Nov 30, 2021 – Dec 4, 2021 Marathon
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.
Dec 1, 2021 – Jan 1, 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.”
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.
Dec 2, 2021 – Dec 5, 2021 Islamorada
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.
Dec 2, 2021 – Dec 30, 2021 Key West
This annual winter members’ show is a celebration and serves as a kick off for the season of events at Studios of Key West. Stop in to see what the artist members have been up to lately, and view the exhibition. Gallery is open Tue-Sat., 12-4 p.m., and admission is free of charge.
Dec 2, 2021 – Dec 30, 2021 Key West
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.
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.
Dec 3, 2021 – Dec 5, 2021
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.
Dec 3, 2021
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.
Dec 4, 2021
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 Smather’s 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 Smather’s Beach. Friends, family and music welcome the athletes through the finish line.
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.
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.
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!
Dec 5, 2021
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.
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.
Dec 5, 2021
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.
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!
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.
Dec 10, 2021 – Dec 12, 2021
Islamorada Junior Sailfish Tournament
Tammy Gurgiolo 305-240-9337 Email
The Florida Keys’ oldest sailfish tournament for kids age 16 and under, this event has been held since 1964.
Dec 11, 2021
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.
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.
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.
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.
Dec 11, 2021
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.”
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.
Dec 12, 2021
(305) 743-7214 Website
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.
Dec 14, 2021 – Mar 24, 2022
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.
December 14 7pm at St. Paul’s Episcopal Church • 401 Duval St Tickets $30 • Seating is Limited PLEASE RESERVE online at keyschoralarts.org, or Keys Choral Arts Facebook page. Tickets may be purchased at the front door if space is available. We suggest the use of masks for our audience members during the concert.
Dec 15, 2021 – Dec 17, 2021
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.
Dec 18, 2021
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.
Dec 19, 2021
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.
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.
Dec 31, 2021
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.