Calendar of Events
Current Florida Keys Events




- Sponsored Event
- Jan 13, 2024 - Jan 14, 2024 Key West
- Key West Half Marathon & Runfest
- Website Key West Historical Seaport
- 231 Margaret Street Key West FL 33040
- 305-240-0727 E-mail
- View video
- The 26th Anniversary of the Key West Half Marathon & 5k will take place during the week-end of January 13-14, 2024. On top of previous years race day events, this years race day will include the Papa’s Pilar Rum Stroll and Key West Beach N’ Beer Mile!
- Buy tickets!




- Sponsored Event
- May 01, 2023 - Dec 31, 2023 Islamorada
- History of Diving Museum
- Website History of Diving Museum
- 82990 Overseas Highway (MM83), Islamorada FL 33036
- 305-664-9737 E-mail
- Open daily. Be amazed by over 4,000 years of “the quest to explore under the sea” and celebrate the special role South Florida and the Florida Keys had in this untold story. Dive in to see “Aquanauts to Astronauts” a limited-time featured exhibit.




- Sponsored Event
- Dec 04, 2023 - Aug 31, 2024 Key West
- Christopher Peterson's Eyecons at LaTeDa
- Website LaTeDa Cabaret
- 1125 Duval St Key West FL 33040
- LaTeDa 305-296-6706 E-mail
- View video
- Christopher Peterson is a master of impersonations, both visually and vocally, and his comic timing is impeccable. The show is All Live, no lip-sync, and audiences will be thrilled with his many characterizations. Tickets available now!
- Buy tickets!
- May 20, 2023 - Dec 31, 2023 Islamorada Arts & Culture
- History of Diving Museum: Aquanauts to Astronauts Exhibit
- Website
- The Aquanauts to Astronauts exhibit focuses on the fascinating relationship between diving and space travel, how NASA uses diving to train future astronauts, and the incredible people who have both been to space and visited the bottom of the sea. The exhibit includes artifacts from NASA. The museum is located at 82990 Overseas Highway bayside.
- 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.
- 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.
- Dec 1, 2023 - Jan 7, 2024 Islamorada Arts & Culture
- The Protect Center: Sea of Trees
- Website
- The Florida Keys Sea of Trees is the Keys' newest holiday tradition, showcasing over 100 uniquely-themed trees and displays with thousands of lights, plus vendors for holiday shopping. Find photo opportunities, especially during select nights with Santa and his workshop on Dec. 2nd, 9th, 16th, 22nd and 23rd. Admission is $10, benefitting the Protect Center, the only whale and dolphin hospital in the Keys. Open nightly through Jan. 7 from 6 to 9 p.m. at mile marker 82 bayside.
- Dec 8, 2023 - Dec 10, 2023 Islamorada Fishing
- Islamorada Junior Sailfish Tournament
- Tammy Gurgiolo 305-240-9337 E-mail
- The Florida Keys’ oldest sailfish tournament for kids age 16 and under, this event has been held since 1964. It is designed to teach teens fishing skills they can apply in competition.
- Dec 8, 2023 - Dec 23, 2023 Key West Arts & Culture
- Old Town Trolley's Holiday Sights & Festive Nights Tours
- Website
- The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m.
- 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.
- Dec 9, 2023 - Dec 10, 2023 Islamorada
- Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N' Beer Mile
- Website
- Participants of all ages and skill levels are invited to register for these popular, annual subtropical footraces. Races start and finish this year at La Siesta Resort & Villas, mile marker 80 oceanside. Saturday's 5k starts at 8 a.m., followed by the Beach 'n Beer Mile "fun run" at noon. The half marathon and 10k races start at 7 a.m. Sunday as the sun rises, with runners headed across the Tea Table Channel Bridge. Registration is filling fast but some spots are still available.
- Dec 10, 2023 Key West Arts & Culture
- 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.10 starting at 5 p.m. 1320 Truman Avenue.
- 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.
- Dec 10, 2023 Marathon Arts & Culture
- Key Colony Beach Christmas Boat Parade
- Website
- Key Colony Beach holds its annual Christmas Boat Parade beginning at dusk with boats of all sizes and shapes. The parade starts at the 7th Street Canal. Find public viewing along the Sadowski Causeway at mile marker 53.5.
- Dec 10, 2023 Key Largo
- Meowliday Party & Key Largo Cat Cafe Grand Opening
- Website
- The Upper Keys Humane Society is opening the Key Largo Cat Cafe with a Meowliday Grand Opening party Sunday, Dec. 10 from 11 a.m. to 2 p.m. Attendees can enjoy the Kitten Den - a room full of playful, loose kittens - and tour the facility's state-of-the-art operating room for spay and neuter surgeries. Enjoy a cocktail, mock-cocktail or coffee and hors d'oeuvres, play with the cats and learn about plans for the next project, which is to be a large indoor/outdoor cat aviary that will serve as a play area for cage-free indoor cats. Mile marker 101.6 oceanside. Additional parking is to be available at the Tradewinds Publix parking lot with free shuttle service.
- Dec 10, 2023 Key West Arts & Culture
- Key West Artisan Market: Merry Marketplace on the Beach
- Website
- Shop for holiday treasures from local artisans while enjoying live music, tasty treats, fun drinks, activities for the kids – including a ‘snowman’ building contest and even a visit from old St. Nick. 10 a.m. to 3 p.m., Southernmost Beach Resort, 1317 Duval St.
- 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.
- Dec 10, 2023 Islamorada Environmental
- Florida Keys Brewing Company: CNN Hero Watch Party
- Website
- Come to the beer garden to watch the live stream of the 2023 CNN Hero of the Year announcement to find out if I.CARE co-founder Mike Goldberg has won this prestigious award! Enjoy spending time with the I.CARE team and our community coral reef supporters. Enjoy the delicious brews at FKBC. Light refreshments will be provided. 7 to 9 p.m.
- Dec 11, 2023 Islamorada Arts & Culture
- REEF: Merry Fishmas Trivia Night
- Website
- Test your "fishy knowledge" at a Merry Fishmas-themed trivia night with ocean, holiday and Florida Keys-themed trivia. It's free to play and prizes will be awarded to the top scoring teams. A portion of the proceeds from the event will be donated to REEF's marine conservation programs. 7 to 9 p.m., Florida Keys Brewing Company, mile marker 81.6 oceanside.
- 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.
- 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.
- Dec 12, 2023 The Lower Keys Arts & Culture
- Big Pine Key Pet Photos With the Grinch
- Website
- Strike a pose with your pet and the Grinch to create a Who-tastic holiday picture in exchange for a donation to the Florida Keys SPCA. Pets should be on a leash or in a carrier. 5 to 7 p.m. at Berkshire Hathaway, 30085 Overseas Highway.
- 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.
- 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.
- 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.
- 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.
- Dec 15, 2023 Marathon Arts & Culture
- Pigeon Key: Movies by the Sea - The Polar Express
- Website
- Pigeon Key invites you to come dressed in your holiday pajamas to the island Friday, Dec.15 for a holiday-themed Movies by the Sea Night featuring the film, The Polar Express! Free hot chocolate and popcorn are included with each ticket, with other concessions available for purchase. Round trip train rides for the movie are sold out; but tickets for walkers and bikers are still available at $15 each. The movie begins at 7:30 p.m.
- 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.
- 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.
- Dec 15, 2023 Marathon Arts & Culture
- Tropical Holiday Fun Fest
- Website
- Holiday fun for all with Santa, the Grinch, the Prodigy Dancers, bounce houses and more. 6 to 8 p.m. at Marathon Community Park, 200 36th Street Ocean.
- Dec 16, 2023 Marathon Arts & Culture
- Marathon Community Theatre: Club MCT Ugly Christmas Sweater Party
- Website
- Club MCT is back with an Ugly Christmas Sweater-themed, age 21 and over dance party! Dance the night away from 8 p.m. until midnight with music by DJ Trae Dae. Tickets $15, available online in advance or cash at the door. 5101 Overseas Highway.
- 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.
- Dec 16, 2023 - Dec 18, 2023 The Florida Keys Arts & Culture
- Holiday Follies
- Website
- The Provincetown Business Guild and The Crown & Anchor with AQUAPLEX and The Key West Business Guild present The Holiday Follies: Make The Yuletide Gay! featuring Yoli Mayor (America’s Got Talent), Matthew Darren (American Idol), Tina Burner (RuPaul’s Drag Race), and Boomer Banks, with a wonderful cast of favorite Key West and Provincetown talent. Tickets start at $40. Show at 8 p.m. at Sidebar at Aquaplex, 504 Angela Street.
- Dec 16, 2023 Marathon Arts & Culture
- Crane Point Hammock: Winter Wonderland
- Website
- At Crane Point Hammock Museum & Nature Trails, 5550 Overseas Highway, families can enjoy an evening winter wonderland from 4:30 to 8 p.m. Attractions are to include reindeer ponies, Santa and Mrs. Claus, performers from Marathon Community Theatre, sleigh rides, holiday decorations, a chocolate fountain, other seasonal treats and alcoholic drinks for purchase — plus a forecast of snow!
- 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.
- Dec 16, 2023 The Lower Keys Arts & Culture
- Kiki's Lighted Boat Parade
- Website
- Lighted and festively decorated boats cruise the waters past Kiki's Sandbar Bar and Grille, 183 Barry Avenue on Little Torch Key, from 7 to 10 p.m. Watch from Kiki's restaurant, the beachfront or from the dock extending into the water.
- 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.
- 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.
- Dec 17, 2023 Marathon Arts & Culture
- Marathon Community Theatre: Drag Queen Bingo - Jingle All the Way
- Website
- Jingle all the way with host J.J. Mills at this month's Drag Queen Bingo event. Holiday-themed costumes are welcome but not required. If you choose to dress up, you can strut your holiday stuff by walking the runway. 5 to 7 p.m. Tickets $10 for attendees 18 and over only. 5101 Overseas Highway.
- Dec 18, 2023 The Lower Keys Environmental
- Full Moon Kayak Excursion
- Capt. Bill Keogh, 305-872-7474 Website
- Paddle the waters surrounding the National Key Deer Refuge in Big Pine Key as the sun sets and the full moon rises. Leading the tour is Captain Bill Keogh of Big Pine Key Kayak Adventures. Reserve your spot with a $30 donation to the Florida Keys Wildlife Society. Before you reserve a spot, please text or call Captain Bill at 305-872-7474 to get more details, discuss your preferences on kayaks (single or tandem) and what additional equipment to bring. Meet at 3:30 p.m. at Old Wooden Bridge Marina, 1791 Bogie Road. The trip will be from The trip will be from 4 to 6 p.m.
- 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.
- 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.
- Dec 21, 2023 Islamorada Arts & Culture
- Morada Way Third Thursday Art Walk
- Website
- The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.
- 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.
- Dec 22, 2023 Islamorada Arts & Culture
- Florida Keys Brewing Company: Holiday Hat Party
- Website
- Everybody loves an ugly sweater contest, but it's a little too warm to wear those! The solution? A holiday hat party! Wear your favorite holiday hat or create a new festive masterpiece. There will be prizes for Most Creative, Most Festive and Funniest hats, along with holiday drinks and decor. The brewery is located in the Morada Way Arts and Cultural District, between mile markers 81 and 82 oceanside.
- Dec 24, 2023 Key West Arts & Culture
- 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 7:30 p.m. 526 Angela St.
- 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.
- Dec 27, 2023 - Dec 31, 2023 The Florida Keys Arts & Culture
- Fringe Theater: An Evening with Lillian Baxter
- Website
- This clever cabaret-style show celebrates the ups and downs of the almost-famous Lillian Baxter, whose career careened from MGM to television to obscurity in the 1970s. Sharing the stage for this colorful ride is Lillian’s faithful accompanist (and favorite ex-husband) Corky Weinstopper. Don’t miss this musical memoir of the greatest star nobody's ever heard of, performed by John Vessels and Jay Schwandt. Tickets start at $45. Shows at 7 p.m. at the Little Room Jazz Club, 821 Duval St.
- 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.
- 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.
- Dec 30, 2023 - Dec 31, 2023 Marathon Arts & Culture
- Marathon Community Theatre: Murder at the Office New Year's Eve Party
- Website
- Enjoy dinner and a delightful murder mystery performance with shows on Saturday night and Sunday (New Year's Eve). Doors open at 6 p.m. with the show and dinner at 7 p.m. $75 per person tickets include dinner, which is a three-course surf-and-turf meal plus a champagne toast. Get tickets online in advance. 5101 Overseas Highway.
- 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.
- 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.
- 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.
- Dec 31, 2023 Key West Arts & Culture
- Schooner Wharf Bar: New Year's Eve Pirate Wench Drop
- Website
- Schooner Wharf Bar invites you to join the party to witness the annual tradition of the Lowering of Pirate Wench Evalena, who will once again descend from the towering mast of Schooner America 2.0 to welcome in 2024. The fun starts in the afternoon with live music continuing into the New Year.
- 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.
- Dec 31, 2023 Key West
- Key West Artisan Market: New Year's Eve Edition
- Website
- Start your New Year's Eve celebration at the market located near Higgs Beach at 1801 White St. from 10 a.m. to 2 p.m. with great food, libations, entertainment, arts and crafts, jewelry and much more.