Calendar of Events

Current Key West Events

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Image for Key West Holiday Fest 2024 Image for Key West Holiday Fest 2024 Image for Key West Holiday Fest 2024 Image for Key West Holiday Fest 2024
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 Nutcracker Key West
  • Dec 5, 2024 - Dec 15, 2024 Key West Arts & Culture
  • Nutcracker Key West
  • Website
  • Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Show dates Dec. 5-8 and 13-15. Showtimes vary. Tennessee Williams Theater, 5901 College Rd.
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 Old Town Trolley: Holiday Nights Tours
  • Dec 9, 2024 - Dec 23, 2024 Key West Arts & Culture
  • Old Town Trolley: Holiday Nights Tours
  • Website
  • Take the trolley for a tour of the Key West residential neighborhoods known for going all-out with holiday home decorations. Make this your new holiday tradition with friends and family. Narrated tours depart from Mallory Square and last for one hour. Advance tickets are available to book online.
Image for Conch Tour Train's Holiday Sights & Festive Nights Tours
  • Dec 9, 2024 - Dec 23, 2024 Key West Arts & Culture
  • Conch Tour Train's Holiday Sights & Festive Nights Tours
  • Website
  • The lively holiday Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 7:30, 8 and 8:30 p.m. on evenings from Dec. 9 to 10 and 13 to 23. Included are holiday lights glasses as keepsake items. The one-hour tour takes riders past the island's most elaborately decorated houses, buildings and neighborhoods, with holiday caroling.
Image for Red Barn Theatre: The Foreigner
  • Dec 12, 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 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 Snowy Days Children's Concert at Key West Botanical Garden
  • Dec 15, 2024 Key West Arts & Culture
  • Snowy Days Children's Concert at Key West Botanical Garden
  • Website
  • Snowy Days, the Key West Tropical Forest & Botanical Garden's annual children's winter concert, features Key West vocalist, Belle Jampol performing favorite holiday tunes for children, followed by snow cones (while they last) and delightful holiday arts and crafts, face painting and special food and beverage treats. 12 noon to 2 p.m.; tickets $10 per family at the door.
Image for Key West Artisan Market: Fill the Pantry Edition
  • Dec 15, 2024 Key West
  • Key West Artisan Market: Fill the Pantry Edition
  • Website
  • Stock your pantry and fridge with fresh produce, exotic fruits, artisan cheeses, local seafood, honey, pickles, nuts and so much more. 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. Listen to awesome local musicians and give canned good or donations to our featured charity, the SOS Foundation, that feeds Key West's underprivileged children. 10 a.m. to 2 p.m., 1801 White St. in Indigenous Park.
Image for Fringe Theater's Holiday Train Ride
  • Dec 18, 2024 Key West Arts & Culture
  • Fringe Theater's Holiday Train Ride
  • Website
  • Don't miss this crowd favorite fundraiser for Fringe Theater. Check-in at 7 p.m. at the beautiful Gardens Hotel, 526 Angela St., and enjoy a tasty beverage at the cash bar while you catch up with your Fringe friends and enjoy the live holiday music. Then at 8 p.m., it's "All Aboard" our Holiday Train for a festive ride about town to see the holiday lights of Key West. Pickup and return at the Gardens Hotel. Tickets $60.
Image for Comedy Key West: Jim Florentine
  • Dec 18, 2024 - Dec 21, 2024 Key West Arts & Culture
  • Comedy Key West: Jim Florentine
  • Website
  • For nearly 25 years Jim Florentine has been making audiences around the world laugh across nearly every type of media. Jim has recorded six stand-up comedy albums and shot four full-length specials. Showtimes 8:30 p.m. 218 Whitehead St.
Image for Key West Art & Historical Society Historic Seaport Sail: Plant a Million Corals Project
  • Dec 18, 2024 Key West Arts & Culture
  • Key West Art & Historical Society Historic Seaport Sail: Plant a Million Corals Project
  • Website
  • Enjoy a 2-hour Historic Harbor Tour with Plant A Million Coral Project’s Dee Dee Vaughan on the S/V Argo Navis, talking about the Project to Restore Florida Keys' Coral Reef. The morning seafaring excursion aboard luxury catamaran SV Argo Navis departs from the dock at 0 Margaret Street at 10 a.m. and returns at 12 p.m. Passengers will enjoy Bloody Marys, mimosas or non-alcoholic beverages along with lite breakfast fare as Vaughan explains the Plant A Million Coral’s focus on active reef restoration and the transfer of coral restoration technology. Book tickets online in advance.
Image for Walk on White Third Thursday Art Walk
  • Dec 19, 2024 Key West Arts & Culture
  • Walk on White Third Thursday Art Walk
  • Website
  • Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets. In December, The KWHS marching band will parade down White Street and perform at various locations along the way. City Hall and the NOAA National Weather Station will also participate.
Image for Key West Art & Historical Society Distinguished Speaker Series: Storms, Shipwrecks & Saints' Names
  • Dec 19, 2024 Key West Arts & Culture
  • Key West Art & Historical Society Distinguished Speaker Series: Storms, Shipwrecks & Saints' Names
  • Website
  • This talk focuses on the dangers associated with early Caribbean and Gulf travel in the first generations of Spanish colonialism. The Florida Keys were a late and important, but also particularly treacherous, final leg of a roundtrip journey from Spain, through the Caribbean, and back to Spain. Dr. Kevin Kokomoor talks on the subject and brings to light discoveries covered in his recent book, "La Florida: Catholics, Conquistadores and other American Origin Stories." 6 to 7 p.m. at Tropic Cinema, 416 Eaton St.
Image for Tropic Cinema: Movies Under the Stars - Elf
  • Dec 21, 2024 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - Elf
  • Website
  • Don't miss the monthly free Movies Under the Stars screening - this month, the movie is Elf! The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins at 6 p.m. 416 Eaton St.
Image for Running of the Elves 5k Run/Walk & Jingle Bell Mile
  • Dec 21, 2024 Key West
  • Running of the Elves 5k Run/Walk & Jingle Bell Mile
  • Website
  • Put on your best festive holiday costume and run, jog, stroll or jingle all the way to the finish line, where organizers promise to make it snow! This first annual fun run benefits Reef Relief. Gates open at 4 p.m. at Coffee Butler Amphitheater, 21 E. Quay Rd., and the run starts at 5 p.m. Your run registration comes with a free ticket to Waterfront Winter Wonderland at the amphitheater along with an elf T-shirt, holiday race medal, Christmas cookies, candy canes and a photo with holiday characters including Buddy the Elf!
Image for Key West Artisan Market: Shop Local Edition
  • Dec 22, 2024 Key West Arts & Culture
  • Key West Artisan Market: Shop Local Edition
  • Website
  • This week's market will be stocked with Keys-made items perfect for gift giving this holiday season. 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. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians doing your favorite Christmas standards, and get photos with Santa! 10 a.m. to 2 p.m. in Indigenous Park, 1801 White St.
Image for The Gardens Hotel: Holiday Jazz in the Gardens
Image for Old Island Restoration Foundation: Noche Buena
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 Key West Lighting of the Menorah
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 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 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 Schooner Wharf Bar: New Year's Eve Lowering of the Pirate Wench
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
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