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 Harbor Walk of Lights
  • Nov 23, 2023 - Dec 31, 2023 Key West Arts & Culture
  • Harbor Walk of Lights
  • Website
  • The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harbor walk area in the Historic Seaport glimmers with holiday displays throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.
Image for Waterfront Playhouse: Little Shop of Horrors
  • Nov 29, 2023 - Dec 16, 2023 Key West Arts & Culture
  • Waterfront Playhouse: Little Shop of Horrors
  • Website
  • The deviously delicious Broadway and Hollywood sci-fi smash musical Little Shop of Horrors comes to Waterfront Playhouse for a three-week run. Tickets range from $40 to $75. Showtimes at 8 p.m. along with an additional 2 p.m. matinee on Dec. 9. 407 Wall Street at Mallory Square.
Image for Old Town Trolley's Holiday Sights & Festive Nights Tours
Image for Conch Tour Train's Holiday Sights & Festive Nights Tours
  • Dec 8, 2023 - Dec 23, 2023 Key West Arts & Culture
  • Conch Tour Train's Holiday Sights & Festive Nights Tours
  • Website
  • Lively 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. 8 to 12 and 15 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 Sheriff's Animal Farm: Christmas on the Farm
  • Dec 10, 2023 Key West
  • Sheriff's Animal Farm: Christmas on the Farm
  • Website
  • Don't miss the special Christmas on the Farm open house at the Sheriff's Animal Farm from 1 to 3 pm. Visit the animals and enjoy holiday crafts, music, gifts, and Santa! The farm is located at 5525 College Rd. at the Sheriff's Office Headquarters complex. The event is free to attend, but the family-friendly farm welcomes donations. In addition to cash, suggested donations include fresh produce for the animals or items from the MCSO Animal Farm Amazon wishlist.
Image for Key West Lighting of the Menorah
Image for Key West Artisan Market: Merry Marketplace on the Beach
Image for Eaton Street Christmas Stroll
  • Dec 10, 2023 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, starting with a concert at Key West United Methodist at 3:30 p.m. Then stop in at multiple venues for shopping or special presentations, including Key West Theater, Woman's Club of Key West, Salt Gallery, the Bahama Village Music Program at Williams Hall, an open house at The Studios of Key West, classic cartoons at Tropic Cinema, and a final Keys Choral Arts Christmas concert at St. Paul's Episcopal at 7 p.m. The event is free but tickets are required. Sign up at Tropic Cinema's website.
Image for 24 North Hotel: Paint & Sip Night with Artist Lance Berry
  • Dec 12, 2023 Key West Arts & Culture
  • 24 North Hotel: Paint & Sip Night with Artist Lance Berry
  • Website
  • Get ready to laugh and have a blast with the whole family or a couple of pals at Paint and Sip night with Key West artist, character and life-of-the-party, Lance Berry. Your $40 ticket includes your first drink, plus all the art supplies and instruction you'll need to create your own masterpiece. The class takes place the second Tuesday of the month at Republica Bar & Lounge at 24 North Hotel, 3820 N. Roosevelt Blvd.
Image for The Studios of Key West: Ann Hampton Callaway
  • Dec 12, 2023 Key West Arts & Culture
  • The Studios of Key West: Ann Hampton Callaway
  • Website
  • Ann Hampton Callaway is one of America’s most gifted artists in pop and jazz. A leading champion of the great American Songbook, she’s made her mark as a singer, pianist, composer, lyricist, arranger, actress, educator, TV host and producer. 7 p.m. in the Helmerich Theater. Tickets $55. 533 Eaton St.
Image for Fringe Theater: The Best Christmas Pageant Ever
  • Dec 12, 2023 - Dec 16, 2023 Key West Arts & Culture
  • Fringe Theater: The Best Christmas Pageant Ever
  • Website
  • Mischief and mayhem ensue at the annual Christmas pageant when the town's young hoodlums enact a coup and unexpectedly teach the town the true meaning of Christmas. An endearing family show with performances Dec. 12 through 17 at 7 p.m., and Dec. 16 at 2 p.m. Tickets $35 adults; $20 for ages 15 and under. Shows at the Historic Armory, 600 White St.
Image for Key West Art & Historical Society: Happy Hour With the Historian
  • Dec 14, 2023 Key West Arts & Culture
  • Key West Art & Historical Society: Happy Hour With the Historian
  • Website
  • Join historian Dr. Cori Convertito for a talk about how Florida's east coast became known as the "American Riviera" as Henry Flagler constructed numerous luxury hotels during the Gilded Age. This talk explores the assorted hotels’ histories to provide insight into what life was like for the leisure class in the 19th and 20th centuries. $15 ticket includes one glass of wine, beer or a soft drink. 5 to 6 p.m. at Comedy Key West, 218 Whitehead Street.
Image for Gay Holiday Getaway
  • Dec 14, 2023 - Dec 17, 2023 Key West LGBTQ
  • Gay Holiday Getaway
  • Website
  • Cuban-inspired hotel Havana Cabana is about to serve up a festive fiesta in partnership with the iconic Provincetown, Massachusetts, premier LGBTQ+ hotel and entertainment complex Crown & Anchor. From December 14th-17th, Havana Cabana is bringing Key West a falala-fabulous experience with their Gay Holiday Getaway that you won’t want to miss! Sip on punchy poolside cocktails and engage in sensational sunset performances that'll have you caroling all the way home. From classic holiday sing-alongs hosted by Tina Burner to Vibrator Races at Mary Ellen’s Bar (yes, you read that right), this is a yuletide experience that's anything but ho-hum. Whether you’ve been naughty or nice, all travelers can warm up their winter with this memorable holiday getaway. Accommodations start from just $169 per night and reservations can be booked online.
Image for Holiday Historic Inn Tours: Night #2
  • Dec 15, 2023 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: Papa’s Pilar Distillery, Island City House, The Conch House Heritage Inn, and the Lighthouse Hotel. The tours are self-guided. $40 tickets available online, but must be picked up in person at the first location - Hemingway's Library at Papa's Pilar Distillery, 201 Simonton Street.
Image for Key West Museum of Art & History: Our Working Waterfront
  • Dec 15, 2023 - Feb 11, 2024 Key West Arts & Culture
  • Key West Museum of Art & History: Our Working Waterfront
  • Website
  • The "Our Working Waterfront" exhibit opens Dec. 15 with a free reception from 5 to 7 p.m. at the Customs House Museum, 281 Front St. The exhibit explores the diversity of maritime industries and occupations along the Key West waterfront and reveals the complex interconnections of seafront work, while integrating never before exhibited historic photos and a range of special artifacts from the museum's permanent collection. The exhibit continues through Feb. 11.
Image for Coffee Butler Amphitheater: Key West Waterfront Winter Wonderland
  • Dec 15, 2023 - Dec 30, 2023 Key West Arts & Culture
  • Coffee Butler Amphitheater: Key West Waterfront Winter Wonderland
  • Website
  • The Coffee Butler Amphitheater at Truman Waterfront Park transitions into the Key West Waterfront Winter Wonderland for an all ages, family friendly holiday experience Dec. 15 through 30, including stunning light displays, an ice skating rink, games, rides, attractions, music and more. A vendor village is to offer a variety of food options and local artisans perfect for holiday shopping. Special holiday experiences include photos with Santa, crafts and more. Admission $12 per person, with children 5 and under free. For an additional $20 per person, you can enjoy a one-hour ice skating session. $10 all-you-can-ride wristbands are available for rides including carousels, swings and slides. 4 to 10 p.m. nightly, except Dec. 25. 21 Quay Rd.
Image for 'A Positive Step' 5k Rudolph Red Nose Run
  • Dec 16, 2023 Key West
  • 'A Positive Step' 5k Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join in the 15th '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 Tennessee Williams Theatre: Fiesta de Navidad Tropical
  • Dec 16, 2023 Key West Arts & Culture
  • Tennessee Williams Theatre: Fiesta de Navidad Tropical
  • Website
  • Featuring grooves such as salsa, bachata, and cha cha cha, this high energy live performance event presented by the Key West-based Pasión Project studio features World Salsa Champion dancers Carine & Rafael and Mambo royalty Eddie Torres, Jr. with his partner Princess. With live music by Caribe and friends, get ready to move, shake and celebrate all night long, and even dance onstage with the band. Tickets $30-$75. 8 p.m. at 5901 College Rd.
Image for Holiday Classic Car Show
  • Dec 17, 2023 Key West Arts & Culture
  • Holiday Classic Car Show
  • Website
  • See classic cars from a variety of eras at the official show of the Florida Keys Southernmost Car Club, and choose a People’s Choice winner with your votes. Located at the Conch Republic Seafood Company parking lot at the corner of Greene and Elizabeth Streets. Attendees are asked to bring an unwrapped toy for the Monroe County Domestic Abuse Shelter. 11 a.m. to 3 p.m.
Image for Key West Artisan Market: Shop Local Edition
  • Dec 17, 2023 Key West
  • Key West Artisan Market: Shop Local Edition
  • Website
  • Shop for fine arts and crafts, jewelry, apparel and more items that would make great gifts, along with fresh produce, delicious foods and drinks at this open-air bazaar from 10 a.m. until 2 p.m. Santa Claus will be onsite starting at noon for free pictures with anyone who wants one! Located in the park at Higgs Beach, 1801 White St.
Image for Red Barn Theatre: A Tuna Christmas
  • Dec 19, 2023 - Jan 13, 2024 Key West Arts & Culture
  • Red Barn Theatre: A Tuna Christmas
  • Website
  • In the third-smallest town in Texas, radio station OKKK news personalities report on Yuletide activities.The hilarity never lets up in this comedic romp for all seasons featuring many colorful Tuna denizens played by two very funny actors, Brandon Beach and David Black. Showtime 8 p.m. Tickets $49 to $60.
Image for Key West Theater: Peter Mayer Stars & Promises Christmas Tour
  • Dec 20, 2023 Key West Arts & Culture
  • Key West Theater: Peter Mayer Stars & Promises Christmas Tour
  • Website
  • Peter Mayer, singer, songwriter and guitarist brings the 24th anniversary of his widely acclaimed “Stars and Promises” Christmas tour to Key West. Mayer has released 25 of his own albums, toured internationally with his own band, and has been lead guitarist for Jimmy Buffett’s Coral Reefer band for three decades. Don't miss this "Christmas show like now other." Doors open at 6:30; show at 7:30 p.m. Tickets $35 to $55.
Image for The Studios of Key West: MicroPARTY with Electric Blue Yonder
  • Dec 21, 2023 Key West Arts & Culture
  • The Studios of Key West: MicroPARTY with Electric Blue Yonder
  • Website
  • Electric Blue Yonder examines the mysteries of the universe and reports their findings through song. The MicroPARTY is a unique live performance of the band's upcoming music that also includes a special sneak peak at unreleased animated music videos, and some info about their next big adventure. MicroPARTY is music and fun for everyone – the young and the young at heart. Performance at 6 p.m. in the Helmerich Theater. Tickets $35. 533 Eaton St.
Image for Jazz in the Gardens
Image for Schooner America 2.0: Christmas Day Brunch Sail
  • Dec 25, 2023 Key West Arts & Culture
  • Schooner America 2.0: Christmas Day Brunch Sail
  • Website
  • Enjoy your holiday in Key West aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. This two-hour Christmas morning sail features complimentary mimosas, Bloody Marys, champagne, wine, beer, soft drinks, and water, as well as a generous brunch buffet. 10 a.m. to 12:30 p.m. Adults $136; children age 4 to 17, $63. Meet at Key West Bight Marina, 202 William Street.
Image for Key West Home Tours: Holiday Style
  • Dec 29, 2023 - Dec 30, 2023 Key West Arts & Culture
  • Key West Home Tours: Holiday Style
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 64th series features self-guided tours of several Key West homes and gardens, each festively dressed for the holidays. Home Tour tickets provide entry to 5 homes at your self-guided pace, between 1-4 p.m. during the Friday-Saturday tour. Address are to be provided when tickets are purchased.
Image for Marriott Key West Beachside: 2023 Fireworks and Glow Party
  • Dec 30, 2023 Key West Arts & Culture
  • Marriott Key West Beachside: 2023 Fireworks and Glow Party
  • Website
  • Marriott Beachside's annual family-friendly Fireworks and Glow Party is back for another year. The resort is giving away thousands of free glow items, and there is to be a fun party atmosphere with music by DJ Sanaris. A memorable fireworks display begins at 9 p.m. Food from the Grill Stand will raise money for United Way, and there is to be a cash bar. The event is free to attend from 6 to 10 p.m. at 3841 N. Roosevelt Blvd.
Image for Hard Rock Cafe: New Year's Eve Guitar Drop
  • Dec 31, 2023 Key West Arts & Culture
  • Hard Rock Cafe: New Year's Eve Guitar Drop
  • Website
  • Reserve your table with VIP outdoor balcony seating for Hard Rock Cafe's New Year's Eve celebration that includes a live DJ, prime rib dinner, one complimentary cocktail and the best view of the Hard Rock Guitar Drop at midnight! Reservations available for $150 per person on Open Table. 313 Duval Street.
Image for New Years Eve Red Shoe Drop
  • Dec 31, 2023 Key West Arts & Culture
  • New Years Eve Red Shoe Drop
  • Website
  • The iconic Key West New Year's Eve "Red Shoe Drop" at Bourbon St. Pub features a new queen riding in the shoe, after the 25-year reign of queen Sushi came to an end after New Year's Eve 2022. Christopher Peterson, famous for his EYECONS female impersonation show, will ride the shoe on New Year's Eve 2023 leading into the 2024 New Year. The public can watch for free from the street in front of the club at 724 Duval St. A limited number of VIP balcony tickets go on sale Dec. 1.
Image for First Flight: Great Gatsby New Year's Eve with Plane Drop
  • Dec 31, 2023 Key West Arts & Culture
  • First Flight: Great Gatsby New Year's Eve with Plane Drop
  • Website
  • Dress to impress in your best Gatsby era outfits at First Flight. Enjoy an open bar, champagne toasts, chef-manned food stations and live music. At the stroke of midnight, a replica of an old Pan Am airplane with a real-life flight attendant will take flight in the garden for a "plane drop" to ring in 2024. Tickets $250. 301 Whitehead St.
Image for Schooner Wharf Bar: New Year's Eve Pirate Wench Drop
Image for Sloppy Joe's Bar: Dropping of the Conch Shell
  • Dec 31, 2023 Key West Arts & Culture
  • Sloppy Joe's Bar: Dropping of the Conch Shell
  • Website
  • This year at Sloppy Joe's, the conch shell will drop at the approach of midnight for the 30th time at the corner of Duval and Greene Street to ring in the New Year! Watch it live in the street or watch from inside the bar on the Sloppy-Tron. No reservations for New Year's Eve inside the bar, tables are on a first-come basis.
Image for Key West Artisan Market: New Year's Eve Edition
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