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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 2022

  • February 05 - Jan 07, 2023 Key West
  • Market on the Green
  • Website
  • Held the first Saturday of every month from 10 a.m.- 2 p.m., visitors and residents are invited to browse and shop amazing local artisans. The monthly market is located at the Sunset Green Event Lawn, at Key West’s 24 North Hotel.

  • March 31 - Dec 11, 2022 Key West
  • Key West Bicentennial Exhibit at The Custom House Museum
  • Website
  • Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

  • November 23 - Dec 31, 2022 Key West
  • 2022 Harbor Walk of Lights
  • Website
  • The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harbor walk area in the Historic Seaport glimmers with holiday displays throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.

  • December 01 - Jan 01, 2023 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 07 - 11, 2022 Key West
  • Nutcracker Key West
  • Website
  • A unique subtropical version of the classic holiday ballet "The Nutcracker" awaits Keys visitors, flavored with characters and settings that depict Key West's colorful history, vibrant coral reef environment and even free-roaming local roosters. Blending professional dancers and local talents, the production features exquisite costumes and sets inspired by island lore. Performances take place at the Tennessee Williams Theatre at 5901 College Road.

  • December 09 Key West
  • Holiday Lighted Boat Parade of Stock Island
  • The Rotary Club of Key West and the Perry Hotel & Marina invite you to enjoy a boatload of maritime merriment as a colorful fleet decked in holiday lights parades by the Perry Hotel lawn. This will be a family-fun evening to that also includes entertainment, photos with Santa and more. 7001 Shrimp Road.

  • December 09 Key West
  • Holiday Historic Inn Tour
  • Website
  • During this enchanted Friday evening, visit and tour four beautifully decorated island locales: Key West Butterfly & Nature Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation between 6 and 8 p.m. Explore the unique architecture and history at each stop while enjoying sweet and savory holiday treats and libation samplings. Limited trolley transportation will be provided between properties, but participants are encouraged to bike, walk or use their own transportation. Purchase tickets online, then pick up tickets after 5 p.m. on Dec. 9 at Butterfly & Nature Conservatory.

  • December 10 Key West
  • Ninth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park in Key West 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 2022 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 10 Key West
  • Schooner Wharf Annual Key West Lighted Boat Parade
  • Website
  • A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights. Music begins at 6 p.m., parade starts at 8.

  • December 11 Key West
  • Key West Triathlon
  • Website
  • The Key West Triathlon challenges participants to swim in the waters of the Atlantic Ocean, bike along a portion of the Florida Keys’ scenic Overseas Highway and run on a fast, flat course beside the Atlantic. As well as the Olympic-distance and sprint-distance triathlons, Aquabike and sprint duathlon competitions are featured. Higgs Memorial Beach Park, 1000 Atlantic Boulevard, Key West.

  • December 11 Key West
  • Christmas on the Farm
  • Website
  • The Monroe County Sheriff's Animal Farm invites everyone for a "Christmas on the Farm" Open House Sunday, Dec. 11 from 1 to 3 p.m. Santa will be there and each child will receive a gift. There will be live local musicians, and farm veterinarian Dr. Doug Mader will be signing copies of his new book, "The Vet at Noah's Ark." Books are for sale for $25 (cash or check only) with all proceeds donated to the farm. The event is free but donations are appreciated. 5501 College Road, Stock Island.

  • December 16 Key West
  • Holiday Historic Inn Tour
  • Website
  • Visit and tour four beautifully decorated island locales: Hemingway’s Library at Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel, and Island City House, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings between 6 and 8 p.m. Purchase tickets online, then pick them up after 5 p.m. on the night of the tour at the first property, Hemingway’s Library at Papa's Pilar Distillery. Participants will need to walk, bike or use their own transportation between locations.

  • December 16 - 17, 2022 Key West
  • The 12 Days of Christmas: Burlesque Show Spectacular
  • Website
  • This extravaganza, based on the classic Christmas song, combines the talents of world class burlesque performers, circus style entertainers and singers. The cast, lead by Julliard School graduate Shelly Watson along with all your favorite Key West Burlesque dancers, is sure to dazzle audience members. Doors open at 7 p.m., show at 8. Tickets $45 to $100, available online. Key West Theater, 512 Eaton Street.

  • December 17 Key West
  • Key West Botanical Garden Native Plant Sale
  • Website
  • The plant nursery offers native Florida trees, shrubs, vegetables and vines for sale from 9 a.m. to noon the third Saturday of the month. Master Gardener volunteers will be on site to help answer any plant questions. There are 165 species of plants available with an inventory totaling more than 2,000 plants that attract birds and butterflies in 1-gallon to 10-gallon pots. Key West Botanical Garden members receive a discount. The Garden, located at 5210 College Road on Stock Island, is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.

  • December 17 Key West
  • 14th Annual 5K Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join! Starts and ends at 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. Pre-race packet pickup is Friday, Dec. 16 from 5-7 p.m. at the Café. Runners and walkers of all ages and abilities are welcome to participate. Registrants receive a free t-shirt; prizes for most festive and unusual PJ’s. Presented by nonprofit group, A Positive Step for Monroe County.

  • December 18 Key West
  • Key West Artisan Market: Shop Local Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and splendid ocean views as we offer everything you need to cross off your holiday shopping list. Supporting the Key West Shop Mom & Pop and #shoplocalkey west movement to keep our resources right here in our community. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

  • December 18 Key West
  • Key West Lighting of the Menorah
  • Website
  • The City of Key West's annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec.18 from 5 to 6 p.m. 1320 Truman Avenue.

  • December 18 Key West
  • Snowy Sunday Children's Concert at Key West Botanical Garden
  • Website
  • Snowy Sunday, the Key West Tropical Forest & Botanical Garden's annual winter concert, features local classical guitarist, Mateo Jampol performing songs especially for children. The event opens at 1 p.m. and Jampol's concert starts at 1:30 p.m., followed by snow cones (while they last) and delightful holiday activities. Tickets $5 per child at the door with a maximum cost of $10 per family.

  • December 28 - 29, 2022 Key West
  • Old Island Restoration Foundation's Home Tours "Holiday Style"
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating back to 1960. This 63rd series of tours features self-guided tours of homes festively dressed for the holidays on Dec. 28 and 29. After the holidays, home tour dates are Jan. 13-14, Feb. 17-18, and March 17-18. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

  • December 31 Key West
  • New Year's Eve at Sunset Pier
  • "Come Together" for New Year’s Eve with The Beatle Band at the famous Sunset Pier at Ocean Key Resort, located at 0 Duval Street. The party starts at 9 p.m. right over the water. Enjoy a complimentary champagne toast and the annual Key Lime Drop at midnight. $10 donation requested to benefit Mote Marine Laboratory's Center for Coral Reef Research & Restoration.

  • December 31 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2023 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 05 - 08, 2023 Key West
  • Pole Vault in Paradise Competition
  • Website
  • Pole Vault in Paradise brings together pole vaulters from ages 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, with the main event Saturday. 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. Pancake Breakfast from 8 am – 10 am. Admission Free. Pancake Breakfast tickets are sold onsite.

  • January 07 Key West
  • Pancake Breakfast - Higgs Beach
  • Website
  • 8 am – 10 am in support of the Key West High School Track Team and the Mays Sands Montessori School. Pancake Booth is located near the African Cemetery and at the Pole Vault in Paradise competition. Unlimited pancakes and one mimosa (adults only) are included. $20 Adults, $10 Children Tickets at the website and on the day of the event.


  • January 12 - 15, 2023 Key West
  • Key West Literary Seminar
  • Website
  • Each year, the Key West Literary Seminar features a particular theme. "Singing America," the 40th seminar, will center on Black American experiences through poetry, fiction, biography, and history. From slavery and Reconstruction to the Harlem Renaissance, the civil rights movement, today, and into the future. All presentations take place at Coffee Butler Amphitheater, 21 Quay Road, within Truman Waterfront Park. Selected portions of the seminar are free-of-charge and open to the public. Find information and registration online.

  • January 12 - 15, 2023 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 13 - 15, 2023 Key West
  • 25th Annual 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 2023 25th anniversary 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. Ranked among 13 must-do U.S. half-marathons by Competitor.com.

  • January 13 - 14, 2023 Key West
  • Old Island Restoration Foundation's 63rd Annual Key West Home Tours
  • Website
  • Enjoy tours of beautiful and historic Key West homes and gardens. Your ticket purchase supports the ongoing mission of preserving and promoting Key West's unique architecture, culture and history. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

  • January 14 - 15, 2023 Key West
  • 17th Annual Florida Keys Seafood Festival
  • Website
  • Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen. This event is a fundraiser for the Florida Keys Commercial Fishermen's Association FKCFA and goes to support sustainable fishing programs, marine restoration projects and college scholarships. A $10 admission is good for BOTH Saturday and Sunday and the festival is to be held at Bayview Park.

  • January 16 - 20, 2023 Key West
  • The Southernmost Regatta
  • Website
  • Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort's marina, 617 Front Street, after each day’s races.

  • January 17 - 21, 2023 Key West
  • RokIsland Fest 2023
  • Website
  • Staged at the Truman Waterfront Park Amphitheater, the world’s greatest rock bands descend upon the island of Key West for this 4-day music festival in paradise. Single- and multi-day passes available. Performers include Styx, Tesla, Loverboy, Vince Neil, 38 Special, Queensryche, Stryper, Quiet Riot and more.

  • January 24 - 20, 2023 Key West
  • Mile 0 Fest Key West
  • Website
  • Mile 0 Fest Key West is a "must see" boutique destination music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.

  • January 24 - 30, 2023 Key West
  • Kelly McGillis Classic
  • Website
  • Women from countries far and wide will be descending upon Key West for flag football competition, fun and learning. It is anticipated this event is to represent the most international countries, and organizers have hosted teams from USA, Morocco, Spain, Mexico, India, Jamaica, Honduras, El Salvador, and Sweden.

  • January 25 - 29, 2023 Key West
  • Key West Food and Wine Festival
  • Email Website
  • Adventurous aficionados of fine food and vintages can explore creative cuisine, premium wines and unique events in a subtropical island setting during the annual celebration. Whet your appetite for island-style excellence, showcasing local chefs’ culinary flair and favorite indigenous ingredients, intriguing libations and distinctive Florida Keys atmosphere. Ticket sales available online.

  • January 28 - 29, 2023 Key West
  • 38th Annual Key West Craft Show
  • 305-294-1243 Email Website
  • The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.

  • January 31 - Feb 04, 2023 Key West
  • Key Western Fest
  • Website
  • More than 20 of the very best classic country bands bring their massive hits to the Southernmost City in the U.S. for a week of unforgettable songs, sun & sand. Take in the warm sunshine and tunes during the day at the island’s iconic bars, snag a bite from one of the renowned restaurants, leave your troubles on land during a live-music sail on a comfy catamaran, and then sing your heart out under the stars at night at the Truman Waterfront Amphitheater, 21 Quay Rd, Key West. Passes and packages available online.