Key West Festivals 2026: A Planning Guide to the Year’s Top Events

Key West Festivals 2026: A Planning Guide to the Year’s Top Events

Planning a trip to Key West in 2026? The island’s festival calendar runs year-round, from January’s Literary Seminar, Mile 0 Fest, and Food & Wine Festival to the Songwriters Festival in spring, Hemingway Days and Lobsterfest in summer, Fantasy Fest and the Offshore World Championship in fall, and holiday festivities closing out the year. This month-by-month guide covers the Key West festivals and events travelers plan their trips around. While we don’t dive into every detail of each celebration, this guide gives you a look at what’s happening when so you can time your visit around the events that matter most to you.
Photo credit: Coffee Butler Amphitheater.

2026 Key West Festivals: At a Glance

Jan 8–11: Key West Literary Seminar
Jan 17–18: Key West Half Marathon & Runfest
Jan 27–31: Mile 0 Fest
Jan 28 – Feb 1: Key West Food & Wine Festival
March 23: Taste of Key West
April 17–26: Conch Republic Independence Celebration
April 29 – May 3: Key West Songwriters Festival
June 3–7: Key West Pride
July 1–5: Key Lime Festival
July 22–26: Hemingway Days
Aug 5–9: Key West Lobsterfest
Aug 12–16: Key West Rum Fest
Sept 3–7: Just a Few Friends (Jimmy Buffett Tribute)
Oct 16–25: Fantasy Fest
Nov 1–8: Offshore World Championship Week
December: Holiday Season

Details are still in progress for some of the festivals and events above, so to stay updated, we recommend visiting each festival’s official website as you plan.

Winter: Literary, Live Music & Food

It’s not just about the weather — though it’s close to perfection. Winter in Key West brings a love of music, food, and the spirit of storytelling.

Key West Literary Seminar (Jan 8–11)

A premier literary gathering where readers from around the world enjoy presentations by some of the best writers of our time. Now in its 43rd year, the 2026 theme is “Pay Attention! The Novel in a Time of Short Attention,” with four days of readings and workshops at the historic San Carlos Institute. This year’s lineup includes Rachel Kushner, Richard Russo, Claire Messud, Colm Tóibín, and Gary Shteyngart.

More info: kwls.org

Key West Half Marathon & Runfest (Jan 17–18)

The 28th annual race weekend features a half marathon, 10K, 8K, and 5K on flat, scenic waterfront courses through Old Town, past the Southernmost Point, and along Smathers Beach. Also on tap: the Papa’s Pilar Rum Stroll, the Beach N’ Beer Mile, and pool parties to recover.

More info: keywesthalfmarathon.com

Mile 0 Fest (Jan 27–31)

The destination for fans of Red Dirt and Americana music. While the main stage is at the Coffee Butler Amphitheater, venues across Old Town keep the music going day and night. The 2026 lineup features Randy Rogers Band, Shane Smith & The Saints, Stephen Wilson Jr., Paul Cauthen, Kaitlin Butts, Silverada, American Aquarium, and James McMurtry, among others. Be sure to see who’s performing poolside at The Marker during Mile 0 Fest.

More info: mile0fest.com

Key West Food & Wine Festival (Jan 28 – Feb 1)

Now in its 17th year, the Key West Food & Wine Festival celebrates the wine and cuisine of the West Coast of North and Central America through a series of tastings and events held around the island.

More info: keywestfoodandwinefestival.com

Spring: Secession & Songwriters

Spring layers on waterfront tastings, tongue-in-cheek “secession” celebrations, and one of the largest songwriter festivals in the world.

Taste of Key West (March 23)

For one night only, 40+ local restaurants set up at Truman Waterfront Park for an open-air tasting with wines and craft beers. Admission is free, with food and beverage tickets available for purchase. The event runs 6–9 PM, timed perfectly for sunset views over the waterfront. Photo credit: Nick Doll.

More info: tasteofkeywest.org

Conch Republic Independence Celebration (April 17–26)

The 44th annual celebration of Key West’s playful “secession” from the U.S. in 1982. Ten days of parades, parties, pirates, bed races, and the Great Sea Battle in the harbor.

More info: conchrepublic.com

Key West Songwriters Festival (April 29 – May 3)

As the largest festival of its kind, the Key West Songwriters Festival celebrates its 30th anniversary this year and 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. While the lineup hasn't yet been announced, the festival has helped launch the careers of artists like Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser, and Maren Morris. Expect five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.

More info: keywestsongwritersfestival.com

Summer: Pride, Key Lime, Hemingway, Lobster & Rum

Summer celebrates community, the island’s signature dessert, its most legendary residents, and the bounty of the Gulf.

Key West Pride (June 3–7)

A week of pool parties, drag shows, comedy nights, street fairs, and sunset sail cruises celebrating the island’s “One Human Family” spirit. The festival wraps with the Pride Parade down Duval Street, featuring a 100-foot section of Key West’s famous Sea-to-Sea rainbow flag.

More info: Key West Pride Fest

Key Lime Festival (July 1–5)

Five days celebrating the island’s favorite citrus. Highlights include the Key Lime Pie Drop from the Key West Lighthouse, the World Famous Key Lime Pie Eating Championship on July 4th, the Key Lime Cocktail Sip & Stroll, mini pie baking classes, and rum tastings at the Key West First Legal Rum Distillery. So fun!

More info: keylimefestival.com

Hemingway Days (July 22–26)

Step into the world of Ernest Hemingway with five days celebrating his life and legacy. Now in its 45th year, the festival features a marlin fishing tournament, literary readings, the Lorian Hemingway Short Story Competition, and the iconic Hemingway Look-Alike Contest at Sloppy Joe’s Bar. Another highlight is the playful Running of the Bulls, where look-alikes parade with faux bulls down Duval Street. The festivities wrap with a Papa Birthday Bash and the Hemingway Rum Bar Stroll, a celebration that reflects Hemingway’s adventurous spirit and deep love for Key West.

Planning to visit the Hemingway Home while you’re in town? Here’s A Local’s Guide to Hemingway’s Home & Cats.

More info: Hemingway Days

Key West Lobsterfest (Aug 5–9)

The 28th annual celebration of the opening of Florida's spiny lobster season with an island-wide party including the kickoff Lobster Boil, the Duval Street Fair with live music, and lobster prepared every way imaginable. The Key West Lobsterfest supports the Key West High School Scholarship Fund.

More info: keywestlobsterfest.com

Key West Rum Fest (Aug 12–16)

A five-day celebration of rum featuring tastings, live music, sunset sails, sandbar trips, culinary pairings, pool parties, and more held around National Rum Day (August 16). Photo credit: @the_rum_traveler from our 2024 pool party.

More info: rumfestkeywest.com

Fall: Just a Few Friends, Fantasy Fest & Offshore Racing

Fall is peak festival season, when the harbor and the streets transform into world-class venues.

Just a Few Friends (Sept 3–7)

Labor Day weekend honors Jimmy Buffett in the place where it all began — five days of music, food, and island traditions. Photo credit: Nick Doll.

“The greatest gift Jimmy ever gave me was bringing me to Key West. And there’s never any place I want to be on Labor Day weekend, ever again for as long as I have breath, except for Key West.”
 — Lucy Buffett

The 2026 schedule is coming soon.
 
Want to explore more of Buffett’s Key West? Check out Jimmy Buffett’s Key West.

More info: justafewfriendskeywest.com

Fantasy Fest (Oct 16–25)

2026 Theme: Musical Icons and Iconic Musicals
Key West’s biggest party of the year is a 10-day celebration of costumes, creativity, and imagination. Expect colorful parades, themed events, pool parties, quirky competitions, and nonstop fun, all leading up to the Masquerade March and the iconic Fantasy Fest Parade. Photo credit: Nick Doll.

More info: fantasyfest.com

Key West Offshore World Championship Week (Nov 1–8)

The ocean transforms into a high-speed battleground as powerboat teams from around the world race for glory. Cutting-edge boats, fearless competitors, massive crowds, a boat parade, concerts, and Race Village make this one of the most adrenaline-fueled weeks of the year.

More info: raceworldoffshore.com

December: The Holiday Season

It’s the most festive time of year in Key West. Palm trees sparkle with lights, the Lighted Boat Parade glides through the Seaport, bikes and boats dress for the season, Santa sightings pop up around town, and the island closes the year with its famous New Year’s Eve drops. By land and sea, Key West becomes 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 part of the island's celebrations. As a proud sponsor of many of the festivals above, we host singer-songwriters, live music, cocktail competitions, and special events poolside throughout the year. The fun doesn't stop when the festival ends. If you're planning to join us for the festivities, check out our Tips for an Unforgettable Festival Experience. There's always something happening in Key West — this guide is just the beginning. Book your stay and be part of the celebration.

Our Key West Harbor Resort is steps from the action, but quiet enough to recharge when you need it. There's a reason we were named the #2 Resort in the Florida Keys. #lovethemarker