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.
Events calendar provided by

Events in the Florida Keys for December, 2019
Year: Month:  
June 03 to December 31,  in Islamorada
Diving With a Purpose, 15 Year Odyssey: Restoring Our Oceans, Preserving Our Heritage
Multiple groups such as Diving With a Purpose, the Florida Keys National Marine Sanctuary, Biscayne National Park, and more have spent 15 years working together to showcase cultural and natural resources throughout the country. They focus in the protection, documentation, and interpretation of African slave trade shipwrecks and the maritime history and culture of African-Americans. This new exhibit at the History of Diving Museum, mile marker 82.9, highlights several shipwrecks and aircraft and the archaeological processes used to study them.

November 14 to December 07,  in Marathon
Marathon Community Theater presents: A Greater Tuna
What do Arles Struvie, Thurston Wheelis, Aunt Pearl, Petey Fisk, Didi Snavely, and Bertha Bumiller have in common? In this hilarious send-up of small-town morals and mores, they are all among the upstanding citizens of Tuna, Texas’ third-smallest town. Greater Tuna, the prequel to the Theater’s 2014-15 season’s "A Tuna Christmas,”features two actors creating the entire population of Tuna, Texas. A tour-de-farce of quick change artistry, our two actors travel across the stage like two whirling dervishes donning costume after costume, persona after persona. Two actors, twenty characters, and a barrel of laughs, y’all. Showtimes 8 p.m.; Sunday matinee 3 p.m.

November 27 to December 31,  in Key West
Key West Holiday Fest
A merry range of celebrations during Key West's busy holiday season 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, pet photos with Santa, a “Violins in Motion” concert and multiple New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”

December 01 to July 31,  in Key West
Key West Fishing Tournament
Anglers of all ages and abilities can target more than 40 species of fish in the Key West Fishing Tournament, a free-entry multi-division challenge that takes place Dec. 1 to July. 31, 2020. The tournament features divisions for men, women, junior anglers ages 10 to 15 and Pee Wees under 10 years old — making it ideal for extended families and multigenerational groups who want to share the angling experience.

December 01,  in Big Pine
I Love Stock Island Holiday Lighting Ceremony
Join the businesses and community of Stock Island as they kickoff and celebrate the season with a festive holiday tree lighting ceremony. Free admission; held 5:30 pm - 6:30 pm. Enjoy a Welcome reception, Tree lighting, Social gathering and refreshments. Hearts are to be available for display in honor/memory of your loved ones. Located at Fishbusterz parking lot, at the corner of Maloney and 4th Street.

December 01,  in Key West
Key West Artisan Market: Red Ribbon Day Edition
Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. Bring your own bags! We invite you to "Rock the Red Ribbon Together" and wear a ribbon or pick up a free ribbon from volunteers of the Key West Business Guild.

December 01,  in Key West
Key West Theater presents: Max Weinberg
The longtime drummer of Bruce Springsteen’s E Street Band and bandleader for Conan O’Brien’s previ-ous late-night television show, Max Weinberg, creates a truly interactive experience with “Jukebox”, inviting the audience to choose the set list, in real time, that he and his crack four-piece group will play. Doors open 7 p.m., show starts 8 p.m.

December 04 to December 07,  in Marathon
Zonta’s Festival of Trees
The annual Festival of Trees is to take place at the Florida Keys Country Club. 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 between 5-9 p.m., and Saturday, Dec. 7 from noon to 4 p.m. Wednesday, December 4, begins at 5 pm with an all-new Children’s Night. Santa Clause will be there to visit with all the good little boys and girls and to hear what they want for Christmas this year. There will be juice and cookies and, of course, lots of decorated trees for your enjoyment.

December 04,  in Key West
Key West Lighted Bike Ride
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride - registration begins October 1 online. This year the Coke Florida Caravan will be in Bayview Park to provide free photos with Santa along with cookies (from Winn Dixie) and milk - 5pm – 7:30pm. The Lighted Bike Ride will leave Bayview Park at 7pm Entry fee for the Bike Ride is one unwrapped toy for Holiday Helpers or monetary donation
Contact: Claire Hiller at 305-809-5000
Email: [email protected]

December 05 to December 08,  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.
Contact: Dianne Harbaugh 305-522-4868
Email: [email protected]

December 05 to December 07,  in Key West
COAST is Clear Music & Arts Festival
Coast Projects — along with Key West Art & Historical Society, Green Parrot and Blue Heaven — are to host the Third Annual COAST Is Clear Music & Arts Festival throughout Bahama Village. The festival will feature local arts events and music by a top-notch lineup of internationally acclaimed performers including Rayland Baxter, SUSTO and Tim Reynolds, to name a few.

December 05,  in Key West
Tennessee Williams Theater presents: Sutton Foster
Sutton Foster is an award-winning actor, singer and dancer who has performed in 11 Broadway shows – most recently the revival of Violet – and originated roles in the Broadway productions of The Drowsy Chaperone, Little Women, Young Frankenstein, Shrek The Musical, and her Tony Award-winning performances in Anything Goes and Thoroughly Moder. Showtime 8 p.m., Tennessee Williams Theater, 5901 College Rd.

December 06 to December 23,  in Key West
Old Town Trolley Lights & Sights Holiday Tour
The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition. Along with the awesome sights and excellent narration highlighting fun facts about the island, you’ll also enjoy some complimentary tasty treats like cookies and hot cider. Give you and yours the gift of Key West this year! This tour has a duration of approximately 60 minutes and departs from Mallory Square. Check website for dates and times. Tickets must be purchased online.

December 06,  in Marathon
Marathon Lighted Bike Ride
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Marathon for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Begins at the Frontage Road at the Marathon Airport. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride - registration is available online. This year the Coke Florida Caravan will be at the Marathon Airport to provide free photos with Santa along with cookies and milk 5 p.m. – 7:30 p.m. Lighted Bike Ride will leave the Frontage Road at 7pm.
Contact: Claire Hiller at 305-809-5000
Email: [email protected]

December 06,  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 gift bazaar. Other activities include caroling and a holiday parade.
Contact: 305-664-4503

December 07,  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 07,  in Key West
TRIKW Sprint & Olympic Triathlon
The Key West Triathlon expects up to 1,000 participants and some of the sport's best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances. Event highlights feature an Aquabike competition this year, along with a .76 km Atlantic Ocean swim from Higgs Beach, a 20km U.S. 1 cycling ride along South Roosevelt Boulevard and a 5km run along Smathers Beach.
Email: [email protected]

December 07,  in Key Largo
Light Up Key Largo!
Come get into the spirit of the holidays with the lighting of the Key Largo Xmas tree and loads of fun activities for the kids. Sponsored by the Key Largo Chamber of Commerce, holiday happenings with live music, decorations, food and drinks are to spark the seasonal spirit. The annual tree lighting is to be held at the Murray E. Nelson Government Center and Key Largo Cultural Center, MM 102, from 5-9 p.m. Eggnog, caroling and an appearance from Santa and Mrs. Claus are virtually guaranteed to put everyone in a festive mood.
Contact: 305-451-1414

December 07,  in Marathon
Second Annual Lighting of the Lighthouse & Boat Parade
From 4-9 p.m., enjoy food, music, performances, holiday shopping, Santa Claus and a boat parade all centered around the lighting of the iconic lighthouse at Faro Blanco Resort & Yacht Club, 1996 Overseas Highway. The boat parade is to start at 7 p.m. and is open to everyone!

December 08,  in Islamorada
Fifth Annual Islamorada Half Marathon and 10K
Winter distance runners in the Florida Keys can welcome warmer climes and the return of Islamorada's annual Half Marathon, 10k and the run-for-fun Beach N' Beer Mile. The subtropical road race is open to bucket list runners or newbies of all ages and skill levels. Registration is open for the half-marathon and 10k events Saturday, Dec. 7. At noon the fun-while-you-run Beach N' Beer Mile kicks off from the iconic Robbie's Marina, mile marker 77.5 bayside. The main half-marathon and 10k events Sunday also begin at Robbie's Marina.
Contact: Robbie McClung 305-587-0901
Email: [email protected]

December 08,  in Marathon
Tucker Degraw Memorial Christmas Boat Parade
Christmas lights on outriggers, Santa's elves and brightly lit deck displays highlight the beautiful festivities during the Key Colony Beach Boat Parade. Set to begin at dusk from the 7th Street canal, the parade is open to all boats, and the route visits canals and cuts, and passes city hall three times. Great viewing spots include Sadowski Causeway at MM 53.5 and the dock area behind city hall and the post office. The public is welcome. Sponsored by the Key Colony Beach Fishing & Boating Club

December 08,  in Key West
Third Annual Eaton Street Christmas Stroll
Key West Theater, The Studios of Key West, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts & Key West United Methodist Church reunite for a “new” Christmas tradition! During this new holiday tradition on Eaton Street, each venue will host a short Christmas-themed performance with caroling as you walk from presentation to presentation. The evening will begin at 4 p.m. at St. Paul’s Church. Tickets are $25 per person, available online

December 08,  in Key West
Heirloom Art Auction
Staged at the Hemingway Rum Company, 201 Simonton St., this evening begins at 5:30 p.m. with appetizers prepared by Iron Chefs and signature rum drinks, followed by a live art auction of pieces from the estate of Judge Tegan Slaton and his widow Rosemary Enright. Proceeds are to benefit the Wesley House. Admission is $20, and is applied toward any art purchase.

December 09 to December 22,  in Key West
Conch Tour Train - Holiday Lights Tour
Join the Conch Tour Train for their annual holiday lights tour of the island. To get things started we will serve up some holiday cheer with cider and cookies. Then it is all aboard for an hour tour that takes you to all of the island’s most elaborately decorated houses, buildings and neighborhoods and caroling. Departs from Key West High School, 2100 Flagler Ave., tour is approximately 60 minutes and departs from Mallory Square. Check website for dates and times.

December 12,  in Key West
Key West Art & Historical Society presents: Perpetual Groove
Perpetual Groove continues to create a cultivated, unique experience for each live show. The Georgia jam veterans make a return to the live stage, equipped with a new album, revamped sound and lyrics, along with special guests, The Happy Dog Band. At Fort East Martello, 3501 S. Roosevelt Blvd. From 6-10 p.m. General Admission tickets $25, children 12 and under are free.

December 12,  in Key West
Full 'Cold' Moon Kayak Tour and Adventure with Blue Moon Kayak
Paddle under the glowing sunset and the rising moon. Perfect for all ages and skill level. This trip will have you howlin’ at the moon with the cool breeze and sounds of water splashing against your kayak as you paddle. During the paddle, we break for our popular S’Mores, an American tradition consisting of graham cracker, marshmallow and Hershey chocolate sandwiched together. A delight with everyone. Guests are welcome to bring small coolers filled with favorite beverages and snacks. From 6-8 p.m., depart from Sunset Marina, 5555 College Rd. Book online or call to reserve.
Contact: SIGN UP 305-209-8303
Email: [email protected]

December 12 to December 28,  in Key West
Waterfront Playhouse presents: Around the World in 80 Days
Stampeding elephants! Raging typhoons! Runaway trains! Unabashedly slapstick! Hold onto your seats for the original amazing race! Characters such as Phileas Fogg, Detective Fix, Passepartout, Sir Francis, Aouda and the British Council make for an evening of live entertainment. Showtimes 8 p.m.

December 13 to December 15,  in Big Pine
Third Annual I Love Stock Island Festival
Celebrate Stock Island's culture and heritage with culinary offerings featuring fresh-off-the-boat seafood, wine and beer tastings, history and art studio tours, live music and other elements that showcase the eclectic island and its working waterfront. Highlights include a lighted boat parade from Stock Island Marina Village; kid's activities & Little Mr. & Miss contest, and more.
Contact: Jill Snodgrass 573-680-5468
Email: [email protected]

December 13 to December 15,  in Islamorada
Islamorada Junior Sailfish Tournament
Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates to tie a bimini or rig ballyhoo. One weekend each year anglers aged 16 and younger can apply such lessons in this competition. A maximum of six anglers is allowed per boat. Proceeds aid Florida Keys charities. This tournament has been held since 1964, one of the oldest sailfish events in the Keys.
Contact: Tammie Gurgiolo 305-240-9337
Email: [email protected]

December 13,  in Big Pine
Stock Island Lighted Boat Parade
Kick off the holiday season and the start of the I Love Stock Island Festival at the Stock Island Marina with a procession of lighted vessels in all sizes – kayaks, dinghies, fishing boats, sailing ships, private yachts and more!  Get merry with plenty of free parking, food from Matt's Stock Island, Salty Oyster, The Barrel House, food trucks and more, along with easy viewing of the parade of watercraft. Free, family-friendly and open to the public! Starts at 7 p.m.

December 13,  in Big Pine
Taste of Stock Island
Get off the beaten path and eat your way across Stock Island in a matter of hours as part of the annual I Love Stock Island Festival. From 4-7 p.m., taste a selection of curated plates and beverages at the locals’ favorite spots, and experience one of the Keys’ hidden gems. Plus, be some of the first to experience The Perry's new BBQ & Brews restaurant, The Barrel House! Limited tickets available, purchase online here.

December 14,  in Key West
12th Annual Rudolph Red Nosed 5k Run
Don your festive holiday running attire, affix your ruby-red nose, and join in the fun, starting and ending 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, fun, prizes and a huge silent auction.

December 14,  in Islamorada
Free Outdoor Pops-in-the-Park Band Concert: Suite Dreams
Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.

December 14,  in Marathon
Boot Key Harbor Christmas by the Sea Lighted Boat Parade
Hosted by Marathon Marina and Resort, boats of all sizes, dinghies to yachts, sail or power, are invited to show off their holiday decorating skills. Parade starts at 6 p.m. and winds through Boot Key Harbor and ends with a festive gala at Marathon Marina and Resort at 8:30 p.m. Spectators welcome! A $500 Grand Prize is up for grabs with additional prizes for best in each division.

December 14,  in Key West
29th Annual Schooner Wharf Bar Lighted Boat Parade
Lighted and decorated vessels from rowboats to tall ships proceed around Key West's Historic Seaport and harbor areas. Festivities are to begin at 6 p.m. with the children of Gerald Adams Elementary Steel Your Heart Band! Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport as vessels of all shapes and sizes dazzle the crowd.
Contact: 305-292-3302

December 14,  in Key West
Sixth Annual Parade of Paws and Shopping Bazaar
Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet's photo! Shopping Bazaar inside the dog park features entertainment, food vendors, a Kissing Booth, holiday gifts for that special snuggle bug and more! A unique opportunity to support the lifesaving mission caring for the Keys' community's homeless animals, the event supports the Florida Keys SPCA. Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends to meet the reigning King and Queen.
Contact: 305-294-4857

December 15,  in Key West
Christmas on the Sheriff's Animal Farm
From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff's Office Animal Farm is situated at the county's detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff's Animal Farm is open the second and fourth Sundays of the month.
Contact: 305-293-7300

December 15,  in Key West
Rams Head Production presents: Bret Michaels at Key West Theater
As front man for the legendary rock band Poison, Bret Michaels has sold 25 million records and scored an amazing 15 chartbusting Top 40 singles including "Talk Dirty To Me," "Something To Believe In," "Nothing But A Good Time" and the timeless #1 smash "Every Rose Has Its Thorn." After more than 25 years in the business this award winning, multi platinum superstar's career continues to move at warp speed. Doors open 7 p.m., show starts 8 p.m.

December 15,  in Marathon
Winter Wonderland at Crane Point Museum & Nature Center
Did someone say Reindeer Ponies? From 4-8 p.m., families of all ages can visit with Santa, who will be there to meet with the kids. Other events include: sleigh rides, hot chocolate bar, chocolate fountain, Keys Dance Academy Dancers and more. There are even predictions of snow!

December 15,  in Key West
Key West Artisan Market: Holiday Shop Local edition
Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. From 10 a.m. to 2 p.m., at Clarence H. Higgs Memorial Beach. Bring your own bags. A fantastic, family-friendly, free event. The show will be stocked with keys-made items perfect for gift giving this holiday season.

December 17,  in Key West
South Florida National Parks Trust presents 'Tortugas Tales'
Staged at the Florida Keys Eco Discovery Center, 35 E. Quay Rd., the event is to feature stories from the Dry Tortugas as presented by award-winning authors James Kushlan and Kirsten Hines and updates on Dry Tortugas National Park and its education programs by park manager Glenn Simpson and lead ranger Curtis Hall. 'Tortugas Tales' coincides with the release of a new history book on the Dry Tortugas as an opportunity to feature Dry Tortugas National Park, its human and natural history, current stewardship, visitor opportunities, and to highlight Dry Tortugas National Park educational programs supported by the South Florida National Parks Trust. Event is free and open to the public. Doors open 6 p.m., presentations begin 6:30 p.m. RSVP online.

December 18,  in Islamorada
History of Diving Museum: Immerse Yourself! Free Lecture Series
The Florida Keys were never a hub for the Transatlantic Slave Trade, but because of their location as a gateway to the Caribbean, many significant, associated events occurred here. Archaeologist Dr. Corey Malcom of the Mel Fisher Maritime Heritage Society will speak about his organization’s efforts to document the history and archaeology of the Transatlantic Slave Trade.

December 18,  in Key West
Key West Art & Historical Society Hosts Holiday Concert & Bazaar at Custom House Museum
From 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum. The immensely popular celebration will feature some of Key West’s finest artisans, musicians and choirs, food and libations, free entrance to the museum and its two stories of exhibits, and a dazzling holiday light show of magical vector projections on the face of the Custom House. Browse hundreds of unique gift options while enjoying the music, food and libations on and around the island’s architectural crown jewel, with eggnog to lift the frazzled ‘final shopping days’ spirits and Santa on hand for last minute requests and ‘selfie’ photos.

December 18,  in Marathon
Paint Night Class: Keys Style Holiday Ornaments
Follow along for step-by-step instructions to paint a mermaid and starfish ornament, or choose from several stencils and create your own. Starts at 5:30 p.m., at Overseas Pub & Grill, registration required, cost is $35 pp, sign up online here. A $5 donation per painter benefits the Florida Keys SPCA of Marathon.

December 19 to December 20,  in Key West
Tennessee Williams Theater presents: The Play That Goes Wrong
This Olivier Award-winning comedy is a hilarious hybrid of Monty Python and Sherlock Holmes. Welcome to opening night of The Murder at Haversham Manor where things are quickly going from bad to utterly disastrous. With an unconscious leading lady, a corpse that can’t play dead, and actors who trip over everything (including their lines). Showtimes 8 p.m., Tennessee Williams Theater, 5901 College Rd.

December 19 to December 21,  in Key West
Key West Burlesque presents: Sugar Rum Cherry, A Burlesque Nutcracker
Inspired by the holiday classic “Nutcracker” ballet, this spirited and naughty two-act “reverie” is presented by Key West Burlesque. Clara, a young ingénue, celebrates the season with sugar rum cherry cocktails and is transported in a dream to the “Land of Libations.” The performance is staged at 8 p.m. at the Key West Theater, 512 Eaton St., with doors opening at 7:30 p.m.

December 19,  in Big Pine
Pop & Pour at The Perry: Holiday Ornament Edition
Join artist Jasmine Jones of Ocean Blues Studio for The Perry's version of a 'paint & sip’ class! In true island style, attendees will be painting under the palm trees, but with a holiday twist. This class starts at 7 p.m. at the Salty Oyster, will feature ornament painting, perfect for decorating your own home or for gift-giving. Great for all-ages, and 21+ get a complimentary drink ticket with class purchase! Class $50, includes three ornaments. Limited seats, reserve spot online.

December 19,  in Islamorada
Morada Way Arts & Cultural District presents: Third Thursday Art Walk
Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82 - formerly named Industrial Road - as well as "culinary art" and live music from 6-9 p.m. Free admission. Art Walk is held the third Thursday of each month.

December 21,  in Key West
Discovery Saturday Educational Series: Coral Crafts
Kids in kindergarten through fifth grade are invited to join the free, fun-filled Discovery Saturday at the Florida Keys Eco-Discovery Center (35 East Quay Road, Key West) from 10-11 a.m. Hosted by Reef Relief, children will make candy coral crafts and learn. Free admission, free parking. Discovery Saturday is held the third Saturday of every month. Pre-registration is recommended. The Florida Keys Eco-Discovery Center is located at 35 East Quay Road on the Truman Annex waterfront in Key West.

December 21,  in Key Largo
Key Largo Boat Parade
Blackwater Sound will shimmer as decorated boats parade along the shoreline in celebration of the holiday season.  The best viewing and libations are to be found at Jimmy Johnson’s Big Chill, Sundowner’s Restaurant and the Caribbean Club, MM 103-104 Bayside.  The parade is free to enter; one grand prize winner and one randomly selected lucky boat are to receive $500 each.  Hosted by The Rotary Club of Key Largo Sunset, the parade starts at 7:30 p.m.
Contact: Marlen Weeks 305-394-1680

December 22,  in Key West
Candy Canes and Kayaks
From 5:30 - 7:30 p.m., Blue Moon Kayak Key West will take you on the Gulf and around Stock Island to view the twinkling holiday lights across the water. Join a family-friendly event with candy canes for everyone! $50 per person. Departs from Sunset Marina, 5555 College Rd.

December 22 to December 28,  in Key West
Truman Little White House - Little White House Holiday Tours
Imagine how it must’ve been to celebrate the holidays with the Truman’s in the 1940s. An impeccably appointed tree decked with the finest ceramic and glass ornaments. The intoxicating aroma of cinnamon and spruce. Now you can travel back to a simpler time with this exclusive tour with some very special treats in store! Dates: Dec. 22, 23, 27 & 28; from 6:30 - 8:30 p.m.

December 26 to December 31,  in Key West
Fringe Theater presents: An Evening Lost with Lillian Baxter
1970s TV icon Lillian Baxter just had her show cancelled. What’s a "everything's coming up roses" girl to do? Industrial musicals, game shows, sitcoms, and Broadway for a start! Lillian reminds us that what is lost can always be found. Performance 7 p.m. at Little Room Jazz Club, 821 Duval St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
Contact: 305-731-0581
Email: [email protected]

December 27 to December 28,  in Key West
60th Annual Key West Home Tours
Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-6 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $35 in advance, $40 day-of-tour. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in the Key West local community fulfilling OIRF’s mission of “Celebrating and sustaining Key West’s unique architecture, culture and history.” 
Contact: 305-294-9501

December 28,  in Key West
Rams Head Productions presents: Blackberry Smoke
Scorched-blues and Southern rock fans are going to love this show! Performances also from Georgia Satellites and Bishop Gun, of Natchez, Mississippi, rooted in the history and sounds of their home and the surrounding Delta, featuring a blend of rock and roll, soul and blues. Starts at 4 p.m. Key West Amphitheater, Truman Waterfront at 21 Quay Rd. Tickets available online.

December 29,  in Key West
Key West Artisan Market: Bring in the New! edition
Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. From 10 a.m. to 2 p.m., at Clarence H. Higgs Memorial Beach. Bring your own bags. A fantastic, family-friendly, free event. The artists will be stocked with keys-made items perfect to treat yourself to the gift you always wanted! Plus check out the selection of wine by the bottle, great snacks for your New Year's Eve festivities and fabulous cuisine worthy of a special dinner celebrating 2020.

December 29,  in Marathon
Banana Bay Bazaar
The Banana Bay Bazaar is a premier art and culture event held the last Sunday of every month at the infamous sunset bar, The Pointe. This outdoor, fully immersive experience will showcase diverse arts and local vendors bringing together some of the best attractions to give attendees a wonderful taste of The Florida Keys. Celebrate the afternoon with live local music, food trucks and drinks offered at The Pointe, from 1-6 p.m., inside Banana Bay Resort, mile marker 45.9 bayside.  

December 31,  in Big Pine
Sun Salutations and Health & Fitness Fair
Enjoy the new event lawn at The Perry Hotel for '108 Sun Salutations' from 8 a.m. to 12 p.m. to end 2019 on a fit note! This donation-based event is open to the public with donations to benefit the Florida Keys SPCA animal rescue shelter. Celebrate your practice with a mimosa toast, then shop health & fitness booths including FYT Key West, Amber Air Essentials, and more. Booths open at 9:30 following yoga - please BYOM (bring your own mat).

December 31,  in Marathon
Isla Bella Beach Resort's New Year's Eve Dinner, Dancing & Celebration
Ring in the New Year at Marathon’s new Isla Bella Beach Resort for a night of food, spectacular views and dancing the night away.  Evening includes a one-hour cocktail reception overlooking the water, dinner buffet featuring a seafood bar, carving station, creative sides, and dessert bar, followed by dancing the night away. Open to the public, reservations required. Per person fees apply.

December 31,  in Key West
Old Island Restoration Foundation presents: 1860s or 1960s Costume Gala
Travel back to the 1960’s for our 60th year anniversary themed NYE party. The fabulously dressed 21-plus crowd sets the scene. This is an exclusive event at the Garden at the Oldest House Museum, 322 Duval St. Limited Seating. The porch will also be open to watch the revelers promenade on Duval Street. Gate opens 6:00 pm; Dinner 8:15pm; Countdown at midnight. Tickets $225pp, available online.

December 31 to January 01,  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 to January 01,  in Key West
New Year's Eve: Conch Shell Drop at Sloppy Joe's
The arrival of 2020 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. Thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. and featuring dancing in the street and a countdown to midnight recorded on a huge clock.

December 31 to January 01,  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 2020. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

December 31 to January 01,  in Islamorada
New Year's Eve Celebrations in Islamorada
Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the beach at Morada Bay Beach Café at MM 81.6 bayside, who is to host a colorful large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.
Contact: 305-664-0604

December 31 to January 01,  in Key Largo
Sundowners Key Largo New Year's Eve Celebration
The back bay is the setting for the annual New Year's Eve fireworks extravaganza hosted by Sundowners, mile marker 104 bayside, with live music to accompany the night. Check website for details and to reserve seats for a special NYE dinner. Midnight fireworks to follow.
Contact: 305-451-5566

December 31 to January 01,  in Islamorada
New Year's Eve at Cheeca Lodge & Spa
For a casually elegant celebration, Cheeca Lodge & Spa, located at MM 82 oceanside, is planning live music and a midnight fireworks display over the Atlantic Ocean. Known for its renowned cuisine and beachside location, Cheeca is an ideal spot for revelers and romantics to ring in 2020. Call for more information about dining and reservations.
Contact: 305-664-4651, ext. 4580.

December 31,  in Key West
Key West Dachshund Walk
Frost-free Key West becomes a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.

December 31 to January 01,  in Key West
New Year's Eve Dockside Bash on Schooner America 2.0
Enjoy a front-row seat for the famous "Lowering of the Wench" at Schooner Wharf Bar! This special adults-only event features complimentary beer, wine, champagne, well drinks, soda, and water and delicious hot and cold hors d' oeuvres! From 9:30 PM- 12:30 AM; tickets for purchase are limited so reserve early.
Contact: 646-772-4880
Email: [email protected]

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]

© The Lodging Association of the Florida Keys and Key West. All rights reserved.
Design & Hosting by