Event calendar courtesy of fla-keys.com
The Tourism & Development Council of the Florida Keys

  • 12/7/2019 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.
  • 12/7/2019 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.
  • 12/7/2019 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 pu
  • 12/7/2019 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!
  • 12/8/2019 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 Su
  • 12/8/2019 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
  • 12/8/2019 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.
  • 12/8/2019 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
  • 12/9/2019 - 12/22/2019 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.
  • 12/12/2019 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.
  • 12/12/2019 Full "Cold" Moon Kayak Tour

    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
  • 12/12/2019 - 12/28/2019 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.

Check Availability