Events & Festivals

November 2017

  • November 1 – 5, 2017 – 26th Annual Meeting of the Minds 2017
    Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows include members of Jimmy Buffett’s band. Highlights include the Margaritaville Street Fest on Friday from 1pm – 5:30pm on the 500 block of Duval Street (near Fleming Street) which is FREE and open to the public.
  • November 4, 2017 – 25th Annual ABC 5K Walk/Run
    Sponsored by Zonta, this running race benefits women’s health screenings and breast cancer awareness in the Lower Florida Keys. Race begins and ends at Salute on Higgs Beach. Registration cost is $25 – $35, depending on when you register at For more information, call 305-393-5200.
  • November 5 – 12, 2017 – 36th Annual Key West World Championship
    Considered the pinnacle of offshore powerboat racing. Top powerboat & superboat offshore racers compete for title of World Champion. Spectators line the Key West harbor to see the 100+ mph action. Good viewing from Fort Zachary Taylor State Park at the end of Southard Street. For more information, call 305-296-6166.
  • November 12, 2017 – 20th Annual Taste of the Islands
    A day of food, art, music and fun. No admission fee, taste tickets will be sold to sample culinary treats from area restaurants. Presented by the Marathon chapter of Business & Professional Women, from 11 a.m. to 5 p.m., at Marathon Community Park. Proceeds benefit local scholarships.
  • November 15 – 19, 2017 – Key West Film Festival
    Features independent cinema with awards for narrative feature film, LGBT feature film, documentary, Florida feature film, and foreign feature film. Events include movie screenings, kick-off party, and awards gala.

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.