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, 2022 Year: 2022 2023 Month: January February March April May June July August September October November December   March 31 to December 11,  in Key West Key West Bicentennial Exhibit at The Custom House Museum 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. October 25 to December 31,  in Islamorada History of Diving Museum: Sponge Hunters 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. November 23 to December 31,  in Key West 2022 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. December 01 to January 01,  in Key West Key West Holiday Fest 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.” December 01 to July 31,  in Key West Key West Fishing Tournament 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. December 01 to January 22,  in Islamorada Florida Keys Gold Cup Sailfish Championship Anglers are to pursue sailfish, the most plentiful billfish in the waters off the Keys, in a series of three competitions - the Islamorada Sailfish Tournament, Dec. 1-4, 2022; the Islamorada Fishing Club Captain's Cup Sailfish Tournament, Jan.17-18, 2023; and the Cheeca Lodge Presidential Sailfish Tournament Jan. 20-22, 2023 - after which the Gold Cup is awarded. Contact: 305-852-2102 Email: [email protected] December 01 to December 04,  in Key West COAST is CLEAR Music and Arts Festival 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. December 01 to December 04,  in Islamorada Islamorada Sailfish Tournament The Florida Keys Gold Cup Sailfish Championship triple-crown series is to open with the Islamorada Sailfish Tournament, a primary fundraiser for the Islamorada Charter Boat Association Thursday, Dec. 1 through Sunday, Dec. 4. Social events are to be headquartered at the Whale Harbor Inn and Marina complex at mile marker 83. December 01,  in Key West World AIDS Day Processional and Service at Key West AIDS Memorial 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. December 01 to December 03,  in Key West Tropic Cinema: Neil Young "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. December 02 to December 03,  in Key West Revival Roadshow at Sunset Pier 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. December 02,  in Islamorada Florida Keys Holiday Fest in Islamorada 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. Contact: 305-664-4503 December 02,  in Key West Holiday Village & BeLighted Bike Ride The Wesley House Family Services’ Holiday Village & BeLighted Bike Ride is a great family-friendly event to help kick off the holiday season. The Holiday Village from 4-8 p.m. features community and vendor booths, food trucks, a best bike contest at 7 p.m. and photos with Santa. The bike ride leaves at 8 p.m. Admission $15 adults, $10 children, kids 4 and under free. Find tickets, information and bike contest registration online. December 03,  in Big Pine Grand Opening: Plant a Million Corals 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. December 03,  in Key West City of 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. Seeing Santa is a highlight for kids. December 03,  in Islamorada Florida Keys History & Discovery Special Event: Redbone Gallery Show 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. December 03,  in Marathon Faro Blanco Resort Lighting of the Lighthouse 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. December 03,  in Key West Surfrider Florida Keys Key West Beach Cleanup at Smathers Beach 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. December 03 to December 04,  in 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. December 03,  in Key West Friends of the Key West Library Book Sale 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. December 03,  in Key West Pet Pictures with the Grinch 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. December 04,  in 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. December 04,  in Key West Key West Woman's Club Holiday Open House 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. December 04,  in Key West Pet Pictures with Santa 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. December 04,  in Key West Eaton Street Christmas Stroll 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. December 04,  in Key West Key West Artisan Market: 10th Anniversary Edition 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. December 07,  in Islamorada Smuggling in the Florida Keys: Part IV 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. December 07,  in Islamorada Full Moon Yoga Meditate and relax under the glow of the full moon and the twinkling stars at Postcard Inn, Islamorada from 6 to 7:30 p.m. Zenfully Aware Yoga, the Islamorada Resort Collection, and Coral Restoration Foundation™ are bringing you on an adventure – a yoga practice centered around how the full moon affects the coral reefs and the spawning and growth of the reefs as the lungs of the earth. 50% of all proceeds will be donated to Coral Restoration Foundation™. Non-guests may register online for $25; free for resort guests. December 07 to December 11,  in Key West Nutcracker Key West 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. December 07,  in Key West Friends of the Key West Library 50th Anniversary Celebration 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. December 09,  in 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. December 09,  in Marathon Tropical Holiday Fun Fest 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. December 09,  in Islamorada "Ocean to Everglades: Stories of the Sea" Film & Discussion 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. December 09,  in Key West Holiday Historic Inn Tour 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. December 10 to December 11,  in Islamorada Eighth Annual Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N' Beer Mile 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. December 10,  in Islamorada Pops in the Park: Keys Community Concert Band Holiday Concert “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. December 10,  in Key West Ninth Annual Florida Keys SPCA Parade of Paws 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. December 10,  in 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. December 10,  in Key West Schooner Wharf Annual Key West Lighted Boat Parade 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. December 10,  in Key Largo The Flamingo Who Stole Christmas, Featuring The Grinch 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 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. December 10,  in Marathon Boot Key Harbor Christmas Boat Parade 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., December 11,  in Marathon Key Colony Beach Christmas Boat Parade The Key Colony Beach Christmas Boat Parade happens on Sunday night, Dec. 11, beginning at dusk, around 5 p.m. December 11,  in Key West Key West Triathlon 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. December 12,  in Marathon The Tackle Box Monthly Fishing Seminar: Wahoo 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. December 15,  in Islamorada Morada Way Third Thursday Art Walk in Islamorada 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. December 16,  in Key West Holiday Historic Inn Tour 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. December 16 to December 17,  in Key West The 12 Days of Christmas: Burlesque Show Spectacular 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. December 16 to December 18,  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. Hosted at the Coconut Palm Inn, mile marker 92 bayside. Contact: Tammy Gurgiolo 305-240-9337 Email: [email protected] December 17,  in Key West 14th Annual 5K Rudolph Red Nose Run 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. December 17,  in Marathon Marathon Latin Festival 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. December 17,  in Marathon Winter Wonderland at Crane Point 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. December 17,  in Key West Key West Botanical Garden Native Plant Sale 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. December 18,  in Key West Key West Artisan Market: Shop Local Edition 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. December 18,  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.18 from 5 to 6 p.m. 1320 Truman Avenue. December 18,  in Key West Snowy Sunday Children's Concert at Key West Botanical Garden 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. December 28 to December 29,  in Key West Old Island Restoration Foundation's Home Tours "Holiday Style" 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. December 31,  in Key West New Year's Eve Shoe Drop Celebration 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. Email: [email protected] December 31,  in Key West New Year's Eve: Conch Shell Drop at Sloppy Joe's 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. December 31,  in Key West New Year's Eve: Pirate Wench Drop at Schooner Wharf 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 2022. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St. December 31,  in Islamorada New Year's Eve Party at Postcard Inn 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. December 31,  in Key Largo Ring in the New Year with Exit Left at Gilbert's Resort 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. December 31,  in 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. December 31,  in Marathon Boogie Into 2023 with Havana Jack's 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. Please make your reservations by Dec. 24. 305-743-4849. December 31,  in Key Largo Bungalows Key Largo New Year's Eve Celebration Guests at Bungalows Key Largo can 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.