Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday. Events calendar provided by www.fla-keys.com.

Events in Key West for December, 2018
Year: Month:  
November 21 to December 31,  in Key West
Key West Holiday Fest
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.


December 01,  in Key West
Key West Triathlon and Expo
The Key West Triathlon and Expo expects to host a maximum of 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.
Email: lizlovekw@gmail.com

December 05,  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. 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.
Contact: Claire Hiller at 305-809-5000
Email: claire.hiller@wesleyhouse.org

December 06,  in Key West
Sixth Annual POSH Event
The Paws Often Steal Hearts, or POSH, party is to be held at the Audubon House & Tropical Gardens, 205 Whitehead St., from 6-9 p.m., to benefit the Florida Keys Society for the Prevention of Cruelty to Animals. Attendees are encouraged to wear island-style formal attire and "fascinator" hats. General admission tickets are $40 pre-purchased and $45 at the door, per person.
Contact: 305-304-1232


December 07,  in Key West
Holiday Historic Inn Tours
Enjoy an enchanted evening to include trolley transportation between several participating inns, each decorated for the holidays. Treats and libations are offered at each inn. Event-goers also can provide their own transportation or bicycle to the inns. Contact the Lodging Association of the Florida Keys and Key West to purchase tickets.
Contact: 305-296-4959


December 07 to December 16,  in Key West
Nutcracker Key West
Inspired by the unique and colorful environment of the Florida Keys, Clara and her young Prince encounter enchanted landscapes complete with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea-Star Fairy, and "underwater" sequences of almost unimaginable beauty. Local children, adults and community leaders are cast alongside a nationally-cast corps de ballet in this spectacularly crafted semi-annual production of a beloved classic. Shows held at the Tennessee Williams Theatre.
Contact: Box office 305-295-7676


December 07,  in Key West
Rams Head Productions presents: Paula Poundstone
With smart, observational humor and a legendary spontaneous interaction with the crowd, Paula Poundstone is one of our country's pre-eminent comedians. She improvises with a crowd like a Jazz musician, swinging in unexpected directions without a plan, without a net. There's a disarming ease in her craft, an immediate sense that she's so quick on her feet you need never worry about the possibility of something going wrong. Doors open 7 p.m., show starts 8 p.m., at Key West Theater, 512 Eaton St.


December 07 to December 22,  in Key West
Conch Tour Train Holiday Lights Tours
During its annual holiday lights tours of the southernmost island in the continental United States, the Conch Train travels past decorated historic homes, buildings and neighborhoods. Tours are offered at multiple times with departures from Key West High School, 2100 Flagler Ave. TOUR DATES: Dec. 7, 15, 19, 21 and 22
Contact: 305-294-5161


December 08,  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 Bayview Park's Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.
Contact: 305-809-3881


December 09,  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 09 to December 22,  in Key West
Old Town Trolley’s Holiday Lights and Sights Tours
The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best decorated historic neighborhoods, buildings and homes. TOUR DATES: Dec. 9, 15, 19, 21 and 22
Contact: 305-296-6688


December 13 to January 06,  in Key West
Waterfront Playhouse presents: Peter and the Star Catcher
Who doesn't love the magic of the story of Peter Pan? Peter and the Starcatcher is the Tony Award-winning smash that is packed with theatrical razzle dazzle. This play with music is a prequel to Peter Pan, as we learn how a young orphan boy becomes The Boy Who Won't Grow Up. Based on the best-selling novels of Dave Barry and Ridley Pearson, Peter... uses ingenious stagecraft to bring the adventures of Peter to life.  See website for show dates. Showtimes 8 p.m.
Contact: Box-Office (305-294-5015)
Email: Box-Office@waterfrontplayhouse.org

December 14,  in Key West
Holiday Historic Inn Tours
Enjoy an enchanted evening to include trolley transportation between several participating inns, each decorated for the holidays. Treats and libations are offered at each inn. Event-goers also can provide their own transportation or bicycle to the inns. Contact the Lodging Association of the Florida Keys and Key West to purchase tickets.
Contact: 305-296-4959


December 15,  in Key West
Florida Keys Eco-Discover Center's Discovery Saturday: Building a Coral Reef
Discovery Saturday from 10-11 a.m. is hosted by Mote Marine and includes a lesson for children to learn how corals grow and they will make their own reef using clay, pipe cleaners and beads. Space is limited. The Florida Keys Eco-Discover Center, operated by Florida Keys National Marine Sanctuary, hosts Discovery Saturday for children in kindergarten through fifth grade on the third Saturday of each month. Located in NOAA's Dr. Nancy Foster Florida Keys Environmental Complex on the Truman Annex waterfront in Key West, the Eco-Discovery Center features more than 6,000 square feet of interactive exhibits, which interpret the resources and management efforts of Florida Keys National Marine Sanctuary, two national parks, and four national wildlife refuges.
Contact: Register at 305-809-4750
Email: FKEDC@noaa.gov

December 15,  in Key West
Fifth 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 reigning King and Queen, Tigger and Cat!
Contact: 305-294-4857


December 15,  in Key West
28th Annual Schooner Wharf Bar Annual 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 15,  in Key West
Rudolph Red Nose Run
Don your festive holiday running attire, affix your ruby-red nose, and join in the 11th Annual 5K Rudolph Red Nose Run, Saturday Dec. 15, starting and ending at the Southernmost Beach Café. Race day check-in starts at 7 a.m. with an 8 a.m. start. After the race, enjoy refreshments, fun, prizes and a huge silent auction.


December 15,  in Key West
Maser Gardener Speaker Series at Key West Botanical Garden
The Key West Botanical Garden Society presents Master Gardener, Michelle Leonard-Mularz to begin its 6-month Speaker Series. Held at 1:30 p.m. in the Toppino Nature Chapel. Michelle will speak on "Gardening in the Keys and the Master Gardener Program." Admission is free for members, $5 for non-members. All proceeds directly benefit the Garden's conservation program. The Garden is located at 5210 College Road, Stock Island.
Contact: 305-296-1504


December 22,  in Key West
Key West Full Moon
Locals and visitors come together to Experience the culture of the Florida Keys through dance, performances, food, and drink. All are welcome to join us on this beautiful beach, under a full moon, with a friendly atmosphere that helps compliment what is truly a "celebration of us".  Everyone comes for the explosion of Sound and visual performances, but they all stay for the limbo! Tickets $12 pp.


December 27 to December 31,  in Key West
Fringe Theater presents: Terri White’s Blue Evening
Broadway star Terri White shares her personal journey to Broadway and back again. The evening intersperses personal stories and show tunes, triumphs and challenges. Accompanied by Pianist Megan Clay. Little Room Jazz Club, 821 Duval Street. Show starts 7 p.m.
Contact: Rebecca Tomlinson 305-587-8961


December 28 to December 29,  in Key West
59th 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. Proceeds benefit the foundation's museum and programs.
Contact: 305-294-9501


December 30,  in Key West
Key West Artisan Market
Browse among culinary, textile, jewelry, wood, artists & crafters, curiosities, live music, craft beer, wine and art and food concessions. From 10 a.m. to 2 p.m.,  at a NEW location this year, at Higgs Beach. Bring your own bags. A fantastic, family-friendly, free event. 


December 31,  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: schroedkw@aol.com

December 31,  in Key West
New Year's Eve: Conch Shell Drop at Sloppy Joe's
The arrival of 2019 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,  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 2018. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.


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.






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