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Annual Key West Events (2025)

Annual Key West Events (2025)

Key West is full of sunshine, stunning beaches, dreamy vacation homes, and a never-ending list of things to do, but it’s also an internationally renowned destination for events.

From costumed parades to seafood feasts by the sea, Key West knows how to throw a party. Our vibrant island blends quirky charm with rich history, offering events that range from world-famous spectacles like Fantasy Fest to laid-back locals’ favorites like the Conch Republic Days.

Whether you’re drawn to the music, the food, or the colorful characters who call Key West home, there’s something happening every month to keep the good times rolling.

Here’s your guide to the biggest and best annual events in Key West for 2025.

January

Key West Literary Seminar

  • January 9th – 12th, 2025
  • kwls.org/seminar
  • San Carlos Institute, 516 Duval Street

A 4-day celebration of the written word, the Key West Literary Seminar on colorful Duval Street features writers, poets, and other literary artists from around the world. Sit in on seminars, workshops, round table discussions, and more, led by some of your favorite authors.

You can also explore local talent, of past and present, with a literary walking tour through downtown Key West.

Key West Half Marathon and Runfest

Dubbed a bucket list destination race by Runner’s World, the Key West Half Marathon and Runfest is a must-do for runners. This 4-day event features several races along the breathtaking waterfront of Key West, including a half-marathon, 5k, 8k, 10k, sunset run, or the popular “Beach n’ Beer Mile.”

Pro-tip: Races and accommodations fill up fast, so be sure to reserve your spot early. Book a private vacation rental to relax in comfort after the race!

Mile 0 Fest

  • January 21st – 25th, 2025
  • mile0fest.com
  • Truman Waterfront Amphitheater, 21 Quay Road

Rock out to your favorite tunes with some epic waterfront views at the Mile 0 Fest. This 5-day music event features dozens of Americana and “red dirt” style country, from headliners to new artists. 

Enjoy live music at the main stage every day from about 5:00 pm to midnight. And be sure to stop by the vendor village, where you can find all sorts of brews, bites, and band merch.

Key West Food and Wine Festival

A culmination of international and local cuisine, the Key West Food and Wine Festival brings all the flavors to the island every January. This 5-day festival takes place throughout Key West, with events popping up at restaurants, beaches, and even historic sites.

You’ll find everything from rum tastings and tapas at the iconic Papa’s Pilar Distillery to multi-course wine dinners, cooking demonstrations, beach brunches, and more.

February

Florida Keys Seafood Festival

Calling all seafood lovers, the Florida Keys Seafood Festival is THE place to be in February in Key West! Get your fill of fish, shrimp, crab, oysters, lobster rolls, conch fritters, and seasonal delights like stone crab claws, plus plenty of tasty sides, Key lime pie, craft cocktails, kid-friendly favorites, and more. Come for the seafood, stay for the fun!

Key West Art and Craft Festival

Showcasing local and visiting artists, the Key West Art and Craft Festival is the perfect place to browse for one-of-a-kind artwork, jewelry, pottery, home decor, leather goods, souvenirs, and more. Stroll through dozens of booths along the water, chat up the artists, and find that special piece to bring home.

March

Key West Air Show

An action-packed event that’s fun for the whole family, the Key West Air Show is a must-see if you’re visiting in March. Watch as the famous Blue Angels, USSOCOM, and others take to the skies to perform all their signature tricks. But the fun doesn’t stop there; on the ground, you’ll find car shows, live entertainment, food, kid zones, and more.

Taste of Key West

A foodie favorite for 30 years and running, Taste of Key West serves up island eats from over 40 local restaurants, plus local wine, beer, and spirits.

Key West is known for its vibrant and varied cuisine that incorporates local seafood, a unique fusion of Floridian and Caribbean flavors, known as Floribbean cuisine, and, of course, Key lime-infused dishes and desserts. And you can sample all of them all at the Taste of Key West — so be sure to bring your appetite.

April

Conch Republic Independence Celebration

A 10-day celebration of the birth of the “Conch Republic,” the Conch Republic Independence Celebration showcases all the fun, history, and quirkiness Key West is known for. Learn about local history, party with some pirates, and enjoy music, dancing, battle reenactments, parades, food, drink, and so much more. It’s a swashbuckling good time!

May

Key West Songwriters Festival

One of the largest events of its kind in the world, the Key West Songwriters Festival features over 100 singers and songwriters. Enjoy 5 days of live performances, special events at local bars, food vendors, unique merch, and much more.

June

Key West Pride

One of the most famous Pride events in the US, Key West Pride is a week-long celebration honoring the LGBTQ community featuring parades, street fairs, live music, pool parties, costume contests, drag shows, and more. From the big Pride Parade down Duval Street to smaller celebrations in local pubs, everyone in Key West gets in on the fun for Pride Week.

July

All over the country 4th of July weekend is a big deal but in Key West, July also brings 2 of the most unique events.

Key Lime Festival

Celebrating the island’s most famous fruit, the Key Lime Festival is your one-stop shop for all things Key lime flavored, and we’re not just talking pie — although there’s plenty of that to go around too!

Sample and shop for Key lime sweets, savory Key lime-marinated seafood dishes, Key lime beer, wine, spirits, sauces, and so much more. And of course, there’s the famous Key Lime Pie Hop, where you’ll stroll the city sampling some of the best Key lime pies in Key West, and if you have the appetite, the pie-eating contest.

Annual Hemingway Days Celebration

Honoring one of the greatest literary figures of all time, and former Key West resident, novelist Ernest Hemingway, the Hemingway Days event celebrates Hemingway’s life and legacy with 4 days of learning, laughter, and, of course, lots of rum.

You can also tour the historic Hemingway Home, shop the street fair for unique Hemingway-themed art, souvenirs, and books, taste his namesake Papa’s Pilar rum, and watch as hordes of Hemingways take to the streets during the running of the bulls and Hemingway look-alike contest.

August

Rumfest

If you’re a rum lover, there’s no better place to be in August than in Key West! Enjoy daily rum tastings, rum history, sandbar trips, Caribbean music and food, cigars, games, and even day trips to Cuba to explore the local rum scene (pre-booking and passport required).

September

Just a Few Friends Festival 2025

  • Dates: August 29 – September 1, 2025
  • Website: justafewfriendskeywest.com
  • Location: Various venues throughout Key West, Florida, including Duval Street, Truman Waterfront Park, and select local bars and restaurants

This one technically straddles the tail end of August going into September! This newer festival will be on just its second iteration in 2025.

Expect a heartfelt, music-filled Labor Day weekend celebration honoring Jimmy Buffett’s legacy. Expect a run/walk, a Margarita bar crawl, guided island tours, rum tastings, live performances across town, and a lively Second Line Parade that culminates in a free concert at Truman Waterfront Park.

October

Fantasy Fest

The mother of all Key West events, Fantasy Fest is famous worldwide for its elaborate parades, parties, costumes, body painting, cocktails, and overall “Mardi Gras meets Halloween” vibes.

Enjoy 10 days of parties, live music, costume contests with cash prizes, drag shows, and so much more.

While Fantasy Fest may be best known for some of its wilder, adults-only parties, nowadays, there are some family-friendly events, like the Bahama Village Goombay Festival featuring food, art, and music, so there’s something for everyone.

November

Apart from spending your Thanksgiving in Key West, it’s also the time of the year people from all over the world flock here for our film festival and in 2025, visit for Race World Offshore.

Key West Film Festival

  • November 12th – 16th, 2025
  • keywestff.com 
  • Multiple locations throughout Key West

A must-attend for film buffs, the Key West Film Festival is 5 days of special screenings, documentaries, short stories, and panel discussions surrounding the cinematic arts. From internationally acclaimed masterpieces to independent films, there’s so much to see at the Key West Film Festival.

December

Holiday and New Year Celebrations

Key West in December is full of festive events for the holidays. From tree lightings and Santa sightings to boat parades and parties, there are lots of holiday happenings. And of course, nothing beats ringing in the New Year in Key West, where you can attend the famous Conch Shell Drop at Sloppy Joe’s and party the night away on Duval Street.

Book Your Key West Event Stay Now

While we’ve only covered some of the biggest events, rest assured that whenever you visit, there will be plenty going on. And in between the big events? There are plenty of smaller, more localized events, such as Key West museum tours, pub crawls, ghost tours, and more.

From seasonal events like the Key West Artisan Market and 4th of July celebrations, to fishing tournament events like the Key West Marlin Tournament, there’s an event for everyone.

Book your stay with VHKW to enjoy all the comforts of home, with easy access to all the best events!

August 25, 2025
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