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Events in Key West

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Key West for 2021

  • November 24 - Jan 01, 2022 Key West
  • Key West 'Bight' Before Christmas
  • Website
  • Enjoy a free Keys holiday event to celebrate the spirit of the season. ‘Harbor Walk of Lights’ comes alive each evening at dusk, through New Year’s Eve, and runs along water past Greene St., William St., Margaret St., to the Key West Ferry Terminal. Traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree. Colorful lights and nautical holiday displays include ship’s anchors, tropical birds, tropical fish, pink flamingos, pelicans, manatees, animated sea turtles and dolphins, and even a festive moray eel, along with thousands of lights all around and in lighted palm trees.

  • December 01 - Jan 01, 2022 Key West
  • Key West Holiday Fest
  • A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”

  • December 02 - 30, 2021 Key West
  • The Studios of Key West presents: Winter Members' Show
  • Website
  • The winter members’ exhibition ‘Piece by Piece’ is to be on display in all four galleries: Sanger, XOJ, Zabar Lobby and Zabar Project Galleries. The annual winter members’ show is a celebration and serves as a kick off for TSKW’s season of events. Galleries are open Tue-Sat, 10 a.m.- 4 p.m., and are free to visit, at 533 Eaton St.

  • December 03 - 05, 2021 Key West
  • COAST is CLEAR Music and Arts Festival
  • Website
  • Enjoy a weekend in the sun surrounded by close compadres — or simply folks you’ve only just met because of a shared love of music and art. The festival's main event is an all-day concert Saturday. VIP and General Admission tickets still available, at $225 pp and $105, respectively. Festival is to be held rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd.

  • December 04 Key West
  • Key West City Hometown Holiday Parade
  • 305-809-3881 Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Bayview Park's Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.

  • December 04 Key West
  • Tri Conch Republic
  • Email Website
  • Athletes will converge on the southernmost island on the United States and enjoy a break from the ordinary. Staged at Higgs Beach, athletes will enjoy a warm Atlantic Ocean swim in full view of spectators.  The bike course is set against along US1 by Smathers Beach. The Olympic distance athletes will have two loops on the course, while the sprint distance will do so once. The run also consists of a scenic view along Smathers Beach. Friends, family and music welcome the athletes through the finish line. 

  • December 05 Key West
  • Key West Artisan Market, 'For the Birds' Edition
  • Website
  • From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote community causes. All artists who show at the event are carefully selected and live and create in the Keys. This month's Market benefits the Key West Wildlife Center.

  • December 05 Key West
  • Eaton Street Christmas Stroll
  • Website
  • Family Friendly Holiday Event The Stroll begins at 4:00PM at St Paul’s Episcopal Church • 401 Duval St. Keys Choral arts presents a short program of secular & religious music for the season. Continue strolling to: Old Stone First United Methodist Church • Christmas Music, with Voices, Bells, Instruments, Piano & Organ. Tropic Cinema • Classic Christmas short film. Studios of Key West • Open for special hours with a happy hour at Hugh’s View on the roof. Key West Theater • Stop in for some hot cocoa or cider, and listen to holiday songs performed by local musicians, at any time during the entire duration of the event. Williams Hall • See their newly rehabbed space all dressed up for the holidays. Featuring live music by Mateo Jampol & fresh baked pastries and cookies.

  • December 10 Key West
  • Holiday Historic Inn Tours 2021
  • Website
  • During this enchanted Friday evening, the annual Holiday Historic Inn Tours offer an opportunity for locals and visitors alike to explore the beautiful architecture and unique history of some of Key West’s most charming inns while making merry with tasty holiday treats and libation samplings. From 6-8 p.m. each night, revelers can avail themselves of free trolley transportation or use their own bikes, trikes, or vehicles to travel to the various properties, enjoy self-guided tours, and delight in the island’s warm tropical holiday ambience. Participating destinations are the Key West Butterfly and Nature Conservatory, The Gardens Hotel, Island City House Hotel, and Amsterdam’s Curry Mansion Inn.

  • December 10 Key West
  • Fifth Annual Holiday Concert and & Bazaar
  • Website
  • Join the Key West Art & Historical Society, from 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum.  The immensely popular celebration is to feature some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show of magical vector projections on the face of the Custom House Museum. Browse hundreds of unique gift options while enjoying the music, food and libations, on and around the island’s architectural crown jewel.  

  • December 11 Key West
  • Rams Head presents: The Temptations at Coffee Butler Amphitheater
  • Website
  • The Temptations, often referred to as “American Music Royalty,” are world-renowned superstars of entertainment, revered for their phenomenal catalog of music, and prolific career. Otis Williams, the sole surviving original Temptation, Ron Tyson, a lead vocalist with the group for 37 years, Terry Weeks, a lead vocalist for 23 years, and Willie Greene, Jr., base vocalist with the group for four years, are still serenading fans with their soulful voices, lighting up stages with their famous Temptations’ Walk, and bringing joy to audiences of all ages. Doors open 5:30 p.m., show starts 7 p.m.

  • December 11 Key West
  • Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
  • 305-292-3302 Website
  • Decorated dinghies, fishing craft and classic tall ships are to light up the Key West Historic Seaport and harbor areas during the 30th annual Schooner Wharf Bar Lighted Boat Parade. Spectators can view the dozens of creatively bedecked vessels from the Schooner Wharf, the parade’s headquarters where the judges stand is located, and from other bars, restaurants and resorts on and around the seaport’s harborwalk and docks. Festivities including steel band performances begin at 6 p.m.

  • December 11 Key West
  • Eighth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park from 10 a.m. - 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2021 Royal Court.  Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach!  Costumes encouraged!  All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.

  • December 12 Key West
  • The Kingston Trio at Key West Theater
  • Website
  • All three current members, Mike Marvin, Tim Gorelangton and Don Marovich, have intrinsic links to and experience with the original group: Mike is the adopted son of founding member Nick Reynolds, who was also his musical mentor; Tim, a close friend since boyhood, is one of the few musicians outside the Trio who has recorded with Nick Reynolds; and Don Marovich, who has performed with the Trio and who plays the guitar, banjo and mandolin. Many of their personal memories recall the iconic trio’s performances and journey as folk music made its extraordinary ascent to the pinnacle of popular culture – and the top of the music charts. Doors open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.

  • December 15 - 17, 2021 Key West
  • Sugar Rum Cherry: A Burlesque Nutcracker
  • Website
  • Slip into your stockings and pull out your sugarplums for the outrageously cheeky production of Sugar Rum Cherry: A Burlesque Nutcracker. This naughty but nice two-act holiday reverie showcases a bevy of burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

  • December 17 Key West
  • Holiday Historic Inn Tours 2021
  • Website
  • During an enchanted Friday evening, the annual Holiday Historic Inn Tours offer an opportunity for locals and visitors alike to explore the beautiful architecture and unique history of some of Key West’s most charming inns while making merry with tasty holiday treats and libation samplings. From 6-8 p.m. revelers can avail themselves of free trolley transportation or use their own bikes, trikes, or vehicles to travel to the various properties, enjoy self-guided tours, and delight in the island’s warm tropical holiday ambience. December 17 destinations are The Mermaid & The Alligator, Winslow’s Bungalows, Wicker Guesthouse, and the Weatherstation Inn.

  • December 18 Key West
  • 13th Annual Rudolph Red Nose 5K Run/Walk
  • Website
  • Don your festive holiday jammies and join in the fun! Race starts and ends at the Southernmost Beach Café,1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, prizes and a fabulous silent auction. Runners and walkers of all ages and abilities are welcome to participate; first 100 registrants receive a free t-shirt. Register online.

  • December 19 Key West
  • Key West Artisan Market Market, 'Holiday/Shop Local' Edition
  • Website
  • From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote community causes. All artists who show at the event are carefully selected and live and create in the Keys. This week's Market benefits Keys-crafted local, artists and creators.

  • December 19 Key West
  • Children’s Concert at Key West Botanical Garden
  • Website
  • The Key West Tropical Forest & Botanical Garden hosts this family friendly children’s concert featuring local classical guitarist, Mateo Jampol, who is to perform songs especially for children. Performance is to start at 1 p.m. until 1:30 pm in the Garden’s Courtyard.   Following the concert a craft project will be available for to create their own holiday ornament.    This “Snowy Sunday” event is to have snow cones, beverages and treats for sale. Cost is $5 per child with a maximum cost of $10 per family. The Garden is located at 5210 College Road on Stock Island. 

  • December 29 - Jan 15, 2022 Key West
  • Fringe Theater presents: Diva! Live From Hell
  • Website
  • The high school drama club president literally kills for a role and finds himself starring in a "flaming hot" cabaret presented nightly -- live from hell. Wickedly fun. Tickets, show dates and times online. Performances begin at 7 p.m., Fringe Theater, 600 White St.

  • December 31 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2022 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock.

  • December 31 Key West
  • New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Website
  • For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2022. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

  • December 31 Key West
  • New Year's Eve Shoe Drop Celebration
  • Email Website
  • The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

  • January 06 - 08, 2022 Key West
  • Pole Vault in Paradise Competition
  • Website
  • Pole Vault in Paradise brings together pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Higgs Beach. Prize monies for male and female challengers are up for grabs, including additional prize money for any man or woman who breaks the island record.

  • January 06 - 27, 2022 Key West
  • South of Southernmost by Mark Hedden
  • Website
  • Ballast Key is a backcountry island seven miles west of Key West, south of the Southernmost point, once listed for sale for $15.8 million. It was owned and used as a getaway for the influential and the creative by David Wolkowsky, a friend of Tennessee Williams and Truman Capote, and a member of a family with deep and storied Florida roots. Wolkowsky died recently at 99. Under the guidance of the Nature Conservancy, the island was donated to the National Wildlife Refuge system, with the intention of it becoming a backcountry research station. So this amazing, coveted, living fantasy of an island is going back to nature, or at least to being primarily managed for the benefit of the natural world. South of Southernmost is a photography project that documents the shift in Ballast Key’s gravity, as the arc of its story switches from the human to the wild. View the exhibition in The Studios of Key West’s Sanger Gallery, open Tue-Sat., 12-4 .m., free of charge.

  • January 06 - 09, 2022 Key West
  • Key West Literary Seminar
  • Website
  • Each year, the Key West Literary Seminar explores a particular literary theme. For “A Seminar Named Desire” we’re interested in literary explorations of the profane and the profound, the inventive, the graphic, and the deeply felt. This will be a unique gathering of some of today’s most acclaimed writers in conversation about the elemental urge at the center of human activity: desire.

  • January 09 Key West
  • Key West Artisan Market Market, 'Preserve Island Life' Edition
  • Website
  • From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote community causes. All artists who show at the event are carefully selected and live and create in the Keys. This week's Market spotlights the City of Key West's efforts to preserve local culture.

  • January 13 - 16, 2022 Key West
  • Key West Kingfish Mayhem
  • Website
  • This the first tournament of the five-leg Kingfish Mayhem Pro Series. In the winter, Key West is the staging ground for King Mackerel before they start their annual migration in the Gulf. Big fish from the 50-70 lb. range are common in these areas, which creates an exciting and competitive environment at the weigh-in. This event has been enhanced by adding tuna, mahi and wahoo, for a four-species tournament. Teams from all around travel to join this world-class event for their shot at claiming King of Key West!

  • January 15 - 16, 2022 Key West
  • 16th Annual Florida Keys Seafood Festival
  • Website
  • Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen. A $10 admission is good for BOTH Saturday and Sunday. New location this year is to be at Truman Waterfront Park at the end of Southard Street. This event is a fundraiser for the Florida Keys Commercial Fishermen's Association FKCFA and goes to support sustainable fishing programs, marine restoration projects & college scholarships.

  • January 15 - 16, 2022 Key West
  • Key West Half Marathon & 5k Run
  • Barbara Wright 305-240-0727 Email Website
  • Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate. Named as one of the United States' leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by Competitor.com.