Calendar of Events

December 2022: Florida Keys Events

• Sponsored Event
• Oct 19, 2023 - Oct 19, 2023 Key West Arts & Culture
• The Black Crowes
• Website Coffee Butler Amphitheater
• 21 Quay Road Key West FL 33040
• Rams Heads Presents 305-985-0433 E-mail
• Get ready to rock the amp as The Black Crowes perform their hit singles "Jealous Again," Twice As Hard," "She Talks To Angels," and the break-through cover of Otis Readding's "Hard To Handle!". Doors open at 5:30P, show starts at 7:00P.
• Buy tickets!

• Sponsored Event
• Oct 19, 2023 - Oct 22, 2023 Key Largo
• REEF Fest - A Celebration of Marine Conservation
• Website Hosted by Reef Environmental Education Foundation
• 98300 Overseas Hwy Key Largo FL 33037
• 305-852-0030 E-mail
• Calling all ocean lovers! Join us for diving, snorkeling, kayaking, educational ocean presentations, and more. Explore the marine life of the Florida Keys, learn from ocean experts, and celebrate marine conservation.
• Buy tickets!

• Sponsored Event
• Oct 20, 2023 - Oct 29, 2023 Key West
• Fantasy Fest 2023
• Website Key West
• 305-295-9112 E-mail
• This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions, and over 30 cleverly themed Parties and performances. Togas, Tutu’s, Body Paint and Burlesque, Halo’s, and Homemade Bikinis. Join the fun!

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

• Sponsored Event
• Nov 25, 2023 - Nov 25, 2023 The Lower Keys Arts & Culture
• Island Art Festival 2023
• Website Lower Keys Chamber Grounds MM31
• 31020 Overseas Hwy Big Pine Key FL 33043
• Lower Keys Chamber of Commerce 305-872-2411
• View video
• Come from 9am-3pm to celebrate the holiday season at this family-friendly event. Enjoy local arts and crafts with live music and delicious food at MM 31. Experience original one-of-a-kind Island art and a wide array of crafts. FREE ADMISSION & PARKING!

• Mar 31, 2022 - Dec 11, 2022 Key West Arts & Culture
• Key West Bicentennial Exhibit at The Custom House Museum
• Website
• Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

• Oct 25, 2022 - Dec 31, 2022 Islamorada Arts & Culture
• History of Diving Museum: Sponge Hunters
• Website
• Sponge Hunters: Key West Hookers, Bahamian Free Divers, and the Hard Hat Divers of Tarpon Springs will be on display May 19 through December 31, 2022. Learn about the sea sponge and its uses, from the long history of fishers to modern fisheries, current restoration efforts and the various dive methods used in seeking out this treasured aquatic animal. Mile marker 83 bayside, Islamorada. 10 a.m. - 5 p.m. daily except Thanksgiving, Christmas Day, and New Year’s Day.

• Dec 1, 2022 - Jul 31, 2023 Key West Fishing
• Key West Fishing Tournament
• Website
• More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.

• Dec 1, 2022 - Dec 4, 2022 Key West Arts & Culture
• COAST is CLEAR Music and Arts Festival
• Website
• Enjoy a weekend in the sun surrounded by close compadres — or simply folks you’ve only just met because of a shared love of music and art. The festival's main events are concerts at the festival grounds Saturday and Sunday. Two-day General Admission, VIP tickets and detailed information is available online. Festival is to be held rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd.

• Dec 1, 2022 Key West
• World AIDS Day Processional and Service at Key West AIDS Memorial
• Website
• All are welcome to gather to celebrate the lives of friends and loved ones taken from us far too soon and honor those that we lost in 2022. There will be a processional starting at 4:30 p.m. from Key West City Hall, located at 1300 White Street, ending at the Key West AIDS Memorial. The names currently inscribed will be read by those walking and by those gathered at the memorial. The actual ceremony will take place from 6 to 7 p.m. at the memorial located at the Edward B. Knight pier, 1707 White Street. The names of those lost in 2022 will be unveiled. Participating in the processional this year will be the Key West Mile Markers SMART Ride team with the Riderless Bike in recognition of those lost to HIV/AIDS.

• Dec 1, 2022 - Dec 3, 2022 Key West Arts & Culture
• Tropic Cinema: Neil Young
• Website
• "Neil Young: Harvest Time" is a fan piece that has never before been seen. Performance and rehearsal content is intertwined into creative storytelling and includes most of the tracks from the iconic 1972 album Harvest. Created in 1971, this docu-film takes us on a journey to Neil Young’s farm in Northern California for the ‘Harvest Barn’ sessions, to London for an iconic performance with the London Symphony Orchestra and to Nashville where Young worked on various tracks of this signature album. Screenings at 7:30 p.m. on Dec. 1 and Dec. 3. 416 Eaton Street.

• Dec 2, 2022 - Dec 3, 2022 Key West Arts & Culture
• Revival Roadshow at Sunset Pier
• Website
• The Revival is a gathering of Nashville’s biggest hit writers sharing their songs, considered some of the best music in Nashville. In 2022 the Revival took the pew on the road with some of Nashville's greatest songwriters. The tour ends in Key West with two days of live music at Ocean Key Resort's Sunset Pier, Dec 2-3, with performances of 31 Number 1 hit songs by the songwriters that created them. Tickets available online. Single day pass $40; weekend pass $66.50.

• Dec 2, 2022 Islamorada
• Florida Keys Holiday Fest in Islamorada
• 305-664-4503 Website
• The fun is set for 4-10 p.m. at the Founders Park beach area, mile marker 87. The crowd-pleasing celebration centerpiece, a 35-foot-tall holiday tree with “magical” snow blowing from its branches, is to be lighted at 6 p.m. Kids can frolic on a 30-ton snow mountain during the event. Parents can bid on one-of-a-kind, Keys-designed ornaments during a silent auction, and explore a holiday gift bazaar. Other activities include caroling, Santa's Sweet Shoppe with gourmet desserts and coffee, and a holiday parade at 7:30 p.m.

• Dec 3, 2022 The Lower Keys Environmental
• Grand Opening: Plant a Million Corals
• Website
• Plant a Million Corals invites you to a Grand Opening and Coral Cutting celebration Sat. Dec. 3 from 3 to 5 p.m. Take a tour of the new Restoration Park, see demonstrations of the coral restoration operation and meet the team. Founder Dave Vaughn will be signing copies of his new book, “The Secret Life of Corals: Sex, War, and Rocks that Don’t Roll.” The event is free to attend at 23801 Overseas Hwy, Summerland Key.

• Dec 3, 2022 - Dec 4, 2022 Marathon
• Bethlehem in the Keys
• Bethlehem in the Keys, a Christmas-themed dinner theater performance, will be performed at Marathon Community Church on Friday, Dec. 3rd. Doors open at 6 p.m., show starts at 7. There will be a matinee on Saturday, Dec. 4 with doors open at 2 p.m. and performance at 3. Tickets are $50 for dinner and $30 for the matinee. Call 305-481-7233 to reserve tickets.

• Dec 3, 2022 Key West
• Friends of the Key West Library Book Sale
• Website
• The Friends of the Key West Library will hold the December Book Sale outside in the library's Palm Garden on Saturday, Dec. 3, from 10am-1pm. Most books are priced at $1, although for this sale, there is a nice selection of art books suitable for holiday gifts priced in the $10-20 range. 700 Fleming Street.

• Dec 3, 2022 Key West
• Pet Pictures with the Grinch
• Website
• Bring your critters to Hank’s Hair of the Dog Saloon, 409 Caroline Street from 11 a.m. to 2 p.m. for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a non-profit senior dog sanctuary.

• Dec 3, 2022 Islamorada Arts & Culture
• Florida Keys History & Discovery Special Event: Redbone Gallery Show
• Website
• The museum opens for a special event Saturday, Dec. 3 to support the Redbone Gallery's mission to "Catch the Cure" for cystic fibrosis. Redbone is selling the remainder of its gallery originals and giclee artwork from some of the foremost saltwater angling artists including Millard Wells, Kathleen Denis, Pasta Pantaleo, Tim Borski, Don Ray, and many more. 82100 Overseas Highway, from 6 to 8 p.m. on the grounds of the Islander Resort. In addition to the special event, all artwork, Redbone holiday ornaments, books and more are for sale at the museum through January 8. Consider your holiday shopping here at the museum and help "Catch the Cure" for cystic fibrosis.

• Dec 3, 2022 The Florida Keys Environmental
• Everglades National Park 75th Anniversary Celebration
• Website
• Everglades National Park was dedicated Dec. 6, 1947. On Saturday, Dec. 3, as part of a year of celebration of the park's 75th anniversary, the public is invited to attend a re-dedication ceremony between 1:30 and 5 p.m. at the Flamingo portion of the park, which is located inside the park's main entrance. There will be live music, historical reenactors, the re-dedication of Flamingo's Guy Bradley Visitor Center including a reception with refreshments and cash bar, and guided tours of the new Flamingo Lodge facilities, which are under construction. The Flamingo portion of the national park is located in Monroe County at the top of the Upper Keys.

• Dec 3, 2022 Key West Environmental
• Surfrider Florida Keys Key West Beach Cleanup at Smathers Beach
• Website
• Join members of Surfrider's Florida Keys Chapter and others for a cleanup of Smathers Beach from 9 to 11 a.m. Free, limited edition t-shirts will be given to the first 25 attendees. Gloves, buckets, grabbers, cold water and good times provided. Please wear close-toed shoes and bring a reusable water bottle to fill. Kids are welcome.

• Dec 3, 2022 Marathon
• Faro Blanco Resort Lighting of the Lighthouse
• Website
• Celebrate the holiday season at Faro Blanco Resort in Marathon for their annual Lighting of the Lighthouse event from 4 until 9 p.m. Enjoy food, drinks, music by Abstract Radio and Santa and Mrs. Claus arriving by train. Mile marker 48.5.

• Dec 4, 2022 Key West
• Key West Woman's Club Holiday Open House
• Website
• Members have decked the halls of the historic mansion at 319 Duval Street for all to enjoy at Sunday's open house from 4 to 6 p.m. Enjoy appetizers, desserts and Amsterdam eggnog, and an appearance by Santa. Music from the Bahama Village Children's Choir and the Key West Community Orchestra. Official tree lighting by Mayor Teri Johnston. Donations of new, unwrapped clothes for students ages K-12 are appreciated.

• Dec 4, 2022 Key West
• Pet Pictures with Santa
• Website
• Pack up Fifi and Fido and delight in Pet Pictures with Santa Sunday, Dec. 4 from 6 to 8 p.m. at the Christmas tree at the foot of William Street at the Key West Bight Marina. Proceeds benefit the Boys & Girls Club of the Keys.

• Dec 4, 2022 Key Largo
• Key Largo Shop, Jingle & Mingle
• Shop for gifts from local vendors and enjoy some holiday cheer from 11 a.m. to 4 p.m. at this annual event at the Cirque Salon Studios at Tradewinds Plaza, mile marker 101 oceanside in Key Largo.

• Dec 4, 2022 Key West
• Key West Artisan Market: 10th Anniversary Edition
• Website
• Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and breathtaking ocean views as we celebrate 10 years of the Key West Artisan Market with old and new friends. Also supporting Friends of the Aids Memorial which is located across the street at White & Atlantic at the entrance to the Edward B. Knight Pier. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

• Dec 4, 2022 Key West Arts & Culture
• Eaton Street Christmas Stroll
• Website
• Key West Theater, The Studios of Key West, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts and the Key West United Methodist Church unite for the annual Eaton Street Christmas Stroll. Each venue hosts a short Christmas-themed performance with caroling as you walk from presentation to presentation. At The Studios of Key West, sip Christmas cocktails with a view and get an extra chance to catch the Members Show for some holiday shopping. The Stroll begins at 4 p.m. at St. Paul's.

• Dec 7, 2022 - Dec 11, 2022 Key West Arts & Culture
• Nutcracker Key West
• Website
• A unique subtropical version of the classic holiday ballet "The Nutcracker" awaits Keys visitors, flavored with characters and settings that depict Key West's colorful history, vibrant coral reef environment and even free-roaming local roosters. Blending professional dancers and local talents, the production features exquisite costumes and sets inspired by island lore. Performances take place at the Tennessee Williams Theatre at 5901 College Road.

• Dec 7, 2022 Key West
• Friends of the Key West Library 50th Anniversary Celebration
• Website
• The Friends of the Key West Library kick off their 50th Anniversary celebration with an event at the library, located at 700 Fleming Street, from 4 to 6 p.m. There will be a short program, tours and refreshments in the library lounge.

• Dec 7, 2022 Islamorada Arts & Culture
• Smuggling in the Florida Keys: Part IV
• Website
• The Florida Keys History & Discovery Center lecture series "Smuggling in the Florida Keys" Part IV, the final panel in the series, consists of State Prosecutor Allison DeFoor speaking on what it took to convict those who were involved in Smuggling in the Florida Keys, along with Richard "Dickie" Lynn, who served over 30 years in federal custody and was granted compassionate release by a federal judge in 2021. Doors open at 5 p.m. to explore the museum with light appetizers and cash bar available. Presentation 6-7:30 p.m. Advance registration required, $10. Located on the Islander Resort property, mile marker 82.

• Dec 9, 2022 Key West
• Holiday Historic Inn Tour
• Website
• During this enchanted Friday evening, visit and tour four beautifully decorated island locales: Key West Butterfly & Nature Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation between 6 and 8 p.m. Explore the unique architecture and history at each stop while enjoying sweet and savory holiday treats and libation samplings. Limited trolley transportation will be provided between properties, but participants are encouraged to bike, walk or use their own transportation. Purchase tickets online, then pick up tickets after 5 p.m. on Dec. 9 at Butterfly & Nature Conservatory.

• Dec 9, 2022 Marathon
• Tropical Holiday Fun Fest
• Website
• Come out to Marathon Community Park for a night of Holiday fun. Enjoy live holiday music, entertainment by the Marathon Community Theater dancers and the Prodigy Dancers, face painting, bounce houses, cotton candy and other treats, and see Santa! Mile marker 49 oceanside.

• Dec 9, 2022 Islamorada Environmental
• "Ocean to Everglades: Stories of the Sea" Film & Discussion
• Website
• Join Surfrider Florida Keys and Sereia Films on Friday, December 9th for "Ocean to Everglades: Stories of the Sea" - a night of film screenings and discussion on sustainable seafood in Florida and the ocean livelihoods that depend on it. Happy hour will be from 6:30 to 7 p.m., film screening from 7 to 8:15, followed by a panel discussion on sustainable seafood in Florida and the Keys. Mile marker 80.5 bayside. Online advance registration required.

• Dec 9, 2022 Key West
• Holiday Lighted Boat Parade of Stock Island
• The Rotary Club of Key West and the Perry Hotel & Marina invite you to enjoy a boatload of maritime merriment as a colorful fleet decked in holiday lights parades by the Perry Hotel lawn. This will be a family-fun evening to that also includes entertainment, photos with Santa and more. 7001 Shrimp Road.

• Dec 10, 2022 Key Largo
• The Flamingo Who Stole Christmas, Featuring The Grinch
• Website
• Bring the family for this free event featuring holiday treats, activities, and the one who needs holiday cheer the most - the Grinch! Stop by Keys Chocolates & Ice Cream at mile marker 100 bayside in Key Largo between 2 and 6 p.m. on Saturday for pictures with the Grinch, Christmas cookie decorating, sweet treats (including popcorn, cotton candy, and snowcones), ice cream cocktails for those over 21, games, and more. Face painting for children will be available from 3 pm to 5 pm.

• Dec 10, 2022 Key West
• Schooner Wharf Annual Key West Lighted Boat Parade
• Website
• A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights. Music begins at 6 p.m., parade starts at 8.

• Dec 10, 2022 Marathon
• Boot Key Harbor Christmas Boat Parade
• Website
• The parade will start in from the west side of the harbor (7 mile bridge side) at 6 p.m. and slowly meander east past Lazy Days, Marathon Marina, Pancho's and Burdines, then down to Dockside past the condo's and turn around in the basin at Yacht Haven Marina. Parade awards and party will be at Dockside café following the parade.,

• Dec 10, 2022 Islamorada
• Kringle's Garden Holiday Market
• Website
• Island Home Garden in Islamorada invites you for holiday fun Saturday, Dec. 10 from 10 a.m. to 2 p..m. Enjoy Gardenia Bistro's hot chocolate bar, cookie decorating and a visit from Santa. Shop for plants, home decor and many other items at the pop up market with island vendors. They will also be collecting donation items for the local children's shelter and animal rescue.

• Dec 10, 2022 Key Largo
• Key Largo Boat Parade - A Cartoon Christmas
• Key Largo's annual holiday boat parade on Blackwater Sound lights up the night beginning at 7:30 p.m. Saturday, Dec. 10 with boats decked out for the holidays. Watch from waterfront locations including various restaurants and nightspots such as Caribbean Club and Jimmy Johnson's Big Chill - both at MM 104 bayside - as well as the public Rowell's Waterfront Park.

• Dec 10, 2022 Key West
• Ninth Annual Florida Keys SPCA Parade of Paws
• Website
• Join the Florida Keys SPCA at the Higgs Beach Dog Park in Key West from 10 a.m. - 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2022 Royal Court.  Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach!  Costumes encouraged!  All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.

• Dec 10, 2022 - Dec 11, 2022 Islamorada
• Eighth Annual Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N' Beer Mile
• Website
• Whether bucket-list runners or newbies, participants of all ages and skill levels are invited to register for this annual subtropical footrace. In the Beach N’ Beer Mile, runners must consume four beers over a 1-mile course in Islamorada. Organizers said the best time to beat for the event is seven minutes. Participants in the Rumrunner 5k receive a finisher medal and a free Rumrunner from the World Famous Tiki Bar. Cash prizes are to be awarded the top three male and female half-marathon finishers, as well as awards for the top three finishers of the 10k. Events start and end at Postcard Inn, mile marker 84.

• Dec 10, 2022 Islamorada Arts & Culture
• Pops in the Park: Keys Community Concert Band Holiday Concert
• Website
• “Joy to the World” with a free, outdoor concert from Keys Community Concert Band at Founders Park (mm 87, bayside), 4 to 5 p.m. in Islamorada. Bring a blanket or lawn chair and pack a picnic basket for a family-friendly concert of holiday music, sing-along and a visit from Santa. Special guests: Burton Handbell Ringers.

• Dec 11, 2022 Key West
• Key West Triathlon
• Website
• The Key West Triathlon challenges participants to swim in the waters of the Atlantic Ocean, bike along a portion of the Florida Keys’ scenic Overseas Highway and run on a fast, flat course beside the Atlantic. As well as the Olympic-distance and sprint-distance triathlons, Aquabike and sprint duathlon competitions are featured. Higgs Memorial Beach Park, 1000 Atlantic Boulevard, Key West.

• Dec 11, 2022 Key West
• Christmas on the Farm
• Website
• The Monroe County Sheriff's Animal Farm invites everyone for a "Christmas on the Farm" Open House Sunday, Dec. 11 from 1 to 3 p.m. Santa will be there and each child will receive a gift. There will be live local musicians, and farm veterinarian Dr. Doug Mader will be signing copies of his new book, "The Vet at Noah's Ark." Books are for sale for $25 (cash or check only) with all proceeds donated to the farm. The event is free but donations are appreciated. 5501 College Road, Stock Island.

• Dec 11, 2022 Marathon
• Key Colony Beach Christmas Boat Parade
• Website
• The Key Colony Beach Christmas Boat Parade happens on Sunday night, Dec. 11, beginning at dusk, around 5 p.m. All participating boat captains and crew are invited to the awards ceremony immediately following the parade at Key Colony Beach Inn.

• Dec 12, 2022 Marathon Fishing
• The Tackle Box Monthly Fishing Seminar: Wahoo
• Website
• This month's free fishing seminar, presented by The Tackle Box, offers tips on ways to fish for and catch wahoo. The seminar takes place from 5:30 to 8 p.m. at Marathon Community Theatre, mile marker 49.5 oceanside.

• Dec 13, 2022 Key Largo
• REEF Holiday Party
• Website
• Join the team from REEF Environmental Education Foundation for their annual get together to celebrate the holidays with light snacks, refreshments, and festive fun with friends. It takes place at the REEF campus at mile marker 98.3 in the median from 6 to 7:30 p.m. This event is free and open to the public.

• Dec 15, 2022 Islamorada Arts & Culture
• Morada Way Third Thursday Art Walk in Islamorada
• Website
• Showcasing the area’s fine arts, music and culinary nuances, the Morada Way Arts & Cultural District features national and local artisans whose work is showcased in galleries at Morada Way between mile markers 81 and 82, as well as beer tastings and live music, 6-9 p.m. Admission is free to this outdoor pre-holiday celebration. Art Walk is held the third Thursday of each month.

• Dec 16, 2022 Islamorada
• Joanne Mackell Live
• Website
• Experience Joanne Mackell Live brought to you by Island Community Entertainment Friday night from 7 to 10 p.m. at Florida Keys Brewing Company, mile marker 81 oceanside in Islamorada. Joanne Mackell is a veteran singer/songwriter whose passionate delivery, outstanding vocal range and commanding stage presence consistently raise the roof and rock the house. Born in Boston and raised in Montreal, Joanne is the daughter of hockey legend Fleming Mackell, who played with the Toronto Maple Leafs and Boston Bruins.

• Dec 16, 2022 Key Largo Environmental
• REEF Citizen Science Fish Survey Dive Trip
• Website
• Certified divers are invited to participate in a two-tank dive this Friday with Rainbow Reef Dive Center, and contribute to REEF Environmental Education Foundation's Volunteer Fish Survey Project. The event begins with a morning class and orientation at 9:15 a.m. on procedures for identifying and properly surveying fish. Then you'll be provided with a dive slate, underwater survey materials and fish ID materials. Kids 10 years old and up who are certified juniors can participate. Cost for the class, materials and dives is $125. Rainbow Reef is located at 100 Ocean Drive, Key Largo. Call 305-451-7171 to sign up.

• Dec 16, 2022 - Dec 17, 2022 Key West LGBTQ
• The 12 Days of Christmas: Burlesque Show Spectacular
• Website
• This extravaganza, based on the classic Christmas song, combines the talents of world class burlesque performers, circus style entertainers and singers. The cast, lead by Julliard School graduate Shelly Watson along with all your favorite Key West Burlesque dancers, is sure to dazzle audience members. Doors open at 7 p.m., show at 8. Tickets $45 to $100, available online. Key West Theater, 512 Eaton Street.

• Dec 16, 2022 Key West
• Holiday Historic Inn Tour
• Website
• Visit and tour four beautifully decorated island locales: Hemingway’s Library at Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel, and Island City House, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings between 6 and 8 p.m. Purchase tickets online, then pick them up after 5 p.m. on the night of the tour at the first property, Hemingway’s Library at Papa's Pilar Distillery. Participants will need to walk, bike or use their own transportation between locations.

• Dec 17, 2022 Marathon
• Winter Wonderland at Crane Point
• Website
• There's a forecast for snow in the tropical forest at Crane Point Hammock Museum & Nature Trail during Winter Wonderland from 4:30 to 7:30 p.m. Bring the entire family to encounter reindeer ponies, holiday decorations, Santa and snow! Enjoy Santa stew, the chocolate fountain, roasted chestnuts and adult beverages for purchase. 5550 Overseas Highway, Marathon.

• Dec 17, 2022 Key West
• Key West Botanical Garden Native Plant Sale
• Website
• The plant nursery offers native Florida trees, shrubs, vegetables and vines for sale from 9 a.m. to noon the third Saturday of the month. Master Gardener volunteers will be on site to help answer any plant questions. There are 165 species of plants available with an inventory totaling more than 2,000 plants that attract birds and butterflies in 1-gallon to 10-gallon pots. Key West Botanical Garden members receive a discount. The Garden, located at 5210 College Road on Stock Island, is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.

• Dec 17, 2022 Key West
• 14th Annual 5K Rudolph Red Nose Run
• Website
• Don your festive holiday jammies and join! Starts and ends at Southernmost Beach Café, 1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, prizes and a fabulous silent auction. Pre-race packet pickup is Friday, Dec. 16 from 5-7 p.m. at the Café. Runners and walkers of all ages and abilities are welcome to participate. Registrants receive a free t-shirt; prizes for most festive and unusual PJ’s. Presented by nonprofit group, A Positive Step for Monroe County.

• Dec 17, 2022 Marathon Arts & Culture
• Marathon Latin Festival
• Website
• Hosted by Baby Lores, one of the pioneers in the Cuban music scene, this all-day music fest is from 10 a.m. to 10 p.m. at Marathon Community Park at mile marker 49. Enjoy family-free entertainment and activities during the day and a grand fiesta of music from 5 to 10 p.m. by several dozen top Latin musical entertainers. Partial proceeds from this event are to support the Somos Esperanza foundation, that helps provide for sick children, providing necessary medical attention and equipment. Advance purchase tickets are online for $50 per adult, $25 for ages 13-21, with kids 12 and under free. VIP tickets also available. Tickets are also to be on sale the day of the event.

• Dec 17, 2022 The Florida Keys
• Captains of Sea Base Fundraiser
• Website
• The Sea Base Alumni and Friends Association is holding a fundraiser Saturday from 4 to 10 p.m. at Florida Keys Brewing Company to help the captains of Sea Base whose boats were damaged by Hurricane Ian. In September, many of the Sea Base captains took their vessels to Port Charlotte for haul out and maintenance, and the hurricane made a direct hit on the marina, damaging 18 boats. The event includes a silent auction and raffle beginning at 4 p.m., with live music by the Barstool Sailors beginning at 6 p.m. All proceeds support the repair of damaged vessels so the captains can get their boats on the water for the 2023 spring and summer season. Sea Base is a unique Scouting program offering aquatic learning found nowhere else including sailing, diving, fishing and now, work in coral restoration in conjunction with Plant a Million Corals. The brewery is at mile marker 81 in the Morada Way arts district.

• Dec 17, 2022 The Florida Keys
• Kiki's Holiday Huddle & Lighted Boat Parade
• Website
• Kiki's Sandbar plans a full day of holiday fun and cheer beginning at 7 in the morning with holiday sunrise yoga and culminating with the Lighted Boat Parade at 7 p.m. There will be live music throughout the day, the holiday paint and sip session at 1 p.m., and the gingerbread house contest and pet pictures with Santa at 2 p.m.

• Dec 17, 2022 - Dec 24, 2022 Key Largo Environmental
• Gift Wrapping Fundraiser for Coral Shores High School Marine Science
• Website
• Marine science students from Coral Shores High School will be running a gift wrapping fundraising event in front of Divers Direct in Key Largo to raise money for their upcoming coral planting dive trips and supplies. Donations accepted. Bring gifts from anywhere to be wrapped by students. Wrapping sessions take place from noon to 5 p.m. Dec 17 and 18, and again daily from Dec. 21 through 24. Mile marker 99 oceanside, Key Largo.

• Dec 18, 2022 Key West Arts & Culture
• Snowy Sunday Children's Concert at Key West Botanical Garden
• Website
• Snowy Sunday, the Key West Tropical Forest & Botanical Garden's annual winter concert, features local classical guitarist, Mateo Jampol performing songs especially for children. The event opens at 1 p.m. and Jampol's concert starts at 1:30 p.m., followed by snow cones (while they last) and delightful holiday activities. Tickets $5 per child at the door with a maximum cost of $10 per family.

• Dec 18, 2022 Key West
• Key West Artisan Market: Shop Local Edition
• Website
• Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and splendid ocean views as we offer everything you need to cross off your holiday shopping list. Supporting the Key West Shop Mom & Pop and #shoplocalkey west movement to keep our resources right here in our community. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

• Dec 18, 2022 Key West Arts & Culture
• Key West Lighting of the Menorah
• Website
• The City of Key West's annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec.18 from 5 to 6 p.m. 1320 Truman Avenue.

• Dec 20, 2022 - Jan 14, 2023 Key West Arts & Culture
• Red Barn Theatre: Dear Jack, Dear Louise
• Website
• Ken Ludwig's "Dear Jack, Dear Louise" opens the Red Barn Theatre's 43rd season. Sparks fly and love blossoms from a world away when U.S. Army doctor, Jack, begins a correspondence with aspiring actress, Louise during WWII. Winner of the Helen Hayes and Charles MacArthur Award for Best New Play of 2020. Order tickets online or at the box office. Showtime 8 p.m. 319 Duval Street.

• Dec 28, 2022 - Dec 29, 2022 Key West Arts & Culture
• Old Island Restoration Foundation's Home Tours "Holiday Style"
• Website
• The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating back to 1960. This 63rd series of tours features self-guided tours of homes festively dressed for the holidays on Dec. 28 and 29. After the holidays, home tour dates are Jan. 13-14, Feb. 17-18, and March 17-18. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

• Dec 30, 2022 Key West
• Fireworks & Glow Party
• Website
• The annual Fireworks & Glow party takes place December 30th from 6 to 10 p.m. at Key West Marriott Beachside, 3841 N. Roosevelt Blvd. This free event is open to the public. Party organizers will give away two thousand glow items to brighten up your night. DJ Sanaris gets the party started at 6 p.m. Food will be available for purchase, with all proceeds benefiting Take Stock in Children. The fireworks show is at 9 p.m.

• Dec 30, 2022 Key West
• Fireworks Celebration at 24 North Hotel
• Website
• Start celebrating New Year's Eve a day early with a fireworks celebration on Friday night, Dec. 30 at the Sunset Green Event Lawn between 24 North Hotel and the Gates Hotel in Key West. There will be live music by The Marshall Morlock Band, food, drinks and fireworks. The lawn opens at 6 p.m., fireworks start at 9 p.m. A portion of food and beverage sales support the Highgate Charitable Foundation. 3820 N. Roosevelt Boulevard.

• Dec 30, 2022 - Jan 1, 2023 Key West Arts & Culture
• Wilson Signature Collection Fine Art Gallery Grand Opening
• Website
• Explore the works of husband and wife artistic duo D. Arthur and Lisa Wilson during the grand opening of their signature collection fine art gallery from 3 to 8 p.m. Dec. 30 and 31; and from 2 to 7 p.m. Jan. 1. 407 Front St., Key West.

• Dec 31, 2022 Marathon
• Lighthouse Grill "Anchor Drop" New Year's Eve Party at Faro Blanco Resort & Yacht Club
• Website
• The Lighthouse Grill at Faro Blanco invites partiers to toast the New Year with a complimentary glass of champagne and its famous anchor drop from the Faro Blanco Lighthouse at midnight. The free party starts at 9 p.m. with a DJ, dancing, photo booth and more. No reservations required. The Lighthouse Grill's pre-party New Year’s Eve dinner is fully booked, but those interested can call 305-434-9039 to join the waiting list.

• Dec 31, 2022 Key Largo
• Baker's Cay Glow Party, Ball Drop & Fireworks
• Website
• For the first time, Baker's Cay Resort has opened up a limited number of New Year's Eve resort passes for locals and non-guests to attend the resort's famous glow party and annual ball drop from 8 p.m. until midnight. Enjoy a live DJ, photo booth, beachfront s'mores and a dazzling display of fireworks over Florida Bay. $70 adults, $35 children 3 to 12; age 2 and under free. Find more information and buy passes online. The resort is located at mile marker 97 in Key Largo.

• Dec 31, 2022 Islamorada
• Keys Island Grill New Year's Eve Beach Party
• Website
• Keys Island Grill at mile marker 85 oceanside rings in the New Year with a bang with a beach party featuring two live bands, a Brazilian Carnival Dance show, a DJ and more. General admission tickets are $25 and VIP tables for four or six with bar package are available to purchase. Tickets include one complimentary glass of wine and there will be a cash bar on the beach and deck. Sushi, barbecue and ice cream will be available for purchase. Deck doors open at 8:30 p.m.; the beach opens at 9 p.m. The nearby Hog Heaven midnight fireworks should be visible.

• Dec 31, 2022 Islamorada
• Hog Heaven New Year's Eve Party
• Website
• Hog Heaven Sports Bar & Grill at mile marker 85 oceanside is having a New Year’s Eve party with live music by “Ego Free” from 8 p.m. up until the midnight fireworks show. Living up to the bar’s reputation as a top late-night spot in the Upper Keys, DJ Louis keeps the party rocking until 4 a.m. No reservations required.

• Dec 31, 2022 Islamorada
• New Year's Eve Dinner and Fireworks at Cheeca Lodge & Spa
• Website
• Cheeca Lodge & Spa's restaurants will be serving an elegant New Year's Eve menu with multiple seatings before the resort's annual fireworks display. Access is open to non-guests as long as you have confirmed dinner reservations. Call 305-517-4447. The resort is located at mile marker 81 oceanside.

• Dec 31, 2022 The Florida Keys
• Gatsby New Year's Eve Party
• Website
• Ring in the New Year with the crew at First Flight Restaurant and Brewery in Key West, known as the birthplace of Pam American World Airways. At the stroke of midnight, a replica Pan Am plane "drops" with a flight attendant to join guests dressed to the nines in black tie or their finest Gatsby-era outfits. All-inclusive $250 per person tickets include full open bar, heavy hors d'oeuvres, chef stations, live music and a champagne toast. 310 Whitehead Street.

• Dec 31, 2022 Key West
• Tuna Drop at Smokin' Tuna Saloon
• Party on New Year's Eve at Key West's Smokin' Tuna Saloon. Drink specials, live music and the offbeat "tuna drop" at midnight. 4 Charles Street.

• Dec 31, 2022 Islamorada
• New Year's Eve Party at Postcard Inn
• Website
• Ring in the new year island-style at Postcard Inn's New Year's Eve party at Raw Bar on the water with tropical cocktails, the Touch of the Keys seafood buffet, a live band from 7 to 10 p.m., a DJ from 10 p.m. until the ball drops, and a complimentary midnight champagne toast. $85 per person, $35 for children 12 and under. The public is invited to attend as well as resort guests. Book reservations online in advance.

• Dec 31, 2022 Key Largo
• Ring in the New Year with Exit Left at Gilbert's Resort
• Website
• Celebrate New Years Eve at Gilbert's Resort with live music by Exit Left, playing high-energy rock, pop and alternative hits from the 70s to today starting at 7 p.m. Call 305-451-9242 for more information or to book a room.

• Dec 31, 2022 Key West
• New Year's Eve at Sunset Pier
• "Come Together" for New Year’s Eve with The Beatle Band at the famous Sunset Pier at Ocean Key Resort, located at 0 Duval Street. The party starts at 9 p.m. right over the water. Enjoy a complimentary champagne toast and the annual Key Lime Drop at midnight. $10 donation requested to benefit Mote Marine Laboratory's Center for Coral Reef Research & Restoration.

• Dec 31, 2022 Marathon
• Boogie Into 2023 with Havana Jack's
• Website
• Havana Jack's Oceanside Restaurant at 401 East Ocean Drive in Key Colony Beach invites you to boogie into the new year with live music from The Lady A Band on New Year's Eve starting at 4 p.m., along with dinner and drink specials starting at 5 p.m. A DJ will be spinning tunes from 9 p.m. up until a complimentary midnight toast. Call 305-743-4849 for reservations.

• Dec 31, 2022 Key Largo
• Bungalows Key Largo New Year's Eve Celebration
• Website
• Registered guests at Bungalows Key Largo will enjoy an elegant New Year's Eve dinner buffet and dessert bar followed by live music from Patrick and the Las Vegas Band, followed by an elaborate fireworks display and champagne toast at midnight.

• Dec 31, 2022 Key West
• New Year's Eve Shoe Drop Celebration
• E-mail Website
• The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne. This is the 25th anniversary "Red Shoe Drop."

• Dec 31, 2022 Key West
• New Year's Eve: Conch Shell Drop at Sloppy Joe's
• Website
• The arrival of 2023 is to be heralded on the island'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.

• Dec 31, 2022 Key West
• New Year's Eve: Pirate Wench Drop at Schooner Wharf
• Website
• For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2023. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.