January 21, 2025

An Insider's Look at the Best Festivals and Events

Key West buzzes with energy and celebration all year long. From legendary festivals to quirky local traditions, there’s always something happening. Whether you’re planning your first visit or returning for another unforgettable adventure, 2025 is brimming with can’t-miss events that showcase the very best of Key West. This Key West events calendar breaks down everything from air shows and parades to music festivals and island-wide celebrations, helping you make the most of your visit. (Photo credit: Coffee Butler Amphitheater)

January

Key West Literary Seminar
January 9–12

Literature lovers converge in Key West each January for the prestigious Key West Literary Seminar. Bringing together world-renowned authors, poets, and readers, this four-day event offers panel discussions, readings, and workshops that celebrate storytelling in all its forms. A perfect addition for visitors who want to engage with the island’s artistic and literary community. Learn more about the Key West Literary Seminar.

Key West Half Marathon & Runfest
January 16–19

Start the year off strong with one of the most scenic half marathons in the U.S. Runners wind through Old Town, along the waterfront, and past Key West landmarks. Whether you're participating or cheering from the sidelines, the atmosphere is electric.
Learn more about the Key West Half Marathon & Runfest.

Mile 0 Fest
January 21–25

One of the premier Red Dirt and Americana music festivals, Mile 0 Fest brings together over 60 solo performers and bands! This dynamic festival blends rock, country, and American roots music with top-tier artists like The Red Clay Strays, Randy Rogers Band, Shane Smith & The Saints, Steve Earle, Reckless Kelly, Kaitlin Butts, and many more. Performances happen at iconic landmarks and the Truman Waterfront Amphitheater, where the main shows take place each evening. Passes and packages are available.
Learn more about Mile 0 Fest.

February

Presidential Families Weekend
February 15–17

Celebrate Presidents' Day Weekend at the historic Harry S. Truman Little White House. On Saturday, February 15, enjoy a lively panel featuring descendants of past U.S. presidents. The weekend continues with multiple performances of the acclaimed one-man play "Give 'Em Hell, Harry!" on Sunday and Monday. Cap off the celebrations with a traditional Presidents' Day cookout on Monday, February 17, from 11:30 a.m. to 1:30 p.m., serving picnic-style favorites. For more details and ticket information, visit Harry S. Truman Little White House Events.

concert

February Concert Lineup: Gipsy Kings, Debbie Gibson, Willie Nelson & The Beach Boys

February in Key West brings a star-studded lineup of performances featuring legendary artists across multiple venues. From intimate theater shows to outdoor concerts at the Coffee Butler Amphitheater at Truman Waterfront.

The Gipsy Kings – February 8 at the Coffee Butler Amphitheater (Get tickets here)
Debbie Gibson – February 16 at the Key West Theater (Learn more and purchase tickets)
Willie Nelson & Family – February 17 at the Coffee Butler Amphitheater
The Beach Boys – February 28 at the Coffee Butler Amphitheater

This February concert lineup is just a preview of the incredible performances Key West has in store. Stay tuned for more artists taking center stage throughout the year. For the latest updates and tickets, visit the Coffee Butler Amphitheater. Tickets sell out quickly, so be sure to book early!

March

Blue Angels Return to Key West: Southernmost Air Spectacular
March 29–30

The Blue Angels return to Key West for a breathtaking air show at NAS Key West’s Boca Chica Field. This two-day event features military and civilian acts soaring across the sky, drawing aviation lovers from around the world.
Learn more about the Southernmost Air Spectacular.

April/May

Conch Republic Independence Celebration
April 18–27

Immerse yourself in the rich history and lively spirit of Key West during Conch Republic Days. This 10-day festival commemorates Key West’s symbolic secession from the United States in 1982. The celebration features parades, reenactments, and lively parties across the island—including the famous Bed Races on Duval. Don’t miss the whimsical Naval Battle in Key West Harbor, where schooners and water cannons stage a hilarious and entertaining "fight" for independence.
Learn more about Conch Republic Days.

markersongwriter

29th Annual Key West Songwriter’s Festival
April 30 – May 4

As the largest festival of its kind, the Key West Songwriters Festival draws top talent from across the country. Spanning five days, the festival features 150+ artists performing at different venues throughout the island - including poolside at our resort. This is your chance to experience intimate acoustic performances and get an inside look at the stories behind the songs. The festival has helped launch the careers of stars like Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser, and Maren Morris. Although the lineup for this year hasn't been announced, stay tuned for exciting updates as the event approaches. (Photo credit: Key West Songwriter’s Festival)
Learn more about the Key West Songwriters Festival.

July

Key Lime Festival
July 3–7

Celebrate Key West’s favorite citrus event with five days dedicated to all things key lime. Enjoy the Key Lime pie-eating contest on the beach, scavenger hunt, cocktail tastings, brunches, and dinners, along with culinary demonstrations featuring lime-infused dishes. From tangy key lime cocktails to decadent pies, every event is a flavorful experience. Don’t miss the quirky Key Lime Pie Drop, a festival highlight inspired by Key West’s playful spirit. In this unique event, participants attempt to drop pies from the top of the iconic Key West Lighthouse without them breaking, adding a fun and competitive twist to the festivities. This festival serves up a perfect slice of Key West’s fun and flavor! Learn more about the Key Lime Festival.

Hemingway Days
July 22–27

Step into the world of Ernest Hemingway with a week of events celebrating his life and legacy. There’s the marlin fishing tournament, literary readings, and the iconic Hemingway Look-Alike Contest at Sloppy Joe's Bar. Another highlight of the festival is the playful Running of the Bulls, where Hemingway look-alikes parade with faux bulls down Duval Street. The festivities end with a Papa Birthday Bash and a Hemingway Rum Bar Stroll. This six-day celebration reflects Hemingway’s adventurous spirit and his love for Key West. Learn more about Key West’s Most Whimsical Tribute to Papa.
just a few friends

August/September

Just a Few Friends Key West
August 29 - Sept. 1

Celebrate the life and legacy of Jimmy Buffett at the 2nd Annual Just a Few Friends memorial during Labor Day Weekend. On August 28th, the City of Key West will officially declare 'State of Florida Jimmy Buffett Day,' setting the stage for a weekend of island-style fun, live music, and community gatherings.

Highlights include a run/walk, Margarita Bar Crawl, guided tours, rum tastings, and performances across Key West’s iconic venues. On Sunday, the Second Line Parade kicks off at 5 pm, leading to a free music festival at Truman Waterfront Park featuring local and national artists, food trucks, and vendors. The festivities continue into Monday with more entertainment and community events to cap off the holiday weekend.

brew

Marking the second anniversary of Buffett’s passing, this year’s memorial will feature heartfelt tributes and special performances celebrating his impact.
(Photo credit: Just a Few Friends Key West)
Learn more about Just a Few Friends Key West.

Key West BrewFest
(Dates TBD)

Beer lovers unite! Key West BrewFest returns for a weekend of craft beer tastings, pairing dinners, and poolside parties. Sample over 150 craft beers at the signature beachside tasting event and join in on tap takeovers throughout the island. Dates for this year's event are yet to be announced, so stay tuned for updates. (Photo credit: Key West Brewfest)
Learn more about Key West BrewFest.

October

Fantasy Fest
October 17–26

2025 Theme: Bedtime Stories and Magical Monsters

fantasyfestforblog

Every October, visitors from around the world descend on Key West, transforming the island into a playground of creativity, imagination, and fun during Fantasy Fest – 10 days of colorful costumes, lively parades, pool parties, themed events, and non-stop excitement. From quirky competitions to the iconic masquerade march and Fantasy Fest parade, we can’t wait to see you all decked out for the festivities. (Photo credit: Fantasy Fest)
Learn more about Fantasy Fest.

November

Race World Offshore Key West Championships
November 2–9

Step into the exhilarating world of Race World Offshore, where the ocean transforms into a high-speed battleground for cutting-edge boats and fearless competitors. Experience the thrill as powerboat teams from around the world race for glory, drawing massive crowds to the shores of Key West. Every moment is a celebration of nautical prowess and the relentless pursuit of victory.
Learn more about the Race World Offshore Championships.

December

Celebrate the holiday season in true Key West style! Experience the dazzling lighted boat parade at the Seaport, decorated bike parades, local hometown parade, and so much more. By land and sea, the island sparkles with holiday spirit as Key West transforms into a tropical winter wonderland.

Stay Where the Celebration Never Ends

The Marker Key West Harbor Resort is more than just a place to stay—we’re a part of the island’s celebrations! From live music and poolside parties to on-site events, the fun doesn’t stop when the festival ends. If you’re planning to join us for the festivities, be sure to check out our Festival Tips for an unforgettable experience.

There’s always something happening in Key West. This guide is just the beginning—start planning now and make sure you don’t miss out. The island’s best events are around the corner, so book your stay today and be part of the celebration. #lovethemarker

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