Key West Events Calendar

key west holiday fest
November 21 - Dec 31, 2018, in Key WestKey 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. 
key west artisan market
December 02 - 30, 2018, in Key WestKey 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., every three weeks (except Easter), at a NEW location this year, at Higgs Beach. Bring your own bags. A fantastic, family-friendly, free event. Dates: Dec. 2, 16 & 30.
key west lighted bike ride
December 05, in Key WestKey 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.
POSH Key West
December 06, in Key WestSixth 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. 
The Nutcracker
December 07 - 16, 2018, in Key WestNutcracker 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. 
historic inns in key west
December 07, in Key WestHoliday 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. 
the conch tour train in key west
December 07 - 22, 2018, in Key WestConch 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
paula poundstone
December 07, in Key WestRams 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. 
key west holiday parade
December 08, in Key WestKey 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. 
key west sheriff animal farm
December 09, in Key WestChristmas 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. 
holiday lights and sights tours
December 09 - 22, 2018, in Key WestOld 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
peter and the star catcher
December 13 - Jan 06, 2019, in Key WestWaterfront 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. 
peachy poo holiday revue
December 14 - 21, 2018, in Key WestChief Peachy-Poo’s Holiday Revue 
Deck the halls and jingle your balls, it's time for Chief Peachy-Poo's Holiday Revue! Key West's smallest strongman and drag-tastic super star, Chief Peach, hosts two evenings of holiday cheer. Peach is joined by the Conch Republic's Queen of Burlesque, Tatah DuJour, along with Nick Mazza, and the Key West Burlesque Dancers to celebrate the season. The show will feature festive weekly guest performers including Sofia Luna, Aurora Natrix, and Cheeky Derrière. Doors open at 7:30 p.m., show starts at 8 p.m. Show nights Dec. 14 & 21 at the Backroom at Sidebar 504 Angela St. 
rudolph red nose run
December 15, in Key WestRudolph 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. 
building a coral reef
December 15, in Key WestFlorida Keys Eco-Discover Center's Discovery Saturday: Building a Coral Reef 
Discovery Saturday from 10-11 a.m. is hosted by Reef Relief 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.
pet parade
December 15, in Key WestFifth 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! 
December 15, in Key West28th 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.
December 27 - 31, 2018, in Key WestFringe 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.
December 28 - 29, 2018, in Key West59th 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. 
December 31, in Key WestNew 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 WestNew 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 WestNew 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. 
December 31, in Key WestKey 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.