Calendar of Events

December 2021: Florida Keys Events

• Sponsored Event
• Dec 04, 2023 - Aug 31, 2024 Key West
• Christopher Peterson's Eyecons at Birdcage Cabaret
• Website SideBar featuring the Birdcage Cabaret
• 504 Angela St. Key West FL 33040
• Birdcage Cabaret
• View video
• Christopher Peterson is a master of impersonations, both visually and vocally, and his comic timing is impeccable. The show is All Live, no lip-sync, and audiences will be thrilled with his many characterizations. Tickets available now!
• Buy tickets!   

• Sponsored Event
• Jul 17, 2024 - Jul 21, 2024 Key West Arts & Culture
• Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest
• Website Sloppy Joes
• 201 Duval Street Key West FL 33040
• 305-294-5717 E-mail
• Key West’s most iconic and whimsical tribute to one of the greatest literary figures of the 20th century, Ernest Hemingway. This event celebrates Hemingway’s life in Key West and enduring legacy in a way that’s as unique and spirited as the man himself.
• Call now!

• Sponsored Event
• Mar 25, 2024 - Aug 13, 2024 Key Largo
• Fish & Friends Seminar
• Website REEF Environmental Education
• 98300 Overseas Hwy Key Largo FL 33037
• Amy Lee 305-852-0030 E-mail
• REEF Fish & Friends is a free, monthly community social and seminar series. Join us for light snacks and drinks plus an engaging, educational ocean-themed presentation. Seminars are live-streamed and recorded.
• Call now!

• Sponsored Event
• Jun 05, 2024 - Jun 09, 2024 Key West LGBTQ
• Key West Pride
• Website Key West Business Guild
• 808 Duval Street Key West FL 33040
• 305-294-4603 E-mail
• Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. Show us your pride, we will show you our Key West Pride!
• Buy tickets!    Call now!

• Sponsored Event
• Apr 27, 2024 - Apr 27, 2024 Key Largo
• ART & SCIENCE FESTIVAL
• Website REEF Environmental Education
• 98300 Overseas Hwy Key Largo FL 33037
• Amy Lee 305-852-0030 E-mail
• Come see how the arts, science, and conservation are connected in our Florida Keys community and beyond! This family-friendly event includes hands-on activities, interactive displays, take-home art and science kits, and more!
• Call now!

• Sponsored Event
• Jul 20, 2024 - Jul 20, 2024 Key West
• Hemingway 5k Sunset Run & Paddleboard Race
• Website Start of Paddle Board Race Higgs Beach & Start of 5K Southernmost Point
• Higgs Beach & Southernmost Point Key West FL 33040
• Key West Half Marathon E-mail
• View video
• Runners, walkers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 20th during the Hemingway 5k Sunset Run and Paddleboard Race. The athletic challenges are part of Hemingway Days!
• Buy tickets!   

• Sponsored Event
• Apr 19, 2024 - Apr 28, 2024 Key West
• 42nd Annual Conch Republic Independence Celebration
• Website
• E-mail
• Party with Pirates, Admirals, Generals, Ambassadors & Island Royalty. 10 Days of FUN-Filled festivities for all ages! 20+ events at historic and unique venues in Key West. We Seceded… Where Others Failed!

• Sponsored Event
• Apr 17, 2024 - Apr 17, 2024 Key Largo
• LIONFISH JEWELRY WORKSHOP
• Website REEF Environmental Education
• 98300 Overseas Hwy Key Largo FL 33037
• Amy Lee 305-852-0030 E-mail
• REEF Lionfish Jewelry Workshops encourage a consumer market that promotes lionfish removal. Workshop instructors will provide a step-by-step tutorial on how to make lionfish jewelry, while also giving an informative presentation on the invasive species.
• Call now!

• 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.

• Nov 30, 2021 - Dec 4, 2021 Marathon Arts & Culture
• Zonta’s Festival of Trees
• Website
• Zonta Club of Marathon, a women’s service organization, offers a free-admission display of decorated trees free at its 13th Annual Festival of Trees at Marathon Garden Club, 5270 Overseas Highway. View and bid to purchase the decorated trees during open hours: Tue.-Thur. 5-8 p.m., Fri. 3:30-10 p.m., Sat. 10 a.m. to 8 p.m. (from 10 a.m. to 12 p.m., kids can enjoy cookies and photos with Santa and the Grinch). Raffle tickets can be purchased for a chance to win a favorite tree. A drawing for all trees is set for Dec. 2 at 8 p.m.

• 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 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.

• 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.

• 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!

• 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 Largo
• Santa’s Sip & Sail Christmas
• 305-747-2600 E-mail 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.

• 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!

• 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 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 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.

• 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 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.”

• 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.

• 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.

• 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.

• Dec 16, 2021 Islamorada Arts & Culture
• Morada Way Arts & Cultural District presents: Third Thursday Art Walk
• Website
• Morada Way Arts and Cultural District is located in the heart of downtown Islamorada and is comprised of affiliated galleries, Morada Way Clay, Jessica Ann Art, the Rum Brush, Limelight Studio/Gallery, and Creative Partners. Join the monthly Art Walk on the third Thursday of every month from 6-9 p.m. Check out the galleries, shops, restaurants, and brewery located on Morada Way at MM81.6.

• 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.

• 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.

• 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.

• 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. 

• 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.

• 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.

• 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
• 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.

• 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.

• 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.