Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
Events calendar provided by www.fla-keys.com.

Events in the Florida Keys for December, 2023 Year: 2023 2024 Month: January February March April May June July August September October November December   May 20 to December 31,  in Islamorada History of Diving Museum: Aquanauts to Astronauts Exhibit 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. November 11 to December 03,  in Key West Key West Art & Historical Society: Headdress Ball - 40 Years of Creativity 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. November 23 to December 31,  in Key West Harbor Walk of Lights 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. November 29 to December 16,  in Key West Waterfront Playhouse: Little Shop of Horrors 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. November 30 to December 03,  in Islamorada Islamorada Sailfish Tournament The Florida Keys Gold Cup Sailfish Championship triple-crown series opens with the 60th Islamorada Sailfish Tournament, Thursday, Nov. 30 through Sunday, Dec. 3. Social events are to be headquartered at the Whale Harbor Inn and Marina complex at mile marker 83. The tournament is the primary fundraiser for the Islamorada Charterboat Association. November 30 to December 03,  in Key West Coast is Clear Festival 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. December 01 to January 07,  in Islamorada The Protect Center: Sea of Trees 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. December 01,  in Key West Holiday Village & BeLighted Bike Ride 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. December 01,  in Islamorada Islamorada Holiday Fest 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. December 01,  in Key West World AIDS Day Processional and Service 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. December 01,  in Key West Pet Pictures with Santa 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. December 02,  in Marathon Marathon Community Theatre: Christmas Cabaret with Jaimie Roberts 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. December 02,  in Key West Key West Hometown Holiday Parade 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. December 02,  in Key Largo First State Bank Key Largo Bridge Run 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. December 02,  in Islamorada Lignumvitae Christmas 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. December 03,  in Key West Key West Artisan Market: Red Ribbon Edition 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. December 03,  in Key Largo Shop, Jingle & Mingle 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. December 03,  in Key West Mote's Ocean Fest: A Community Celebration 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. December 03,  in Key West Montessori United 5k Run/Walk 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. December 03,  in Key West Key West United Methodist Church: Handel's Messiah All are welcome for this annual performance of George Frederic Händel's Messiah. 7 p.m. at the church at 600 Eaton Street. December 03,  in Key West Key West Woman's Club: Santa, Sweets and Holiday Tree Lighting 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. December 03,  in Key West Conch Republic Seafood Company: Santa Meet and Greet 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. 5 to 8 p.m. at 631 Greene Street. December 04,  in Islamorada Florida Keys History & Discovery Museum: Afro-Caribbean Migration to Florida 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. December 04,  in Marathon Marathon Community Theatre: Monthly Fishing Seminar - Sailfish The Tackle Box in Marathon presents an evening seminar on sailfish. Learn about fishing for, catching and releasing this majestic fish. Fantastic door prizes and a 50/50 Raffle - you could win up to $250 or more. Free to attend starting at 6 p.m. at Marathon Community Theatre, located at 5101 Overseas Highway oceanside. December 07,  in Key West Florida Keys SPCA - POSH Fundraiser 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. December 07,  in Big Pine Taste of Stock Island Trolley Tour with a Holiday Twist Board the Old Town Trolley for I Love Stock Island's whirlwind 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. Included are up to 9 chef-inspired small plates and a dessert, all with cocktail pairings. The trolley departs from the Perry Hotel, 7001 Shrimp Road. Each participant is asked to bring an unwrapped toy for the Wesley House Family Services Holiday Helpers Toy Drive. Check in at 3:30 p.m. for a 4 p.m. start at Matt's Stock Island Kitchen at the Perry Hotel, 7001 Shrimp Rd. December 07,  in Key West Key West Theater: Colin Quinn - Small Talk Stand-up comedian Colin Quinn is known for his observational humor. In his new show, Small Talk, he shines a light on the way we communicate in person and online. Tickets range from $37.50 to $57.50. Doors open at 7 p.m., show at 8 p.m. 512 Eaton Street. December 08 to December 23,  in Key West Old Town Trolley's Holiday Sights & Festive Nights Tours 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. December 08 to December 23,  in Key West Conch Tour Train's Holiday Sights & Festive Nights Tours 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. December 08,  in Marathon Marathon Pet Photos With the Grinch 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. December 08 to December 09,  in Marathon Marathon Community Theatre: Holiday Show & Sing-Along 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. December 08,  in Key West Holiday Historic Inn Tours: Night #1 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. December 08,  in Big Pine Plant a Million Corals: Cocktails for Corals 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. December 08 to December 10,  in Islamorada Islamorada Junior Sailfish Tournament 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. Contact: Tammy Gurgiolo 305-240-9337 Email: [email protected] December 08,  in Key West Key West Art & Historical Society: Annual Holiday Concert & Bazaar 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. December 09,  in Key Largo Key Largo Lighted Boat Parade 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. December 09 to December 10,  in Islamorada Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N' Beer Mile 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. December 09,  in Key West Carl Hiaasen in Conversation With Judy Blume 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 WRECKER, his new middle-grade novel for young readers. It's 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. December 09,  in Key West Key West Pet Pictures With the Grinch 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. December 09,  in Key West 32nd Annual Schooner Wharf/Abosult Vodka Lighted Boat Parade 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. December 09,  in Key West 10th Annual Parade of Paws & Holiday Bazaar 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. December 09,  in Key Largo Santa at the Park: Harry Harris Beach & Park 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. December 09,  in Marathon Boot Key Harbor Christmas Boat Parade 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. December 10,  in Key Largo Meowliday Party & Key Largo Cat Cafe Grand Opening 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. December 10,  in Key West Key West Lighting of the Menorah 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. December 10,  in Key West Sheriff's Animal Farm: Christmas on the Farm 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. December 10,  in Key West Key West Artisan Market: Merry Marketplace on the Beach 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. December 10,  in Key West Eaton Street Christmas Stroll 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. December 10,  in Marathon Key Colony Beach Christmas Boat Parade 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. December 11,  in Islamorada REEF: Merry Fishmas Trivia Night 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. December 12,  in Key West The Studios of Key West: Ann Hampton Callaway 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. December 12 to December 16,  in Key West Fringe Theater: The Best Christmas Pageant Ever 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. December 12,  in Big Pine Big Pine Key Pet Photos With the Grinch 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. December 12,  in Key West 24 North Hotel: Paint & Sip Night with Artist Lance Berry 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. December 14,  in Key West Key West Art & Historical Society: Happy Hour With the Historian 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. December 14 to December 17,  in Key West Gay Holiday Getaway 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. December 15,  in Key West Holiday Historic Inn Tours: Night #2 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. December 15,  in Marathon Pigeon Key: Movies by the Sea - The Polar Express 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. December 15 to December 30,  in Key West Coffee Butler Amphitheater: Key West Waterfront Winter Wonderland 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. December 16,  in Key West 'A Positive Step' 5k Rudolph Red Nose Run 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. December 16,  in Marathon Crane Point Hammock: Winter Wonderland 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! December 16,  in Key West Tennessee Williams Theatre: Fiesta de Navidad Tropical 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. December 16,  in Big Pine Kiki's Lighted Boat Parade 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. December 17,  in Key West Holiday Classic Car Show 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. December 17,  in Key West Key West Artisan Market: Shop Local Edition 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. December 18,  in Big Pine Full Moon Kayak Excursion 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. Contact: Capt. Bill Keogh, 305-872-7474 December 19 to January 13,  in Key West Red Barn Theatre: A Tuna Christmas 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. December 20,  in Key West Key West Theater: Peter Mayer Stars & Promises Christmas Tour 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. December 21,  in Islamorada Morada Way Third Thursday Art Walk 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. December 21,  in Key West The Studios of Key West: MicroPARTY with Electric Blue Yonder 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. December 22,  in Islamorada Florida Keys Brewing Company: Holiday Hat Party 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. December 24,  in Key West Jazz in the Gardens 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. December 25,  in Key West Schooner America 2.0: Christmas Day Brunch Sail 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. December 29 to December 30,  in Key West Key West Home Tours: Holiday Style 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. December 30,  in Key West Marriott Key West Beachside: 2023 Fireworks and Glow Party 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. December 31,  in Key West First Flight: Great Gatsby New Year's Eve with Plane Drop 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. December 31,  in Key West Schooner Wharf Bar: New Year's Eve Pirate Wench Drop 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. December 31,  in Key West Sloppy Joe's Bar: Dropping of the Conch Shell 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. December 31,  in Key West New Years Eve Red Shoe Drop 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. December 31,  in Key West Key West Artisan Market: New Year's Eve Edition 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.