Events & Festivals

December 2017

  • December 1 – December 31st – Key West Holiday Fest
    Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.
    December 6, 2017 – 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. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration/checkin at 6 p.m. with the Lighted Bike Ride beginning at 7:00 p.m. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Key West Holiday Store. Register online.
  • December 8-10, 2017 – Inaugural Southernmost Spirits Festival
    Enjoy what organizers expect to be the cocktail, culinary and cultural extravaganza celebrated annually each fall in Key West Florida. Appealing to industry insiders, consumer cocktail and culinary lovers alike, the event is to encompass product innovation, education, and of course, a good time filled with entertainment camaraderie and just good fun. Tastings, celebrity bartender competitions and more. Visit website for details.
  • December 8-10, 2017 – Inaugural Key West Grand Prix of the Sea
    Experience non-stop racing action as Sea-Doo, Yamaha, and Kawasaki personal watercraft racers take to the water averaging 75 mph. This race is the final round in 2017 and serves as the overall championship for the PRO Enduro and International Amatuer Championship. Jetcross Jet Ski stand up races will also be a part of this family friendly event free to the public.
  • December 8-10, 2017 – I Love Stock Island
    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, watersports, 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; festival at the park with a free concert; kid’s activities & Little Mr. & Miss contest; a new Stock Island Seamanship Olympics; Discovery Stock Island trolly tours; food events; art studio tours; bike rides and more.
  • December 9, 2017 – 8th Annual TRIKW Triathalon
    Athletes swim, run, and bike among Key West’s ideal scenery and conditions. More than 500 competitors are expected. Two race distances are available: Sprint and the twice-as-long Olympic. For more information, call 305-394-3469.
  • December 2, 2017 – Key West Holiday Parade
    Extremely popular with children due to the shower of candy given out by the parade. Parade begins at Bayview Park in Key West, then heads down Truman Ave to Duval Street. Best viewing is along Truman Ave in Old Town, Key West. FREE. Call 305-292-8100 for more information.
  • December 8 – 10, 2017 – AquaX World Championship
    Personal watercraft (waverunners) racers, both pro and amateur, compete for world championship title.
  • December 9, 2017 – 27th Annual Key West Lighted Boat Parade
    Vessels of every size and shape deck their hulls and light up the night with their creativity and originality to the delight of locals and visitors alike. Santa Claus has been spotted at the helm, ditching his sleigh for a center console or sailboat with mistletoe hanging from the mast. His first mates have included gingerbread men and the Grinch. Other times, dolphins have replaced cold-weather reindeer, ushering in Santa’s sleigh packed with lighted presents. Boats will come into the Key West Bight (Historic Seaport) and pass in front of the judges’ stand at Schooner Wharf Bar. Festivities start at 6 p.m. with the Gerald Adams Steel Your Heart Band, and the parade begins at 8 p.m. Live music all evening with yuletide favorites, plus a traditional ham dinner served from our galley. Captains’ meeting is Friday, December 8 at 8pm. To register your boat or for more information, please call (305) 292-3302.
  • December 9, 2017 – 4th Annual Parade of Paws & Holiday Bazaar
    For the benefit of the the animals at the local Florida Keys SPCA (FKSPCA), this pledge-parade event has pet owners competing for prizes and bragging rights. 10am – 2pm, Higgs Beach Dog Park (across from White Street pier). FREE.
  • December 12 – 20, 2017 – Hanukkah in Key West 2017
    Key West is home to one of Florida’s oldest Jewish communities – with Jews settling here when the City was incorporated in 1832. The first Key West Congregation, B’nai Zion was founded in 1887. Today, during Hanukkah, a large menorah is lit in from of the synagogue each night of the holiday, with Rabbi and congregants gathering for the “festival of lights”. A latke and salmon feast is held the first night. Stop by 750 United Street and celebrate. For more information, call 305-294-3437.
  • December 25, 2017 – Christmas in Key West 2017
    Whatever gift you wish for, spending Christmas in Key West might be at the top of the list. While it never snows, and sometimes a palm tree is substituted for a traditional tree, there still is plenty of Christmas spirit in Key West. Look for historic homes that have added twinkle and magic with lights and displays. And to all a good night!
  • December 27-28, 2017 – 58th Annual Key West House & Garden Tours
    Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-7 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation’s museum and programs.
  • December 31, 2017 – Key West New Year’s Eve
    Celebrations include the lowering of the Conch Shell over Sloppy Joe’s on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.

January 2018

  • Dec. 14, 2017 – Jan. 6, 2018
    Waterfront Playhouse presents: Inspecting Carol
    Grab a large helping of holiday cheer with this hilarious, madcap comedy! It’s a cross between A Christmas Carol and Noises Off. Behind the scenes of a struggling theatre’s annual slapdash production of A Christmas Carol, rehearsals are at a standstill. Tim is no longer Tiny, Scrooge wants to do the play in Spanish (Feliz Navidad), and their funding is on hold pending an inspection. This laugh out loud spoof makes for a night at the theatre that is anything but show business as usual. “Inspecting Carol” is a delightful mix of “A Christmas Carol,” “Noises Off,” “Waiting for Guffman.”
  • Jan. 1, 2018 – Aug. 31, 2018
    Key West Fishing Tournament
    More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) 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.
  • Jan. 11, 2018 – Jan. 14, 2018
    Key West Kingfish Mayhem
    Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.
  • Jan. 11, 2018 – Jan. 14, 2018
    36th Annual Key West Literary Seminar
    The 2018 topic is “Writers of the Caribbean.” Literary aficionados from around the world are to gather for readings, discussions and lectures led by some of contemporary literature’s most acclaimed writers. The island nations of the Caribbean have produced some of the most powerful and exciting writers of our time. For the 36th annual Key West Literary Seminar, we look across the waves to the vital literature that has emerged from this region.
  • Jan. 12, 2018 – Jan. 13, 2018
    58th Annual Key West House & Garden Tours
    Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.
  • Jan. 13, 2018 – Jan. 14, 2018
    13th Annual Florida Keys Seafood Festival
    A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.
  • Jan. 22, 2018 – Jan. 29, 2018
    Kelly McGillis Classic International Flag Football Championship
    Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate.
  • Jan. 24, 2018 – Jan. 28, 2018
    Key West Food & Wine Festival
    Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.
  • Jan. 26, 2018 – Jan. 27, 2018
    Key West Theater presents: Arlo Guthrie
    Arlo Guthrie has been known to generations as a prolific songwriter, social commentator, master storyteller, actor and activist. Born in Coney Island, New York in 1947, Arlo is the eldest son of Marjorie Mazia Guthrie, a professional dancer with the Martha Graham Company and founder of The Committee to Combat Huntington’s Disease, and America’s most beloved singer/writer/philosopher/artist Woody Guthrie. Arlo has become an iconic figure in folk music in his own right with a distinguished and varied career spanning over fifty years. Show starts 8 p.m. each night.
  • Jan. 28, 2018
    Key West Artisan Market presents: Culinary & Wine Show
    Culinary & Wine Show features local chef specialties, exotic cheeses, wine tasting and dozens of great vino by the bottle and case. Guests are encouraged to ride bikes or the bus which conveniently stops in front of the Restaurant Store. Parking is available in the Old Town Parking Garage at 300 Grinnell Street. Please bring your own bags.
  • Jan. 28, 2018
    24th Annual Key West Master Chefs Classic
    Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens.