The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
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Events in the Florida Keys for December, 2021
Year: Month:  
April 21 to December 31,  in Islamorada
History of Diving Museum Exhibit: Diving in Pop Culture
Visit the museum at 82990 Overseas Highway (mile marker 83) to see the latest exhibit with representations of diving in literature, advertising, film, television, games, music, attractions, collectibles, and more, while examining connections amongst these works. Museum staff has been collecting and researching all of the creative ways diving has been incorporated into pop culture for over 100 years.

November 30 to December 04,  in Marathon
Zonta’s Festival of Trees
The annual Festival of Trees is to take place at the Marathon Community Theater, 5101 Overseas Highway. Holiday trees are festively displayed, and decorated by members of the Zonta Club of Marathon, a humanitarian service organization. Visitors and residents can view and bid to purchase the decorated trees during open hours: Tue-Thur 3:30-8 p.m., Fri 3:30-9 p.m., Sat 10 a.m. to 9 p.m. (from 10 a.m. to 12 p.m., kids can enjoy cookies and photos with Santa). No charge for admission; just come and enjoy the trees or purchase raffle tickets for a chance to win your favorite tree.

December 01 to July 31,  in Key West
Key West Fishing Tournament
More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.

December 01 to January 01,  in 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 to December 30,  in Key West
The Studios of Key West presents: Winter Members' Show
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 02 to December 05,  in Islamorada
Islamorada Sailfish Tournament
The first leg of the triple-crown Florida Keys Gold Cup Championship series is the only tournament in the series to offer a junior division for anglers age 16 and younger. Unlimited anglers are allowed per vessel. Two subsequent fishing events in the Gold Cup Series include the Cheeca Lodge Presidential Sailfish Tournament scheduled Jan. 21-23, 2022, and the Islamorada Fishing Club Sailfish Tournament scheduled Jan. 26-27, 2022, when the series culminates and an overall Gold Cup Series champion is crowned.
Email: [email protected]

December 02 to December 05,  in Islamorada
Islamorada Sailfish Tournament
Continuing a 50-plus-year tradition, the Florida Keys Gold Cup Sailfish Championship triple-crown series is to open with the Islamorada Sailfish Tournament, a primary fundraiser for the Islamorada Charter Boat Association.  Social events are to be headquartered at the Whale Harbor Inn and Marina complex at mile marker 83.

December 03,  in Islamorada
Islamorada Chamber of Commerce Florida Keys Holiday Festival
The fun is set for 4-10 p.m. at the Founders Park beach area, mile marker 87. The crowd-pleasing celebration centerpiece, a 35-foot-tall holiday tree with “magical” snow blowing from its branches, is to be lighted at 6 p.m. Kids can frolic in a magical 30-ton snow mountain during the event and watch the lighting of a 35-foot-tall community tree. Parents can bid on one-of-a-kind Keys-designed ornaments during a silent auction and explore a holiday gift bazaar. Other activities include caroling and a holiday parade at 7:30 p.m.
Contact: 305-664-4503

December 03 to December 05,  in Key West
COAST is CLEAR Music and Arts Festival
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 03,  in Big Pine
Green Pineapple at The Perry Holiday Artist Showcase
From 5:30 - 7:30 p.m. at The Perry Hotel, 7001 Shrimp Road on Stock Island, shop new collections, find the perfect gift, and sip on wine & champagne while exploring each of the featured artists including local favorite ZEN by Karen Moore, a holistic jewelry & accessory company that specializes in one-of-a-kind, meaningful pieces that are just right for you or for gift giving. Come say hello, find the perfect holiday gifts and support small businesses and local Keys artists.

December 04,  in Key West
Tri Conch Republic
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. 
Email: [email protected]

December 04,  in Key West
Key West City Hometown Holiday Parade
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.
Contact: 305-809-3881

December 05,  in Marathon
Pet Photos with Santa
Hosted by Courtyard Marathon, Santa is to pose for photos with pets from 2-4 p.m. The event supports the medical and special needs for the shelter animals at Florida Keys SPCA campus in Marathon. With a $50 cash donation, you will get a 10 min professional photo shoot (by McLaughlin Photo & Video) with your pet and Santa. Pets can also join us on the beach before/after their photo shoot at our Doggie Beach Party with a cash bar for their humans. Contributions of pet food, toys, beds or financial donations for the FKSPCA are also welcomed.
Contact: 305-743-DOGS

December 05,  in Marathon
Annual Lighting of the Lighthouse
From 3-6 p.m., enjoy food, music, performances, holiday shopping in a marina walk marketplace, Santa Claus and holiday buoy decorating, all centered around the lighting of the iconic lighthouse at Faro Blanco Resort & Yacht Club, 1996 Overseas Highway. Open to everyone!

December 05,  in Key West
Key West Artisan Market, 'For the Birds' Edition
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,  in Key Largo
Santa’s Sip & Sail Christmas
This holiday fundraiser takes place at the Upper Keys Sailing Club from 12 - 4 p.m. at 100 Ocean Bay Drive (MM 99.5 Bayside). Santa and his elves are to arrive on his water sleigh at noon, kicking off an afternoon of family fun. For a $10 donation, have a family photo taken with Santa aboard a sailboat overlooking the beautiful Florida Bay! The fun continues with a petting zoo, Christmas cookie decorating and ornament design, and adult beverages. Sailing lessons will be raffled off. Proceeds support youth sailing instruction for local children.
Contact: 305-747-2600
Email: [email protected]

December 05,  in Key West
Eaton Street Christmas Stroll
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,  in Key West
Holiday Historic Inn Tours 2021
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 to December 11,  in Marathon
Home for the Holidays
Enjoy a family friendly evening filled with cheer, joy and music at Marathon Community Theatre's Annual Holiday Show & Sing-Along concert. Doors open 7 p.m., show starts at 8 p.m.; tickets $10 per person, available online. The annual family-friendly show is to run one hour with no intermission and include musical selections from the Island Harmony Singers, the MCT Children’s Chorus as well as local church groups and singers. Be entertained by dancers from Prodigy Dance Center and the MCT Dance Department as they dance to classic Holiday Tunes!

December 10,  in Key West
Fifth Annual Holiday Concert and & Bazaar
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 10 to December 12,  in Islamorada
Islamorada Junior Sailfish Tournament
The Florida Keys’ oldest sailfish tournament for kids age 16 and under, this event has been held since 1964.
Contact: Tammy Gurgiolo 305-240-9337
Email: [email protected]

December 11,  in Key West
Eighth Annual Florida Keys SPCA Parade of Paws
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 11,  in Key West
Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
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.
Contact: 305-292-3302

December 11,  in Key Largo
Key Largo Holiday Lighted Boat Parade
Boats of all sizes are to show off festive decorations in a lively procession of vessels on Key Largo’s Blackwater Sound. Presented by the Key Largo Sunset Rotary Club, the parade is to be themed “Nauty-cal & Nice!” in salute to the community’s lighthearted holiday spirit. Spectators can enjoy the fun from viewing spots at Sundowners, Cactus Jack’s, Señor Frijoles, the Key Largo Bay Marriott Beach Resort and Caribbean Club, all around mile markers 103-104.

December 11,  in Big Pine
Kiki's Annual Lighted Boat Parade
All boats are welcome to enter the Pine Channel Causeway parade including deep-sea cruisers, dinghies, kayaks and canoes. Santa and Mrs. Claus are expected to arrive and hand out candy to the kids. The best recommended viewing is from Kiki's Sandbar, 183 Barry Ave. on Little Torch Key. Parade begins at 7 p.m.

December 11,  in Key West
Rams Head presents: The Temptations at Coffee Butler Amphitheater
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,  in Islamorada
Seventh Annual Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N' Beer Mile
Whether bucket-list runners or newbies, participants of all ages and skill levels are invited to register for the subtropical footrace. In the Beach N’ Beer Mile, runners must consume four beers over a 1-mile course in Islamorada. Organizers said the best time to beat for the event is seven minutes. Cash prizes are to be awarded the top three male and female half-marathon finishers, as well as awards for the top three finishers of the 10k.

December 11,  in Islamorada
Pops in the Park with Keys Community Concert Band
Some of the best things in life are free, at least in the Florida Keys. Through the dedication and talent of Florida Keys Community Concert Band members and supporters, music enthusiasts can enjoy an entire Pops in the Park season of themed outdoor concerts free, Saturdays at 4 p.m., at Founder’s Park, mile marker 87 bayside in Islamorada. This month’s theme is “(Not So) White Christmas.”

December 12,  in Key West
The Kingston Trio at Key West Theater
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 12,  in Marathon
Key Colony Beach Lighted Boat Parade
Christmas lights on outriggers and displays on boat decks are part of the beautiful festivities at the Key Colony Beach Boat Parade, set to begin at the 7th Street canal at 6 p.m. Great viewing spots include Sadowski Causeway at mile marker 53.5. Sponsored by the Key Colony Beach Fishing and Boating Club, participants vie for awards in Best Boat Overall, Best Boat under 30 ft, Best Boat over 30 ft.
Contact: (305) 743-7214

December 14 to March 24,  in Key West
Southernmost Chamber Music Society 2021-22 Season
The Dec. 14 concert celebrates the holidays with Keys Choral Arts! Other concerts of the season include a January concert featuring music from the baroque period, with composers like Bach, Handel, Soler and others. February welcomes the Classic and Romantic periods, Mozart, Brahms, Schubert, and others. In March, the French romantic literature. Performance dates: January 20; February 24; March 24. Guest musicians have been invited to join throughout the season, both local and from across the country. Concerts will be on Thursday evenings at 7 p.m., held in the Parish Hall at the rear of the property of St Paul's Episcopal Church, 401 Duval St.
Contact: 305-296-5142
Email: [email protected]

December 15 to December 17,  in Key West
Sugar Rum Cherry: A Burlesque Nutcracker
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 16,  in Key West
Walk on White
From 5-8 p.m. enjoy a monthly art walk through the White Street Arts District, from Southard St to United St. Walk on White is to continue on the Third Thursday of each month. Participants include galleries (such as Stone Soup, Harrison Gallery, Shade Ceramics and Shutter Photography, and Bone Island Graphics), studios such as Artists at the Armory and Coffee Mill Dance Studios, eateries such as Mayanjali Cafe, and other fine businesses.

December 17,  in Key West
Holiday Historic Inn Tours 2021
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,  in Key West
13th Annual Rudolph Red Nose 5K Run/Walk
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,  in Key West
Children’s Concert at Key West Botanical Garden
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 19,  in Key West
Key West Artisan Market Market, 'Holiday/Shop Local' Edition
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 29 to January 15,  in Key West
Fringe Theater presents: Diva! Live From Hell
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,  in Key West
New Year's Eve Shoe Drop Celebration
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.
Email: [email protected]

December 31,  in Key West
New Year's Eve: Conch Shell Drop at Sloppy Joe's
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,  in Key West
New Year's Eve: Pirate Wench Drop at Schooner Wharf
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,  in Marathon
New Years Eve Party at Faro Blanco Resort
Toast to the New Year with complimentary champagne and the resort’s famous anchor drop from the iconic Faro Blanco lighthouse at midnight! Dinner at Lighthouse Grill is to be served 5-9 PM. Reservations are highly encouraged. Enjoy DJ music, dancing, photo booth & more, from 9 p.m. to midnight.

The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

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