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. Make plans to grab a cocktail and stroll the streets to see all of the wonderful decorations. 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?? 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 so much more. 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 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 dropping 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. Overal, warm temperatures, 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: Aquanauts to Astronauts Exhibit – through December 31
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.
Harbor Walk of Lights – through December 31
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.
Waterfront Playhouse: Little Shop of Horrors – through December 16
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.
Holiday Village & Belighted Bike Ride – December 1
The Wesley House Family Services’ Holiday Village & BeLighted Bike Ride from 4 to 8 p.m.at Truman Waterfront Park’s Coffee Butler Amphitheater, 21 Quay Rd., is a fun-filled, festive evening for all ages and a great way to kick off the Keys’ Holiday season. The Holiday Village is the pre-party to the bike ride, featuring over 20 community booths offering games, goodies, and crafts for the kids, bounce houses, DJ, food trucks, and photos with Santa. Enter the “best bike” contest at 7 p.m. and then cruise Duval St. at 8 pm on your ultra-lighted bike. Costumes are encouraged.
World AIDS Day Procession and Service – December 1
All are welcome to gather to celebrate the lives of friends and loved ones taken from us too soon, and to honor those lost in 2023. A processional starts at 4:30 p.m. from Key West City Hall, located at 1300 White Street, ending at the Key West AIDS Memorial at Edward B. Knight pier, 1800 White Street. A ceremony is to follow upon arrival at the memorial.
Pet Pictures with Santa – December 1
Bring your festively outfitted kids and 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. Photos are $25 each (cash only) with proceeds benefitting the Boys and Girls Club of the Keys.
Islamorada Holiday Fest – December 1
The forecast for Dec. 1 calls for snowballs in Founder’s Park as Snow Mountain returns to the 19th annual Holiday Fest. Kids will need their mittens to play on the icy mound made of 30 tons of snow. The annual holiday tree will be blowing snow from its branches during the celebration. The holiday bazaar is the perfect place to shop for holiday treasures including art, jewelry and unique gift items. Fifty special holiday ornaments crafted by local artists are available through an online auction during the event. Don’t miss Santa’s Sweet Shoppe and the annual Holiday Parade with the theme “Happy Holiday and Best Fishes.” Festivities run from 4 to 10 p.m. with the parade at 7:30 p.m. MM 87 bayside.
KEY WEST HOMETOWN HOLIDAY PARADE – December 2
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local 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.
MOTE’S OCEAN FEST: A COMMUNITY CELEBRATION – December 3
Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment at Mote Marine Laboratory’s annual Ocean Fest from 10 a.m. to 4 p.m. Enjoy an outdoor community celebration of the oceans at Truman Waterfront Park. Enter at 100 Southard Street for a day of family activities, raffles, live music, shopping and environmental exhibits. Mote scientists will be there to answer questions about coral reef research and restoration. Family activities include children’s fishing clinics, live animals, bounce houses and a rock wall. Adult attendees will get a free beer ticket with the donation of a new-unused toy in Mote’s Toys for Tots bin.
Marathon Community Theatre: Christmas Cabaret with Jaimie Roberts – December 2
This one-night event featuring Jaimie Roberts with Randy Morris will be the perfect holiday date night. It’s a Christmas cabaret that will knock your stockings off! 18-and-over only. Tickets $35 each plus tax. Doors and concessions open at 7 p.m. Show at 8 p.m. 5101 Overseas Highway, oceanside.
Garden Club of the Upper Keys: Holiday Market – December 2
The annual Holiday Market takes place on the shaded grounds of the Francis Tracy Garden Center at mile marker 94 bayside from 9 a.m. to 4 p.m. Browse and shop for beautiful plants, artwork and a wide range of artisan-made gift items. Food trucks will be available.
First State Bank Key Largo Bridge Run – December 2
Close to 500 runners from around the U.S. and other countries are to challenge their best times amid spectacular scenery during this 5k run/walk event over the beautiful Jewfish Creek Bridge. Race time is 7:30 a.m. Runners will access the northbound lanes of the bridge from Gilbert’s Access Road, run toward the Key Largo side, then turn around and run back across the bridge to finish back at the start line. Registrations are filling fast, but there are a few spaces available. Northbound traffic out of the Keys will be diverted to County Road 905/Card Sound Road between 6 and 9 a.m.
Lignumvitae Christmas – December 2
Celebrate the history and heritage of Lignumvitae Key Botanical State Park on this special day of exploration and holiday celebration from 10 a.m. to 4 p.m. Purchase tickets online for boat transportation from Robbie’s to the park with departures at various times. Enjoy guided nature hikes, tours of the 1930s era caretaker’s home, history presentations and stories by Brad Bertelli, old fashioned games including croquet, and art and craft stations to make ornaments to take home. Free cookies and limeade will be offered, with other snacks on sale to benefit the Friends of Islamorada Area State Parks.
Key West Art & Historical Society: Headdress Ball – 40 Years of Creativity – through December 3
Combining captivating entertainment and creative competition, the Key West Headdress Ball has been the premier LGBTQ+ event of the Fantasy Fest celebration for the last 40 years. The ball typically features up to 25 contestants showcasing their unique headdresses, some that tower high above their designers. This special exhibition showcases the works of art worn in the 2023 competition. On display daily from 10 a.m. to 5 p.m. at the Custom House Museum, 281 Front St.
Coast is Clear Festival – through December 3
As another Atlantic hurricane season closes, the Coast is Clear Festival kicks off the high season in Key West with a weekend of music and cultural events throughout Old Town. Highlights include a series of nighttime ticketed events, plus multiple free shows daily at the Green Parrot, and a public sandlot baseball tournament Saturday at Bayview Park. Tickets are available for single events or there is a full weekend pass available at www.coastisclearfest.com.
KEY WEST ARTISAN MARKET: RED RIBBON EDITION – December 3
Key West Artisan Market supports World Aids Day December 3, from 10 a.m. to 2 p.m. Pick up a free ribbon to wear from the volunteers of the Friends of the Aids Memorial. Shop for fine arts and crafts, jewelry, apparel, produce, delicious foods and drinks and more. In the park near Higgs Beach, 1801 White St.
MONTESSORI UNITED 5K RUN/WALK – December 3
Runners and walkers are invited to participate in the Montessori United 5k and Kids Fun Run beginning and ending at Truman Waterfront Park. The 5k run, walk and stroller divisions are $35 and begin at 8 a.m. The Kids 1-Mile and Kids Half-Mile registration fees are $20 and races start at 9 a.m. Spectators can register for VIP tickets to enjoy a light breakfast and mimosa while cheering on race participants. The run benefits Montessori education in Key West.
KEY WEST UNITED METHODIST CHURCH: HANDEL’S MESSIAH – December 3
All are welcome for this annual performance of George Frederic Händel’s Messiah. 7 p.m. at the church at 600 Eaton Street.
KEY WEST WOMAN’S CLUB: SANTA, SWEETS AND HOLIDAY TREE LIGHTING – December 3
Celebrate the season with the Key West Woman’s Club and Key West Mayor Teri Johnston at the historic Hellings Curry Museum at 319 Duval St. Enjoy appetizers, desserts, Amsterdam eggnog, and holiday music performed by the Bahama Village Children’s Choir and the Key West Community Orchestra. Donations of unwrapped, new clothing items for students K-12 appreciated.
CONCH REPUBLIC SEAFOOD COMPANY: SANTA MEET AND GREET – December 3
Come out to meet Santa and get your holiday photos with the jolly old elf. Donations support the Key West Police Department Love Fund, which provides aid to any department member in crisis.
Shop, Jingle & Mingle – December 3
The Cirque Salon Studios at Tradewinds Plaza hosts the 6th annual Shop, Jingle & Mingle event Sunday, Dec. 3 from noon to 4 p.m. Browse for gifts at this popular pop-up holiday market. Find unique gifts created by local artists along with Key Largo Chocolates, locally made honey, children’s clothing and other handmade gift items. Raffle tickets are to be sold for custom gift baskets with all proceeds supporting Good Health Clinic of Key Largo. Mile marker 101.4 oceanside.
Florida Keys History & Discovery Museum: Afro-Caribbean Migration to Florida – December 4
In this Lunch & Learn program, Historian Magdalena Lamar presents a program on the historical ties that Florida and Afro-Caribbean people have shared since the time Ponce de Leon first arrived on Florida shores. She’ll examine the history and unique characteristics of Florida settlement patterns from the Spanish colonization period to the present. It covers some of the Spanish, English and French-speaking Caribbean islands and the significant contributions those groups have made to Florida’s cultural, economic, political, social, and environmental development. Tickets are $25, with the program from 12 noon to 1 p.m. at the museum, located on the Islander Resort property at mile marker 82 oceanside.
FLORIDA KEYS SPCA – POSH FUNDRAISER – December 7
The 10th annual POSH (Paws Often Steal Hearts) fundraiser benefitting Florida Keys SPCA takes place from 6 to 9:30 p.m. at Audubon House and Gardens, 205 Whitehead St. The gala affair encourages guests to dress up and don their favorite fascinators. Silent auctions, raffle prizes, a tapas-style dinner and live music are all part of the fun. Follow the Second Line Procession at the end of the night to continue the party.
Taste of Stock Island Trolley Tour with a Holiday Twist – December 7
Board a trolley for an early-evening culinary tour of favorite Stock Island restaurants. Attractions include a small plate and beverage pairing at each stop as well as insights from the chef, owner, sommelier and/or brew master. For participating restaurants, tickets and trolley schedule, visit ilovestockisland.org.
HOLIDAY HISTORIC INN TOURS: NIGHT #1 – December 8
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: the Key West Butterfly and Nature Conservatory, Wicker Guesthouse, The Mermaid and the Alligator, and the Marquesa Hotel. The tours are self-guided. $40 tickets available online, but must be picked up after 5:30 p.m. on Dec. 8th at the first location, the Butterfly and Nature Conservatory, 1316 Duval Street. The second inn tour takes place Dec. 15.
OLD TOWN TROLLEY’S HOLIDAY SIGHTS & FESTIVE NIGHTS TOURS – December 8 – 23, 2023
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.
CONCH TOUR TRAIN’S HOLIDAY SIGHTS & FESTIVE NIGHTS TOURS – December 8 – 23, 2023
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.
KEY WEST ART & HISTORICAL SOCIETY: ANNUAL HOLIDAY CONCERT & BAZAAR – December 8
This popular annual celebration features 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. The bazaar offers shoppers a treasure trove of unique gift items and there will be plenty of food and festive libations Free and open to the public, the event takes place on the front porch and the street in front of the Customs House Museum at 281 Front Street.
Plant a Million Corals: Cocktails for Corals – December 8
The Plant a Million Corals Foundation hosts a Cocktails for Corals event to raise funds and awareness for coral restoration. Enjoy a variety of coral-inspired cocktails, delicious food, a silent auction, live music and updates on operations, future plans and activities at Coral Restoration Park. The event takes place at South of the Seven restaurant, 17075 Overseas Highway bayside from from 6 to 9 p.m. $150 per person. Tickets available online.
Marathon Pet Photos With the Grinch – December 8
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. 4:30 to 6:30 p.m. at Berkshire Hathaway, 9141 Overseas Highway.
Marathon Community Theatre: Holiday Show & Sing-Along – December 8
Enjoy a family-friendly evening filled with cheer, joy, music and dancing at Marathon Community Theatre’s annual Holiday Show and Sing-A-Long concert. Doors and concessions open at 6 p.m.; show at 7 p.m. Tickets $10 each. 5101 Overseas Highway oceanside.
Key Largo Lighted Bike Ride – December 8
All are invited to join the Key Largo Lighted Bike Ride, Friday Dec. 8. Decorate your bike with lights and wear Christmas sweaters or other festive attire. Participants are to register at 5:30 p.m. at Florida Mortgage Lab, mile marker 102.9 oceanside. The ride begins at 6:30 p.m., proceeding up and down U.S. 1 with a Monroe County Sheriff’s Department escort. Donations at registration support Mrs. Clause a Merry Cause, which helps Keys children in need.
10TH ANNUAL PARADE OF PAWS & HOLIDAY BAZAAR – December 9
Celebrate dogs at this annual dog parade and holiday bazaar with local vendors. Santa will be there for photos with the pups along with the Smooch-a-Pooch booth, raffles and tons of fun. Higgs Beach Dog Park, corner of Atlantic and White St. from 10 a.m. to 2 p.m.
Holiday Lighted Boat Parade of Stock Island – December 8
Enjoy live entertainment, holiday treats, photos with Santa and a great view of the annual lighted boat parade of Stock Island from the waterfront at The Perry Hotel & Marina. 5:30 to 9 p.m.at 7001 Shrimp Rd.
CARL HIAASEN IN CONVERSATION WITH JUDY BLUME – December 9
Best-selling “Florida Fiction” author Carl Hiaasen appears Saturday, Dec. 9 at 3 p.m. in conversation with Judy Blume at the Helmerich Theater at the Studios of Key West, hosted by Books & Books. They’ll discuss his new middle-grade novel for young readers, WRECKER, about the teenage descendent of a Key West shipwreck salvager and his exploits with shady characters after he finds them wrecked in their speedboat. The event is sold out but there is a waiting list. Access the online ticket link to sign up. The event takes place at 533 Eaton Street.
KEY WEST PET PICTURES WITH THE GRINCH – December 9
Bring your critters for pet pictures with the Grinch Saturday, Dec. 9 at the Hard Rock Cafe, 313 Duval St. from noon to 3 p.m. $20 per photo session. Proceeds benefit River’s Wish, a non-profit senior dog sanctuary.
32ND ANNUAL SCHOONER WHARF/ABOSULT VODKA LIGHTED BOAT PARADE – December 9
Deck the hulls, it’s time for the annual Schooner Wharf Lighted Boat Parade along Key West Bight and Historic Seaport. The glittering parade of illuminated watercraft begins at 8 p.m. There are multiple viewing spots from bars and restaurants and from spots all along the Harbor Walk. Family fun begins at 6 p.m. with the Bahama Village Music Program’s House of Pans steel band playing calypso Christmas carols at Schooner Wharf Bar, 202 William Street.
Boot Key Harbor Christmas Boat Parade – December 9
Everything from lighted and decorated dinghies to yachts are to cruise in the 27th annual Boot Key Harbor Christmas Boat Parade. The festive parade begins at dusk and meanders past popular Boot Key Harbor waterfront restaurants. Parade awards and a party are to take place after the parade at Dockside at Boot Key Harbor, 35 Sombrero Blvd. Visit bootkeyharbor.com or call 561-542-2727.
Santa at the Park: Harry Harris Beach & Park – December 9
Monroe County Fire Rescue and Monroe County Parks and Beaches invite the public to take a picture with Santa and meet local firefighters on Saturday, Dec. 9, from 12 noon to 2 p.m. at Harry Harris Park, at 50 E. Beach Rd. in Tavernier. The first 100 children will receive a frisbee, and there will also be candy canes and fire truck tours.
Key Largo Lighted Boat Parade – December 9
The theme for this year’s lighted boat parade on Blackwater Sound is Christmas Around the World. Decorated boats begin their procession at 7:30 p.m. Viewing available from bayside waterfront bars, restaurants and resorts around mile markers 103-104.
Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N’ Beer Mile – December 9 – 10, 2023
Whether bucket-list runners or newbies, participants of all ages and skill levels are invited to register for these annual subtropical footraces. Races start and finish this year at La Siesta Resort & Villas, MM 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. Only registration is filling fast but some spots are still available.
Key Colony Beach Christmas Boat Parade – December 10
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.
SHERIFF’S ANIMAL FARM: CHRISTMAS ON THE FARM – December 10
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.
KEY WEST LIGHTING OF THE MENORAH – December 10
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.
KEY WEST ARTISAN MARKET: MERRY MARKETPLACE ON THE BEACH – December 10
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.
EATON STREET CHRISTMAS STROLL – December 10
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.
Meowliday Party & Key Largo Cat Cafe Grand Opening – December 10
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.
REEF: Merry Fishmas Trivia Night – December 11
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.
THE STUDIOS OF KEY WEST: ANN HAMPTON CALLAWAY – December 12
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.
FRINGE THEATER: THE BEST CHRISTMAS PAGEANT EVER – December 12 – 16, 2023
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.
24 NORTH HOTEL: PAINT & SIP NIGHT WITH ARTIST LANCE BERRY – December 12
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.
Big Pine Key Pet Photos With the Grinch – December 12
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.
KEY WEST ART & HISTORICAL SOCIETY: HAPPY HOUR WITH THE HISTORIAN – December 14
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.
GAY HOLIDAY GETAWAY – December 14 – 17, 2023
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.
KEY WEST WATERFRONT WINTER WONDERLAND – December 15 – 30, 2023
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. The amphitheater’s vendor village is to offer a variety of food options and local artisans perfect for holiday shopping. Don’t miss out on special holiday experiences including photo opportunities with Santa, crafts and more. Admission $10 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. Tickets go on sale mid-November.
HOLIDAY HISTORIC INN TOURS: NIGHT #2 – December 15
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.
Pigeon Key: Movies by the Sea – The Polar Express – December 15
Pigeon Keys invites you to come dressed in your holiday pajamas and ride the Pigeon Key Express to the island Friday, Dec.15 for a holiday-themed Movies by the Sea Night featuring The Polar Express! Free hot chocolate and popcorn are included with each ticket, with other concessions available for purchase. Round trip train rides plus movie tickets are $25; for walkers and bikers $15. Trains depart the depot, located at 1090 Overseas Highway, at 6:15 and 6:45 p.m. The movie begins at 7:30 p.m.
‘A POSITIVE STEP’ 5K RUDOLPH RED NOSE RUN – December 16
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.
Holiday Follies – December 16
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.
TENNESSEE WILLIAMS THEATRE: FIESTA DE NAVIDAD TROPICAL – December 16
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.
Kiki’s Lighted Boat Parade – December 16
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.
Crane Point Hammock: Winter Wonderland – December 16
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!
HOLIDAY CLASSIC CAR SHOW – December 17
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.
KEY WEST ARTISAN MARKET: SHOP LOCAL EDITION – December 17
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.
Full Moon Kayak Excursion – December 18
Capt. Bill Keogh, 305-872-7474
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.
Red Barn Theatre: A Tuna Christmas – December 19 – January 13, 2024
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.
KEY WEST THEATER: PETER MAYER STARS & PROMISES CHRISTMAS TOUR – December 20
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.
THE STUDIOS OF KEY WEST: MICROPARTY WITH ELECTRIC BLUE YONDER – December 21
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.
Florida Keys Brewing Company: Holiday Hat Party – December 22
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.
JAZZ IN THE GARDENS – December 24
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.
Fringe Theater: An Evening with Lillian Baxter – December 27 – 31, 2023
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.
KEY WEST HOME TOURS: HOLIDAY STYLE – December 29 – 30, 2023
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.
NEW YEARS EVE RED SHOE DROP – December 31
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.
GREAT GATSBY NEW YEAR’S EVE WITH “PLANE DROP” – December 31
Dress to impress in your best Gatsby era outfits at First Flight, Enjoy an open bar, champagne toasts, chef-manned stations and live band. At the stroke of midnight, a replica of an old Pan Am airplane with a real-life “stewardess” will take flight in the garden for a “plane drop” to ring in 2024. Tickets $250. 301 Whitehead St.
SCHOONER WHARF BAR: NEW YEAR’S EVE PIRATE WENCH DROP – December 31
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.
SLOPPY JOE’S BAR: DROPPING OF THE CONCH SHELL – December 31
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.
KEY WEST ARTISAN MARKET: NEW YEAR’S EVE EDITION – December 31
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.
The Protect Center: Sea of Trees – through January 7, 2024
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.
