise money for local student’s scholarships. The main tasting event takes place on Saturday, September 5th from 3-8pm. Expect over 60 beer vendors, more than 225 types of beers, live entertainment, and a guaranteed great time! Plus the Southernmost Beach Café will be open with beer hall food specials and cocktails for those who want to change it up! Read More

September 2nd-6th, 2026

Key West Womenfest 2026

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

October 16th to October 25th, 2026

Fantasy Fest 2026

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! The theme for Fantasy Fest 2026 will be "Musical Icons and Iconic Musicals" Read More

November 1st-8th, 2026

Race World Offshore Key West Championships 2026

The Race World Offshore Key West Championships will be November 1st-8th, 2026. 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 26th 2026

Key West Thanksgiving 2026

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 sports bars! 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