The Florida Keys & Key West

Calendar of Events

Current Key West Events

Image for Key West Holiday Fest
Image for Key West Artisan Market
  • Dec. 2, 2018 - Dec. 30, 2018 Location: Key West
  • Key West Artisan Market
  • Website
  • 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.
  • Dec. 7, 2018 - Dec. 22, 2018 Location: Key West
  • Conch Tour Train Holiday Lights Tours
  • 305-294-5161 Website
  • 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
Image for Nutcracker Key West
  • Dec. 7, 2018 - Dec. 16, 2018 Location: Key West Category: Arts & Culture
  • Nutcracker Key West
  • Box office 305-295-7676 Website
  • 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.
Image for Waterfront Playhouse presents: Peter and the Star Catcher
  • Dec. 13, 2018 - Jan. 6, 2019 Location: Key West Category: Arts & Culture
  • Waterfront Playhouse presents: Peter and the Star Catcher
  • Box-Office (305-294-5015) Email Website
  • 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.
  • Dec. 14, 2018 - Dec. 21, 2018 Location: Key West
  • Chief Peachy-Poo’s Holiday Revue
  • Tickets 305.294.0555 Website
  • 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.
Image for Holiday Historic Inn Tours
  • Dec. 14, 2018 Location: Key West
  • Holiday Historic Inn Tours
  • 305-296-4959 Website
  • 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.
Image for 28th Annual Schooner Wharf Bar Annual Lighted Boat Parade
  • Dec. 15, 2018 Location: Key West
  • 28th Annual Schooner Wharf Bar Annual Lighted Boat Parade
  • 305-292-3302 Website
  • 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.
  • Dec. 15, 2018 Location: Key West
  • Maser Gardener Speaker Series at Key West Botanical Garden
  • 305-296-1504 Website
  • 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.
Image for Florida Keys Eco-Discover Center's Discovery Saturday: Building a Coral Reef
  • Dec. 15, 2018 Location: Key West
  • Florida Keys Eco-Discover Center's Discovery Saturday: Building a Coral Reef
  • Register at 305-809-4750 Email Website
  • 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.
Image for Fifth Annual Parade of Paws and Shopping Bazaar
  • Dec. 15, 2018 Location: Key West
  • Fifth Annual Parade of Paws and Shopping Bazaar
  • 305-294-4857 Website
  • 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!
Image for Rudolph Red Nose Run
  • Dec. 15, 2018 Location: Key West
  • Rudolph Red Nose Run
  • Website
  • 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.
Image for Fringe Theater presents: Terri White’s Blue Evening
Image for 59th Annual Key West Home Tours
  • Dec. 28, 2018 - Dec. 29, 2018 Location: Key West
  • 59th Annual Key West Home Tours
  • 305-294-9501 Website
  • 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.
Image for New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Dec. 31, 2018 Location: Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • 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.
Image for New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Dec. 31, 2018 Location: Key West
  • New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Website
  • 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.
Image for Key West Dachshund Walk
  • Dec. 31, 2018 Location: Key West
  • Key West Dachshund Walk
  • Website
  • 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.
Image for New Year's Eve Shoe Drop Celebration
  • Dec. 31, 2018 Location: Key West
  • New Year's Eve Shoe Drop Celebration
  • Email Website
  • 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.