One of the best times of year to visit Key West is over the Holiday season. From Thanksgiving to New Year’s the island offers a lot of activities and fun. But, what are the best things to do in Key West in December?
Holiday lights start to go up around Thanksgiving. The palm trees are in full glory around the Historic Seaport and Key West Bight. Other areas of the island follow suit. It’s a great time to grab a cocktail and stroll the streets to see all of the wonderful decorations. Maybe even grab a slice of Key Lime Pie? Each year, the residents, and businesses, go all out to show off their holiday spirit.
So… let’s dive into some of the fun you can have while visiting Key West
Historic Homes
Come check out historic homes all decorated with lots and lots of Christmas lights.
Year Round Historic Walking tour (self guided)
Lighted Boat Parade
Schooner Wharf Bar hosts the lighted boat parade every year. It is a crowd favorite for sure. This family fun event starts early (plan 6pm). Head over and enjoy a stroll through the Historic Seaport, shopping the stores and tasting the wonderful food from the many restaurants. But stay for the parade, it’s the Florida Keys and Key West’s tropical tribute to the season. (for date and time)
Mallory Square
Of course, no trip is complete without a trip to Mallory Square. Traveling with kids, or a kid at heart? Then plan to visit Santa during the day. As the sun starts to set, head over to shop the local artists’ booths and see the world famous Key West sunset celebration.
Trolleys and Trains
A great way to explore Key West is by one of the Conch Train or Old Town Trolley Tours. These are offered year round, but they have fun themed ones during the Holiday season. Explore the most decorated neighborhoods and maybe even a bit of caroling!
Looking for more fun? Check out the official calendar of events.
Water Activities
I know, you’re saying what, water sports?? It’s December. Well, if there are no cold fronts you can plan to spend some time on the water. Parasailing, snorkeling, dolphin watching, and other outdoor activities. Take advantage of the sunny days and be out on the water.
Not sure you want to go in the water? One of the best ways to see the coral reef is by glass bottom boat.
The Best Key West Glass Bottom Boat tours
Looking to enjoy a beautiful sunset cruise?
Other amazing water activities
New Year’s Eve
A very popular night in Key West is New Year’s Eve. Parties, fun, music and so much more can be found. Key West is so popular that CNN broadcasts this annual event live from Duval Street every year. Instead of watching the fun… plan to be there in all of the action. There are four ball drops to choose from to ring in the New Year.
- Conch Shell Drop – outside of Sloppy Joe’s, in the heart of Old Town and Duval Street the party is in the street.
- Pirate Wench Drop – want to see a Pirate Wench lowered from a schooner mast? Then head over to Schooner Wharf for the fun.
- Red Shoe Drop – As seen on CNN, Sushi will be lowered in a large red shoe outside of Bourbon Street. A lot of fun!
- Key Lime Wedge Drop – Sunset Pier drops a giant Key Lime wedge to ring in the New Year.
Oh my… so many choices… I’m thinking you will need to plan multiple vacations to experience all that Key West offers for the Holidays and New Year’s. But, what kind of weather can you expect?
Weather – What to Expect
Well… since Key West has never experienced snow, you can probably bet it will feel very tropical. But, the evenings can be a bit brisk so plan to bring a light jacket. I always check the weather forecast before traveling to make sure my clothes match the expected weather. However, I have been caught and had to go shopping (or did I plan that on purpose???) Either way, no need to pack boots, hats, and gloves for this tropical destination.
Key West weather is very moderate for December. During the day, the average temperature is in the mid-70’s while at night average temperatures drop to mid to upper 60’s. It is less muggy in December than in the summer months. Rainy days are a bit behind us (with hurricane season ending in November – but there could always be an outlier) On average, December sees about three rainy days. The water temperature is in the mid-70’s. Overall, average high temperatures will be warm, a few days of sunny skies and a bit of cloud cover. Sounds perfect right?
How to Get to Key West
We’ve planned your events and talked about the weather, but let’s plan how you are getting to Key West. The best way is to fly into Key West International Airport and take a cab to your hotel. Parking spots can be really hard to find and probably will have a daily fee. If you need to drive, then plan to be near a public parking garage/lot and plan to pay for parking.
Ultimate Road Trip from Miami to Key West (Best places to stop)
Best Breakfast Places in Key Largo
Key West is one of the best places to be in December. The warm weather, live music, and fun activities are some of the best reasons to escape to one of the warmest places in the winter months. I would even say… it’s the most wonderful time of the year.
Keep scrolling to see the full list of activities for December. Can’t make it this year? Well, now you have an idea of what to expect!
Calendar of Events
History of Diving Museum: Salvaging the Deep – Until December 31, 2024
Learn about some of the world’s deepest wrecks and how salvage divers got there in the museum’s featured exhibit, on display through Dec. 31. Mile marker 82.9.
Waterfront Playhouse: Into the Woods – until December 14, 2024
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.
The Protect Center: Sea of Trees – until January 5, 2025
Over 100 uniquely decorated and sponsored trees light your way nightly from 10 a.m. to 6 p.m. daily from Nov. 29 through Jan. 5. In addition to the beautiful lights and trees, you’ll find photo opportunities and shopping. On these select nights – Nov. 29, 30; Dec. 1, 6, 7, 13, 14, 20, 21, 22 from 6 to 9 p.m. – enjoy Santa’s Village with holiday-themed cocktails and snacks, workshops for kids and visits with Santa. Admission of $10 adults; $5 kids supports the Dolphin ICU at The Protect Center. MM 82 bayside.
Key West Artisan Market: Rock the Red Ribbon Edition – December 1
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.
Key West End of Prohibition Celebration – December 1 -5, 2024
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.
Comedy Key West: Brendan Eyre – December 4 – 7, 2024
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.
Sloppy Joe’s Bar: End of Prohibition Repeal Party – December 5
Party like it’s 1933 at the End of Prohibition Repeal Party! Live entertainment runs all day beginning at 10 a.m. The party really begins in the 5 o’clock hour with the Repeal Party commemorating the historic 5:32 pm. repeal. Costume anti-Prohibition revelers will enjoy swinging bands, costume contests, period cocktails and more. The fun runs through 2 a.m. Find the action and fun at Sloppy Joe’s Bar, 201 Duval Street.
Key West International Dance Co.: Fiesta de Navidad Tropical – December 5 -6, 2024
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.
Pet Pictures with Santa – December 5
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.
Nutcracker Key West – December 5 -15, 2024
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.
Holiday Historic Inn Tours: Night #1 – December 6
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.
Coffee Butler Amphitheater: Holiday Village & BeLighted Bike Ride – December 6
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.
Key West Art & Historical Society: Opening Reception for Collecting Key West – The Works of Mario Sanchez – December 6
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.
Key West Theater: Under the Streetlamp – December 6
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.
Islamorada Holiday Fest – December 6
Bundle up for one of the most exciting events of the year in Islamorada – the annual Holiday Fest at Founders Park – to kick off the Upper Keys holiday season. The forecast calls for lots of snow, with a 30-ton mound of the cold, white stuff brought in to delight mitten-clad kids, along with the 35-foot tall holiday tree that “blows” snow through its branches. The festival includes a holiday gift bazaar, an auction of more than 60 prized ornaments crafted by local artists and Santa’s Sweet Shoppe. The festivities are capped off with the annual Holiday Parade starting at 7:30 p.m. Mile marker 87 bayside.
Key West Theater: The Kingston Trio – December 7
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.
Key West Hometown Holiday Parade – December 7
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.
Eaton Street Christmas Stroll – December 8
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.
Key West Artisan Market at Southernmost Beach Resort – December 8
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.
Sheriff’s Animal Farm Open House: Christmas on the Farm – December 8
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!
Old Town Trolley: Holiday Nights Tours – December 9 – 23, 2024
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.
Conch Tour Train’s Holiday Sights & Festive Nights Tours – December 9 -23, 2024
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.
LaTeDa Christmas Party – December 10
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.
Fringe Theater: Tony Konrath’s A Christmas Carol – December 10
‘Tis the season! It’s a fresh take on the Charles Dickens ghost story of holiday transformation and redemption. Showtimes at 7 p.m. at the Armory, 600 White St.
Gay Key West Holiday Lights Trolley Tour – December 11
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.
Pigeon Key Holiday Spectacular – December 13 – 14, 2024
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.
Holiday Historic Inn Tours: Night #2 – December 13
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.
Waterfront Winter Wonderland – December 13 – 28, 2024
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.
Key West Art & Historical Society: Holiday Concert & Bazaar – December 13
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.
Key West Outdoor Movies – Nightmare Before Christmas – December 13
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.
Key West Theater: The Magic of Christmas – December 13
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.
Schooner Wharf Bar Lighted Boat Parade – December 14
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.
‘A Positive Step’ 5k Rudolph Red Nose Run – December 14
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.
Snowy Days Children’s Concert at Key West Botanical Garden– December 15
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.
Key West Artisan Market: Fill the Pantry Edition – December 15
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.
Fringe Theater’s Holiday Train Ride – December 18
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.
Key West Art & Historical Society Historic Seaport Sail: Plant a Million Corals Project – December 18
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.
Comedy Key West: Jim Florentine – December 18 -21
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.
Walk on White Third Thursday Art Walk– December 19
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.
Key West Art & Historical Society Distinguished Speaker Series: Storms, Shipwrecks & Saints’ Names – December 19
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.
Tropic Cinema: Movies Under the Stars – Elf – December 21
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.
Running of the Elves 5k Run/Walk & Jingle Bell Mile – December 21
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!
Key West Artisan Market: Shop Local Edition – December 22
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.
The Gardens Hotel: Holiday Jazz in the Gardens – December 22
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 Street.
Old Island Restoration Foundation: Noche Buena – December 24
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.
Key West Lighting of the Menorah – December 29
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.
Sunset Green Lawn: Early New Year’s Eve Celebration– December 30
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.
Schooner Wharf Bar: New Year’s Eve Lowering of the Pirate Wench – December 31
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.
New Year’s Eve Red Shoe Drop– December 31
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.
New Year’s Eve Conch Shell Drop at Sloppy Joe’s– December 31
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.
New Year’s Eve Gatsby Gala at First Flight Island Restaurant & Brewery– December 31
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.
