Key West has never needed much of an excuse to throw a party. Give the island a plate of Key lime pie, a famous author, a freshly caught lobster or its own wonderfully strange history, and someone will turn it into a festival.
That makes choosing when to visit almost as much fun as deciding what to do after you arrive. The 2027 calendar brings waterfront concerts, literary gatherings, road races, food festivals, costumed celebrations, powerboat racing and plenty of only-in-Key-West traditions.
Use this month-by-month guide to find the Key West event that fits your kind of getaway. Some celebrations are worth building an entire vacation around, while others are a happy surprise waiting to join an already-great island trip.
Planning note: Event information can change. Dates below were checked on September 3, 2026. Events labeled “dates to be announced” are expected to return, but travelers should confirm schedules, venues and ticket requirements with the organizers before booking.
Dates: January 7–10, 2027
Key West’s long relationship with writers takes center stage during the Key West Literary Seminar. The 2027 theme is “Poetry,” with readings, lectures, conversations, book signings and special programs featuring an impressive collection of poets and literary voices.
The main seminar takes place at the historic San Carlos Institute on Duval Street. Registration is required for much of the four-day program, although selected closing events and related activities may be open to the public.
Dates: January 15–17, 2027
Trade the treadmill for palm trees at the Key West Half Marathon & Runfest. The 2027 weekend includes a 5K and 10K on Saturday, followed by the half marathon and 8K on Sunday. Scenic waterfront stretches, historic neighborhoods and post-race celebrations make this feel more like an island party with finish lines.
Not chasing a personal record? The weekend’s concerts, rum stroll, beer mile and spectator-friendly course offer plenty of ways to join the fun without logging 13.1 miles.
Dates: January 26–30, 2027
Five days of Red Dirt, Americana and country music take over waterfront stages, theaters, resorts and intimate Old Town venues during Mile 0 Fest. The 2027 gathering marks the festival’s 10th anniversary, with the Coffee Butler Amphitheater serving as its main evening venue.
This is not a festival where you sit in one field all day. Music appears across the island, making Key West itself part of the experience. Popular passes, lodging packages and nearby rooms can disappear early, so this is one trip to plan well ahead.
Dates: January 27–31, 2027
Come hungry—and curious. The Key West Food & Wine Festival serves up tastings, pairing dinners, wine strolls and chef-driven experiences at venues around the island. Events are generally sold individually, and the most popular tastings can sell out in advance.
The festival overlaps with Mile 0 Fest in 2027, creating one remarkably busy week. Visitors hoping to enjoy both should secure accommodations and transportation early.
Dates: February 13–14, 2027
Local fishermen bring the flavor at the Florida Keys Seafood Festival at Truman Waterfront Park. Expect Florida spiny lobster, stone crab, fish, conch and other Keys favorites, plus live music, local vendors and family-friendly activities.
This is a relaxed, come-as-you-are celebration with a purpose: proceeds support the Florida Keys Commercial Fishermen’s Association and its work on behalf of the local fishing community.
Dates: February 20 & 21, 2027
Artists from around the country fill the streets of Old Town with paintings, photography, sculpture, jewelry, glass and other original work during the annual Old Island Days Art Festival. It is an easy event to explore at your own pace—and an excellent place to find something more memorable than a standard souvenir.
Dates: March 13-27, 2027
March celebrates playwright Tennessee Williams, who made Key West his home for more than three decades. The Tennessee Williams Key West Festival typically blends theatrical performances, films, writing and painting contests, talks and birthday festivities.
The mood is more creative salon than crowded street festival, making it a smart choice for travelers who enjoy theater, literature and Key West history.
Dates: April 16, 2027
Can you turn a conch shell into a musical instrument? The annual contest at the Oldest House invites competitors of different ages and abilities to give it their best blast. Some produce a heroic island call. Others produce something closer to a startled goose. Both belong in Key West.
Dates: April 16-25, 2027
In 1982, Key West responded to a federal roadblock by declaring itself the independent Conch Republic, waging a very brief battle, surrendering and requesting foreign aid. Naturally, the island still celebrates.
The Conch Republic Independence Celebration typically includes parades, parties, historic reenactments, waterfront events and the famously splashy Great Sea Battle. It is quirky, proudly local and nearly impossible to confuse with a festival anywhere else.
Dates: April 28–May 2, 2027
Some of Nashville’s biggest songs come with stories most listeners have never heard. At the Key West Songwriters Festival, the people who wrote those songs perform them in theaters, bars, resorts and waterfront settings across the island.
The intimate performances are the magic here. A songwriter, a guitar and the story behind a familiar lyric can turn a small Key West room into the best seat in the house.
The Songwriters Festival is expected to carry into the first weekend of May. The schedule usually mixes free performances with ticketed shows, so watch for the official lineup and venue announcements before building your plans.
Date: May 8, 2027
Paddlers circle the island by paddleboard, kayak, surf ski and other human-powered craft during this challenging ocean race. Even if you stay safely on shore, watching the colorful fleet move through Key West’s surrounding waters is an impressive sight.
Date: June 2-6, 2027
Key West’s famous “One Human Family” spirit shines during Key West Pride. Pool parties, performances, sunset sails, street events and the Pride parade create several days of color, celebration and community.
Visitors are welcome throughout the festivities, and many events take place in or near Old Town. Some are free, while cruises, parties and special performances may require advance tickets.
Dates: July 1–5, 2027
Key lime pie is only the beginning. The Key Lime Festival turns the island’s signature flavor into five days of tastings, competitions, cocktails and cheerful citrus-colored mischief.
Annual favorites may include the Key Lime Pie Drop, pie-eating contests, culinary events and the spectacularly oversized pie served around the Fourth of July. Individual events have separate schedules and ticket rules, so check the official program before arriving with fork in hand.
Expected: July 21-25, 2027
Ernest Hemingway’s Key West years inspire a festival filled with literary events, fishing, running and a remarkable number of white-bearded men. Hemingway Days traditionally features the famous “Papa” Look-Alike Contest at Sloppy Joe’s, readings, museum events and the Running of the Bulls—a delightfully Key West parade of look-alikes and wooden bulls.
The Hemingway 5K Sunset Run and Paddleboard Race is scheduled for July 24–25, 2027, placing at least part of the celebration firmly on the calendar.
Dates: August 11–15, 2027
Florida spiny lobster season gets a delicious welcome during the Key West Lobsterfest. The five-day celebration is expected to bring back lobster dinners, pool parties, a pub crawl and the free Duval Street fair with food, vendors and live music.
Ticketed meals and special events can fill quickly, but the street fair makes it easy to join the party without planning every bite in advance.
2027 dates: August 11-15, 2027
This adults-only LGBTQ+ celebration traditionally brings several days of pool parties, nightlife and social events to gay-friendly venues around the island. Travelers should review individual event details and admission requirements when the official schedule is released.
2027 dates: September 1-5, 2027
Womenfest brings together women from around the world for comedy, live music, watersports, pool parties and special performances over Labor Day week. The event lineup changes from year to year, giving returning visitors something new to discover alongside longtime favorites.
Dates: October 22-23, 2027
Bahamian food, island rhythms, art and dancing fill the streets of Bahama Village during the Goombay Festival. This free street celebration honors the cultural connection between Key West and the Bahamas and traditionally helps launch the Fantasy Fest season.
Dates: October 22–31, 2027
For ten days each October, imagination takes over Key West. Fantasy Fest fills the island with elaborate costumes, themed parties, parades, performances and people who have been planning their outfits since last year.
The schedule usually offers a mix of playful daytime events, creative costume competitions and adults-oriented nightlife. The grand parade is the biggest draw, while favorites such as the Masquerade March and Pet Masquerade add their own brand of spectacle. Review each event before attending with children, because the atmosphere and age restrictions vary considerably.
Dates: November 7-14, 2027
The harbor roars to life when the world’s fastest offshore race boats come to Key West. Race week traditionally combines multiple days of competition with a boat parade, race-village access and waterfront viewing opportunities.
The boats are impressive even when sitting still. Once they hit the course, the sound and speed make this one of the island’s most dramatic spectator events. Premium viewing and hospitality areas may require tickets, while other shoreline viewing locations can be free.
2027 dates: To be announced
Independent films, documentaries, shorts, filmmaker conversations and special screenings take over island theaters during the Key West Film Festival. The event combines serious cinema with a setting that makes even the walk between screenings feel like part of the vacation.
Expected: Late November through December 2027
Key West does the holidays with boats, bicycles, palm trees and far fewer winter coats. Seasonal celebrations typically include the Harbor Walk of Lights, lighted boat parade, holiday tours, concerts and family activities around the Historic Seaport and Old Town.
It is festive without losing the island flavor. You may see a decorated schooner, a conch-shell ornament and Santa arriving by boat—all before dinner.
Date: December 31, 2027
One midnight countdown would never be enough for Key West. The island is known for several delightfully unconventional “drops,” from a conch shell at Sloppy Joe’s to the Pirate Wench at Schooner Wharf and the famous red high heel on Duval Street.
Streets and venues become extremely busy, so choose your celebration in advance, confirm whether tickets are required and leave plenty of time to walk to your destination.
The best event depends on the Key West experience you want:
Key West has limited space, and the biggest festivals can fill hotels, guesthouses and transportation well in advance. Fantasy Fest, Mile 0 Fest, the Songwriters Festival and peak-winter events deserve especially early planning.
A festival’s advertised dates do not mean every activity runs all day, every day. Some signature events may happen only once, while dinners, cruises and premium performances can require separate tickets.
Many festival venues cluster around Old Town, Duval Street, Truman Waterfront Park and the Historic Seaport. Walking, bicycles, taxis and rideshares are often easier than searching for downtown parking—especially during parades and street closures.
Do not let an ambitious festival itinerary crowd out the destination. Save room for a sunset at Mallory Square, a stroll through the Historic Seaport, a few hours at one of the best Key West beaches or an unplanned stop when live music spills out of an open doorway.
For travelers coming from Southwest Florida, the trip to a Key West festival can begin on the water. Key West Express offers high-speed ferry service from Fort Myers Beach to Key West, replacing the long drive with time to relax, enjoy the view and start shifting into island mode.
The Key West terminal is located at 100 Grinnell Street in the Historic Seaport. From there, many Old Town hotels, restaurants and event venues are within walking distance or a short taxi or rideshare trip.
Festival weekends can be popular, so confirm the sailing schedule and reserve early. If the event spans several days, book your outbound and return trips on separate dates and give yourself enough time to enjoy Key West beyond the headline celebration.
Book your Key West Express trip and let the festival fun begin before you even reach the island.
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