Key West Calendar of Events (2024)

Events in Key West for 2024

• Dec 14, 2024 - Dec 14, 2024
• 33rd Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
• Website Schooner Wharf
• 202 Williams StKey WestFL33040
• Facebook
• Join in spreading the spirit where mistletoe hangs from the mast and strings of lights adorn the riggings: at the 33rd Annual Schooner Wharf Bar & Galley Lighted Boat Parade at 8pm December 14th.

• Nov 18, 2024 - Dec 30, 2024
• Waterfront Winter Wonderland
• Website
• 21 Quay RdKey WestFL33040
• Elizabeth Love E-mail
• Facebook
• Enjoy Visits with Santa, live music performances, and festive celebrations throughout the season! Home to Key Wests only ice rink, we will also have thrilling carnival rides and fun for the whole family at Waterfront Winter Wonderland!
• Buy tickets!

• September 01 - Nov 30, 2024 Key West
• Key West Tropical Forest & Botanical Garden: Scarecrows in the Garden
• Website
• Get your spooky on at the 6th annual Scarecrows in the Forest Art exhibition and Contest. Around the corner, in a meadow or right in front of you, made from natural, recycled and repurposed material, scarecrows are found throughout the Tropical Forest & Botanical Garden. The exhibit runs Sept. 1-Nov. 30.

• November 07 - 28, 2024 Key West
• Studios of Key West: Memory Lane with works by Catherine Solmo
• Website
• This exhibition features works by Catherine Solo. Inspired by old photographs and her grandfather’s vivid stories, Solmo creates nostalgic paintings that pay tribute to past generations of Conchs and their traditions. She crafts unique stories through her art, presenting the island as it once was. The work keeps the spirit of old Key West alive, weaving narratives with humor and compassion. 533 Eaton St.

• November 20 - Dec 14, 2024 Key West
• 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.

• November 27 - Dec 31, 2024 Key West
• 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.”

• November 27 Key West
• Lighting of the Key West Harbor Walk of Lights
• Website
• Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2024 Key West Harbor Walk of Lights with lights and creative displays reflecting the Maritime History of Key West. The Key West Harbor Walk of Lights stays lit nightly through New Year's Eve, stretching along the Key West Historic Seaport and Key West Bight Marina. Festive music starts at 5 p.m., by the Fishing Buoy tree, with the tree lighting at 6 p.m. Music at the Lobster Trap tree begins at 6 p.m. with the tree at 7 p.m. The displays are to remain illuminated nightly through Dec. 31.

• November 28 Key West
• Southernmost Turkey Trot 5k & 1-Mile Rooster Romp
• Website
• Have some fun with family and friends and work up an appetite with the 2nd annual Southernmost Turkey Trot 5k or the 1-mile Rooster Romp walk. Races begin at 8 a.m. at the Southernmost Point Buoy, 1400 Whitehead St. Proceeds benefit Reef Relief.

• November 29 Key West
• Black Friday Shopping Extravaganza
• Website
• This Black Friday, get outside instead of online and join the Key West Artisan Market, the Truman Waterfront Farmers Market and shop Mom & Pop Key West along with local Keys artists, crafters, makers and providers for the fourth annual Black Friday Shopping Extravaganza from 10 a.m. to 6 p.m. at Truman Waterfront Park. Score one-of-a-kind gifts, unique handmade items, exquisite art and meet awesome people offering delicious culinary delights, yummy beverages and the views you won't find at any mall for a memorable shopping experience.

• November 29 - Dec 07, 2024 Key West
• Key West International Dance Co.: Fiesta de Navidad Tropical
• Website
• Fiesta de Navidad delivers a festive extravaganza to ignite the holiday spirit. With world-class Latin dance and vibrant costumes, this joyful celebration also offers the opportunity for audience members of all ages to dance on stage with a live band! Performances take place at 8 p.m. at San Carlos Institute, 516 Duval St.

• November 30 Key West
• Hogfish Bar & Grill 22nd Anniversary Party
• Website
• Hogfish Bar & Grill, home to fresh seafood, great drinks, panoramic waterfront views, outdoor dining and plenty of local characters for a truly authentic Keys experience, is celebrating its 22nd anniversary Sat. Nov. 30. Enjoy great food and special musical guests Mac McAnally - 10-time CMA Entertainer of the Year and member of Jimmy Buffett's Coral Reefer Band - along with Scotty Emerick and Eric Darken. 6810 Front Street, Stock Island.

• November 30 Key West
• Hog Trot 5k
• Website
• Sign up for the 30th annual Hog Trot to run or walk to burn off those Turkey Day calories. The race begins and ends in front of Hogs Breath Saloon, 400 Front Street. Proceeds benefit the Florida Keys SPCA, dedicated to protecting animals and providing them with a safe, loving environment. Race starts at 8 a.m.

• November 30 Key West
• Key West Theater: The Broken Hearts - Tribute to Tom Petty & the Heartbreakers
• Website
• The Broken Hearts were created by former Tom Petty and Mudcrutch band mate, bassist Charlie Souza, along with singer/songwriter Shawn Scheller as a tribute to Petty's passing in October of 2017. Originally intended only as a temporary project, the group of musicians including keyboardist Robin Swenson (Air Supply, Frankie Valli & the Four Seasons, 3 Dog Night), guitarist Joe Sanders, drummer Scott Lockhart, Souza and Scheller became continuously requested to return to events in Tom's honor. In 2018, the decision was made to become an official touring tribute project paying respect and honor to his life and music. Doors open at 7 p.m.; show at 8 p.m. 512 Eaton St.

• December 01 Key West
• Key West Artisan Market: Rock the Red Ribbon Edition
• Website
• Shop the Artisan Market for fine crafts, jewelry and more from talented local makers. Enjoy cocktails, coffee, food from vendor stalls and food trucks. This week's market supports World AIDS Day - all are invited to pick up and wear a red ribbon. Indigenous Park at 1801 White St. from 10 a.m. to 2 p.m.

• December 01 - 05, 2024 Key West
• Key West End of Prohibition Celebration
• Website
• Take a step back into old Key West and celebrate the End of Prohibition with 5 days of fun-filled Prohibition-themed films, cocktails, history, live entertainment and a blowout party at Sloppy Joe's. The final End of Prohibition celebration takes place Thursday, Dec. 5 at Sloppy Joe's with a costume contest, giveaways, a special appearance by the Anheuser-Busch antique truck and much more.

• December 04 - 07, 2024 Key West
• Comedy Key West: Brendan Eyre
• Website
• Brendan Eyre is one of the country's top young comedians. His laid back, observational style is a hit with audiences across the country. Showtimes 8:30 p.m. 218 Whitehead St.

• December 05 Key West
• Pet Pictures with Santa
• Website
• Bring your festively outfitted pets for professional photos with Santa on Friday evening from 6 to 8 p.m. at the Christmas tree at the foot of William Street at Key West Bight Marina, hosted by All Animal Clinic. Photos are $25 each (cash only) with proceeds benefitting the Boys and Girls Club of the Keys.

• December 05 - 15, 2024 Key West
• 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.

• December 06 Key West
• Holiday Historic Inn Tours: Night #1
• Website
• In this first of two holiday historic inn tours, explore four beautifully decorated locations and their unique architecture and history from 6 to 8 p.m. Sample sweet and savory holiday treats and libations. Locations are: Hemingway's Social Club at Papa's Pilar Distillery, Lighthouse Inn, Wicker Guesthouse, and the Gardens Hotel. The tours are self-guided. $40 tickets available online, but must be picked up after 5:30 p.m. on Dec. 6th at the first location, Hemingway's Social Club at Papa's Pilar Distillery, 210 Simonton St. The second inn tour takes place Dec. 13.

• December 06 Key West
• Key West Theater: Under the Streetlamp
• Website
• Under the Streetlamp is an electrifying show driven by an inspired catalog of classic Doo Wop, Motown, and Rock n' Roll hits! Streetlamp has been dazzling audiences across the globe for over a decade. Their five specials airing on PBS have played to more than 300 million viewers and a million people have seen them live. These dynamite Broadway stars are propelled by an ensemble of world-class musicians through a show packed with smooth harmonies, soul-touching music and stories, and thrilling choreography. The audience engagement is palpable, often bringing four generations of music lovers together. Doors at 7 p.m.; show at 8 p.m. 512 Eaton St.

• December 06 Key West
• Key West Art & Historical Society: Opening Reception for Collecting Key West - The Works of Mario Sanchez
• Website
• The Key West Museum of Art & History is pleased to present the opening of the exhibition, “Collecting Key West: The Works of Mario Sanchez" on Friday, December 6. A reception to mark the opening is to take place from 5 to 8 p.m. that evening in the Bryan Gallery, which is free and open to the public. Exploring the crossroads of art and history, this exhibition delves into the legacy of Cuban American folk artist Mario Sanchez (1908 – 2005). Sanchez established himself as the foremost Key West artist in the 1940s, creating hundreds of intricately carved and painted intaglios that portray his birthplace in the first part of the 20th century better than any annals or academic texts. 281 Front St.

• December 06 Key West
• Coffee Butler Amphitheater: Holiday Village & BeLighted Bike Ride
• Website
• The Wesley House Family Services Holiday Village is the family-friendly pre-party for the BeLighted Bike Ride, creating an evening of joy, laughter, and holiday magic for all ages, from 5 to 9 p.m. at Coffee Butler Amphitheater, 21 Quay Rd. The village features over 20 community booths offering games and activities, carnival rides, bounce houses, local food trucks, community performances, snowfalls and Santa! The highlight of the evening is the BeLighted Bike Ride that departs from the event at 8 p.m. The luminous parade of holiday cheer on wheels winds through the streets of Key West. Admission to Holiday Village is $20 per person or four tickets for $70. Children age 3 and under enter free.

• December 07 Key West
• 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.

• December 07 Key West
• 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.

• December 08 Key West
• 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.

• December 08 Key West
• 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.

• December 08 Key West
• 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!

• December 09 - 23, 2024 Key West
• 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.

• December 09 - 23, 2024 Key West
• 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.

• December 10 Key West
• 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.

• December 11 Key West
• 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.

• December 12 - Jan 11, 2025 Key West
• 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.

• December 13 Key West
• 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.

• December 13 Key West
• 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.

• December 13 - 28, 2024 Key West
• 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.

• December 13 Key West
• 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.

• December 13 - 14, 2024 Key West
• 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.

• December 13 Key West
• 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.

• December 14 Key West
• Schooner Wharf Bar Lighted Boat Parade
• Website
• Don't miss this magical nautical display of holiday lights on board every manner of watercraft in Key West Harbor. The judges stand is located at Schooner Wharf, 202 William St. Viewing is available from all along the Harbor Walk. The parade starts at 8 p.m.

• December 14 Key West
• '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.

• December 15 Key West
• 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.

• December 15 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.

• December 18 Key West
• 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.

• December 18 - 21, 2024 Key West
• 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.

• December 18 Key West
• 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.

• December 19 Key West
• 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.

• December 19 Key West
• 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.

• December 21 Key West
• 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.

• December 22 Key West
• 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.

• December 24 Key West
• Old Island Restoration Foundation: Noche Buena
• Website
• This Christmas Eve event is a celebration of Key West Cuban heritage. Enjoy a traditional succulent roast pig dinner loaded with sides and topped off with El Mocho's homemade flan. $50 adults, $15 age 12 and under. Call for information and tickets, 305-294-9501 or visit the website.

• December 24 Key West
• Holiday Jazz in the Gardens
• Website
• Find festive outdoor jazz in The Gardens Hotel's famous outdoor garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly. 5 to 7:00 p.m. 526 Angela St.

• December 29 Key West
• Key West Lighting of the Menorah
• Website
• The City of Key West's annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec. 29 from 5 to 7 p.m. 1320 Truman Avenue.

• December 30 Key West
• 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.

• December 31 Key West
• Schooner Wharf Bar: New Year's Eve Lowering of the Pirate Wench
• Website
• Celebrate the New Year in true Schooner Wharf Bar style with the annual Lowering of the pirate wench down the mast of the Schooner America 2.0 at midnight. Enjoy live music through the afternoon and evening, with cannon's firing, party favors and fun at midnight. 202 William St.

• December 31 Key West
• 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.

• December 31 Key West
• 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.

• December 31 Key West
• New Year's Eve Gatsby Gala at First Flight Island Restaurant & Brewery
• Website
• Dress to impress in your Gatsby-era best for First Flight Island Restaurant & Brewery's New Year's Eve gala. Enjoy live music, DJ tunes and the Plane Drop at midnight. Heavy hors d'oeuvres, chef-manned food stations and an open bar. Purchase tickets in advance to ensure entry.

• January 02 - 04, 2025 Key West
• Waterfront Playhouse: Vagina Monologues
• Website
• Featuring talented local voices, Waterfront Playhouse presents Eve Ensler’s groundbreaking show, “The Vagina Monologues." The show is part of the theater's Spotlight series. Shows at 8 p.m. 407 Wall St. at Mallory Square.

• January 04 Key West
• Pole Vault in Paradise
• Website
• Pole Vault in Paradise is an all-comers pole vault competition taking place from 9 a.m. to 6 p.m. on Jan. 4 at Higgs Beach, 1000 Atlantic Ave. Participants compete in youth, masters and elite categories, with prize money for the elites. All pole vaulters are welcome and should register online. If you're not a pole vaulter, bring a chair or beach towel and watch the competition. Admission is free and food and beverage sales support the Key West High School track team. The event is sanctioned by the USATF and is on the World Athletic Calendar.

• January 05 - 09, 2025 Key West
• Key West Literary Seminar: Writers' Workshop Program
• Website
• Writers at all stages of development have opportunities to explore the craft of writing at eight distinct workshops available through Key West Literary Seminar before the main seminar begins. Workshops available on the January 2025 program are: Small Miracles: An Exploration of the Short Story; Key West and the Queer Home; Paths Through the Labyrinth: Plot and Structure, Structure and Plot; The Poet as Chronicler of Our Times; Writing Into the Unknown; Developing the Young Adult Voice; Writing Poetry Alongside The Iliad; and The Intersection of Home, Memory and Imagery in Memoir.

• January 07 - 08, 2025 Key West
• Studios of Key West: Susan Werner & Jonatha Brooke in Concert
• Website
• Join acclaimed folk rock artists Susan Werner and Jonatha Brooke for a night of innovative songwriting, captivating harmonies, and masterful musicianship. Jan. 7 at 7 p.m. in the Studio's Helmerich Theater and Jan. 8 at 6 p.m. on the rooftop at Hugh's View. 533 Eaton St.

• January 09 - 12, 2025 Key West
• Key West Literary Seminar: Family
• Website
• The Key West Literary Seminar is a four-day literary celebration that explores a different theme each year. The 2025 seminar theme is "Family" — the one we’re born into, those we’ve later built or chosen, and the ones we’ve lost or found or run as far away from as possible. For “Family,” the seminar brings together writers who can help us understand how the ties that bind shape the stories we tell, the worlds we move through, and all the imagination’s possibilities for human connection. Featured writers include John Irving, Brando Skyhorse, Paul Harding, Nathan Hill, Dani Shapiro and many more. Programs take place at the historic San Carlos Institute, 516 Duval St.

• January 09 Key West
• Key West Theater: Paul Poundstone
• Website
• Iconic comedian Paula Poundstone is known for her smart, observational humor and a spontaneous wit that has become the stuff of legend. She performs at Key West Theater for one night. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.

• January 10 Key West
• Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West
• Website
• Enjoy a 2-hour Historic Harbor Tour with Truman Little White House docent Rick Warmbold on the S/V Argo Navis, talking about "Harry S. Truman's Eleven Key West Visits." The trips departs from the Historic Seaport docks at 0 Margaret St. 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 Warmbold dives into Truman’s eleven working vacations, and shares how Key West was not only a place for the President to recharge his batteries – he will tell you how things in Key West would shape the country and world. Book reservations online in advance.

• January 12 Key West
• Key West Artisan Market: Don't Be Trashy!
• Website
• Key West Artisan Market invites you to help keep our island clean and learn more about the efforts of Plogging the Keys and the Keep Key West Beautiful initiative. Find out how you can help and ways to be a part of the solution. 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. 10 a.m. to 2 p.m. 1801 White St.

• January 14 Key West
• Key West Theater: Bitch Trouble
• Website
• Writer performer Alice Johnson Boher takes you on a coming-of-age roller coaster ride of the giddy highs and codependent lows of best friendship. Told in three chronological tales, Bitch Trouble charts Alice from friendless youngster in a lame southern subdivision all the way to one-half of an iconic friend duo in the shadows of Hollywood. Performance takes place in the theater's Back Stage Listening Room. Doors open 6 p.m.; show 7 p.m. 512 Eaton St.

• January 16 - 19, 2025 Key West
• 27th Annual Key West Half Marathon & Runfest Weekend
• Website
• Enjoy a weekend filled with running and camaraderie including 5k, 8k, 10k and half marathon races. Participants can also sign up for the Papa's Pilar Rum Stroll and the Bech N' Beer Mile, and celebrate with recovery and farewell parties.

• January 16 - 11, 2025 Key West
• Key West Kingfish Mayhem
• Website
• Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2025 Key West Kingfish Mayhem tournament. The open division team that weighs in the heaviest kingfish, also known as king mackerel, is to take home a $10,000 first prize.

• January 21 - 25, 2025 Key West
• Mile 0 Fest
• Website
• Mile 0 Festival is a premier music festival that celebrates Red Dirt and Americana music. Artists includes the Red Clay Strays, Randy Rogers Band, Shane Smith & the Saints, Steve Earle, Reckless Kelly, Kaitlin Butts and many more. A variety of passes that include lodging are available along with event-only passes.

• January 22 Key West
• Key West Theater: Melissa Etheridge
• Website
• Don't miss the legendary Melissa Etheridge on the Key West stop of her 2025 tour. Known for her confessional lyrics and raspy, smoky vocals, Etheridge has remained one of America’s favorite female singer-songwriters for more than two decades. Doors at 7 p.m.; show at 8 p.m. 512 Eaton Street.

• January 23 - 16, 2025 Key West
• 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.

• January 25 Key West
• Tropic Cinema: Movies Under the Stars - War Games
• Website
• Don't miss the monthly free Movies Under the Stars screening - this month, the movie is War Games. 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 approximately 6:30 p.m. 416 Eaton St.