Calendar of Events

Current Key West Events

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Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest
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Image for Waterfront Playhouse: Into the Woods
  • Nov 20, 2024 - Dec 14, 2024 Key West Arts & Culture
  • Waterfront Playhouse: Into the Woods
  • Website
  • Into the Woods is one of the late Stephen Sondheim's most well-known musicals. It explores the intertwining of well-known fairytales, but more importantly, the consequences of the actions in those stories. Showtimes nightly at 8 p.m. plus three 2 p.m. Saturday matinees on Nov. 30 and Dec. 7 and 14.
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 Comedy Key West: Brendan Eyre
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 Key West Hometown Holiday Parade
  • Dec 7, 2024 Key West Arts & Culture
  • Key West Hometown Holiday Parade
  • Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local, hometown flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street beside Bayview Park and proceeds down Duval Street. Seeing Santa is a highlight for kids.
Image for Key West Theater: The Kingston Trio
  • Dec 7, 2024 Key West Arts & Culture
  • Key West Theater: The Kingston Trio
  • Website
  • In celebration of 60-plus years of music, the iconic folk group performs their best-loved songs as part of the ‘Keep The Music Playing’ national tour. All three current members, Mike Marvin, Tim Gorelangton and Buddy Woodward, have intrinsic links to the original group: Mike is the “adopted son” of founding member Nick Reynolds, who was also his musical mentor; Tim, a friend of John Stewart since he was in his early twenties, is one of the few musicians outside the Trio who has recorded with Nick Reynolds; and Buddy Woodward, a highly regarded musician who has worked with former Trio member George Grove. Doors 7 p.m.; show 8 p.m. 512 Eaton St.
Image for Key West Artisan Market at Southernmost Beach Resort
  • Dec 8, 2024 Key West Arts & Culture
  • Key West Artisan Market at Southernmost Beach Resort
  • Website
  • Join the Key West Artisan Market and the Southernmost Beach Resort for a very special holiday event on the beach. Find some of your favorite local artists with the perfect gifts for everyone on your list along with lots of activities for the kids, great food, tasty treats, fun drinks and even a visit from old St. Nick himself! Live music all day and a fun sand 'snowman' building contest. Free to attend from 10 a.m. to 3 p.m. 504 South St.
Image for Sheriff's Animal Farm Open House: Christmas on the Farm
  • Dec 8, 2024 Key West Arts & Culture
  • Sheriff's Animal Farm Open House: Christmas on the Farm
  • Website
  • Celebrate Christmas at the Monroe County Sheriff's Animal Farm from 1 to 3 p.m. This will be the only open house during the month of December. Visit with the animals and participate in joyful holiday-themed activities including crafts, music and visits with Santa! Gifts of fresh produce and other items, as well as cash gifts for the animals, are greatly appreciated!
Image for Eaton Street Christmas Stroll
  • Dec 8, 2024 Key West Arts & Culture
  • Eaton Street Christmas Stroll
  • Website
  • Eaton Street becomes a southernmost North Pole Sunday afternoon and evening. Wander the blocks between Whitehead and Simonton, stopping at multiple venues for shopping and special presentations, including United Methodist with a 3:30 p.m. concert, Woman's Club of Key West, Salt Gallery, an open house at The Studios of Key West, classic cartoons at Tropic Cinema at 6 p.m., a 7 p.m. choral concert at St. Paul's Episcopal, and more. The event is free but tickets are recommended.
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 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 LaTeDa Christmas Party
  • Dec 10, 2024 Key West Arts & Culture
  • LaTeDa Christmas Party
  • Website
  • All are welcome to attend the annual LaTeDa Christmas Party Dec. 10 from 6 to 9 p.m. For entry, please bring an unwrapped gift for a child in need. Enjoy holiday music by DJ Rude Girl with other special appearances along with a Christmas buffet and drinks. Dress is holiday festive. 1125 Duval St.
Image for Fringe Theater: Tony Konrath's A Christmas Carol
Image for Gay Key West Holiday Lights Trolley Tour
  • Dec 11, 2024 Key West LGBTQ
  • Gay Key West Holiday Lights Trolley Tour
  • Website
  • Slip into your fabulous festive gear and jump aboard this Holiday Lights extravaganza for a dazzling night showcasing the island’s sparkliest displays. Kick things off at Bobby's Monkey Bar, 900 Simonton St., at 5:30 p.m. with a jingle and mingle before the trolley rolls in at 6:30 p.m. Then it’s a two-hour joyride and a few merry pit stops for cheer-fueling. Bring your favorite holiday goodies to share with our fabulous guests. We’ll wrap up the adventure around 8:30 p.m. back at Bobby's. Register now so you don't miss out. After you sign up, we’ll slide into your inbox for payment details.
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 Key West Outdoor Movies - Nightmare Before Christmas
  • Dec 13, 2024 Key West Arts & Culture
  • Key West Outdoor Movies - Nightmare Before Christmas
  • Website
  • Key West Outdoor Movies presents Tim Burton's The Nightmare Before Christmas, Friday, Dec. 13, at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk.
Image for Pigeon Key Holiday Spectacular
  • Dec 13, 2024 - Dec 14, 2024 Key West Arts & Culture
  • Pigeon Key Holiday Spectacular
  • Website
  • The wonderment and excitement of the holiday season takes over Pigeon Key with a festive event that kicks on Friday, Dec. 13 with a VIP viewing of the island in full holiday splendor. On Saturday, the "Polar Express" starts running at 1 p.m. with trips throughout the day and into the evening. Families can spend the entire day on the 5-acre island enjoying marine science activities along with delicious holiday food, drinks, guided tours, activities, holiday-themed movies on the big screen, Santa Claus encounters and snow! Admission $5 for walkers/bikers; ride the Polar Express for $10 if you book in advance or $15 the day of the event.
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 Holiday Historic Inn Tours: Night #2
  • Dec 13, 2024 Key West Arts & Culture
  • Holiday Historic Inn Tours: Night #2
  • Website
  • In this second of two holiday historic inn tours, explore four beautifully decorated locations from 6 to 8 p.m. while enjoying sweet and savory holiday treats and libation samplings. Locations are: Key West Butterfly Conservatory, The Mansion on the Sea, Island City House and The Mermaid & the Alligator. The tours are self-guided. $40 tickets available online, but must be picked up in person after 5:30 p.m. at the first location - Key West Butterfly Conservatory, 1316 Duval Street.
Image for Key West Art & Historical Society: Holiday Concert & Bazaar
  • Dec 13, 2024 Key West Arts & Culture
  • Key West Art & Historical Society: Holiday Concert & Bazaar
  • Website
  • Join the Key West Art & Historical Society for the 7th Annual Holiday Concert & Bazaar from 5 pm to 9 pm. The event is located on the sweeping historic porch and street in front of the Custom House Museum. The immensely popular celebration will feature some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House. There will be plenty of food and festive libations at this event along with excellent holiday shopping. The event is free and open to the public. 281 Front St.
Image for Key West Theater: The Magic of Christmas
  • Dec 13, 2024 Key West Arts & Culture
  • Key West Theater: The Magic of Christmas
  • Website
  • The Magic of Christmas is an adult- and kid-friendly magic show that combines different genres of magic into one fantastic show. Enjoy a complimentary cookie and candy bar along with pictures with Santa by photographer Rob O'Neal. Special appearance by our dancing grinch and some say it even may snow that night. Doors open at 5 p.m.; show at 6 p.m. 512 Eaton St.
Image for 'A Positive Step' 5k Rudolph Red Nose Run
  • Dec 14, 2024 Key West Arts & Culture
  • 'A Positive Step' 5k Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join in the 16th 'A Positive Step' 5k Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café, 1405 Duval Street. Race day check-in starts at 7 a.m. with start time at 8 a.m. Prizes are awarded for most festive and most unusual PJ's. After the race, enjoy refreshments and a fabulous silent auction to benefit A Positive Step of Monroe County, a non-profit serving at-risk kids and their families.
Image for Schooner Wharf Bar Lighted Boat Parade
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. The event opens at 1 p.m. and the concert starts at 1:30 p.m., followed by snow cones (while they last) and delightful holiday arts and crafts, face painting and special treats. Tickets $5 per child at the door with a maximum cost of $10 per family.
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. The run starts at 5 p.m. at Coffee Butler Amphitheater. 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 Lighting of the Menorah
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 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
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.
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