Take a deep breath and pace yourself. Holiday Happenings in the Keys go full throttle in December and include a jam-packed roster of events that will keep your engine running every night of the week. Here’s a detailed list of what to expect.
ONGOING
Randy Roberts Live!
Key West: Spotlighted on television’s hit series “America’s Got Talent,” Randy Roberts shines in this live, multi-media tribute to some of the world’s most beloved performers. His uncanny impersonations of Cher, Better Midler, and Mae West are spot-on. He’ll have you rolling in the aisles when he performs a titillating striptease as the bawdy Gypsy Rose Lee. Catch this fantastic show at La Te Da’s Crystal Room Cabaret, 1125 Duval St. Tickets and info: 305-296-6706; lateda.com.
Christopher Peterson’s Eyecons
Key West: Christopher Peterson is, without a doubt, one of North America’s foremost female impressionists — visually and vocally. Often compared to the legendary Jim Bailey, master of impersonations, Christopher’s hit show EYECONS, is one of the hottest tickets in town. You’ll be amazed by how he transforms himself into more than a dozen famous women right before your eyes with the help of his “magic closet.” See him in the Crystal Room Cabaret at La Te Da, 1125 Duval St. Tickets and info: 305-296-6706; lateda.com.
DAILY
Mario Sanchez Original Works & Lecture
Key West: Learn about the real “Old Key West” from Mario Sanchez, Florida’s most important folk artist. Nance Frank has curated multiple exhibits of famed Cuban artist Mario Sanchez with catalogs for his exhibition presented by The American Folk-Art Museum, The Museum of the City of New York, and Cuba’s National Museum. Takes place daily at 2 pm at Gallery on Greene, 606 Greene St. Info: 305-304-2323; galleryongreene.com.
The Alan Maltz Collection
Key West: As the official wildlife and fine art photographer for the State of Florida, Alan Maltz’ evocative studies of birds, animals, and landscapes hang in public and private collections worldwide, including the Carter Presidential Library in Atlanta. You can see his vibrant collection of cutting-edge fine art photography and limited edition prints on aluminum, canvas, and glass at his beautiful multi-level gallery and studio at 1210 Duval Street in Key West. Open daily at 10 am. Info: 305-294-0005; alanmaltz.com.
NIGHTLY
Cabaret @ D’Vine Wine Gallery
Key West: This is an excellent hang if you want to kick back with a fine glass of wine and settle in for an intimate cabaret performance by some of Key West’s favorite performers, like classical guitarist Matteo Jampol and pianist Bobby Green. Takes place from 5 – 7 pm at The Gardens Hotel and Cottages, 526 Angela St. Info: 305-294-2661; gardenshotel.com.
Jazz at Tavern N’ Town
Key West: Some of Key West’s top talent, including “Island Chanteuse” Carmen
Rodriquez and Michael Thomas perform nightly from 5 – 7 pm during Key West’s best Happy Hour. Takes place at Marriott Beachside Resort, 3841 N. Roosevelt Blvd. Info: 305-296-8100; tavernntown.com.
The Aquanettes
Key West: Key West’s talented female impressionist troupe transforms into a bevy of beauties using elaborate costuming, makeup, and lip-sync. Renowned for its outrageous and comic numbers, this adult-oriented, interactive show is one of the hottest tickets in town. Takes place M – W at 9 pm and Th – Su at 7 pm and 9 pm. See it at the Aquaplex, 711 Duval St. Info: 305-294-0555; aquakeywest.com.
WEEKLY
Monday & Tuesday
Glow Hours: Rooftop Happy Hour on Hugh’s View
Key West: For a headier Happy Hour, head up to Hugh’s View, where the bar is open, admission is free, and everyone looks great in the golden twilight. The Studios of Key West’s rooftop bar is an ideal spot to catch the sunset with friends and enjoy panoramic vistas from the Gulf of Mexico to the Atlantic. Takes place from 6-8 pm at The Studios of Key West, 533 Eaton St. Info: tskw.org.
Tuesday – Saturday
Movies at the Museum
Islamorada: This ongoing series of fascinating “Shorts” runs throughout the day and includes films about Henry Flagler’s Overseas Railroad, the Keys 1935 Hurricane, and an overview of Islamorada area State Parks. Films begin at 10:30 and continue throughout the day, with the last showing at 4 pm. Takes place at the Florida Keys History & Discovery Center, 82100 Overseas Hwy (on the grounds of the Islander Resort) in Islamorada. Info: 305-922-2237; keysdiscovery.com.
Wednesday – Saturday
Cabaret in The Gardens
Key West: Key West’s Gardens Hotel is one of the most beautiful boutique hotels on the island. Every Wednesday through Saturday from 5 – 7 pm, you can enjoy outstanding live piano music in the Hotel’s intimate Cabaret. Full bar and stellar wines are the coup de gras. Find the Gardens Hotel at 526 Angela St. Info:
305-294-2661; gardenshotel.com.
Every Sunday
Jazz in the Gardens
Key West: Enjoy terrific jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne, and fabulous wines. Jazz in the Gardens from 5:30 – 8 pm at the Gardens Hotel, 526 Angela St. Info: 305-294-2661; gardenshotel.com.
MONTHLY
Third Wednesday
Immerse Yourself!
Islamorada: Islamorada/Virtual: This free monthly presentation takes place both on-site and virtually. Come by the museum or tune in from wherever you are as experts share fascinating information related to maritime history, archeology, diving, and marine science. Coming up: History of the Habakkuk, Search for the Last Missing WASP, and Coral Creations. To learn about each month’s topic, call 305-664-9737
or visit divingmuseum.org. Virtual registration: programs@divingmuseum.org.
First Thursday
Open House At The Studios
Key West: See what’s new, enjoy a drink with a view on the rooftop terrace and
explore three floors of exhibition space. Takes place from 6 – 8 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Third Thursday
Art Walk Key West
Key West: Take an intimate two-hour walking tour of our local galleries and studios in Key West’s Historic Seaport District and get an inside look at the island’s vibrant
culture. Leaves at 9:30 am from the Custom House Museum, 281 Front St. Info:
305-850-8343; keywestartwalk.com.
Third Thursday
Morada Way Arts & Cultural District Art Walk
Islamorada: Fine arts, live music, and “culinary art” are the hallmark of this festive
local happening from 6 – 9 pm along the Morada Way Arts District on Old Hwy, MM 81.5, Oceanside. Info: 305-664-2471; moradawayarts.org.
First Fridays
Upper Duval Street Stroll
Key West: Galleries, boutiques, and cafes open late for exhibitions and receptions on Duval St from Truman to United. Starts at 6pm.
First Fridays
First Fridays On Fleming
Key West: “The Fabulous 500 Block of Fleming Street” showcases boutiques, galleries, and eateries with all kinds of cool events, including jewelry trunk shows, art openings, book signings, tastings, and libations. It takes place from 6 – 9 pm. Info: 305-304-9001; shoplocalkeywest.com.
First Fridays (December 19 – January 13)
A Tuna Christmas
Key West: One of the popular “Tuna” series of plays, this is the perfect show to kick off the holidays. Two of Key West’s most popular and accomplished actors,
Brandon Beach and David Black will star, and between them, will bring dozens of characters and voices to life in the hilarious production. On stage at the Red Barn Theatre, 319 Duval St. Info and tickets: 305-296-9911; redbarntheatre.com.
SPECIAL EVENTS
Now – November 30
Scarecrows in the Garden
Key West: This lighthearted outdoor exhibit showcases scarecrows crafted from natural and recycled materials by local artists, students, and other community members. The scarecrows are all freestanding and no more than six feet tall, so they can withstand outdoor weather conditions for the exhibit’s duration. On display daily from 10 am – 4 pm at the Key West Tropical Forest & Botanical Garden at 5210 College Road, Stock Island (Key West). Info: 305.296.1504; keywest.garden.
Now – November 30
EXHIBITION: Patchwork Perspectives –
Margo Ellis & Gayle Antonides
Key West: Two Florida Keys artists share their quilting-inspired techniques through fiber art and sculpture. Ellis’ works showcases intricate quilting through patterned seams and layered fabrics, while Antonides’ creations explore new ways to embody patchwork through clay, basket weaving, high fire metal wire and bead work. On view from Tu – Sa from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Now – November 30
EXHIBITION: Changing of the Guard –
Ralph De Palma
Key West: For well over a decade, Ralph De Palma has been documenting the
musicians of Key West. The old guard remains, but there are also now second and third generation musicians making their voices heard. DePalma’s explores this legacy through richly textured photography. On view from Tu – Sa from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Now – November 30
EXHIBITION: Rising Waters –
Barb Grad, Ilana Manolson & Lisa Reindork
Key West: Three abstract painters ignite the conversation around climate change and rising sea levels where the natural bumps up against the structural world. On view from Tu – Sa from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Now – December 3
SPECIAL EXHIBITION: Key West Headdress Ball –
Celebrating 40 Years of Creativity
Key West: Combining captivating entertainment and creative competition, the Key West Headdress Ball has been the premier LGBTQ+ event of the island’s annual
10-day Fantasy Fest for the last 40 years! The ball typically features up to 25
contestants showcasing their unique headdresses, some that tower high above their designers. Takes place daily from 9:30 am – 4:30 pm at the Custom House
Museum, 281 Front St. Info: 305-295-6616; kwahs.org.
Now – December 31
History of Diving Museum Presents: Aquanauts
to Astronauts
Islamorada: This limited-time featured exhibit examines the connections between space and underwater exploration. The exhibition features stories and artifacts from NASA, including how they use diving to train future astronauts. Takes place daily from 9 am – 5 pm at The History of Diving Museum, 82990 Overseas Hwy. Info:
305-664-9737; divingmuseum.org.
Now – January 1
SPECIAL EXHIBITION: Key West Shutter Stories
by Elizabeth Devries
Key West: Elizabeth Devries’ has been a craftsman in the Keys for over 36 years and is known as ‘Lizzee the Shutter Lady’. Her artwork/woodwork catalogs Key West’s authentic artifacts, and many of her elements are over a hundred years old. The main vehicle for her brilliant creations are old shutters salvaged from historic homes owned by famous artists and writers. Takes place daily from 9:30 am – 4:30 pm at the
Custom House Museum, 281 Front St. Info: 305-295-6616; kwahs.org.
Now – January 31
SPECIAL EXHIBITION: Living In Harmony
Members Show
Key West/Key Largo: Members of the Florida Keys Council of the Arts showcase works that express the theme “Living in Harmony.” The exhibition includes paintings, drawings, photographs and any related media. Takes on M – F from 9 am – 5 pm at the Gato Building, 1100 Simonton St, Key West; and on M – Sa 9 am – Close
(various times) at the Key Largo Library, Tradewinds Shopping Center, 101485 Overseas Hwy. Info: 305-295-4369; keysarts.com.
November 29 – December 16
Little Shop of Horrors
Key West: Don’t miss the limited three-week run of this deviously delicious Broadway and Hollywood sci-fi smash musical that devours the hearts of theatergoers in New York. Takes place at the Waterfront Playhouse, 407 Wall St. in Mallory Square. Info and tickets 305-294-5015; waterfrontplayhouse.org.
November 30
Distinguished Speaker Series: American Volunteers
in Cuba’s Insurgent Army
Key West: Guest speaker, Paula Michael Taylor explores the role of Cuban-American civilian volunteers who mustered at Tampa and places it within the broader history of the Spanish-American War and the history of Florida and of US-Cuban relations.
Takes place from 6 – 7 pm at the Custom House Museum, 281 Front St. Info: 305-295-6616; kwahs.org.
December 1 – 31
Key West Holiday Fest
Key West: A merry range of celebrations during Key West’s busy holiday season includes the Harbor Walk of Lights, Holiday Historic Inn Tours, a spectacular lighted boat parade, and lots of 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, bazaars, and multiple New Year’s Eve “drops” that spoof New York City’s annual Times Square Ball Drop. For more info, go to keywestholidayfest.com.
December 1
3rd Annual Wesley House Holiday Village & BeLighted Bike Ride
Key West: This fun annual “pre-party” kicks off Key West’s annual BeLighted Bike Ride. A magical Holiday Village features photos with Santa, community booths with games, crafts, and goodies for the kids, food booths, music, local performances and more! Rumor has it that it may even snow! Takes place from 4 – 8 pm with the festively creative “Best Bike Contest” at 7:30pm. The BeLighted Bike Ride follows at 8pm from the Coffee Butler Amphitheater. It all takes place at Truman Waterfront Park, 21 E Quay Rd. Tickets and info: 305-809-5000; wesleyhouse.org.
December 1
Pet Pictures with Santa
Key West: Santa returns to Key West’s Historic Seaport to pose for a photo with your entire brood — whether it includes your dog, cat, rooster, or even the kids. All participating pets and kids receive goodies and treats along with a professional
high-resolution photo by renowned photographer Rob O’Neal. Proceeds benefit the Boys & Girls Club of the Keys. Takes place from 6 – 8 pm at the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St. Info: keywestchristmas.org.
December 2
Key West Hometown Holiday Parade
Key West: The most charming hometown parade you’ll ever see with holiday floats and tons of kids of all ages. Of course, Santa will make a guest appearance! The festivities kick off at 7 pm on Truman Ave at White St. The parade then proceeds down to Duval and ends at Eaton. Info: 305-809-3881; keywesthistoricseaport.com
December 3
Schooner Wharf Bar’s Annual
Tree Trimming Party & Toy Drive
Key West: Bring your nautical ornament for Schooner Wharf Bar’s big beautiful 8′ Christmas Tree or an unwrapped kids’ gift and enjoy a complimentary holiday cocktail — rum eggnog, Swedish glog, or hot applejack. Prizes for most original, most nautical, and most popular with the crowd. Schooner Wharf’s annual Toy Drive benefits a variety of children organizations. FYI: Be sure to visit Santa’s southernmost workshop at Schooner Wharf where local artists and authors sign and sell original works for holiday gift giving. Local musicians will also be on hand, playing holiday tunes, Reggae, and Calypso with the island sound of Steel Drums to round out the festivities. Takes place at 6 pm at the Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3773; schoonerwharf.com.
December 3
Family Day at the Museum
Key West: You and the kids are welcome to join Mrs Kassandra and Mrs Jenni on the porch of the Custom House on a fun exploration of the art and history of the Florida Keys. Takes place from Noon – 1:30 pm at the Custom House Museum, 281 Front St. Info: 305-295-6616; kwahs.org.
December 3
Eaton Street Christmas Stroll
Key West: Keys Choral Arts presents a short program of sacred and secular music for this festive season. Takes place at 3:30pm and stroll follows at 4pm from St Paul’s Episcopal Church, 401 Duval St.
December 3
Mote Marine Laboratory’s Ocean Fest:
A Community Celebration
Key West: Underwater and outdoor enthusiasts, eco-travelers, and families celebrate the marine environment at this fun Upper Keys festival that includes crafts, games, music, food, shopping, and a fabulous silent auction. Takes place from 10 am – 4 pm at Truman Waterfront Park, Info: 941-356-0964; mote.org
December 7
Historic Seaport Sail On S/V Argo Navis:
Naval Blockade of Southern Commerce
Key West: Dry Tortugas National Park Service Ranger, Curtis Hall leads this
illuminating morning seafaring excursion about the American Civil War and how
the slow strangulation of commerce in and out of the Gulf of Mexico impacted the Confederacy. The two-hour sailing tour includes Bloody Marys, Mimosas,
non-alcoholic beverages, and a light breakfast. Shoves off at 9 am on the luxury catamaran, S/V Argo Navis docked at 0 Margaret St in Key West’s Historic Harbor. Info and tickets: 305-295-6616; kwahs.org.
December 7 – 29
Winter Member’s Show
Key West: This annual kickoff event for The Studios of Key West’s upcoming season includes the launch of their upcoming season catalog, along with a special exhibition of over 100 artworks on display throughout all four gallery spaces. This season, artists are prompted to reexamine, but then look forward. This perpetual crowd favorite opens on Th, Nov 7 from 6 – 8 pm and continues throughout the month on Tu – Sa from
10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 8
7th Annual Holiday Concert & Bazaar
Key West: One of Key West’s most popular holiday celebrations boasts some of the island’s finest artisans, musicians, and choirs; lots of great food, eggnog, and other festive libations; and a holiday light show which will be projected on the face of the Custom House. You’ll also be able to shop for unique gifts, including handcrafted jewelry, clothing, textiles, home decor, and more. FYI: Santa will be on hand for last-minute requests and “selfie” photos. Takes place from 5 – 9 pm on the historic porch of the Custom House Museum, 281 Front St., and spills out onto Front St. Info and tickets: 305-295-6616; kwahs.org.
December 8
Holiday Historic Inn Tours
Key West: Enjoy two enchanted self-guided tours of five different decorated inns and a sampling of holiday treats and cheer at each property. The properties on the tour include the Wicker Guest House, Mermaid & Alligator and the Marquesa Hotel.
Takes place from 6 – 8 pm. FYI: Tickets can ONLY be picked up the night of the tour at the first property on the tour after 5:30pm (*Key West Butterfly & Nature Conservatory, 1316 Duval St). Info: 305-296-4959.
December 9
33rd Annual Schooner Wharf Bar Lighted Boat Parade
Key West: A magical nautical display of lights and creativity is the hallmark of this favorite holiday maritime event in the Key West’s Historic Seaport. The boats come very close to the docks of the Schooner Wharf Bar, where the Judge’s Stand is located, which makes it a great vantage point. Festivities kick off at 6 pm. The parade starts at 8 pm, followed by a big Awards Party. Info:305-292-3773; schoonerwharf.com.
December 9
Key Largo Lighted Boat Parade
Key Largo: The waters of Blackwater Sound in Key Largo shimmer as decorated boats put on “A Cartoon Christmas” along the shoreline to celebrate the holiday season. Kicks off at 7:30 pm. The top spots for viewing are between MM 103 – 104. Info: 305-451-4502; keylargoboatparade.com.
December 9
10th Annual Parade of Paws & Holiday Bazaar
Key West: Join the Florida Keys SPCA for a fun-filled day of live music, a Holiday Bazaar, and the crowning of the 2022 Royal Court. Enjoy pictures with Santa, sloppy kisses at the “Smooch-A-Pooch” Booth, fun raffles, and a dog parade where all pups are welcome to strut their stuff. Costumes encouraged! All proceeds benefit the homeless animals of the Middle and Lower Keys. Registration takes place at 9 am; parade begins at 10 am at Higgs Beach, 100 Atlantic St at the end of White St.
December 9
Annual Winter Wonderland At Crane Point
Marathon: Snow is in the forecast for this fun annual event that features reindeer ponies, a chocolate fountain, hot chocolate, Santa Stew, a visit from Santa Claus, and much more. Takes place from 4:30 – 7:30 pm at Crane Point Hammock, 5550 Overseas Hwy. Info: 305-743-9100; cranepoint.net.
December 10
Eaton Street Holiday Stroll
Key West: Neighborhood venues on Eaton St host Christmas-themed events
backdropped by caroling as you walk from place to place. At The Studios of Key West, you can sip on Christmas cocktails on the rooftop of Hugh’s View and do some holiday shopping at the Member’s Show which is on display throughout all four gallery spaces. Takes place from at 4 -10 pm. Info: 305-296-0458; tskw.org.
December 12
Ann Hampton Callaway
Key West: Voted by Broadwayworld.com as “Performer of the Year” and two years in a row as “Best Jazz Vocalist,” Ann Hampton Callaway is one of America’s most gifted and prolific artists. A leading champion of the great American Songbook, she’s made her mark as a singer, pianist, composer, lyricist, arranger, actress, educator, TV host and producer. Ann is a born entertainer. Her unique singing style blends jazz and traditional pop, making her a mainstay in concert halls, theaters, and jazz clubs, as well as in the recording studio, on television, and in film. Showtime: 7 pm at The Studios of Key West at 533 Eaton St. Info: 305-296-0458; tskw.org.
December 12
Hodie, Hodie! Christmas Convert
Key West: Key Choral Arts, in collaboration with the Southernmost Chamber Music, performs together in this heartwarming holiday concert. Takes place at 7pm at St Pauls’ Episcopal Church, 401 Duval St. Tickets may be purchased at the door or online at keyschoralarts.org.
December 12 – 16
The Best Christmas Pageant Ever
Key West: Mischief and mayhem ensue at the annual Christmas pageant when the town’s young hoodlums enact a coup and unexpectedly teach the town the true meaning of Christmas. Produced by Art House Fringe in concert with Bravo Theatre. Showtimes: 7 pm on December 12 – 16 and 2 pm on December 7. Takes place at the Armory, 600 White Street. Showtime: 7pm. Info and tickets: 305-7731-0581; fringetheater.org.
December 14
Happy Hour with the Historian:
The Building the American Riviera
Key West: Historian Cori Convertito explores the history of numerous hotels built by American Industrialist, Henry Flagler during the Gilded Age and how he impacted the transformation of Florida’s East Coast into an elite destination. This fun historical
lecture which includes a complimentary drink (beer, house wine, or soft drink) takes place from 5 – 6 pm at the Custom House Museum, 281 Front St. Info: 305-295-6616; kwahs.org.
December 15 – February 11
SPECIAL EXHIBITION:
Our Working Waterfront
Key West: Integrating never before exhibited historic photos and a range of artifacts, this intriguing exhibit explores the diversity of work along the Key West waterfront and reveals the complex interconnections of waterfront work. The diverse forms of work range from shipbuilding, wrecking, sponging, turtling and shrimping. Takes place daily from 9:30 am – 4:30 pm at the Custom House Museum, 281 Front St. Info: 305-295-6616; kwahs.org.
December 16 – 17
SPECIAL EXHIBITION:
Krystiano DaCosta
Key West: Krystiano DaCosta is renowned for his revolutionary interpretations of
industrial impressionism. His “Recycled Masterpieces” often harness the beauty of
natural objects like crushed abalone shells opals, sea glass, and crushed walnuts
resulting in imaginative works that pop off incongruous canvases that can range from plastic to galvanized steel. See his incredible works at SeasSister Island Gallery, 303
Duval St. Info 954-232-7248; seasisterislandgallery.com.
December 17
Holiday Classic Car Show
Key West: See classic cars from every era decked out for the holidays and vote for your favorites. Takes place from 11am – 3 pm at Conch Republic Seafood Co, 613 Greene St on the Harbor Walk of Lights. Info: keywestchristmas.org.
December 17
Kiki’s Holiday Huddle & Lighted Boat Parade
Little Torch Key: Get a ringside seat for the Lower Keys Holiday Boat parade back dropped with great live music by the CIRCA 22 Duo & Marshall Morlock Band. Holiday Paint & Sip at 1 pm; Gingerbread Contest and Pet Pictures with Santa at 2 pm; Toy for Tots Drive and Lighted Boat Parade at 7pm. It all happens at Kiki’s Sandbar,183 Barry Ave (MM28.5 Gulfside). Info: 305-872-4500; KikisSandbar.com.
December 17
Menorah Lighting
Key West: Join Rabbis Shimon Dudai and Jacob Zucker is this spiritual Lighting of the Menorah. Takes place at 5pm in Bayview Park, 1320 Truman Ave.
December 20
Immerse Yourself!
The Search of the Last Missing Wasp
Islamorada: Host Mark “Sharky” Alexander takes you on a search for the last
missing Women Air Force Service Pilots (WASPS). Formed in 1943, this organization allowed women to become trained pilots, as well as test and ferry aircraft. The live presentation takes place at 7 pm at The History of Diving Museum, 82990 Overseas Hwy. Info: 305-664-9737; divingmuseum.org.
December 21
Electric Blue Yonder
Key West: This traveling troupe of intrepid space folk explorers examines the
mysteries of the universe and report their findings through song. The band draws inspiration from the psychedelic folk, surf, and cosmic country rock of the 60s and the Space Age prog/art rock explorations of David Bowie and Pink Floyd. The result is a genre-bending mix that captures a nostalgic familiarity while simultaneously transporting you into uncharted territory. Showtime: 7 pm at The Studios of Key West at 533 Eaton St. Info: 305-296-0458; tskw.org.
December 25
Christmas Day Brunch Sail
Key West: Dreaming of a crystal clear, blue Christmas? Then, spend Christmas morning aboard the Schooner America 2.0 for a brunch sail that you’ll never forget! This two-hour sail includes a fully catered brunch starting with complimentary Mimosas and Bloody Marys or champagne. Departs from Key West’s Historic Seaport. Info & tickets: 305-292-7245; sail-keywest.com.
December 25
Holiday Jazz in the Gardens
Key West: Enjoy this exceptional jazz performance amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne, and fabulous wines. Jazz in the Gardens from 5:30 – 8 pm at the Gardens Hotel, 526 Angela St. Info: 305-294-2661; gardenshotel.com.
December 27
Holiday Historic Inn Tours
Key West: This enchanted self-guided tour takes you to five different decorated inns for a sampling of holiday treats and cheer at each property. Takes place from 6 – 8 pm. Info and tickets: 305-296-4959.
December 27 – 31
An Evening with Lillian Baxter
Key West: Mischief and mayhem ensue at the annual Christmas pageant when the town’s young hoodlums enact a coup and unexpectedly teach the town the true meaning of Christmas. Produced by Art House Fringe. Showtime: 7pm at the Little Room Jazz Club, 821 Duval St. Info and tickets: 305-731-0581; fringetheater.org.
December 29 – 30
64th Annual Key West Home Tours
Key West: Festively dressed Key West homes and gardens take center stage during this much anticipated annual event which showcases exquisite restorations, creative renovations, and delightful interiors and exteriors. The self-guided tours take place from 1 – 4 pm, benefiting the Old Island Restoration Foundation. Tickets and schedules are available online at OIRF.org. More info: 305-294-9501.
December 31
Key West Dachshund Walk
Key West: Frost – free Key West becomes a “wiener wonderland” when up to 200 dachshunds and their owners take a New Year’s Eve stroll through the island’s picturesque downtown. The “Weiner Walk” begins at noon at the corner of Whitehead and Fleming Streets continue through the 400 block of Fleming St, 500 block of legendary Duval St, and one-block length of Appelrouth Lane. Info: keywestdachshundwalk@gmail.com.
December 31
New Year’s Eve Fireworks on Blackwater Sound
Key Largo: The back bay is the setting for the annual midnight New Year’s Eve fireworks extravaganza hosted by Sundowners, MM 104 bayside, with live music to accompany the festivities. Info: 305-664-4651.
December 31
New Year’s Eve Celebrations in Key West
Key West: Ring in 2023 with a “Conch Shell Drop” at Sloppy Joe’s Bar, 201 Duval St; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St Pub/New Orleans House complex, 724 Duval St; a big New Year’s Eve Bash at the Schooner Wharf Bar, 202 William St; and a massive replica of a Key lime wedge splashing down into a larger-than-life margarita glass at Ocean Key Resort & Spa, 0 Duval St.
December 31
New Year’s Eve at Cheeca Lodge & Spa
Islamorada: This ultra-chic beachside resort hosts a midnight fireworks display over the Atlantic Ocean with live music. Takes place at Cheeca Lodge & Spa at MM 82 oceanside. Info: 305-664-4651; cheeca.com.
January 6 – 7
11th Annual Florida Keys Celtic Festival
Marathon: Break out your kilts and dancing shoes because this festive Gaelic celebration will have you kicking up your heels. Enjoy top acts by international Celtic bands, vendors, Celtic food and beer, highland athletics, and a children’s glen. The festival begins on Sa, January 6, from 10 am – 7 pm and continues on Su, January 7 from 11 am – 5 pm at Marathon Community Park, MM 49. Tickets and info: 305-743-6412; floridakeyscelticfestival.com.
