The Florida Keys & Key West

Calendar of Events

Current Florida Keys 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 History of Diving Museum presents: Immerse Yourself Free Speaker Series
Image for Fringe Theater presents: Terri White’s Blue Evening
Image for Key West Full Moon
  • Dec. 28, 2018 Location: Key West
  • Key West Full Moon
  • Website
  • 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.

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.
  • Dec. 31, 2018 Location: Islamorada
  • New Year's Eve Celebrations in Islamorada
  • 305-664-0604 Website
  • Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the beach at Morada Bay Beach Café at MM 81.6 bayside, who is to host a colorful large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.
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.
Image for New Year's Eve Fireworks on Blackwater Sound
  • Dec. 31, 2018 Location: Key Largo
  • New Year's Eve Fireworks on Blackwater Sound
  • 305-451-4502 Website
  • The back bay is the setting for the annual New Year's Eve fireworks extravaganza hosted by Sundowners, Jimmy Johnson's Big Chill, Senor Frijoles, Cactus Jacks, Gus' Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, MM 103-104. Check website for details.
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.
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