Calendar of Events

December 2024: Florida Keys Events

Image for KEY WEST LITERARY SEMINAR Image for KEY WEST LITERARY SEMINAR Image for KEY WEST LITERARY SEMINAR Image for KEY WEST LITERARY SEMINAR
Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular
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Image for History of Diving Museum: Salvaging the Deep
Image for Marathon Community Theater: Beer for Breakfast
  • Nov 14, 2024 - Dec 7, 2024 Marathon Arts & Culture
  • Marathon Community Theater: Beer for Breakfast
  • Website
  • This comedy features a group of men who gather for a weekend at a cabin to eat, drink and reminisce about their high school and college days in the 70s and indulge their fondness for drinking beer for breakfast. One of the men, the cabin owner, doesn't show up but his estranged wife does. What follows is a battle of wit and stamina over which is the stronger sex. Showtimes at 8 p.m. 5101 Overseas Hwy.
Image for Waterfront Playhouse: Into the Woods
  • Nov 20, 2024 - Dec 14, 2024 Key West Arts & Culture
  • Waterfront Playhouse: Into the Woods
  • Website
  • Into the Woods is one of the late Stephen Sondheim's most well-known musicals. It explores the intertwining of well-known fairytales, but more importantly, the consequences of the actions in those stories. Showtimes nightly at 8 p.m. plus three 2 p.m. Saturday matinees on Nov. 30 and Dec. 7 and 14.
Image for Key West Holiday Fest
  • Nov 27, 2024 - Dec 31, 2024 Key West Arts & Culture
  • Key West Holiday Fest
  • Website
  • A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”
Image for Key West International Dance Co.: Fiesta de Navidad Tropical
Image for Key West Artisan Market: Rock the Red Ribbon Edition
Image for Key West End of Prohibition Celebration
  • Dec 1, 2024 - Dec 5, 2024 Key West Arts & Culture
  • Key West End of Prohibition Celebration
  • Website
  • Take a step back into old Key West and celebrate the End of Prohibition with 5 days of fun-filled Prohibition-themed films, cocktails, history, live entertainment and a blowout party at Sloppy Joe's. The final End of Prohibition celebration takes place Thursday, Dec. 5 at Sloppy Joe's with a costume contest, giveaways, a special appearance by the Anheuser-Busch antique truck and much more.
Image for Pet Photos with the Grinch
  • Dec 2, 2024 The Lower Keys Arts & Culture
  • Pet Photos with the Grinch
  • Website
  • Bring your furry friends for a fun, festive photo with the Grinch! Share some holiday cheer while you capture a paw-some pic. Make sure your pets are leashed or in carriers for a safe and joyful time. It’s the perfect way to create Whoville-worthy memories and help Florida Keys SPCA make a difference for animals in need. 5 to 7 p.m. at Berkshire Hathaway HomeServices, 30085 Overseas Hwy. MM 30.
Image for Trashy Tuesday Cleanup: Harry Harris Park
  • Dec 3, 2024 Key Largo Environmental
  • Trashy Tuesday Cleanup: Harry Harris Park
  • Website
  • Join the team from Sereia Films for a mangrove shoreline cleanup at Harry Harris Park, 50 E. Beach Rd. off of Burton Dr. Wear closed-toed shoes and bring water in your own reusable bottle. Gloves, water refill and buckets will be provided. The event is free, but please register online to attend.
Image for Zonta’s Festival of Trees
  • Dec 3, 2024 - Dec 8, 2024 Marathon Arts & Culture
  • Zonta’s Festival of Trees
  • Website
  • Zonta Club of Marathon, a women’s service organization, offers a free-admission display of decorated trees free at its 14th Annual Festival of Trees at Marathon Garden Club, 5270 Overseas Hwy. View and bid to purchase the decorated trees during open hours: Tue.-Thur. 5-8 p.m., Fri. 3:30-10 p.m., Sat. 10 a.m. to 8 p.m. (from 10 a.m. to 12 p.m., kids can enjoy cookies and photos with Santa and the Grinch). Raffle tickets can be purchased for a chance to win a favorite tree. A drawing for all trees is set for Dec. 7 at 8 p.m.
Image for Pet Photos with the Grinch
  • Dec 4, 2024 Islamorada Arts & Culture
  • Pet Photos with the Grinch
  • Website
  • Bring your furry friends for a fun, festive photo with the Grinch! Share some holiday cheer while you capture a paw-some pic. Make sure your pets are leashed or in carriers for a safe and joyful time. It’s the perfect way to create Whoville-worthy memories and help MarrVelous Pet Rescues & Adoptions make a difference for animals in need. 4:30 to 6:30 at Berkshire Hathaway HomeServices, MM 85.9 bayside
Image for Comedy Key West: Brendan Eyre
Image for Safe Harbor Angler House: Florida Seafood Short Films
  • Dec 5, 2024 Islamorada Environmental
  • Safe Harbor Angler House: Florida Seafood Short Films
  • Website
  • Join the team from Sereia films along with local experts for networking, the screening of short films on sustainable seafood and sponge restoration in the Keys and a panel discussion. Snacks and networking from 6:30 to 7 p.m.; films from 7 to 7:40 p.m.; followed by a panel discussion from 7:45 to 8:15 p.m. The event is free to attend but online registration is requested.
Image for Islamorada Sailfish Tournament
  • Dec 5, 2024 - Dec 8, 2024 Islamorada Fishing
  • Islamorada Sailfish Tournament
  • Website
  • The Florida Keys Gold Cup Sailfish Championship triple-crown series opens with the 61st Islamorada Sailfish Tournament Dec. 5-8. 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.
Image for Pet Pictures with Santa
  • Dec 5, 2024 Key West Arts & Culture
  • Pet Pictures with Santa
  • Website
  • Bring your festively outfitted pets for professional photos with Santa on Friday evening from 6 to 8 p.m. at the Christmas tree at the foot of William Street at Key West Bight Marina, hosted by All Animal Clinic. Photos are $25 each (cash only) with proceeds benefitting the Boys and Girls Club of the Keys.
Image for Nutcracker Key West
  • Dec 5, 2024 - Dec 15, 2024 Key West Arts & Culture
  • Nutcracker Key West
  • Website
  • Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Show dates Dec. 5-8 and 13-15. Showtimes vary. Tennessee Williams Theater, 5901 College Rd.
Image for Divers Direct: Noah Spearfishing Seminar - Spearfishing Techniques, Tips & Gear
Image for Key West Art & Historical Society: Opening Reception for Collecting Key West - The Works of Mario Sanchez
  • Dec 6, 2024 Key West Arts & Culture
  • Key West Art & Historical Society: Opening Reception for Collecting Key West - The Works of Mario Sanchez
  • Website
  • The Key West Museum of Art & History is pleased to present the opening of the exhibition, “Collecting Key West: The Works of Mario Sanchez" on Friday, December 6. A reception to mark the opening is to take place from 5 to 8 p.m. that evening in the Bryan Gallery, which is free and open to the public. Exploring the crossroads of art and history, this exhibition delves into the legacy of Cuban American folk artist Mario Sanchez (1908 – 2005). Sanchez established himself as the foremost Key West artist in the 1940s, creating hundreds of intricately carved and painted intaglios that portray his birthplace in the first part of the 20th century better than any annals or academic texts. 281 Front St.
Image for Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Dec 6, 2024 - May 18, 2025 Key West Arts & Culture
  • Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Website
  • Mario Sanchez (1908-2005), a Key West native, is among this country’s finest and most-recognized folk artists. In hundreds of intricately painted wood carvings created in a lifelong labor of love, Sanchez has provided a better history of Key West in the first part of the 20th century than any annals or academic texts. His bas-relief carvings, or intaglios, are a visual feast filled with the music, smells and passion of Gato’s Village, the Cuban-American community of Key West where Sanchez spent much of his life. In the carvings, each person, chicken, dog and fish has its own singular expression, attitude and identity. The exhibit is on display at the Custom House Museum daily from 10 a.m. to 5 p.m. 281 Front St.
Image for Holiday Historic Inn Tours: Night #1
  • Dec 6, 2024 Key West Arts & Culture
  • Holiday Historic Inn Tours: Night #1
  • Website
  • In this first of two holiday historic inn tours, explore four beautifully decorated locations and their unique architecture and history from 6 to 8 p.m. Sample sweet and savory holiday treats and libations. Locations are: Hemingway's Social Club at Papa's Pilar Distillery, Lighthouse Inn, Wicker Guesthouse, and the Gardens Hotel. The tours are self-guided. $40 tickets available online, but must be picked up after 5:30 p.m. on Dec. 6th at the first location, Hemingway's Social Club at Papa's Pilar Distillery, 210 Simonton St. The second inn tour takes place Dec. 13.
Image for Islamorada Holiday Fest
  • Dec 6, 2024 Islamorada
  • Islamorada Holiday Fest
  • Website
  • 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.
Image for Key West Theater: Under the Streetlamp
  • Dec 6, 2024 Key West Arts & Culture
  • Key West Theater: Under the Streetlamp
  • Website
  • Under the Streetlamp is an electrifying show driven by an inspired catalog of classic Doo Wop, Motown, and Rock n' Roll hits! Streetlamp has been dazzling audiences across the globe for over a decade. Their five specials airing on PBS have played to more than 300 million viewers and a million people have seen them live. These dynamite Broadway stars are propelled by an ensemble of world-class musicians through a show packed with smooth harmonies, soul-touching music and stories, and thrilling choreography. The audience engagement is palpable, often bringing four generations of music lovers together. Doors at 7 p.m.; show at 8 p.m. 512 Eaton St.
Image for Coffee Butler Amphitheater: Holiday Village & BeLighted Bike Ride
  • Dec 6, 2024 Key West Arts & Culture
  • Coffee Butler Amphitheater: Holiday Village & BeLighted Bike Ride
  • Website
  • The Wesley House Family Services Holiday Village is the family-friendly pre-party for the BeLighted Bike Ride, creating an evening of joy, laughter, and holiday magic for all ages, from 5 to 9 p.m. at Coffee Butler Amphitheater, 21 Quay Rd. The village features over 20 community booths offering games and activities, carnival rides, bounce houses, local food trucks, community performances, snowfalls and Santa! The highlight of the evening is the BeLighted Bike Ride that departs from the event at 8 p.m. The luminous parade of holiday cheer on wheels winds through the streets of Key West. Admission to Holiday Village is $20 per person or four tickets for $70. Children age 3 and under enter free.
Image for Key Largo Public Library Branch: First Friday Free Concert - Patchouli and Terra Guitarra
Image for Key West Theater: The Kingston Trio
  • Dec 7, 2024 Key West Arts & Culture
  • Key West Theater: The Kingston Trio
  • Website
  • In celebration of 60-plus years of music, the iconic folk group performs their best-loved songs as part of the ‘Keep The Music Playing’ national tour. All three current members, Mike Marvin, Tim Gorelangton and Buddy Woodward, have intrinsic links to the original group: Mike is the “adopted son” of founding member Nick Reynolds, who was also his musical mentor; Tim, a friend of John Stewart since he was in his early twenties, is one of the few musicians outside the Trio who has recorded with Nick Reynolds; and Buddy Woodward, a highly regarded musician who has worked with former Trio member George Grove. Doors 7 p.m.; show 8 p.m. 512 Eaton St.
Image for Lignumvitae Christmas
  • Dec 7, 2024 Islamorada Environmental
  • Lignumvitae Christmas
  • Website
  • Discover Lignumvitae Key Botanical State Park from 9:30 a.m. to 3:30 p.m. at a holiday event presented by the Friends of the Islamorada Area State Parks. Attractions include guided nature hikes, tours of the island park’s century-old caretaker’s home, storytelling presentations by historian and author Brad Bertelli, 1930s-era games, seasonal live music and an arts and crafts station. Lunch is available for a donation. Tickets include roundtrip ferry transportation to the park from Robbie’s Marina, 77522 Overseas Highway. Advance reservations and ticketing are required.
Image for History of Diving Museum: Guided Tour to Commemorate Pearl Harbor's Salvage Divers
Image for Village Shops: Holiday Sip & Shop
Image for Key Largo Bridge Run
  • Dec 7, 2024 The Florida Keys
  • Key Largo Bridge Run
  • Website
  • Run or walk the bridge that is the gateway to the Keys during the annual Key Largo Bridge Run. The race over the Jewfish Creek Bridge is a timed 5k and begins at 7:30 a.m. with an awards ceremony immediately following.
Image for Key West Hometown Holiday Parade
  • Dec 7, 2024 Key West Arts & Culture
  • Key West Hometown Holiday Parade
  • Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local, hometown flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street beside Bayview Park and proceeds down Duval Street. Seeing Santa is a highlight for kids.
Image for Garden Club of the Upper Keys: Holiday Market
Image for The Protect Center: Pup Pictures with Santa
  • Dec 7, 2024 Islamorada Arts & Culture
  • The Protect Center: Pup Pictures with Santa
  • Website
  • Bring your fur baby for a picture with Santa and sample delicious holiday-themed treats from Keys Re-Treats. You'll also find Key Re-Treats holiday goodies for sale. Enjoy coffee from the Cupacabana coffee camper and holiday shopping in the Protect Center gift shop with 10% off all pet items, including pet toys, collars and more, all made of sustainable and recycled products. Continue on to the center's Sea of Trees exhibit to support our nonprofit organization’s mission and celebrate the season. Sea of Trees admission charges apply.
Image for Eaton Street Christmas Stroll
  • Dec 8, 2024 Key West Arts & Culture
  • Eaton Street Christmas Stroll
  • Website
  • Eaton Street becomes a southernmost North Pole Sunday afternoon and evening. Wander the blocks between Whitehead and Simonton, 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.
Image for Cirque Salon Studios: Shop, Jingle & Mingle
  • Dec 8, 2024 Key Largo Arts & Culture
  • Cirque Salon Studios: Shop, Jingle & Mingle
  • Website
  • The Cirque Salon Studios at Tradewinds Plaza hosts the annual Shop, Jingle & Mingle event Sunday, Dec. 8 from noon to 4 p.m. Browse for gifts at this popular pop-up holiday market. Shop from a wide selection including children's clothes, hand-made bathing suits, sweet and savory treats, wine (enjoy a wine tasting, then make your selection), jewelery, bath and body goodies, books, wooden plant stands, custom bowls and baskets, fairy hair and more! 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.
Image for Sheriff's Animal Farm Open House: Christmas on the Farm
  • Dec 8, 2024 Key West Arts & Culture
  • Sheriff's Animal Farm Open House: Christmas on the Farm
  • Website
  • Celebrate Christmas at the Monroe County Sheriff's Animal Farm from 1 to 3 p.m. This will be the only open house during the month of December. Visit with the animals and participate in joyful holiday-themed activities including crafts, music and visits with Santa! Gifts of fresh produce and other items, as well as cash gifts for the animals, are greatly appreciated!
Image for Key West Artisan Market at Southernmost Beach Resort
  • Dec 8, 2024 Key West Arts & Culture
  • Key West Artisan Market at Southernmost Beach Resort
  • Website
  • Join the Key West Artisan Market and the Southernmost Beach Resort for a very special holiday event on the beach. Find some of your favorite local artists with the perfect gifts for everyone on your list along with lots of activities for the kids, great food, tasty treats, fun drinks and even a visit from old St. Nick himself! Live music all day and a fun sand 'snowman' building contest. Free to attend from 10 a.m. to 3 p.m. 504 South St.
Image for Monthly Fishing Seminar: Reef Fishing in the Keys
  • Dec 9, 2024 Marathon Fishing
  • Monthly Fishing Seminar: Reef Fishing in the Keys
  • Website
  • Reef fishing in the Florida Keys offers an exhilarating experience for both novice and seasoned anglers, thanks to the region's rich marine biodiversity and stunning coral reefs. The Keys, a coral cay archipelago located off the southern coast of Florida, are home to a variety of fish species such as snapper, grouper, it is a premier destination for fishing enthusiasts. Learn valuable tips and tricks to effectively target and catch reef fish species. The free seminar is held at the Marathon Elks Lodge. Doors at 5 p.m.; seminar begins 6 p.m.; dinner service at 6:30 p.m. for $10. 8239 Overseas Hwy.
Image for Conch Tour Train's Holiday Sights & Festive Nights Tours
  • Dec 9, 2024 - Dec 23, 2024 Key West Arts & Culture
  • Conch Tour Train's Holiday Sights & Festive Nights Tours
  • Website
  • The lively holiday Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 7:30, 8 and 8:30 p.m. on evenings from Dec. 9 to 10 and 13 to 23. Included are holiday lights glasses as keepsake items. The one-hour tour takes riders past the island's most elaborately decorated houses, buildings and neighborhoods, with holiday caroling.
Image for Old Town Trolley: Holiday Nights Tours
  • Dec 9, 2024 - Dec 23, 2024 Key West Arts & Culture
  • Old Town Trolley: Holiday Nights Tours
  • Website
  • Take the trolley for a tour of the Key West residential neighborhoods known for going all-out with holiday home decorations. Make this your new holiday tradition with friends and family. Narrated tours depart from Mallory Square and last for one hour. Advance tickets are available to book online.
Image for REEF: Holiday Party
Image for LaTeDa Christmas Party
  • Dec 10, 2024 Key West Arts & Culture
  • LaTeDa Christmas Party
  • Website
  • All are welcome to attend the annual LaTeDa Christmas Party Dec. 10 from 6 to 9 p.m. For entry, please bring an unwrapped gift for a child in need. Enjoy holiday music by DJ Rude Girl with other special appearances along with a Christmas buffet and drinks. Dress is holiday festive. 1125 Duval St.
Image for Gay Key West Holiday Lights Trolley Tour
  • Dec 11, 2024 Key West LGBTQ
  • Gay Key West Holiday Lights Trolley Tour
  • Website
  • Slip into your fabulous festive gear and jump aboard this Holiday Lights extravaganza for a dazzling night showcasing the island’s sparkliest displays. Kick things off at Bobby's Monkey Bar, 900 Simonton St., at 5:30 p.m. with a jingle and mingle before the trolley rolls in at 6:30 p.m. Then it’s a two-hour joyride and a few merry pit stops for cheer-fueling. Bring your favorite holiday goodies to share with our fabulous guests. We’ll wrap up the adventure around 8:30 p.m. back at Bobby's. Register now so you don't miss out. After you sign up, we’ll slide into your inbox for payment details.
Image for Key West Art & Historical Society: Happy Hour with the Historian
  • Dec 12, 2024 The Florida Keys Arts & Culture
  • Key West Art & Historical Society: Happy Hour with the Historian
  • Website
  • This fun historical lecture covers the Life & Art of Winslow Homer, widely regarded a one of the greatest American artists of the 19th century. Historian Cori Convertito focuses her talk on the work created as a result of Homer's travels in South Florida and the Bahamas. These images influenced generations of artists and transformed marine painting in the United States. 5 to 6 p.m at Comedy Key West, 218 Whitehead St.
Image for Red Barn Theatre: The Foreigner
  • Dec 12, 2024 - Jan 11, 2025 Key West Arts & Culture
  • Red Barn Theatre: The Foreigner
  • Website
  • This very funny comedy is an American classic, winning the Best New American Play for 1985 by the Outer Critics Circle. Set at a rural Georgia fishing lodge, a pathologically shy man adopts a persona as a non-English speaking foreigner in an attempt to avoid conversation. Hilarity ensues as an outrageous group of characters reveal secrets and scandals. Shows at 7:30 p.m. 319 Duval St.
Image for Waterfront Winter Wonderland
  • Dec 13, 2024 - Dec 28, 2024 Key West Arts & Culture
  • Waterfront Winter Wonderland
  • Website
  • Make your Key West holiday experience even more magical at Waterfront Winter Wonderland at Truman Waterfront Park. Coffee Butler Amphitheater transforms into an amazing winter wonderland, with an ice-skating, rides, games, music, holiday lights, a vendor village with food and local artisans, and more from Dec. 134-23 and 26-28 (closed Christmas Eve and Christmas). 21 Quay Rd. General admission $10, free for children age 5 and under. Additional fees apply for ice skating and rides.
Image for Stock Island Holiday Lighted Boat Parade
  • Dec 13, 2024 The Lower Keys Arts & Culture
  • Stock Island Holiday Lighted Boat Parade
  • Website
  • 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. Enjoy festivities from 5:30 to 9 p.m., with the parade starting at 7 p.m. Activities and parade viewing at 7001 Shrimp Rd.
Image for Key West Art & Historical Society: Holiday Concert & Bazaar
  • Dec 13, 2024 Key West Arts & Culture
  • Key West Art & Historical Society: Holiday Concert & Bazaar
  • Website
  • Join the Key West Art & Historical Society for the 7th Annual Holiday Concert & Bazaar from 5 pm to 9 pm. The event is located on the sweeping historic porch and street in front of the Custom House Museum. The immensely popular celebration will feature some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House. There will be plenty of food and festive libations at this event along with excellent holiday shopping. The event is free and open to the public. 281 Front St.
Image for Islamorada Junior Sailfish Tournament
  • Dec 13, 2024 - Dec 15, 2024 Islamorada Fishing
  • Islamorada Junior Sailfish Tournament
  • 305-240-9337 E-mail
  • The Florida Keys’ oldest sailfish tournament for kids age 16 and under celebrates its 60th year.
Image for Holiday Historic Inn Tours: Night #2
  • Dec 13, 2024 Key West Arts & Culture
  • Holiday Historic Inn Tours: Night #2
  • Website
  • In this second of two holiday historic inn tours, explore four beautifully decorated locations from 6 to 8 p.m. while enjoying sweet and savory holiday treats and libation samplings. Locations are: 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.
Image for Pigeon Key Holiday Spectacular
  • Dec 13, 2024 - Dec 14, 2024 Key West Arts & Culture
  • Pigeon Key Holiday Spectacular
  • Website
  • The wonderment and excitement of the holiday season takes over Pigeon Key with a festive event that kicks on Friday, Dec. 13 with a VIP viewing of the island in full holiday splendor. On Saturday, the "Polar Express" starts running at 1 p.m. with trips throughout the day and into the evening. Families can spend the entire day on the 5-acre island enjoying marine science activities along with delicious holiday food, drinks, guided tours, activities, holiday-themed movies on the big screen, Santa Claus encounters and snow! Admission $5 for walkers/bikers; ride the Polar Express for $10 if you book in advance or $15 the day of the event.
Image for Key West Outdoor Movies - Nightmare Before Christmas
  • Dec 13, 2024 Key West Arts & Culture
  • Key West Outdoor Movies - Nightmare Before Christmas
  • Website
  • Key West Outdoor Movies presents Tim Burton's The Nightmare Before Christmas, Friday, Dec. 13, at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk.
Image for Key West Theater: The Magic of Christmas
  • Dec 13, 2024 Key West Arts & Culture
  • Key West Theater: The Magic of Christmas
  • Website
  • The Magic of Christmas is an adult- and kid-friendly magic show that combines different genres of magic into one fantastic show. Enjoy a complimentary cookie and candy bar along with pictures with Santa by photographer Rob O'Neal. Special appearance by our dancing grinch and some say it even may snow that night. Doors open at 5 p.m.; show at 6 p.m. 512 Eaton St.
Image for Duck Key Holiday Boat Parade
  • Dec 13, 2024 Marathon Arts & Culture
  • Duck Key Holiday Boat Parade
  • Website
  • Gather at Angler & Ale at Hawk's Cay Resort to watch festively-decorated boats glide through the waters around Duck Key. Participating boats will gather for a post-parade, in-water raft up celebration. The parade is hosted by the Duck Key Fishing Club and Hawk's Cay Resort. Proceeds from the event are to benefit the U.S. Coast Guard Station Marathon.
Image for Key Largo Public Library: Make Pet Toys for Shelter Animals
Image for Florida Keys Community Concert Band: Pops in the Park Holiday Harmony
Image for 7 Mile SantaCon
  • Dec 14, 2024 Marathon Arts & Culture
  • 7 Mile SantaCon
  • Website
  • The inaugural 7 Mile SantaCon celebrates the holiday season in Florida Keys style with drinks, poker, the historic Old 7 Mile Bridge, Pigeon Key, and raising money for scholarships. This holiday-themed poker run - for those age 21 and over - costs $50 to enter. Your poker run card includes 4 stops that you can make by either car or boat from 12 p.m. to 4 p.m., with 1 free drink at each, plus entry to the Pigeon Key Holiday Spectacular on the island of Pigeon Key (go by the Pigeon Key Polar Express train, or walk or bike across the Old 7 Mile Bridge). Dress up in your Santa/holiday best to win prizes for best and worst dressed, to be awarded on the island. The restaurant/bar stops are: Keys Fisheries, Lighthouse Kitchen & Bar, Lazy Days South and Sunset Grille & Raw Bar. Register online or at Marathon Chamber of Commerce, 12222 Overseas Hwy.
Image for Grassy Flats Full Moon Party
  • Dec 14, 2024 Marathon Arts & Culture
  • Grassy Flats Full Moon Party
  • Website
  • Grassy Flats Resort & Beach Club hosts a full moon celebration from 6 to 11 p.m., 58182 Overseas Hwy. Advance passes $25, with day of entry $35. Enjoy live music, food by Bongos, drink specials, fire breathers, a rousing Junkanoo parade and more.
Image for Key Largo Boat Parade: Christmas in the Keys
  • Dec 14, 2024 Key Largo Arts & Culture
  • Key Largo Boat Parade: Christmas in the Keys
  • Website
  • The 39th annual Key Largo Boat Parade and Fireworks Show takes place on Blackwater Sound beginning at 7:30 p.m. This year's parade highlights Key Largo's fun-loving Christmas spirit. Watch from Rowell's Waterfront Park or businesses on Blackwater Sound including Caribbean Club, Sundowners and Jimmy Johnson's Bill Chill.
Image for Boot Key Harbor Christmas Boat Parade
  • Dec 14, 2024 Marathon Arts & Culture
  • Boot Key Harbor Christmas Boat Parade
  • Ilene Clark E-mail Website
  • Everything from lighted and decorated dinghies to yachts are to cruise in the 28th 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. Call Ilene at 561-542-2727.
Image for 'A Positive Step' 5k Rudolph Red Nose Run
  • Dec 14, 2024 Key West Arts & Culture
  • 'A Positive Step' 5k Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join in the 16th 'A Positive Step' 5k Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café, 1405 Duval Street. Race day check-in starts at 7 a.m. with start time at 8 a.m. Prizes are awarded for most festive and most unusual PJ's. After the race, enjoy refreshments and a fabulous silent auction to benefit A Positive Step of Monroe County, a non-profit serving at-risk kids and their families.
Image for Islamorada Half Marathon & 10K; Rumrunner 10K & 5K; and Beach N' Beer Mile
  • Dec 14, 2024 - Dec 15, 2024 Islamorada
  • Islamorada Half Marathon & 10K; Rumrunner 10K & 5K; and Beach N' Beer Mile
  • Website
  • Participants of all ages and skill levels participate in these popular annual subtropical footraces to be hosted at the newly renovated and rebranded Three Waters Resort (formerly Postcard Inn). Saturday's Rumrunner 5k and 10k races start at 8 a.m., followed by the Beach 'n Beer Mile "fun run" at noon. The Islamorada Half Marathon and 10k races start at 7 a.m. Sunday as the sun rises.
Image for Schooner Wharf Bar Lighted Boat Parade
Image for Snowy Days Children's Concert at Key West Botanical Garden
  • Dec 15, 2024 Key West Arts & Culture
  • Snowy Days Children's Concert at Key West Botanical Garden
  • Website
  • Snowy Days, the Key West Tropical Forest & Botanical Garden's annual children's winter concert, features Key West vocalist, Belle Jampol performing favorite holiday tunes for children. The event opens at 1 p.m. and the concert starts at 1:30 p.m., followed by snow cones (while they last) and delightful holiday arts and crafts, face painting and special treats. Tickets $5 per child at the door with a maximum cost of $10 per family.
Image for Key West Artisan Market: Fill the Pantry Edition
  • Dec 15, 2024 Key West
  • Key West Artisan Market: Fill the Pantry Edition
  • Website
  • Stock your pantry and fridge with fresh produce, exotic fruits, artisan cheeses, local seafood, honey, pickles, nuts and so much more. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Listen to awesome local musicians and give canned good or donations to our featured charity, the SOS Foundation, that feeds Key West's underprivileged children. 10 a.m. to 2 p.m., 1801 White St. in Indigenous Park.
Image for Key Colony Beach Christmas Boat Parade
Image for History of Diving Museum: Merry Divemas
  • Dec 18, 2024 Islamorada Arts & Culture
  • History of Diving Museum: Merry Divemas
  • Website
  • Dive into some holiday fun at the museum from 5:30 to 7 p.m. Bring the family for cookie decorating, ornament making, festive snacks and photos with Santa Claus! The event is free but donations are appreciated. The event is to be followed by an Immerse Yourself presentation at 7 p.m. about the Journey of the Christ of the Deep statue.
Image for Fringe Theater's Holiday Train Ride
  • Dec 18, 2024 Key West Arts & Culture
  • Fringe Theater's Holiday Train Ride
  • Website
  • Don't miss this crowd favorite fundraiser for Fringe Theater. Check-in at 7 p.m. at the beautiful Gardens Hotel, 526 Angela St., and enjoy a tasty beverage at the cash bar while you catch up with your Fringe friends and enjoy the live holiday music. Then at 8 p.m., it's "All Aboard" our Holiday Train for a festive ride about town to see the holiday lights of Key West. Pickup and return at the Gardens Hotel. Tickets $60.
Image for Comedy Key West: Jim Florentine
  • Dec 18, 2024 - Dec 21, 2024 Key West Arts & Culture
  • Comedy Key West: Jim Florentine
  • Website
  • For nearly 25 years Jim Florentine has been making audiences around the world laugh across nearly every type of media. Jim has recorded six stand-up comedy albums and shot four full-length specials. Showtimes 8:30 p.m. 218 Whitehead St.
Image for Key West Art & Historical Society Historic Seaport Sail: Plant a Million Corals Project
  • Dec 18, 2024 Key West Arts & Culture
  • Key West Art & Historical Society Historic Seaport Sail: Plant a Million Corals Project
  • Website
  • Enjoy a 2-hour Historic Harbor Tour with Plant A Million Coral Project’s Dee Dee Vaughan on the S/V Argo Navis, talking about the Project to Restore Florida Keys' Coral Reef. The morning seafaring excursion aboard luxury catamaran SV Argo Navis departs from the dock at 0 Margaret Street at 10 a.m. and returns at 12 p.m. Passengers will enjoy Bloody Marys, mimosas or non-alcoholic beverages along with lite breakfast fare as Vaughan explains the Plant A Million Coral’s focus on active reef restoration and the transfer of coral restoration technology. Book tickets online in advance.
Image for Morada Way Third Thursday Art Walk
  • Dec 19, 2024 Islamorada Arts & Culture
  • Morada Way Third Thursday Art Walk
  • Website
  • The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.
Image for Walk on White Third Thursday Art Walk
  • Dec 19, 2024 Key West Arts & Culture
  • Walk on White Third Thursday Art Walk
  • Website
  • Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets. In December, The KWHS marching band will parade down White Street and perform at various locations along the way. City Hall and the NOAA National Weather Station will also participate.
Image for Key West Art & Historical Society Distinguished Speaker Series: Storms, Shipwrecks & Saints' Names
  • Dec 19, 2024 Key West Arts & Culture
  • Key West Art & Historical Society Distinguished Speaker Series: Storms, Shipwrecks & Saints' Names
  • Website
  • This talk focuses on the dangers associated with early Caribbean and Gulf travel in the first generations of Spanish colonialism. The Florida Keys were a late and important, but also particularly treacherous, final leg of a roundtrip journey from Spain, through the Caribbean, and back to Spain. Dr. Kevin Kokomoor talks on the subject and brings to light discoveries covered in his recent book, "La Florida: Catholics, Conquistadores and other American Origin Stories." 6 to 7 p.m. at Tropic Cinema, 416 Eaton St.
Image for Rainbow Reef Dive Center: Mission Iconic Reefs Passive Nursery & Coral Restoration Site Snorkel or Dive
Image for Tropic Cinema: Movies Under the Stars - Elf
  • Dec 21, 2024 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - Elf
  • Website
  • Don't miss the monthly free Movies Under the Stars screening - this month, the movie is Elf! The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins at 6 p.m. 416 Eaton St.
Image for Kiki's Sandbar Lighted Boat Parade & Drone Show
Image for Key West Artisan Market: Shop Local Edition
  • Dec 22, 2024 Key West Arts & Culture
  • Key West Artisan Market: Shop Local Edition
  • Website
  • This week's market will be stocked with Keys-made items perfect for gift giving this holiday season. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians doing your favorite Christmas standards, and get photos with Santa! 10 a.m. to 2 p.m. in Indigenous Park, 1801 White St.
Image for Old Island Restoration Foundation: Noche Buena
Image for Holiday Jazz in the Gardens
Image for Key West Lighting of the Menorah
Image for Key West Artisan Market: Welcome Home Edition
  • Dec 29, 2024 The Florida Keys Arts & Culture
  • Key West Artisan Market: Welcome Home Edition
  • Website
  • Key West Artisan Market invites you to an early New Year's Eve celebration with non-profit partner Habitat for Humanity of the Lower Keys (be sure to donate to them), 10 a.m. to 2 p.m. at Indigenous Park, 1801 White St. Buy yourself the present that you wanted - but didn't get - over the holidays and stock up on treats for your New Year's eve events. Many artists will be offering sales and exclusive merchandise not available anywhere else. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians, meet local authors and support our featured charity.
Image for Sunset Green Lawn: Early New Year's Eve Celebration
  • Dec 30, 2024 Key West Arts & Culture
  • Sunset Green Lawn: Early New Year's Eve Celebration
  • Website
  • This event is the perfect way to kick your New Year's celebrations a day early. Come to the Sunset Green Lawn for a FREE night of music and family-friendly fun to start the countdown to 2025 with the talented Mike Stack and friends! Featuring Mike Stack, The Brickfinders, D-Lew, Sharese, Josh Kiser, Jockey Jord and other special musical guests. The show is to be followed by a fireworks display! Gates open at 6 p.m. with music starting at 6:30 p.m.
Image for Caribbean Club: New Year's Eve Celebration
Image for New Year's Eve Conch Shell Drop at Sloppy Joe's
  • Dec 31, 2024 Key West Arts & Culture
  • New Year's Eve Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2025 is to be heralded on Key West's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock. Customers inside the bar may view the dropping of the conch shell on Sloppy-Tron.
Image for New Year's Eve Gatsby Gala at First Flight Island Restaurant & Brewery
Image for New Year's Eve Red Shoe Drop
  • Dec 31, 2024 Key West LGBTQ
  • New Year's Eve Red Shoe Drop
  • Website
  • Witness Key West's iconic Red Shoe Drop at the Bourbon Street Pub, 724 Duval St. Free to watch from Duval Street; VIP options are to be available for balcony seating. Live entertainment in the street starts at 9 p.m. with the shoe drop at midnight.
Image for Schooner Wharf Bar: New Year's Eve Lowering of the Pirate Wench
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