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Calendar of Events

December 2021: Florida Keys Events

Image for Buccaneer Blast Regatta Image for Buccaneer Blast Regatta Image for Buccaneer Blast Regatta Image for Buccaneer Blast Regatta
Image for Key West Impromptu Classical Concerts Image for Key West Impromptu Classical Concerts Image for Key West Impromptu Classical Concerts Image for Key West Impromptu Classical Concerts
Image for History of Diving Museum Exhibit: Diving in Pop Culture
  • Apr 21, 2021 - Dec 31, 2021 Islamorada Arts & Culture
  • History of Diving Museum Exhibit: Diving in Pop Culture
  • Website
  • Visit the museum at 82990 Overseas Highway (mile marker 83) to see the latest exhibit with representations of diving in literature, advertising, film, television, games, music, attractions, collectibles, and more, while examining connections amongst these works. Museum staff has been collecting and researching all of the creative ways diving has been incorporated into pop culture for over 100 years.
Image for Zonta’s Festival of Trees
  • Nov 30, 2021 - Dec 4, 2021 Marathon Arts & Culture
  • Zonta’s Festival of Trees
  • Website
  • The annual Festival of Trees is to take place at the Marathon Community Theater, 5101 Overseas Highway. Holiday trees are festively displayed, and decorated by members of the Zonta Club of Marathon, a humanitarian service organization. Visitors and residents can view and bid to purchase the decorated trees during open hours: Tue-Thur 3:30-8 p.m., Fri 3:30-9 p.m., Sat 10 a.m. to 9 p.m. (from 10 a.m. to 12 p.m., kids can enjoy cookies and photos with Santa). No charge for admission; just come and enjoy the trees or purchase raffle tickets for a chance to win your favorite tree.
  • Dec 1, 2021 - Jul 31, 2022 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.
Image for Key West Holiday Fest
  • Dec 1, 2021 - Jan 1, 2022 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.”
Image for The Studios of Key West presents: Winter Members' Show
  • Dec 2, 2021 - Dec 30, 2021 Key West Arts & Culture
  • The Studios of Key West presents: Winter Members' Show
  • Website
  • The winter members’ exhibition ‘Piece by Piece’ is to be on display in all four galleries: Sanger, XOJ, Zabar Lobby and Zabar Project Galleries. The annual winter members’ show is a celebration and serves as a kick off for TSKW’s season of events. Galleries are open Tue-Sat, 10 a.m.- 4 p.m., and are free to visit, at 533 Eaton St.
  • Dec 2, 2021 - Dec 5, 2021 Islamorada Fishing
  • Islamorada Sailfish Tournament
  • Email Website
  • The first leg of the triple-crown Florida Keys Gold Cup Championship series is the only tournament in the series to offer a junior division for anglers age 16 and younger. Unlimited anglers are allowed per vessel. Two subsequent fishing events in the Gold Cup Series include the Cheeca Lodge Presidential Sailfish Tournament scheduled Jan. 21-23, 2022, and the Islamorada Fishing Club Sailfish Tournament scheduled Jan. 26-27, 2022, when the series culminates and an overall Gold Cup Series champion is crowned.
  • Dec 2, 2021 - Dec 5, 2021 Islamorada Fishing
  • Islamorada Sailfish Tournament
  • Continuing a 50-plus-year tradition, 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.  Social events are to be headquartered at the Whale Harbor Inn and Marina complex at mile marker 83.
Image for Islamorada Chamber of Commerce Florida Keys Holiday Festival
  • Dec 3, 2021 Islamorada
  • Islamorada Chamber of Commerce Florida Keys Holiday Festival
  • 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 in a magical 30-ton snow mountain during the event and watch the lighting of a 35-foot-tall community tree. 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 and a holiday parade at 7:30 p.m.
Image for Green Pineapple at The Perry Holiday Artist Showcase
  • Dec 3, 2021 The Lower Keys
  • Green Pineapple at The Perry Holiday Artist Showcase
  • Website
  • From 5:30 - 7:30 p.m. at The Perry Hotel, 7001 Shrimp Road on Stock Island, shop new collections, find the perfect gift, and sip on wine & champagne while exploring each of the featured artists including local favorite ZEN by Karen Moore, a holistic jewelry & accessory company that specializes in one-of-a-kind, meaningful pieces that are just right for you or for gift giving. Come say hello, find the perfect holiday gifts and support small businesses and local Keys artists.
Image for COAST is CLEAR Music and Arts Festival
  • Dec 3, 2021 - Dec 5, 2021 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 event is an all-day concert Saturday. VIP and General Admission tickets still available, at $225 pp and $105, respectively. Festival is to be held rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd.
  • Dec 4, 2021 Key West
  • Tri Conch Republic
  • Email Website
  • Athletes will converge on the southernmost island on the United States and enjoy a break from the ordinary. Staged at Higgs Beach, athletes will enjoy a warm Atlantic Ocean swim in full view of spectators.  The bike course is set against along US1 by Smathers Beach. The Olympic distance athletes will have two loops on the course, while the sprint distance will do so once. The run also consists of a scenic view along Smathers Beach. Friends, family and music welcome the athletes through the finish line. 
Image for Key West City Hometown Holiday Parade
  • Dec 4, 2021 Key West
  • Key West City Hometown Holiday Parade
  • 305-809-3881 Website
  • 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 Bayview Park's Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.
Image for Pet Photos with Santa
  • Dec 5, 2021 Marathon
  • Pet Photos with Santa
  • 305-743-DOGS Website
  • Hosted by Courtyard Marathon, Santa is to pose for photos with pets from 2-4 p.m. The event supports the medical and special needs for the shelter animals at Florida Keys SPCA campus in Marathon. With a $50 cash donation, you will get a 10 min professional photo shoot (by McLaughlin Photo & Video) with your pet and Santa. Pets can also join us on the beach before/after their photo shoot at our Doggie Beach Party with a cash bar for their humans. Contributions of pet food, toys, beds or financial donations for the FKSPCA are also welcomed.
Image for Annual Lighting of the Lighthouse
  • Dec 5, 2021 Marathon
  • Annual Lighting of the Lighthouse
  • Website
  • From 3-6 p.m., enjoy food, music, performances, holiday shopping in a marina walk marketplace, Santa Claus and holiday buoy decorating, all centered around the lighting of the iconic lighthouse at Faro Blanco Resort & Yacht Club, 1996 Overseas Highway. Open to everyone!
Image for Key West Artisan Market, 'For the Birds' Edition
  • Dec 5, 2021 Key West Environmental
  • Key West Artisan Market, 'For the Birds' Edition
  • Website
  • From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote community causes. All artists who show at the event are carefully selected and live and create in the Keys. This month's Market benefits the Key West Wildlife Center.
  • Dec 5, 2021 Key West Arts & Culture
  • Eaton Street Christmas Stroll
  • Website
  • Family Friendly Holiday Event The Stroll begins at 4:00PM at St Paul’s Episcopal Church • 401 Duval St. Keys Choral arts presents a short program of secular & religious music for the season. Continue strolling to: Old Stone First United Methodist Church • Christmas Music, with Voices, Bells, Instruments, Piano & Organ. Tropic Cinema • Classic Christmas short film. Studios of Key West • Open for special hours with a happy hour at Hugh’s View on the roof. Key West Theater • Stop in for some hot cocoa or cider, and listen to holiday songs performed by local musicians, at any time during the entire duration of the event. Williams Hall • See their newly rehabbed space all dressed up for the holidays. Featuring live music by Mateo Jampol & fresh baked pastries and cookies.
Image for Santa’s Sip & Sail Christmas
  • Dec 5, 2021 Key Largo
  • Santa’s Sip & Sail Christmas
  • 305-747-2600 Email Website
  • This holiday fundraiser takes place at the Upper Keys Sailing Club from 12 - 4 p.m. at 100 Ocean Bay Drive (MM 99.5 Bayside). Santa and his elves are to arrive on his water sleigh at noon, kicking off an afternoon of family fun. For a $10 donation, have a family photo taken with Santa aboard a sailboat overlooking the beautiful Florida Bay! The fun continues with a petting zoo, Christmas cookie decorating and ornament design, and adult beverages. Sailing lessons will be raffled off. Proceeds support youth sailing instruction for local children.
Image for Home for the Holidays
  • Dec 10, 2021 - Dec 11, 2021 Marathon
  • Home for the Holidays
  • Website
  • Enjoy a family friendly evening filled with cheer, joy and music at Marathon Community Theatre's Annual Holiday Show & Sing-Along concert. Doors open 7 p.m., show starts at 8 p.m.; tickets $10 per person, available online. The annual family-friendly show is to run one hour with no intermission and include musical selections from the Island Harmony Singers, the MCT Children’s Chorus as well as local church groups and singers. Be entertained by dancers from Prodigy Dance Center and the MCT Dance Department as they dance to classic Holiday Tunes!
Image for Holiday Historic Inn Tours 2021
  • Dec 10, 2021 Key West
  • Holiday Historic Inn Tours 2021
  • Website
  • During this enchanted Friday evening, the annual Holiday Historic Inn Tours offer an opportunity for locals and visitors alike to explore the beautiful architecture and unique history of some of Key West’s most charming inns while making merry with tasty holiday treats and libation samplings. From 6-8 p.m. each night, revelers can avail themselves of free trolley transportation or use their own bikes, trikes, or vehicles to travel to the various properties, enjoy self-guided tours, and delight in the island’s warm tropical holiday ambience. Participating destinations are the Key West Butterfly and Nature Conservatory, The Gardens Hotel, Island City House Hotel, and Amsterdam’s Curry Mansion Inn.
Image for Fifth Annual Holiday Concert and & Bazaar
  • Dec 10, 2021 Key West Arts & Culture
  • Fifth Annual Holiday Concert and & Bazaar
  • Website
  • Join the Key West Art & Historical Society, from 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum.  The immensely popular celebration is to feature some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show of magical vector projections on the face of the Custom House Museum. Browse hundreds of unique gift options while enjoying the music, food and libations, on and around the island’s architectural crown jewel.  
  • Dec 10, 2021 - Dec 12, 2021 Islamorada Fishing
  • Islamorada Junior Sailfish Tournament
  • Tammy Gurgiolo 305-240-9337 Email
  • The Florida Keys’ oldest sailfish tournament for kids age 16 and under, this event has been held since 1964.
Image for Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
  • Dec 11, 2021 Key West
  • Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
  • 305-292-3302 Website
  • Decorated dinghies, fishing craft and classic tall ships are to light up the Key West Historic Seaport and harbor areas during the 30th annual Schooner Wharf Bar Lighted Boat Parade. Spectators can view the dozens of creatively bedecked vessels from the Schooner Wharf, the parade’s headquarters where the judges stand is located, and from other bars, restaurants and resorts on and around the seaport’s harborwalk and docks. Festivities including steel band performances begin at 6 p.m.
  • Dec 11, 2021 Key Largo
  • Key Largo Holiday Lighted Boat Parade
  • Website
  • Boats of all sizes are to show off festive decorations in a lively procession of vessels on Key Largo’s Blackwater Sound. Presented by the Key Largo Sunset Rotary Club, the parade is to be themed “Nauty-cal & Nice!” in salute to the community’s lighthearted holiday spirit. Spectators can enjoy the fun from viewing spots at Sundowners, Cactus Jack’s, Señor Frijoles, the Key Largo Bay Marriott Beach Resort and Caribbean Club, all around mile markers 103-104.
Image for Kiki's Annual Lighted Boat Parade
  • Dec 11, 2021 The Lower Keys
  • Kiki's Annual Lighted Boat Parade
  • All boats are welcome to enter the Pine Channel Causeway parade including deep-sea cruisers, dinghies, kayaks and canoes. Santa and Mrs. Claus are expected to arrive and hand out candy to the kids. The best recommended viewing is from Kiki's Sandbar, 183 Barry Ave. on Little Torch Key. Parade begins at 7 p.m.
Image for Rams Head presents: The Temptations at Coffee Butler Amphitheater
  • Dec 11, 2021 Key West Arts & Culture
  • Rams Head presents: The Temptations at Coffee Butler Amphitheater
  • Website
  • The Temptations, often referred to as “American Music Royalty,” are world-renowned superstars of entertainment, revered for their phenomenal catalog of music, and prolific career. Otis Williams, the sole surviving original Temptation, Ron Tyson, a lead vocalist with the group for 37 years, Terry Weeks, a lead vocalist for 23 years, and Willie Greene, Jr., base vocalist with the group for four years, are still serenading fans with their soulful voices, lighting up stages with their famous Temptations’ Walk, and bringing joy to audiences of all ages. Doors open 5:30 p.m., show starts 7 p.m.
  • Dec 11, 2021 Islamorada
  • Seventh 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 the 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. 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.
Image for Eighth Annual Florida Keys SPCA Parade of Paws
  • Dec 11, 2021 Key West
  • Eighth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park 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 2021 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.
Image for Pops in the Park with Keys Community Concert Band
  • Dec 11, 2021 Islamorada Arts & Culture
  • Pops in the Park with Keys Community Concert Band
  • Some of the best things in life are free, at least in the Florida Keys. Through the dedication and talent of Florida Keys Community Concert Band members and supporters, music enthusiasts can enjoy an entire Pops in the Park season of themed outdoor concerts free, Saturdays at 4 p.m., at Founder’s Park, mile marker 87 bayside in Islamorada. This month’s theme is “(Not So) White Christmas.”
Image for The Kingston Trio at Key West Theater
  • Dec 12, 2021 Key West Arts & Culture
  • The Kingston Trio at Key West Theater
  • Website
  • All three current members, Mike Marvin, Tim Gorelangton and Don Marovich, have intrinsic links to and experience with the original group: Mike is the adopted son of founding member Nick Reynolds, who was also his musical mentor; Tim, a close friend since boyhood, is one of the few musicians outside the Trio who has recorded with Nick Reynolds; and Don Marovich, who has performed with the Trio and who plays the guitar, banjo and mandolin. Many of their personal memories recall the iconic trio’s performances and journey as folk music made its extraordinary ascent to the pinnacle of popular culture – and the top of the music charts. Doors open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.
Image for Key Colony Beach Lighted Boat Parade
  • Dec 12, 2021 Marathon
  • Key Colony Beach Lighted Boat Parade
  • (305) 743-7214 Website
  • Christmas lights on outriggers and displays on boat decks are part of the beautiful festivities at the Key Colony Beach Boat Parade, set to begin at the 7th Street canal at 6 p.m. Great viewing spots include Sadowski Causeway at mile marker 53.5. Sponsored by the Key Colony Beach Fishing and Boating Club, participants vie for awards in Best Boat Overall, Best Boat under 30 ft, Best Boat over 30 ft.
Image for Sugar Rum Cherry: A Burlesque Nutcracker
  • Dec 15, 2021 - Dec 17, 2021 Key West
  • Sugar Rum Cherry: A Burlesque Nutcracker
  • Website
  • Slip into your stockings and pull out your sugarplums for the outrageously cheeky production of Sugar Rum Cherry: A Burlesque Nutcracker. This naughty but nice two-act holiday reverie showcases a bevy of burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.
Image for Morada Way Arts & Cultural District presents: Third Thursday Art Walk
  • Dec 16, 2021 Key West Arts & Culture
  • Walk on White
  • Website
  • From 5-8 p.m. enjoy a monthly art walk through the White Street Arts District, from Southard St to United St. Walk on White is to continue on the Third Thursday of each month. Participants include galleries (such as Stone Soup, Harrison Gallery, Shade Ceramics and Shutter Photography, and Bone Island Graphics), studios such as Artists at the Armory and Coffee Mill Dance Studios, eateries such as Mayanjali Cafe, and other fine businesses.
Image for Holiday Historic Inn Tours 2021
  • Dec 17, 2021 Key West
  • Holiday Historic Inn Tours 2021
  • Website
  • During an enchanted Friday evening, the annual Holiday Historic Inn Tours offer an opportunity for locals and visitors alike to explore the beautiful architecture and unique history of some of Key West’s most charming inns while making merry with tasty holiday treats and libation samplings. From 6-8 p.m. revelers can avail themselves of free trolley transportation or use their own bikes, trikes, or vehicles to travel to the various properties, enjoy self-guided tours, and delight in the island’s warm tropical holiday ambience. December 17 destinations are The Mermaid & The Alligator, Winslow’s Bungalows, Wicker Guesthouse, and the Weatherstation Inn.
Image for 13th Annual Rudolph Red Nose 5K Run/Walk
  • Dec 18, 2021 Key West
  • 13th Annual Rudolph Red Nose 5K Run/Walk
  • Website
  • Don your festive holiday jammies and join in the fun! Race starts and ends at the 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. Runners and walkers of all ages and abilities are welcome to participate; first 100 registrants receive a free t-shirt. Register online.
Image for Boot Key Harbor Christmas Boat Parade
  • Dec 18, 2021 Marathon
  • Boot Key Harbor Christmas Boat Parade
  • Parade starts at 7 p.m. from the west end of Boot Key Harbor (7 mile bridge side) near Pancho's fuel dock and Burdines Waterfront Tiki, and will slowly wind its way east into the harbor towards Sombrero Marina Dockside. Large boats will lead the parade with small boats and dinghies following.
Image for Key West Artisan Market Market, 'Holiday/Shop Local' Edition
  • Dec 19, 2021 Key West Environmental
  • Key West Artisan Market Market, 'Holiday/Shop Local' Edition
  • Website
  • From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote community causes. All artists who show at the event are carefully selected and live and create in the Keys. This week's Market benefits Keys-crafted local, artists and creators.
Image for Children’s Concert at Key West Botanical Garden
  • Dec 19, 2021 Key West
  • Children’s Concert at Key West Botanical Garden
  • Website
  • The Key West Tropical Forest & Botanical Garden hosts this family friendly children’s concert featuring local classical guitarist, Mateo Jampol, who is to perform songs especially for children. Performance is to start at 1 p.m. until 1:30 pm in the Garden’s Courtyard.   Following the concert a craft project will be available for to create their own holiday ornament.    This “Snowy Sunday” event is to have snow cones, beverages and treats for sale. Cost is $5 per child with a maximum cost of $10 per family. The Garden is located at 5210 College Road on Stock Island. 
Image for 'Wild Observations in Everglades National Park' Outdoor Art Exhibition
  • Dec 29, 2021 - Jun 1, 2022 Key Largo Environmental
  • 'Wild Observations in Everglades National Park' Outdoor Art Exhibition
  • Website
  • Exploring changes in wildlife corridors and combining scientific research with artistic interpretation, the mixed media work by conservation artist Deborah Mitchell is focused on ecological and cultural changes occurring in our wild places. Mitchell's site-specific exhibition starts at the Ernest F. Coe Visitor Center and continues along trails and boardwalks at the Royal Palm Visitor Center, Gumbo Limbo Trail, Long Pine Key, Pineland Trail, Pa-hay-okee Overlook Trail and Mahogany Hammock Trail. The exhibition is on view 24 hours a day.
Image for Fringe Theater presents: Diva! Live From Hell
Image for New Year's Eve Shoe Drop Celebration
  • Dec 31, 2021 Key West
  • New Year's Eve Shoe Drop Celebration
  • Email 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.
Image for New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Dec 31, 2021 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2022 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.
Image for New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Dec 31, 2021 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 2022. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.
Image for New Year’s Eve: Mermaid ‘Drop’ at Stock Island’s Absinthe House
  • Dec 31, 2021 Key West
  • New Year’s Eve: Mermaid ‘Drop’ at Stock Island’s Absinthe House
  • Website
  • Welcome the new year mermaid-style at Absinthe House on Stock Island with the “drop” of a beautiful Florida Keys mermaid “riding” a 14-foot lobster created by local artist Steve King. After taming the lobster, the lovely mermaid will descend 26 feet at midnight to mark the start of 2022. Other attractions for revelers include a DJ, entertainers, absinthe service, a food truck and more. No cover charge; first come, first served. 6404 Front St. on Stock Island.
Image for New Years Eve Party at Faro Blanco Resort
  • Dec 31, 2021 Marathon
  • New Years Eve Party at Faro Blanco Resort
  • Website
  • Toast to the New Year with complimentary champagne and the resort’s famous anchor drop from the iconic Faro Blanco lighthouse at midnight! Dinner at Lighthouse Grill is to be served 5-9 PM. Reservations are highly encouraged. Enjoy DJ music, dancing, photo booth & more, from 9 p.m. to midnight.
Image for New Year's Eve Black & White Party
  • Dec 31, 2021 Marathon
  • New Year's Eve Black & White Party
  • 305-743-4849
  • Havana Jack's Oceanside Restaurant and Bar, in Key Colony Beach, is hosting live entertainment with a band and DJ, complimentary champagne toast at midnight, dinner and cocktail specials. Reserve dinner times by 12/23, last seating at 10 p.m.
  • Dec 31, 2021 Key West
  • New Year's Eve at First Flight Island Restaurant & Brewery
  • Website
  • New Year’s Eve festivities also are planned at the original home of Pan American World Airways featuring the midnight “flight” of a “stewardess” in a replica Pan Am aircraft. Today called First Flight Island Restaurant & Brewery, the structure now located at 301 Whitehead St. was the place where Pan Am’s first tickets were sold in 1927. Other attractions include a full open bar, champagne, chef-manned food stations and live music. Attendees are encouraged to wear 1920s Gatsby-era costumes.
  • Dec 31, 2021 Islamorada
  • New Year’s Eve Celebration at Cheeca Lodge
  • RSVP 305-517-4447
  • Islamorada’s Cheeca Lodge & Spa, mile marker 82 oceanside, also is staging a New Year’s Eve celebration and midnight fireworks display. Revelers can savor a multicourse gourmet dinner at the flagship Atlantic’s Edge restaurant while enjoying panoramic ocean views. Live music is scheduled from 7 p.m. to 1 a.m. For more information, costs and reservations (required) call in advance.
Image for NYE Beach Bash at Casa Marina Key West, a Waldorf Astoria Resort
  • Dec 31, 2021 Key West
  • NYE Beach Bash at Casa Marina Key West, a Waldorf Astoria Resort
  • Reservations 305.304.3818 Website
  • Welcome in the New Year along the water’s edge; end the year by starting the evening with your toes in the sand, under the Key West stars with a luxurious dinner for 2 or up to 6 people, offered between 5 p.m. – 9 p.m.; cost is $150 per person up to 6 people per party (pre-order seafood enhancements and prime rib for $25 pp additional). Music and dancing is also offered from 9:30 p.m. to 12:30 a.m. at the resort's East Beach. Includes, beach party access, complimentary beer & wine, champagne toast and cash bar, $100 per person. Reservations accepted by phone or through Open Table.
Image for Key Lime Wedge 'Drop' at Ocean Key Resort & Spa
  • Dec 31, 2021 Key West
  • Key Lime Wedge 'Drop' at Ocean Key Resort & Spa
  • Website
  • At the Ocean Key Resort & Spa, 0 Duval St. on Key West Harbor, plans call for a huge replica of a Key lime wedge to splash down into a larger-than-life margarita glass on the property’s Sunset Pier at midnight. The elite event features live entertainment by The Beatle Band as well as dancing, a superpremium open bar and butler-passed appetizers. Only 125 tickets are available for the gala.
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