Calendar of Events

Current Florida Keys Arts & Culture Events

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Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo
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Image for Key West Holiday Fest
  • Nov 27, 2024 - Dec 31, 2024 Key West Arts & Culture
  • Key West Holiday Fest
  • Website
  • A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”
Image for The Protect Center: Sea of Trees
  • Dec 1, 2024 - Jan 5, 2025 Islamorada Arts & Culture
  • The Protect Center: Sea of Trees
  • Website
  • Over 100 uniquely decorated and sponsored trees light your way nightly from 10 a.m. to 6 p.m. daily from Nov. 29 through Jan. 5. In addition to the beautiful lights and trees, you'll find photo opportunities and shopping. On these select nights - Nov. 29, 30; Dec. 1, 6, 7, 13, 14, 20, 21, 22 from 6 to 9 p.m. - enjoy Santa's Village with holiday-themed cocktails and snacks, workshops for kids and visits with Santa. Admission of $10 adults; $5 kids supports the Dolphin ICU at The Protect Center. MM 82 bayside.
Image for Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Dec 6, 2024 - May 18, 2025 Key West Arts & Culture
  • Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Website
  • Mario Sanchez (1908-2005), a Key West native, is among this country’s finest and most-recognized folk artists. In hundreds of intricately painted wood carvings created in a lifelong labor of love, Sanchez has provided a better history of Key West in the first part of the 20th century than any annals or academic texts. His bas-relief carvings, or intaglios, are a visual feast filled with the music, smells and passion of Gato’s Village, the Cuban-American community of Key West where Sanchez spent much of his life. In the carvings, each person, chicken, dog and fish has its own singular expression, attitude and identity. The exhibit is on display at the Custom House Museum daily from 10 a.m. to 5 p.m. 281 Front St.
Image for Waterfront Winter Wonderland
  • Dec 13, 2024 - Dec 28, 2024 Key West Arts & Culture
  • Waterfront Winter Wonderland
  • Website
  • Make your Key West holiday experience even more magical at Waterfront Winter Wonderland at Truman Waterfront Park. Coffee Butler Amphitheater transforms into an amazing winter wonderland, with an ice-skating, rides, games, music, holiday lights, a vendor village with food and local artisans, and more from Dec. 134-23 and 26-28 (closed Christmas Eve and Christmas). 21 Quay Rd. General admission $10, free for children age 5 and under. Additional fees apply for ice skating and rides.
Image for Red Barn Theatre: The Foreigner
  • Dec 18, 2024 - Jan 11, 2025 Key West Arts & Culture
  • Red Barn Theatre: The Foreigner
  • Website
  • This very funny comedy is an American classic, winning the Best New American Play for 1985 by the Outer Critics Circle. Set at a rural Georgia fishing lodge, a pathologically shy man adopts a persona as a non-English speaking foreigner in an attempt to avoid conversation. Hilarity ensues as an outrageous group of characters reveal secrets and scandals. Shows at 7:30 p.m. 319 Duval St.
Image for Key West Theater: Ben Harrison
  • Dec 27, 2024 Key West Arts & Culture
  • Key West Theater: Ben Harrison
  • Website
  • Ben Harrison is a playwright, lyricist and composer who is also an entertainer. What makes his live performances so enjoyable is that, at his core, he is a barroom guitar player/singer/songwriter who somehow manages to blend history, musical theater, Key West and humor into unusual stories that are mostly true. Key West Theater's Backstage Listening Room. Doors at 6 p.m.; show at 7 p.m. 512 Eaton Street.
Image for Old Island Restoration Foundation: Home Tours
  • Dec 27, 2024 - Dec 28, 2024 Key West Arts & Culture
  • Old Island Restoration Foundation: Home Tours
  • Website
  • Key West is home to what is considered the largest predominantly wooden historic district in the United States. One weekend a month, from December through March, five distinctive homes and their gardens open, revealing a range of architectural gems, eclectic art, transformed cigar-makers cottages, shipbuilders’ craft, re-imagined Victorian mansions, and the stories behind the facades. Home tour tickets provide entry to 5 homes at your self-guided pace during the Friday-Saturday tour dates. All tickets for sale online. Your receipt will be your ticket to enter the home. If you prefer to have a physical ticket, you can pick one up at the Oldest House Museum gift shop, 322 Duval St., the week before the tour date.
Image for Key West Artisan Market: Welcome Home Edition
  • Dec 29, 2024 The Florida Keys Arts & Culture
  • Key West Artisan Market: Welcome Home Edition
  • Website
  • Key West Artisan Market invites you to an early New Year's Eve celebration with non-profit partner Habitat for Humanity of the Lower Keys (be sure to donate to them), 10 a.m. to 2 p.m. at Indigenous Park, 1801 White St. Buy yourself the present that you wanted - but didn't get - over the holidays and stock up on treats for your New Year's eve events. Many artists will be offering sales and exclusive merchandise not available anywhere else. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians, meet local authors and support our featured charity.
Image for Key West Lighting of the Menorah
  • Dec 29, 2024 Key West Arts & Culture
  • Key West Lighting of the Menorah
  • Website
  • The community is invited to attend a traditional Menorah lighting ceremony hosted by the City of Key West at Bayview Park, 1320 Truman Ave., Sunday from 5 to 7 p.m. Blessings are to be offered by Rabbi Shimon Dudai from Congregation B’Nai Zion and Rabbi Jacob Zucker from Chabad of the Florida Keys. Conducted just before sunset, the lighting signals the beginning of Hanukkah, the eight-day Jewish Festival of Lights. The Lighting of the Menorah is one of many celebrations that occur during the island-wide Key West Holiday Fest, which runs through December 31.
Image for Sunset Green Lawn: Early New Year's Eve Celebration
  • Dec 30, 2024 Key West Arts & Culture
  • Sunset Green Lawn: Early New Year's Eve Celebration
  • Website
  • This event is the perfect way to kick your New Year's celebrations a day early. Come to the Sunset Green Lawn for a FREE night of music and family-friendly fun to start the countdown to 2025 with the talented Mike Stack and friends! Featuring Mike Stack, The Brickfinders, D-Lew, Sharese, Josh Kiser, Jockey Jord and other special musical guests. The show is to be followed by a fireworks display! Gates open at 6 p.m. with music starting at 6:30 p.m.
Image for Beachside Resort & Residences: Glow on the Beach Party & Fireworks
  • Dec 30, 2024 Key West Arts & Culture
  • Beachside Resort & Residences: Glow on the Beach Party & Fireworks
  • Website
  • Wrap up the year with an unforgettable evening at Beachside Resort & Residences during the annual Glow on the Beach free party that’s open to everyone. Grab complimentary glow gear upon arriving (while supplies last) to help light up the night. Dance to music by JustDJ, then end the evening with fireworks. No tickets required, just show up from 6 to 10 p.m. at 3841 N. Roosevelt Blvd.
Image for Island Grill: New Year's Eve Circus Beach Party
  • Dec 31, 2024 Islamorada Arts & Culture
  • Island Grill: New Year's Eve Circus Beach Party
  • Website
  • Step into 2025 with a night of magic under the stars. The fun begins at 8 p.m. with two live bands and a DJ, plus the Island Grill dancers. Watch the New York Ball Drop live on screen, but enjoy much better weather! Free champagne toast at midnight, party favors, large buffet dinner and free parking. $110 for adults. Drinks sold separately.
Image for Caribbean Club: New Year's Eve Celebration
Image for Hemingway's Distillery: New Year's Eve Cocktail Class
  • Dec 31, 2024 Key West Arts & Culture
  • Hemingway's Distillery: New Year's Eve Cocktail Class
  • Website
  • Step back in time to the 40s where adventures ran high, cocktails lit up the night and men and women were all about fashion, fun and enjoying lots of rum. Participants will be instructed by a Hemingway's Distillery Cocktail Specialist on how to make 2 Papa's Pilar signature cocktails. Each guest has their own station with tools and all the ingredients needed to create these fabulous cocktails, and you get to enjoy what you create. Come dressed in Casablanca-themed attire or Key West cocktail casual. 6:30-9:30 p.m. 201 Simonton St. Tickets available online
Image for New Year's Eve Red Shoe Drop
  • Dec 31, 2024 Key West LGBTQ
  • New Year's Eve Red Shoe Drop
  • Website
  • Witness Key West's iconic Red Shoe Drop at the Bourbon Street Pub, 724 Duval St. Free to watch from Duval Street; VIP options are to be available for balcony seating. Live entertainment in the street starts at 9 p.m. with the shoe drop at midnight.
Image for New Year's Eve Conch Shell Drop at Sloppy Joe's
  • Dec 31, 2024 Key West Arts & Culture
  • New Year's Eve Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2025 is to be heralded on Key West'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. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock. Customers inside the bar may view the dropping of the conch shell on Sloppy-Tron.
Image for New Year's Eve Gatsby Gala at First Flight Island Restaurant & Brewery
Image for Schooner Wharf Bar: New Year's Eve Lowering of the Pirate Wench
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