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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 December

  • November 27 - Dec 31, 2019 Key West
  • Key West Holiday Fest
  • Website
  • A merry range of celebrations during Key West's busy holiday season includes lighting of 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 - Jul 31, 2020 Key West
  • Key West Fishing Tournament
  • Website
  • 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 Key West
  • Key West Artisan Market: Red Ribbon Day Edition
  • Website
  • 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 Key West
  • Key West Theater presents: Max Weinberg
  • Website
  • 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 01 Key West
  • World AIDS Day Service at the Key West AIDS Memorial
  • Website
  • Come out and join your friends in celebrating the lives of loved ones in Key West, the first United States City to have an AIDS Memorial. . The Key West World AIDS Day Service will be held at the AIDS Memorial, at the foot of White Street and the Edward B. Knight Pier, on Sunday, December 1 at 5 pm. The service begins with a candlelight Memorial March from the Key West City Hall down White Street to the Memorial.  Marchers will assemble at 4:30 PM.
  • December 04 Key West
  • Key West Lighted Bike Ride
  • Claire Hiller at 305-809-5000 Email Website
  • 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
  • December 05 - 07, 2019 Key West
  • COAST is Clear Music & Arts Festival
  • Website
  • 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 Key West
  • Tennessee Williams Theater presents: Sutton Foster
  • Website
  • 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 - 23, 2019 Key West
  • Old Town Trolley Lights & Sights Holiday Tour
  • Website
  • 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 07 Key West
  • TRIKW Sprint & Olympic Triathlon
  • Email Website
  • 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.
  • December 07 Key West
  • Key West City Hometown Holiday Parade
  • 305-809-3881 Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Bayview Park's Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.
  • December 08 Key West
  • Heirloom Art Auction
  • Website
  • 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 08 Key West
  • Third Annual Eaton Street Christmas Stroll
  • Website
  • 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 09 - 22, 2019 Key West
  • Conch Tour Train - Holiday Lights Tour
  • Website
  • 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 Key West
  • Full "Cold" Moon Kayak Tour
  • SIGN UP 305-209-8303 Email Website
  • 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.
  • December 12 Key West
  • Key West Art & Historical Society presents: Perpetual Groove
  • Website
  • 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 - 28, 2019 Key West
  • Waterfront Playhouse presents: Around the World in 80 Days
  • Website
  • 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 14 Key West
  • Sixth Annual Parade of Paws and Shopping Bazaar
  • 305-294-4857 Website
  • 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.
  • December 14 Key West
  • 29th Annual Schooner Wharf Bar Annual Lighted Boat Parade
  • 305-292-3302 Website
  • 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.
  • December 14 Key West
  • 12th Annual Rudolph Red Nosed 5k Run
  • Website
  • 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 15 Key West
  • Key West Artisan Market: Holiday Shop Local edition
  • Website
  • 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 15 Key West
  • Christmas on the Sheriff's Animal Farm
  • 305-293-7300 Website
  • 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.
  • December 15 Key West
  • Rams Head Production presents: Bret Michaels at Key West Theater
  • Website
  • 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 17 Key West
  • South Florida National Parks Trust presents 'Tortugas Tales'
  • Website
  • 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 Key West
  • Key West Art & Historical Society Hosts Holiday Concert & Bazaar at Custom House Museum
  • Website
  • 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 19 - 20, 2019 Key West
  • Tennessee Williams Theater presents: The Play That Goes Wrong
  • Website
  • 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 - 21, 2019 Key West
  • Key West Burlesque presents: Sugar Rum Cherry, A Burlesque Nutcracker
  • Website
  • 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 22 - 28, 2019 Key West
  • Truman Little White House - Little White House Holiday Tours
  • Website
  • 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 - 31, 2019 Key West
  • Fringe Theater presents: An Evening Lost with Lillian Baxter
  • 305-731-0581 Email Website
  • 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. 
  • December 27 - 28, 2019 Key West
  • 60th Annual Key West Home Tours
  • 305-294-9501 Website
  • 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.” 
  • December 28 Key West
  • Rams Head Productions presents: Blackberry Smoke
  • Website
  • 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 Key West
  • Key West Artisan Market: Bring in the New! edition
  • Website
  • 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 31 Key West
  • Old Island Restoration Foundation presents: 1860s or 1960s Costume Gala
  • Website
  • 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 - Jan 01, 2020 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.
  • December 31 - Jan 01, 2020 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • 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 - Jan 01, 2020 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 2020. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.
  • December 31 Key West
  • Key West Dachshund Walk
  • Website
  • 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 - Jan 01, 2020 Key West
  • New Year's Eve Dockside Bash on Schooner America 2.0
  • 646-772-4880 Email Website
  • 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.

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