Our complete calendar of major events and festivals across Key West and the Florida Keys features a year round lineup of music, heritage, food, endurance challenges, major headliners, niche cultural traditions, and local sports tournaments into a single comprehensive guide

 

JANUARY

Southernmost Regatta

January 4–8
World-class yacht racing brings international sailing teams to compete in Key West Harbor and the Atlantic waters off Key West. Spectators can watch the action for free from various waterfront vantage points and local beaches.

Key West Literary Seminar

January 7–10
This prestigious gathering of world-renowned writers and avid readers takes place at the San Carlos Institute at 516 Duval Street in Key West. Advance registration is required, and packages for the four-day seminar must be purchased well ahead of time.

Key West Tropical Forest Native Plant Sale

January 9
Located at the Key West Tropical Forest & Botanical Garden at 5210 College Road in Key West, this event showcases local flora. Admission to the plant sale area is free, and plants are available for individual purchase.

Key West Half Marathon & Runfest

January 13–18
Popular scenic running courses wind along the waterfront, with the start and finish lines located near the Historic Seaport in Key West. Registration fees are required for all official race distances, including the Half Marathon, 5K, Beer Mile, and Rum Stroll, with race weekend taking place January 15–17.

The 2027 Key West Half Marathon & Runfest is scheduled for January 13–18, with the primary race weekend spanning January 15–17. Voted one of the top winter half-marathons in the nation, this multi-day event features fast, flat road courses, coastal views, and a large lineup of social activities.

The Race Courses
All event routes feature entirely flat terrain that showcases Key West’s historic landmarks:
• The Half Marathon (13.1 miles): The flagship race takes place on Sunday, January 17, starting at 7:00 AM at the corner of Caroline Street & Trumbo Road. Runners pace down Duval Street, past the Southernmost Point buoy, wind through Old Town, trace along Smathers Beach, and cross the finish line near the Historic Seaport.
• The 8K: Also held on Sunday morning, launching at 7:30 AM from the Caroline Street starting block.
• The 5K & 10K: These races take place a day earlier on Saturday, January 16. The 5K kicks off at 7:00 AM, followed closely by the 10K at 8:00 AM. Both courses start and finish at the Higgs Beach park area along Atlantic Avenue.

Multi-Race Challenges
For athletes looking to stack races across the weekend, the 2027 festival introduces two specific multi-medal combinations:
• The Big Pecker Challenge: Participants enter and complete the 5K, the 10K, and the full Half Marathon, receiving specialized medals for all three separate distances.
• The Lil’ Pecker Challenge: Designed for shorter-distance runners who want to complete the 5K, 8K, and 10K events across the weekend to earn a commemorative challenge hat.

Social Events & Runfest Activities
The weekend is highly structured around community gatherings, live tracking options via the RaceJoy app, and non-competitive novelty challenges:
• Runner’s Expo & Packet Pick-Up: Officially opens on Friday, January 15 from 2:00 PM to 7:00 PM at the Historic Seaport. The area serves as the primary weekend anchor, offering pre-race social hours and runner merchandise options.
• The Papa’s Pilar Rum Stroll: Taking place Sunday afternoon from 1:00 PM to 5:00 PM, this guided walk routes participants through nine distinct Old Town locations, serving a themed rum cocktail at each stop.
• Key West Beach N’ Beer Mile: A fun run held Sunday at 3:00 PM on the sands of South Beach. Participants complete four short running loops, drinking a full craft beer at the completion of each lap.
• Post-Race Concert & Awards: The finish line celebration kicks off Sunday morning from 8:30 AM to 12:30 PM outside the Half Shell Raw Bar. The event features live music, random prize raffles, and a costume contest awarding prizes for the most creative running attire.

Mile 0 Fest

January 26–30
A massive five-day music festival brings the best of Texas Red Dirt and Americana music directly to the Truman Waterfront Park Amphitheater at 21 E Quay Road in Key West. Multi-day festival passes and individual venue packages sell out quickly and must be purchased in advance.

The 2027 Mile 0 Fest marks a major milestone as the festival celebrates its 10th Anniversary from January 26–30. Voted the #1 music festival in the country by USA Today readers, this highly acclaimed 5-day “music vacation” turns the entire 2-by-4-mile island of Key West into a massive playground for Texas Red Dirt, Americana, and country-rock music.

The 2027 Artist Lineup
The 10th-anniversary roster features over 50 artists spanning icons of the genre, major full-circle returns, and specialized regional showcases:
• The Headliners: The main evening stages are anchored by Ryan Bingham, Cross Canadian Ragweed, and Old Crow Medicine Show.
• Featured Acts: The stacked lineup includes Wyatt Flores, Kaitlin Butts, Wade Bowen, 49 Winchester, William Clark Green, Stoney LaRue, American Aquarium, Tanner Usrey, Cody Canada & The Departed, Silverada, and Corb Lund.
• Special Showcases: The 2027 festival introduces unique collaborative sets, including a dedicated “Commonwealth of Kentucky Party” traveling showcase featuring regional acts like The Creekers, Nicholas Jamerson, and The Local Honeys.

Festival Venues & Daily Structure
Music runs daily from roughly 11:00 AM to 11:00 PM, spreading across more than 10 distinct stages around Key West:
• The Daytime Circuit: Late morning through late afternoon sets spill across beach resorts, resort pools, piers, local bars, and the historic Key West Theater. These intimate daytime sets are famous for spontaneous, unannounced artist collaborations and surprise pop-up acoustic jams.
• The Main Stage Centerpiece: The focal point for the massive evening performances is the Coffee Butler Amphitheater at Truman Waterfront Park. Evening concerts here run roughly from 5:00 PM to 10:00 PM. To protect the experience and ensure maximum attendance for the headliners, the festival does not schedule any conflicting daytime venue sets while the main amphitheater shows are running.
• Late-Night & Special Excursions: After the amphitheater gates close, the party moves back to the Duval Street corridor for specialized late-night bar shows. Beyond the land-based stages, the festival coordinates unique ticketed events like live acoustic catamaran sailing trips out on the water.

Weather, Logistics, & Navigation
• Rain or Shine Operations: All performances are scheduled rain or shine. Because the primary amphitheater is an open-air facility right on the Gulf side of the island, massive tents are erected on the grounds to provide storm shelter.
• Getting Around: Because parking in downtown Key West is practically non-existent, the festival leaves all internal transit planning up to the attendees. No official festival shuttles are provided between the various daytime venues, meaning walking, renting a bicycle, or hailing local golf-cart taxis are the standard ways to navigate between sets.

Key West Food & Wine Festival

January 27–31
This premier island culinary event celebrates world-class chefs and fine wine tastings at various venues across Key West, including local beaches, historic properties, and hotels. Separate tickets are required for every individual event, as no general admission pass covers the entire festival.

“Unnecessary Farce” (Stage Play)

January 28 – February 6
Individual ticket purchases are required for all evening and matinee performances of this stage play. Production takes place at the Waterfront Playhouse, located at 407 Wall Street within Mallory Square in Key West.

“The Pirates of Penzance”

FEBRUARY

February 1
This grand touring performance requires reserved seating tickets, which should be purchased in advance through the box office. The show is hosted at the Tennessee Williams Theatre, located at 5901 College Road in Key West.

Florida Keys Seafood Festival

February 13–14
Held at Truman Waterfront Park at the end of Southard Street in Key West, this family-friendly celebration features locally caught seafood and live music. Admission is $10 per person at the gate, while food and beverages inside are sold separately.

The 20th Annual Florida Keys Seafood Festival is scheduled for February 13–14, taking place at Truman Waterfront Park at the end of Southard Street in Key West. Operating from 11:00 AM to 8:00 PM on Saturday and 11:00 AM to 5:00 PM on Sunday, this community event celebrates the region’s commercial fishing heritage.
The festival is organized directly by the Florida Keys Commercial Fishermen’s Association, with local fishermen and their families preparing and serving the food to ensure authenticity and freshness.

The Seafood Menu
The primary draw of the weekend is the extensive menu of native species harvested straight from local waters. Dishes are prepared using traditional recipes and sold individually:
• Main Platters: Grilled Florida spiny lobster halves, fried local fish baskets, and golden-fried Key West pink shrimp.
• Claws & Shareables: Steamed stone crab claws served with traditional mustard sauce, alongside smoked fish dip, conch fritters, and conch ceviche.
• Soups & Sides: Classic conch chowder (a spicy, tomato-based Bahamian style), rich lobster bisque, French fries, and coleslaw.
• Desserts & Drinks: Traditional Key lime pie slices are served alongside a full beverage selection that includes domestic beers, regional craft brews, rum runners, and margaritas.

Entertainment & Attractions
Beyond the food lines, the park grounds are arranged to host a variety of family-friendly activities:
• Live Music: A continuous lineup of local and regional bands performs from the main stage throughout the weekend, covering a mix of classic rock, country, and tropical island music.
• The Artisan Market: Dozens of vendor booths showcase marine-themed art, handmade jewelry, local photography, apparel, and unique crafts.
• Kids Eco-Discovery Zone: A dedicated children’s area featuring interactive games, educational displays about marine conservation, and activities focused on the delicate Florida Keys ecosystem.

Admission & Logistics
• Entry Fee: Admission is $10 per adult, which is valid for both days of the weekend. Children under the age of 12 are admitted for free.
• Raffle Entry: Each paid adult admission automatically doubles as a raffle ticket for a chance to win a grand prize of $250 worth of fresh Keys seafood, which can be packed and shipped directly to the winner’s home.
• Payments: Cash and credit cards are accepted at the main entry gates and major food lines, but bringing cash is highly recommended for faster service at smaller beverage and dessert booths.

Florida Keys Celtic Festival

Mid-February 2027 (Dates TBD)
Marathon Community Park on Ocean Boulevard in Marathon hosts a cultural weekend featuring traditional Irish and Scottish music, Highland athletics, and Celtic food vendors. Daily or weekend passes can be purchased online in advance or directly at the gate.

Key West Art & Craft Festival

February 20–21
This event brings outdoor artist rows and fine handmade crafts to Truman Waterfront Park in Key West. Admission is free for all attendees looking to browse the display booths.

Key West Circus Invasion

February 24–28
A family-friendly showcase of acrobatics, street performers, and interactive theater takes over various locations throughout Old Town Key West. Admission is free for the outdoor street performances, though specialized workshops may require individual tickets.

MARCH

“Come From Away” (Musical)

March 4–20
Individual ticket purchases are required for all performance dates of this hit musical. The production runs at the Waterfront Playhouse, located at 407 Wall Street in Key West.

Spanish Fly Shark Tournament

March 12–13
This premier catch-and-release fishing tournament celebrates marine conservation and sport fishing legacy in Key West, with specific marina headquarters to be determined. Angler registration fees are required for all participating boats and crews.

Original Marathon Seafood Festival

March 13–14
The Middle Keys’ largest seafood celebration serves up fresh-caught mahi-mahi, stone crab, and lobster tail at Marathon Community Park on Ocean Boulevard in Marathon. A small entry fee is required at the gate, and food, drinks, and vendor items are paid for individually inside.

“Beethoven’s Ninth & Grand Opera Arias”

March 20
The Tennessee Williams Theatre at 5901 College Road in Key West hosts a night of classical music and grand orchestration. Reserved seating tickets are required and must be purchased through the theater box office.

The Florida Keys Latin Festival

March 20–21
A high-energy weekend celebrating Latin culture, music, and food takes over Key West at a park location to be determined. General admission tickets are available at the gate, and VIP packages can be purchased in advance.

The Florida Keys Latin Festival is scheduled for March 20–21, transforming the island into a vibrant hub of Hispanic culture, art, music, and cuisine. This high-energy, multi-day celebration unites locals and visitors to honor the deep-rooted Latin heritage that has influenced the Florida Keys for generations.
The festival is designed as a fully immersive cultural experience, combining large-scale concerts with an expansive open-air marketplace.

The Entertainment Lineup
The main stage serves as the focal point of the weekend, featuring a non-stop rotation of regional and international performers:
• Musical Genres: Audiences can expect live performances spanning salsa, merengue, bachata, reggaeton, and traditional Afro-Cuban jazz.
• Dance Showcases: Professional dance troupes perform traditional folkloric dances representing various countries, including Cuba, Puerto Rico, Colombia, and the Dominican Republic.
• Interactive Dance Lessons: In between musical sets, professional instructors take to the floor to teach the crowd basic salsa and bachata steps, turning the entire audience area into a massive dance floor.

The Latin Food Pavilion
A cornerstone of the festival is its extensive food court, which brings together local Hispanic chefs, restaurants, and food trucks to serve up authentic, diverse dishes:
• Savory Specialties: The menu features classic dishes like lechón asado (roast pork), ropa vieja, authentic Cuban sandwiches, empanadas, mofongo, and fresh-cooked paella.
• Sweet Treats & Refreshments: Traditional desserts like flan, tres leches cake, and churros are paired with a wide variety of drinks, including Cuban espresso, fresh sugarcane juice (guarapo), horchata, and tropical fruit smoothies.
• Themed Cocktails: Adults can enjoy dedicated beverage stations serving classic rum-based cocktails like mojitos, daiquiris, and caipirinhas.

Cultural Marketplace & Family Activities
The festival grounds are organized to accommodate a wide range of cultural attractions:
• Artisan Rows: Visual artists, sculptors, and craftsmen display and sell their work, which includes vibrant Caribbean paintings, handmade jewelry, leather goods, and cultural apparel.
• Dominos Tournament: A highly competitive, traditional Latin dominoes tournament is hosted across both days, attracting seasoned local players and offering prizes for the winners.
• Kids Cultural Zone: A dedicated space for children featuring bilingual storytelling, face painting, and arts and crafts projects where kids can create their own carnival masks and musical instruments.

Admission & Logistics
General admission tickets are available for purchase at the entry gates, with single-day and full-weekend passes offered. For an upgraded experience, advance VIP packages are available, which grant access to a dedicated viewing area right in front of the main concert stage, private air-conditioned restrooms, and exclusive bar access.

Spring Migration Mania

March 27
This family-oriented environmental event takes place at the Key West Tropical Forest & Botanical Garden at 5210 College Road in Key West. A general garden admission fee applies at the entrance.

“Short Attention Span Theatre”

March 30 – April 24
This fast-paced collection of short plays showcases works by acclaimed playwrights. Individual ticket purchases are required for all scheduled show dates at the Red Barn Theatre, located at 319 Duval Street in Key West.

APRIL

Taste of Key West

April 5
This open-air gourmet dining experience runs from 6:00 PM to 9:00 PM at Truman Waterfront Park in Key West. Entry to the park is free, but attendees must purchase a tasting plate and a package of food or wine tickets at the venue to exchange for restaurant samples.

“Dial M For Murder” (Stage Play)

April 8–17
Individual ticket purchases are required for all performance dates of this classic suspense thriller. The stage play is presented at the Waterfront Playhouse at 407 Wall Street in Key West.

Conch Republic Independence Celebration

April 16–25
A legendary 10-day celebration marking Key West’s historic secession features mock sea battles, parades, and parties across various locations like Duval Street, the harbor, and local bars. Most public spectator events are free, but select private parties and VIP boat charters require individual advance tickets.

The 45th Annual Conch Republic Independence Celebration is scheduled for April 16–25, across Key West. This legendary 10-day festival commemorates the island’s tongue-in-cheek “secession” from the United States on April 23, 1982, which was staged in protest of a federal border patrol roadblock that paralyzed the Florida Keys economy.
Under the historic motto “We Seceded Where Others Failed,” the celebration blends historical theater, costumed revelry, eccentric sports, and a warm-hearted message of global friendliness.

The Great Battle of the Conch Republic
The absolute highlight of the 10-day celebration is the Conch Republic Naval Battle, taking place on Friday, April 23, at 7:00 PM in Key West Harbor.
• The Combatants: The official Conch Republic Navy (a ragtag fleet of historic schooners, civilian yachts, and local dinghies) squares off against the “United States Evil Empire” forces (represented by a willing local U.S. Coast Guard vessel).
• The Weapons: The battle is fought entirely with water cannons, water balloons, Cuban bread missiles, and stale conch fritters, all accompanied by the booming of black-powder cannons from the tall ships.
• Vantage Points: Thousands of spectators gather for free along the docks of Mallory Square, Ocean Key Resort, and the Historic Seaport to cheer on the local fleet.

Signature Events & Parades
The 10 days are packed with themed traditions that span from high-energy parades to casual block parties:
• The Conch Republic Drag Race (April 17): A hilarious afternoon tradition on the 700 block of Duval Street where local drag queens don full makeup, wigs, and high heels to sprint down the asphalt in a series of elimination heats.
• The World’s Longest Parade (April 22): This satirical parade begins at the Atlantic Ocean on Whitehead Street and marches entirely across the island to the Gulf of Mexico. It features motorized lawn chairs, local marching bands, pirate krewes, and official Conch Republic dignitaries tossing beads to the crowds.
• The Blue Ribbon Bed Race (April 24): A wild race down Duval Street featuring decorated wheel-mounted beds pushed by costumed teams of four, while a passenger rides on top hanging on for dear life.

Food, Craft Markets, & Nautical Gatherings
• Conch Republic Craft Show & Food Fest: Spanning the weekends of the celebration, the outdoor street market takes over Greene Street. Local food stalls serve up heavy portions of conch chowder, conch fritters, cracked conch, and Key lime cocktails alongside rows of local marine-themed arts and crafts.
• Schooner Wharf Republic Military Ball: A high-spirited costume party hosted at the Historic Seaport where sailors, pirates, and citizens dress in “Conch formal” attire, culminating in a raucous sea-shanty sing-along and a pirate costume competition.

Ticketing & Festival Entry
The vast majority of the events—including the Naval Battle, the Duval Street parades, and the bedside races—are entirely free to watch. However, certain exclusive activities require individual tickets. This includes booking a passenger seat onboard one of the fighting tall ships during the Naval Battle, attending the official VIP Secession Dinner, or purchasing a team registration slot to compete in the Drag Race or Bed Race.

Key West Paddle Classic

Late April 2027 (Dates TBD)
This premier 12-mile open-ocean paddleboard race circles the entire island of Key West, launching from Higgs Beach. Registration fees are required for all race participants and board divisions, while shoreline spectator viewing is free.

Key West Songwriters Festival

April 28 – May 2
The largest gathering of its kind in the world features intimate acoustic showcases by hit hitmakers across main street stages on Duval Street, local theaters, and various bars or hotel pools. Main street stages and daytime bar showcases are free to the public, while headlining theater concerts and exclusive pool performances require advance tickets.

MAY

Key West Fishing Tournament Kickoff

May 2027 (Dates TBD)
The launch of a months-long, multi-division angling tournament covers everything from billfish to tarpon in waters across the Florida Keys, with weigh stations located in Key West. Registration fees are required for all anglers entering the tournament categories.

JUNE

Key West Pride

June 2–6
Five days of celebrations take over Duval Street, local pools, and LGBTQ+ community venues across Key West. The main parade and outdoor street fair are free to attend, while specialized pool parties, drag shows, and evening club events require individual tickets or cover charges.

The 2027 Key West Pride celebration is scheduled for June 2–6, transforming the entire island into a vibrant showcase of diversity, inclusion, and high-energy entertainment. Organized by the Key West Business Guild—one of the oldest LGBTQ+ business organizations in the country—this five-day festival embraces Key West’s official city motto, “All Welcome,” and draws visitors from around the globe.

Flagship Parades and Street Festivals
The festival peaks over the weekend with large-scale public events that take over the heart of the historic district:
• The Key West Pride Parade (Sunday, June 6): The crown jewel of the weekend kicks off at 5:00 PM, marching all the way down Duval Street from the Gulf of Mexico to the Atlantic Ocean. The parade features high-production floats, local marching bands, drag icons, and the famous 100-foot portion of the original Sea-to-Sea Rainbow Flag, which was stitched in Key West by prominent activist Gilbert Baker.
• Duval Street Pride Street Fair (Saturday, June 5): A massive daytime block party that closes down traffic on upper Duval Street. Visitors can browse rows of booths featuring local arts and crafts, community organization displays, food vendors, and open-air cocktail stations.

Pool Parties and Day Events
Given the warm June climate, the festival heavily utilizes Key West’s premier resorts and clothing-optional guesthouses for specialized daytime gatherings:
• Splash Pool Parties: Hosted daily from Thursday through Saturday at various prominent island resorts, featuring rotating live DJs, go-go dancers, fluid-art showcases, and poolside cocktail bars.
• Nautical Excursions: Specialized local charters coordinate all-day clothing-optional catamaran trips, taking guests out to the Florida Keys National Marine Sanctuary for snorkeling, paddleboarding, and sandbar parties.

Evening Showcases and Theater
When the sun goes down, the entertainment moves into local theaters, clubs, and cabaret bars:
• The Pride Pageants: Highly competitive evening showcases held early in the week to crown the official “Mr., Miss, and MS Key West Pride,” featuring talent rounds, evening wear modeling, and celebrity judges.
• Drag & Comedy Shows: Key West’s world-famous drag venues (such as 801 Bourbon Bar, Aqua, and La Te Da) run expanded nightly schedules featuring celebrity female impersonators, stand-up comedy specials, and late-night dance parties that spill into the early morning hours.
• Stoli Key West Cocktail Classic: A high-profile bartending competition where mixologists from across the country compete live on stage to create the ultimate island cocktail, accompanied by theatrical entertainment and free samples for the audience.

Admission & Ticketing
The massive Duval Street Parade and the Saturday Street Fair are entirely free to attend and watch. However, individual tickets or cover charges apply to the vast majority of the specialized events. This includes access to the private resort pool parties, entry passes for the nightly theater pageants, seats at the indoor comedy showcases, and boat tickets for the pride-themed catamaran sailing excursions.

JULY

Key Lime Festival

June 30 – July 4
The island’s signature multi-day culinary celebration is dedicated entirely to America’s favorite citrus dessert at various venues across Duval Street, local distilleries, and hotels. Individual tickets are required for specific events such as the Key Lime Pie Drop, cocktail strolls, and the pie-eating championship.

Hemingway Days Festival

July 21–25
Celebrating the literary and lifestyle legacy of Ernest Hemingway, this festival features the world-famous Look-Alike Contest at Sloppy Joe’s Bar at 201 Duval Street and various other island locations. Watching the contest is free on a first-come, first-served basis, while registration fees are required to participate in the Hemingway 5K Sunset Run on July 24.

Lobster Mini-Season

July 28–29
This competitive two-day preview window draws divers to waters throughout the Florida Keys to harvest Florida spiny lobsters ahead of the regular season. No event ticket is required, but all participants must possess a standard Florida saltwater fishing license alongside a spiny lobster permit.

The 2027 Florida Spiny Lobster Mini-Season is scheduled for July 28–29. This highly anticipated, 48-hour competitive window always takes place on the last consecutive Wednesday and Thursday of July, serving as a special preview for recreational divers and snorkelers before the commercial lobster season officially opens in August.
Thousands of saltwater enthusiasts descend upon the waters of the Florida Keys with dive gear, tickle sticks, and net bags to harvest the local spiny lobster, turning the islands into a high-energy hub of nautical activity.

Strict Daily Limits and Measuring Rules
To protect the local marine population, state wildlife officers strictly enforce strict catch limits and physical measurements:
• The Daily Bag Limit: In Monroe County (the Florida Keys) and Biscayne National Park, the legal limit is 6 lobsters per person, per day. This is a strict cap—divers cannot catch a double limit for a friend or boat captain who is not actively in the water harvesting.
• The Carapace Rule: Every diver must carry an official plastic or metal lobster gauge in the water. The carapace (the hard shell of the lobster’s head and body section) must measure larger than 3 inches. Lobsters must be measured in the water immediately upon capture; if the shell fits inside the gauge, it is undersized and must be released immediately.
• Egg-Bearing Females: Harvesting female lobsters carrying visible eggs on their undersides is strictly prohibited year-round. Divers must check the underside of the tail before placing any lobster in their catch bag.
• Tail Separation: Lobsters must remain intact in their whole condition while on the water. Separating the tail from the body can only be done once the boat has safely docked back at a land-based marina or campsite.

Gear Requirements and Safety Regulations
Mini-season requires specific gear and strict adherence to open-water safety laws:
• The Dive Flag: All boats and individual divers must display a standard red-and-white “Divers Down” flag. Boats operating near a dive flag must maintain a safe distance and proceed at idle speed within 300 feet of a flag in open water, or 100 feet within narrow rivers, inlets, and navigation channels.
• Standard Catch Tools: Mechanical spears, hooks, or piercing devices are completely illegal for taking lobsters. Divers must use a soft mesh hand net paired with a flexible “tickle stick” to gently coax the lobsters out of their coral holes and rock ledges.
• Night Diving Restrictions: In Monroe County, night diving for lobsters is strictly banned during the 48-hour mini-season window. Harvesting is only legally permitted between official sunrise and official sunset.

AUGUST

Key West Lobsterfest

August 11–15
The official opening week celebration of the spiny lobster season features street fairs and free concert stages along Duval Street and various historic district restaurants. The street gatherings do not require tickets, but the opening-night lobster boil and official Sunday brunch require advance ticket purchases.

Key West Rum Fest

Mid-August 2027 (Dates TBD)
A dedicated celebration of the island’s favorite spirit features distillery tours, beachside tastings, and pool parties at various beachside hotels and distilleries in Key West. Individual event tickets are required to access the beach parties and general tastings.

SEPTEMBER

Key West Brew Fest

September 1–5
A Labor Day weekend tradition brings expansive craft beer tastings and beachside pairing dinners to South Beach at the Southernmost Beach Resort and other locations across Key West. The signature Saturday afternoon tasting event requires an advance ticket, while surrounding dinners and pool parties are priced individually.

Just a Few Friends Festival (Jimmy Buffett Tribute)

September 2–6
This citywide Labor Day weekend celebration honors the life, music, and lifestyle of Jimmy Buffett across Duval Street, the Key West Theater, and various historic district locations. Outdoor concerts and street gatherings are free, but specialized theater tribute shows and private excursions require individual tickets.

Womenfest

Mid-September 2027 (Dates TBD)
A premier annual gathering for lesbians and the LGBTQ+ community features specialized beach parties, pool gatherings, and comedy shows at various resorts, nightclubs, and beaches across Key West. Festival passes cover major events, or individual tickets can be purchased for specific pool parties, comedy nights, and dinners.

Key West Womenfest is scheduled for September 1–5, aligning with the long Labor Day weekend. For this installment, the official theme is “Alice in Womenfest”—a playful, tropical reimagining of the classic Alice in Wonderland tale. Produced by the Key West Business Guild, this five-day festival is recognized as one of the premier gatherings in North America for lesbians and queer women, bringing together thousands of travelers for connection, empowerment, and artistic expression.

Theme and Creative Elements

The “Alice in Womenfest” theme sets the tone for the entire long weekend. Attendees can expect whimsical costume contests, theatrical elements, and curated sub-events inspired by Wonderland archetypes. This playful direction follows previous successful thematic iterations focused on female empowerment, visibility, and reclaiming space in contemporary music and visual arts.

Festival Highlights and Activities
The multi-day itinerary balances creative day excursions with high-energy nightlife:
• Pool Parties & Day Socials: The physical epicenters for the festival rotate through various prominent LGBTQ+-friendly resorts and guesthouses. These include signature pool gatherings featuring rotating female DJs, beach games, and casual cocktail meetups.
• On-the-Water Excursions: Group charters offer specialized nautical activities, such as late-afternoon sunset sails with live music, alongside clothing-optional snorkeling and sandbar excursions into the Florida Keys National Marine Sanctuary.
• The Arts & Culture Track: Honoring women-owned businesses on the island, the schedule includes guided trolley tours through prominent local art galleries, live poetry readings, performance art installations, and meet-and-greets with regional female artists.
• Interactive Showcases: Popular recurring features include interactive performance workshops (such as Drag King Bootcamps where participants train with professionals before performing live on stage) and the private Jell-O wrestling tournament.
• Themed Nightlife & The Prom: Evening programming includes femme-focused cabaret shows, late-night dance parties, and the centerpiece Womenfest Prom—a massive costume dance party where attendees dress up according to their favorite era or interpretation of the festival theme.

Ticketing and Registration Structure
The festival offers two main paths for entry. Attendees can purchase an all-access VIP Festival Pass online in advance, which covers entry to all major pool parties, the gallery trolley tour, nightly club events, and the prom. Alternatively, individuals can purchase single-entry tickets à la carte at the door for standalone events like the comedy showcases, private boat charters, or the signature Sunday Drag Brunch.

OCTOBER

Fantasy Fest

October 22–31
Key West’s world-renowned 10-day festival of costumed revelry takes over the Duval Street corridor, Truman Waterfront Park, and island-wide venues under the 2027 theme “Summer Camp Couture.” The massive Duval Street parade on October 30 and the Goombay street fair are entirely free to watch, while official themed parties, the Royal Coronation on October 22, and costume competitions require advance tickets.

The 2027 Fantasy Fest is scheduled for October 22–31, transforming the city of Key West into a massive, 10-day celebration of costumed revelry, body art, and creative expression. Founded in 1979 to boost winter tourism, the festival has grown into a world-famous autumn tradition. The official theme for 2027 is “Summer Camp Couture,” inviting attendees to put a high-fashion, eccentric spin on nostalgic summer camp styles.

The 2027 Theme: “Summer Camp Couture”
The theme dictates the creative direction for major costume competitions, float designs, and private parties throughout the week. Participants are encouraged to craft outfits that blend classic campground nostalgia—such as merit badges, retro camp counselors, bunk beds, and campfire ghost stories—with bold, avant-garde glamour and wearable art.

Flagship Parades and Main Events
The festival’s final weekend plays host to the largest public gatherings on the island:
• The Bud Light Fantasy Fest Parade (Saturday, October 30): The official centerpiece of the entire festival draws tens of thousands of spectators to the Duval Street corridor. The multi-hour parade features massive, high-production motorized floats, synchronized dance troupes, and island-style marching bands.
• The Goombay Festival (October 22–23): This family-friendly street party kicks off the 10-day stretch in Key West’s historic Bahama Village neighborhood. It celebrates the island’s deep Caribbean heritage with continuous live reggae and island music, Junkanoo rush parades, and food stalls serving up authentic jerk chicken and conch fritters.
• The Royal Coronation (Friday, October 22): A high-spirited gala where a local King and Queen of Fantasy Fest are crowned based on a multi-month community fundraising campaign.
• The Masquerade March (Friday, October 29): Known locally as the “locals’ parade,” this is a massive, walking costumed promenade that winds through the streets of Old Town, stopping at historic guest houses and neighborhood bars along the way.

Niche Parties and Famous Traditions
Dozens of specialized, themed sub-events run continuously from midday through the late-night hours:
• The Tutu Tuesday Party: A strictly enforced costume tradition where entry requires wearing a tutu. What started as a small gathering has expanded into a massive, multi-venue block party.
• The Pet Masquerade: A lighthearted Wednesday night costume competition hosted at the Truman Waterfront Park Amphitheater, where local owners dress up alongside their dogs, cats, birds, and pocket pets to compete for prizes.
• The Headdress Ball: Considered the premier creative competition of the week, this seated event showcases designers competing live on stage with massive, elaborate, and often motorized headpieces that extend multiple feet into the air.

Street Rules, Logistics, and Safety
Because of the unique nature of the festival, the city of Key West enforces specific municipal guidelines during the 10-day window:
• The Fantasy Zone: A designated section of Old Town where body paint is legally recognized as a costume. Outside of this designated zone and official festival venues, standard public decency laws are strictly enforced.
• Open Container Laws: Open glass containers are strictly banned on public streets. While the city relaxes certain open-container laws for plastic cups along the main Duval Street corridor during peak event hours, alcohol must be kept within designated pedestrian barriers.
• Navigating the Island: Streets throughout the historic district are completely closed to vehicle traffic for major parades and fairs. Walking, riding bicycles, or utilizing designated park-and-ride transit shuttles are the standard ways to travel.

Entry and Ticketing Information
Watching the massive Saturday night Fantasy Fest Parade, the Masquerade March, and attending the daytime Goombay street festivals are completely free to the public. However, tickets must be purchased in advance for specific indoor galas, theater showcases, and official themed parties—including the Royal Coronation, the Headdress Ball, the Pet Masquerade, and private resort pool parties.

NOVEMBER

Race World Offshore World Championship

Mid-November 2027 (Dates TBD)
High-speed powerboat racing transforms Key West Harbor and the Truman Waterfront Park Outer Mole into an extreme motorsports arena. Free viewing is available from various points around the harbor, while VIP hospitality tents and premium outer mole viewing access require paid passes.

Key West Film Festival

November 17–21 (Tentative)
Standout independent films, foreign cinema, and creative documentaries are showcased across historic island venues like the San Carlos Institute and Tropic Cinema. Individual screening tickets, film passes, and all-access VIP badges must be purchased online or at the festival box office.

DECEMBER

Key West Holiday Fest

All Month Long (December 2027)
A festive month-long celebration features holiday light displays, historic inn tours, and the iconic Schooner Wharf Lighted Boat Parade around the historic seaport and local neighborhoods. Street displays and the harbor boat parade are free to watch, while the historic inn tours require a specific ticket purchase.

The 2027 Key West Holiday Fest runs throughout the entire month of December 2027, transforming the tropical island into a festive winter wonderland. Organized by the Key West Business Guild and local historic preservation groups, the month-long festival blends classic holiday nostalgia with Key West’s unique maritime culture.
The schedule features a continuous lineup of historic property tours, light celebrations, and nautical parades.

Flagship Parades and Harbor Events
The ocean serves as the primary backdrop for the island’s most famous holiday traditions, which take place during the first half of the month:
• The Schooner Wharf Lighted Boat Parade: This signature event takes place on Saturday, December 11, at 8:00 PM along the Key West Bight at the Historic Seaport. A massive fleet of vessels—ranging from tall ships and commercial fishing boats to private yachts and local dinghies—cruises the harbor completely wrapped in elaborate, synchronized holiday light displays. The festivities begin hours earlier with a holiday village marketplace featuring local choirs, steel drum bands, and fresh seafood stalls.
• The Key West Holiday Parade: Scheduled for Saturday, December 4, at 7:00 PM

, this traditional hometown parade marches through the streets of Old Town. It features marching bands, local school groups, festive floats, and a special appearance by Santa Claus riding atop a vintage Key West fire truck.

Historic Inn and Architecture Tours
Key West celebrates its rich architectural heritage with specialized evening tours that open up private properties normally closed to the public:
• The Key West Holiday Inn Tours: Taking place across consecutive Fridays in mid-December (specifically December 10 and December 17, from 6:00 PM to 8:00 PM). Visitors board the open-air Conch Tour Train or local trolleys to be transported between five distinct, beautifully decorated historic inns each evening. Every stop features festive holiday light displays, live acoustic music, and a selection of holiday treats, signature cocktails, and wines prepared by local chefs.
• The Custom House Holiday Concert & Bazaar: Hosted on the porch of the historic Custom House Museum in early December. The evening features light projections cast onto the red brick facade of the building, a marketplace filled with regional artisans, and live holiday musical performances by the Key West dynamic orchestration groups.

Neighborhood Light Displays and Celebrations
Local parks and historic sites run continuous light celebrations throughout the month:
• The Harbor Walk of Lights: Illuminated nightly starting the day before Thanksgiving and running through New Year’s Eve. The display stretches along the Historic Seaport, featuring maritime-themed light sculptures including a giant Christmas tree crafted entirely from local lobster traps and another built from colorful fishing buoys.
• The Key West “Bravest and Finest” Holiday Light Challenge: A month-long competitive event where local residential neighborhoods, fire stations, and businesses compete for the title of the best holiday light display. Visitors can grab a map at the local chamber building to conduct self-guided walking or bicycle tours through the most elaborately lit side streets of Old Town.

Ticketing and Entry Information
Attending the Schooner Wharf Lighted Boat Parade, the hometown street parade, and strolling the Harbor Walk of Lights are completely free to the public. However, tickets are strictly required for the Key West Holiday Inn Tours, which must be purchased in advance online or at the Key West Business Guild office, as these trolley slots frequently sell out weeks ahead of time. Individual entry fees also apply to specialized museum gallery nights and evening bazaar events.

And for New Year’s Eve…

33rd Annual Conch Shell Drop

December 31
Location: Sloppy Joe’s Bar, 201 Duval Street, Key West
This iconic Key West tradition serves as the island’s main counter-programming to Times Square. As midnight approaches, thousands of revelers pack the intersection of Duval and Greene Streets to watch a giant, illuminated conch shell descend from the roof of the historic bar. Live musical entertainment runs continuously on the main stage inside from noon until 2:00 AM, while a rooftop DJ anchors the outdoor countdown starting at 10:00 PM. Standing in the street to watch the countdown is entirely free to the public.

26th Annual Red High Heel Drop

December 31
Location: Bourbon St. Pub / New Orleans House Complex, 724 Duval Street, Key West
A world-famous centerpiece of the island’s New Year’s celebrations, this high-energy event features a super-sized, glittering red high-heel shoe containing a prominent drag queen. At the midnight mark, the shoe slowly descends from above the balcony of the pub to the street below amidst a massive confetti blast. The surrounding Duval Street block transforms into an open-air dance party covered by national television broadcasts. Spectating from the street level is free, but exclusive VIP balcony tickets must be purchased well in advance.

Lowering of the Pirate Wench

December 31
Location: Schooner Wharf Bar, 202 William Street, Key West
For a celebration with a distinct maritime flair, the Historic Seaport hosts a raucous, pirate-themed countdown. At midnight, a costumed pirate wench is dramatically lowered from the towering mast of the tall ship America 2.0 docked directly in front of the venue against giant, illuminated numbers. The descent culminates in booming cannon fire, horns, and a pirate-dressed crew toast. The waterfront party features consecutive live musical acts all day and night, champagne specials, and complimentary party favors with no cover charge for general entry.

The Flight Attendant Drop

December 31
Location: First Flight Island Restaurant & Brewery, 301 Whitehead Street, Key West
Steeped in aviation history at the birthplace of Pan American World Airways, this unique countdown features the “flight” of a uniformed stewardess inside a replica section of a Pan Am aircraft. The vessel glides downward to ring in the new year. The venue hosts an upscale, ticketed Gatsby-style gala to accompany the drop, featuring an open bar, chef-attended food stations, and a private dance floor. Tickets must be locked in ahead of time online.

Key Lime Wedge Drop

December 31
Location: Sunset Pier, 0 Duval Street, Key West
Perched directly over the waters of the Gulf of Mexico, this location hosts a giant, glowing Key lime wedge that drops directly into a massive, custom-built margarita glass at midnight. The outdoor pier celebration serves as an extension of the island’s famous sunset celebration, transitioning directly into live beach rock music, tropical drinks, and open-air dancing.

Oceanfront White Night Beach Bash

December 31

Location: Casa Marina Resort / The Reach Key West, Atlantic Boulevard, Key West
These oceanfront luxury resorts host private, upscale holiday packages right on the sand along the Atlantic side of the island. Guests dress in all-white attire for high-end “Tide to Table” multi-course dinners under the stars, followed by lawn dance floors, live bands, and custom cigar-rolling stations. The midnight countdown is accompanied by a complimentary champagne toast by the sea. These are strictly ticketed culinary experiences requiring advance resort reservations.

New Year’s Eve Sunset & Midnight Cruises

December 31
Location: Launches from the Key West Historic Seaport and Mallory Square docks
Various regional catamaran fleets and charter yachts operate specialized excursions on the water to close out the final hours of the year. Travelers can choose between late-afternoon sunset sails that return before the land-based drops begin, or late-night midnight cruises that position boats directly in the harbor. The late-night cruises offer premium views of the waterfront fireworks and seaport celebrations from the open water, complete with onboard live acoustic music, heavy appetizers, and open bars. Every passenger ticket must be booked weeks in advance.