Please confirm details with event organizers or venues in case of changes or cancellations.
The Holiday Season is upon us and there are just so many festive happenings taking place in the Florida Keys & Key West. Here’s what’s happening…
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, Key West. Tickets and info: 305-296-6706; lateda.com.
ONGOING
Christopher Peterson’s Eyecons
Key West: Christopher Peterson is, without a doubt, one of North America’s foremost female impressionists — both visually and vocally. Often compared to the legendary Jim Bailey, master of impersonations, his 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, Key West. Tickets and info: 305-296-6706; lateda.com.
Daily
Mini Golf
Ramrod Key: Come play the southernmost and only mini-golf course in the Florida Keys. This kid-friendly 18-hole course is a perfect family adventure. It boasts a fun caveman theme with two giant waterfalls and four fountains. And get this: If you’re 21+, you and your friends can have a cocktail or glass of wine while you putter around. Happens daily from 10 am – 10 pm at Boondocks Grille & Draft House at 27205 Overseas Hwy (MM 27.5) on Ramrod Key. Be sure to check out their special party packages and tournaments. Info: 305-872-4094; boondocksus.com.
Daily
Green Pineapple Key West Yoga
Key West: Whether you’re a beginner or seasoned practitioner, this Hatha-based yoga studio offers daily classes designed for every skill level. Based on the foundations of traditional yoga practices, categories include Vinyasa, Yin, Restorative, Gentle, Breath and Mindful Movement, Pilates, and Meditation. The Green Pineapple Yoga Shala also offers workshops to feed your body, mind, and soul. Private or Group Classes are also available. Come early or stay after class for a fresh juice, a cup of tea, or a super healthy Zen-Bite in the plant-based Wellness Cafe. Find it nestled inside The Green Pineapple Wellness Center, 1130 Duval Street, Key West. Info: 305-509-7378; greenpineapplewellness.com.
Nightly
Key West Sunset Celebration
Key West: Each evening, about two hours before sunset, flocks of people gather at Key West’s Mallory Square and on the pier behind the Opal Resort & Marina on Front Street to watch the sun slowly sink into the Gulf of Mexico and to revel in the colorful street performers, local artists, psychics and food vendors who have made Key West’s Sunset Celebration a world-famous, multicultural happening.
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. Her daily presentation about Sanchez’s life and work is absolutely fascinating. Takes place daily at 2 pm at Gallery on Greene, 606 Greene St. Info: 305-304-2323; galleryongreene.com.
Daily
Historic Marker Tours
Key West: Discover a little piece of paradise during this self-guided tour which
explores Key West’s 120 Historic Markers in the Largest Historic District of Frame
Buildings in the United States. See photos and listen to the history and stories these buildings tell. Info: 305-295-6616; kwahs.org.
Daily
The Alan Maltz Collection
Key West: As the official wildlife and fine art photographer for The State of Florida, Alan Maltz’s 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. It’s a journey you won’t soon forget! Open daily at 10 am. Info: 305-294-0005; alanmaltz.com.
Nightly
Aquaplex
Key West: With five venues all under one roof, Key West’s state-of-the-art
entertainment complex is where it’s all happening. SideBar, a world-class dance club with high-tech lighting and an industrial vibe, connects each venue, including a lovely outdoor garden bar called the Back Bar. Poké in the Rear is a fun backyard Hawaiian eatery open until 11pm. The 22&CO bar is known for its tutu-wearing clientele, neon flamingo décor, and unique glittering cocktails. There’s also the original Aqua Nightclub, renowned for its outrageous drag shows. What more could you ask for? Find it all at 711 Duval St. Info: 305-294-0555; aquakeywest.com.
Nightly
The Aquanettes
Key West: Key West’s own talented female impressionist troupe transforms themselves into a bevy of beauties using elaborate costuming, makeup, and lip-sync. Renowned for their outrageous and comic numbers, this adult-oriented, interactive show is one of the hottest tickets in town. Takes place Mon – Weds at 9 pm and on Thursday through Sunday at 7 pm and 9 pm. See it at the Aquaplex, 711 Duval St. Info: 305-294-0555; aquakeywest.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.
Nightly
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 – 7pm during Key West’s best Happy Hour. Takes place at Marriott Beachside Resort, 3841 N. Roosevelt Blvd. Info: 305-296-8100; tavernntown.com.
WEEKLY: 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.
WEEKLY: 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.
WEEKLY: Every Thursday
Key West Waterfront Market
Key West: Every week, you’ll find traditional farmer’s market fare, including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh bread, hot sauces, and more. There are food stands and food trucks. Artists, crafters, flea market goods, jewelry, clothing/t-shirts, local organizations, cigars, and CBD. An eclectic group of small businesses who collectively offer one-stop shopping at our weekly pop-up island bazaar. Takes place from 2 pm – 7 pm at the Truman Waterfront (end of Southard St). Bring your own bags. Info: 305-731-3385; keysartisanmarket.com.
WEEKLY: Every Thursday
Glow Hours on Hugh’s View
Key West: This weekly rooftop Happy Hour comes with the best views in town. Hugh’s View sits on the roof of The Studios of Key West. It boasts panoramic vistas across the rooftops of Old Town, from the Gulf of Mexico to the Atlantic. Takes place weekly from 6 – 8 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; TSKW.org.
WEEKLY: Every Saturday
Open-Air Market
Ramrod Key: Forget about driving miles to find local Florida Keys art, handmade jewelry, one-of-a-kind creations, fresh organic produce, greens, and flowers! You’ll find all that and more right at Boondocks. Takes place from 9 am – 2 pm in the parking lot of Boondocks Plaza at MM 27.5 on Ramrod Key. Info: 305-872-4094;
boondocksus.com.
WEEKLY: Every Saturday & Sunday
Big Pine Flea Market
Big Pine Key: Discover all kinds of great finds at unbeatable prices at this long-time Lower Keys Flea Market that showcases an eclectic mix of both used and new merchandise, as well as locally made soaps, tools and tarps, fishing supplies, watches and jewelry, fresh seafood and produce, homemade ice cream, weekend Fish Fry, and inflatable park. Open from 8 am – 2 pm every Sat and Sun. Free admission and parking. Find it at 30250 Overseas Hwy, oceanside, on Big Pine Key. Info: 305-872-4103; bigpinefleamarket.com.
WEEKLY: Every Sunday
Jazz in The Gardens
Key West: Enjoy some hot jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne, and fabulous wines. Takes place from 5:30 – 8 pm at the Gardens Hotel, 526 Angel St, Key West. Info: 305-294-2661; gardenshotel.com.
MONTHLY: Third Wednesday
Immerse Yourself!
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. To find out about each month’s topic, which may include presentations like “Searching for Treasures,” “Great Whites of Guadalupe,” and “Sponge Research,” call 305-664-9737 or visit divingmuseum.org. Virtual registration:
programs@divingmuseum.org.
MONTHLY: First Thursday
Art & Shopping Walk
Key West: Grab a pair of comfortable shoes and stroll this collection of great
galleries, unique boutiques, and design studios, spanning from The Studios of Key West at Eaton and Simonton to Guild Hall Gallery on Duval; as well as all the
galleries and boutiques in the neighboring 500 Block of Fleming. Takes place from
6 – 9 pm. Info: tskw.org.
MONTHLY: Third Thursday
Walk On White Gallery Walk
Key West: One of Key West’s original art walks includes exhibitions and receptions at galleries and shops along White St, from Southward to United. Takes place from 5 – 9 pm. Info: walkonwhitekeywest.com.
MONTHLY: 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 in the Morada Way Arts & Cultural District. Takes place from
6 – 9 pm on Old Hwy, MM 81.5, Oceanside. Info: 305-664-2471;
moradawayarts.org.
MONTHLY: First Friday
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 6 pm.
MONTHLY: First Friday
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.
MONTHLY: Third Wednesday
Immerse Yourself!
Islamorada/Virtual: This free monthly presentation takes place both on-site and
virtually. Come by the History of Diving Museum or tune in from wherever you are. Experts cover topics related to maritime history, archeology, diving, and marine science. Coming up: Deep Water Restoration, Floating Battleship Museums, and Mangrove biology and habitats. For more info or to find out about each month’s presentation, call 305-664-9737; or visit divingmuseum.org.
MONTHLY: 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.
MONTHLY: First Friday
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.
MONTHLY: First Saturday
Market on the Green
Key West: Shop some amazing local arts at this fun artisan market. Takes place from 10 am – 2 pm at the Sunset Green Event Lawn located between the Gates Key West Hotel and 24 North Hotel, 3852 N Roosevelt Blvd. Info: 305-400-4117;
thekeyscollection.com.
MONTHLY: Second Saturday
I Love Stock Island Art Stroll
Key West/Stock Island: Over 10 local artists at several different locations showcase sculptures, woodworking, mosaics, screen printing, soaps, fabric art, and more. Takes place from 11am – 5 pm at the Stock Island Arts District. Info: 305-731-5780;
ILoveStockIsland.org.
MONTHLY: Third Saturday
Native Plant Sale
Key West: Peruse over 2,000 native, rare, and endangered plants from the Keys, Cuba, and the Western Caribbean at this terrific monthly plant sale. Takes place from 9 am-Noon at the Key West Tropical Forest and Botanical Garden, 5210
College Rd. Info: 305-296-1504; keywest.garden.
MONTHLY: Select Sundays
Key West Artisan Market
Key West: Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, a wide variety of food and libations, and local musicians and authors. Takes place from 10 am – 2 pm on Nov 6. & 20; Dec. 14 & 18; Jan 1, 15 & 29 at Sonny McCoy Indigenous Park, 1801 White St. Info: 305-731-3385;
facebook.com/KeyWestArtisanMarket.
November 16 – 26
The Last Five Years
Key West: Two aspiring creatives fall in and out of love in this unconventional and award-winning musical. An emotional tour de force from end to beginning and beginning to end. Produced by Fringe at the Armory, 600 White Street. Showtime: 7pm. Tickets: fringetheater.org.
Now – November 23
Eco Echos, Marianne Vogel
Key West: Vogel’s fiber art serves as a reflection of and response to her natural world, finding deeper meaning in basic shapes through mindful, slow stitching and beading. Each piece celebrates the beautifully unusual arrangements designed by nature. On exhibit, Tu – Sat from 10am – 4pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
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 6′ tall, so they can withstand outdoor weather conditions for the duration of the exhibit. 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 – December 8
EXHIBITION: Complex Curiosity
Key West: After a five year hiatus from the Key West art scene, Michel Delgado with a new series of bold and thought provoking mixed media paintings. COMPLEX
CURIOSITY explores Delgado’s lifelong journey as artist and human delving into the complexities of failure, self doubt and insecurity as well as those elements of the human spirit that Michel has, in his own words, “been able to squeeze out, aligning body and present, all leading to a sense of balance and power “, adding“it has taken a long time to get to this place; emotionally, spiritually and artistically.” On exhibit from Noon – 5 pm Tue – Sun and Mon by appointment at Key West’s acclaimed Jag Gallery, 1075 Duval St. Info: 305-407-6202; jaggallerykeywest.com.
Now – December
Sponge Hunters
Islamorada: Learn about the fascinating maritime industry of history of sponge
hunting with Key West hook boats, Tarpon Springs hard-hat divers, and Bahamian free divers. You’ll also learn about the sponge restoration of contemporary conservationists in the Florida Keys. Takes place daily from 10 am – 5 pm at The History of Diving Museum, 82990 Overseas Hwy, Islamorada. Info: 305-664-9737;
divingmuseum.org.
Now – December 23
Robert the Doll
Key West: Author and photographer Mathew Leifheit takes the haunting story of “Robert the Doll” to a whole new level: that of an older man carrying around an
effigy of his younger self dressed in a little sailor suit—and reinterprets it as a tongue-in-cheek queer story. Leifheit’s photographs meld history with autobiography and commentary on queer culture. On exhibit, Tu – Sat from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Now – December 11
Key West 200th
Key West: This historic curation commemorates Key West’s 200 years of history and explores Key West’s people, culture, and community. The exhibit begins with settlers and government officials arriving on our remote island in 1822. It traces its historical milestones, including the Civil War, Great Depression, and World War II. Open daily from 9:30 am – 4:30 pm at the Custom House Museum, 281 Front Street. Info: 305-295-6616; kwahs.org.
Now – December 11
Tennessee Williams Exhibit
Key West: In celebration of the island’s ongoing bicentennial celebration, the
Tennessee Williams Museum’s educational and historic exhibit now showcases
information about Williams’ writing, filming, and premiering of “The Rose Tattoo” in Key West during the 1950s. Discover how Williams’ many cultural and philanthropic contributions made during his thirty-four-year residency helped place Key West on the cultural and literary map. Located at 513 Truman Avenue, the Tennessee Williams Museum is open for self-guided tours from Thurs – Sun from 9:30 am – 4:30 pm. Info: 305-204-4527; kwahs.org.
November 3 – 26
Everything I Ever Needed to Now I Had to Learn
Over in My Own Language, Katharine Doughty
Key West: Doughty’s series of alphabet self-portraits began with an “A” in 1999 and finished with a “Z” in 2017. The complete series explores personal mythology, archetypes, and the differences between writing and visual imagery. On exhibit, Tu – Sat from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
November 12
Historic Seaport Sail On Argo Navis
Key West: Brad Bertelli leads a historically illuminating seafaring excursion that
explores Captain Benjamin Baker’s foray into pineapple farming during the late 1800s. Enjoy Bloody Marys, mimosas, or non-alcoholic beverages along with a
variety of pastries as you also learn about why the construction of Key West’s Civil War-era Fort Zachary Taylor was so important, as well as about the building’s
relevance through today. The two-hour tour shoves at 9 am at Argo Navis Sailing Charters, 0 Margaret St in Key West’s Historic Harbor. Presented by the Key West Art & Historical Society. Info: 305-295-6616. Tickets: kwahs.org.
November 16
How to Talk About Your Book at a Cocktail Party
with Katrin Schumann
Key West: Bestselling author Katrin Schumann helps writers cut through the noise with tools to succinctly explain their work. More fun than an elevator pitch and certainly more festive, the cocktail party one-liner helps authors grab the attention of would-be readers. Takes place from 1 – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
November 16
6th Annual Smuggler’s Night at the Museum
Islamorada: This signature fundraiser for the Keys History & Discovery Museum is one of the Upper Keys’ most fun annual events. The evening features specialty cocktails, fine wine, an elegant dinner, live music, dancing, and live and online auctions. Takes place from 6 – 10 pm at the Islander Resort, 82100 Overseas Hwy (MM 82 Oceanside). Info and tickets: 305-922-2237; keysdiscovery.com.
November 16
Immerse Yourself:
Deep Water Horizon Open Ocean Restoration
Islamorada: NOAA Marine Habitat Resource Specialist, Kristopher Benson, discusses the restoration of mesophotic and deep benthic communities impacted by the Deepwater Horizon oil spill. Takes place at 7 pm at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Info: 305-664-9737; divingmuseum.org.
November 16 – 20
Key West Film Festival
Key West: This annual event showcases films that exhibit excellence in storytelling and features screenings, visiting filmmakers, workshops, and special events at landmark venues throughout Key West. The festival also looks to support the next generation of local student filmmakers with scholarships and other key awards. Info: kwfilmfest.com.
November 18
Sister Season Fashion Show & Auction
Key West: Local designers show off their original creations and auction them off to the highest bidder. The Grand prize is awarded to the designer who receives the highest bid. Tickets include hors d’oeuvres and an open bar. Doors open at 6:30 pm, and the show begins at 8 pm. Takes place at the Key West Theater, 512 Eaton St. Info: 304-304-9828; sisterseason.com.
November 16 – 20
Key West Film Festival
Key West: Passion meets paradise during this annual event, showcasing films that exhibit storytelling excellence. Screenings and special events take place at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West, and Key West Theater. Info: keywestff.com.
November 19
Preserving Paradise
Key West: George Born, author of “Preserving Paradise,” deciphers the intriguing history of Key West through the island’s unique architecture and building history. Born explains in detail just why Key West is so architecturally unique and why the city’s buildings, streets, and neighborhoods are a repository of history that can be discovered by experts and weekend visitors alike. Takes place at 10 am at The Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
November 23
Lighting of the Bight: Key West Harbor Walk of Lights
Key West: The Key West Harbor lights up the waterfront with a 16′ fresh pine
Nautical Christmas Tree, a Fishing Buoy Tree, and the original 20′ Key West Lobster Trap Tree. This “Harbor Walk of Lights” honors the maritime history of the Key West waterfront and stays lit nightly through New Year’s Eve. Stretches along the seawall past Greene, William, and Margaret Streets to the Key West Ferry Terminal. The opening night event starts with live music at 5 pm and the lighting at 6 pm. Info:
keywestchristmas.org.
November 26
Holiday Artisan Market
Key West: Enjoy cookies and coffee as you stroll through a friendly, festive indoor market where over 20 artisans showcase unique and locally produced gifts: jewelry, textiles, home accessories, and quality crafts. Takes place from 9 am – 1 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
November 26
Big Pine & The Lower Keys Island Art Festival
Big Pine: This fun annual holiday event always draws a big crowd and includes live music, exhibits, arts and crafts, food vendors, and more. Takes place from 9 am – 3 pm at the Lower Keys Chamber of Commerce, MM 31, oceanside. Info: 305-872-2411; lowerkeyschamber.com.
November 28
City of Key West Tree Lighting Ceremony
Key West: Kick off the holiday season with this fun annual tree lighting that also
includes festive music, food and activities. Takes place at 4:30 pm – p pm at Bayview Park, 1320 Truman Ave. Info: keywestchristmas.org.
November 29
ReMARCable Table Top Christmas Tree Auction
Key West: Bid on beautiful Fraser Fir trees, between 3½’ to 4½’ tall, which are
elaborately decorated by local artists, businesses, and private residents. Takes place from 7 pm – 10 pm at the Opal Resort and Marina, with an early preview starting at 6:30 pm. Benefits the Monroe Association for ReMARCable Citizens (MARC). To sponsor a tree and decorate yourself ($100) or to sponsor a tree and have MARC find a decorator for you ($250). Info: 305-294-9526; marchouse.org.
November 29 – 30
Southern Skies Stargazing with Larry Halstead
Key West: Artist and astronomy buff Larry Halstead takes you to the cosmos and back. On night one, you’ll meet in the theater for a presentation on what to expect and how to comprehend where these celestial objects fit in terms of scale, distance, and location in the night sky. The next night, you will use a powerful telescope on the roof for direct observation and stargazing. Takes place at 7 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 1 – 4
COAST is CLEAR Music & Arts Festival
Key West: What began as a backyard gathering has grown organically and continues to take place annually on the first weekend of December to celebrate the official ending of the Atlantic Hurricane Season — when the “coast is clear.” The festival’s main event is an all-day concert on Saturday. Takes place, rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd. Info & tickets: coastisclearfest.com.
December 1
9th Annual POSH (Paws Often Steal Hearts) Fundraiser
Key West: Dance to Miami’s acclaimed nine-piece Latin band, Suenalo, at this
formal attire event that benefits our local SPCA. You are encouraged to don your own ‘Fascinator Hat’ headpiece, which is a large head decoration on a band or clip with elaborate trimmings and decoration. Takes place from 6 – 9 pm at the Audubon House & Tropical Garden, 205 Whitehead St. Tickets & info: 305-304-1232;
fkspca.org.
December 1 – 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 perpetual crowd favorite is on exhibit Tu – Sat from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.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. Info: keywestholidayfest.com
December 2
BeLighted Bike Ride & Holiday Village
Key West: Festively decorated bikes parade through Key West during the Wesley House Family Services fun annual holiday event. The festivities kick off with a
Holiday Village pre-party from 4 – 8 pm at the Coffee Butler Amphitheater in Truman Waterfront Park. The Holiday Village will feature community booths, Santa, food, music, and the Best Bike Contest! The BeLighted Bike ride leaves from the Holiday Village at 8 pm and parades down Whitehead and Duval Streets. Info: 305-809-5000; wesleyhouse.org.
December 2
Annual Florida Keys Holiday Festival
Islamorada: A 35′ holiday tree blows magical snow at this spirited night of holiday fun, which includes a snow mountain, festive parade, community tree lighting, caroling, holiday gift bazaar, delicious food, live music, and a silent auction of masterpiece ornaments created by local artists. Takes place from 4-10 pm at Founders Park, MM 87, Bayside. Info: 305-664-4503; islamoradachamber.com.
December 2
Annual Holiday Tree Lighting
Key Colony Beach: Wear your ugliest Christmas sweater and high tail it over
to the annual lighting of Key Colony’s giant Christmas Tree “Under the Tiki.” Make
a donation to “Presents in Paradise” and add an ornament to the tree. There is lots of egg nog and hot chocolate to get you into the spirit, live music, a 50/50 raffle, food, drinks, and a visit from Santa himself. Kicks off at 5 pm with a tree lighting at 7 pm at Havana Jack’s Oceanside, 401 E Ocean Dr, Key Colony Beach. Info: 305-743-4849; HavanaJacksOceanside.com.
December 2
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 at the 16′ Nautical Christmas Tree on William St on the Harbor Walk of Lights. Info: keywestchristmas.org.
December 3
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 4
Eaton Street Holiday Stroll
Key West: During this holiday tradition on Eaton Street, neighborhood venues host short Christmas-themed performances. 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, displayed throughout all four gallery spaces. Kicks off at 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 4
Schooner Wharf Bar’s Annual
Tree Trimming Party & Toys For Tots Drive
Key West: Bring your nautical ornament for Schooner Wharf Bar’s big beautiful 8′ Christmas Tree 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. Takes place at 6 pm at the Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3773; schoonerwharf.com.
–December 4
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 4
Pet Pictures with Santa
Key West: Dress up your furry family members and head down to the docks for a
holiday snapshot with Santa himself. Takes place from 6 – 8 pm on the Harbor Walk of Lights. Info: keywestchristmas.org.
December 4
Faro Blanco Annual Lighthouse Lighting
Marathon: This fun annual event includes a Marina Walk Marketplace, holiday
music, live performances, holiday buoy decorating, a silent auction, and a visit by Santa and Mrs. Claus. Takes place from 3 – 6 pm at Faro Blanco Marina,
1996 Overseas Hwy. Info: 305-424-9038.
December 7 – 11
Nutcracker Key West
Key West: The highly acclaimed Keys version of the classic seasonal ballet returns to the stage once again. This unprecedented production is the creation of classically trained dancer and choreographer Joyce Stahl, who reinterprets the fabled ballet with original Key West tropical imagery and icons. This is truly a holiday event not to be missed! Showtime at 7:30 pm with a matinee on Saturday, December 10, and Sunday, December 11, at the Tennessee Williams Theater, 5901 College Rd on Stock Island. Info and tickets: 305-295-7676; keystix.com.
December 8
Holidays: The Dark Side with Aaron Sagers
Key West: Until relatively recently, Christmas was a time for “scary ghost stories,” with its lore, traditions, and mythology leaning to the dark side. Former Artist in Residence, Travel Channel/Discovery+ host, and paranormal expert, Aaron Sagers
explores the spookier side of the season. Takes place at 7 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 8
Scary Ghost Stories: A History of
the Holiday’s Spooking Tradition
Key West: Travel Channel/Discovery+ host, host of Netflix’s “28 Days Haunted,” and paranormal historian and journalist, Aaron Sagers explores the spookier side of the season. Long before Ebenezer Scrooge changed his ways on the holiday in 1843 — and 143 years before Andy Williams first sang about the most wonderful time of the year — Christmas had already been established as the season for telling scary ghost stories. Sorry Halloween, Christmas is the season for spooky greetings. Kicks off at 7 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org
December 9
6th 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, as well as a holiday light show projected on the face of the Custom House. You’ll also have an opportunity to shop for lots of 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 and spills out onto the street in front of the Museum at 281 Front St. Info and tickets: 305-295-6616; kwahs.org.
December TBD
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. Takes place on two
consecutive Fridays. Info and tickets: 305-296-4959; keywestinns.com.
December 10
9th 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. Takes place from10 am – 2 pm at Higgs Beach, 100 Atlantic St at the end of White St. Info: keywestchristmas.org.
December 10
32nd 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 10
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 11
Key Colony Beach Lighted Boat Parade
Key Colony Beach: Key Colony’s Lighted Boat Parade shoves off at 6 pm from the 7th Street Canal and makes three passes by the Judges’ Stand before heading up and down the 8th – 12th Street canals. Info: 305-743-7214; kcbca.org/boatparade.htm.
December 11 – 12
Fully Committed
Key West: Becky Mode’s hilarious one-man comedy will have you rolling in the aisles. On stage at the Waterfront Playhouse, 407 Wall St in Mallory Square. Info and tickets 305-294-5015; waterfrontplayhouse.org.
December 15
La Chicharra Story Slam
Key West: This live storytelling competition features a lineup of Key West locals, each with a chance to tell a story based on the theme “One Bad Decision.” No notes are allowed, and stories must be told and not read. Takes place at 7 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 15
Historic Seaport Sail On Argo Navis
Key West: Dr. Cori Convertito leads this historically illuminating seafaring excursion and shares the back story of all of the Florida Keys Lighthouses, including their construction and current status. The two-hour tour shoves at 9am at Argo Navis Sailing Charters, 0 Margaret St in Key West’s Historic Harbor. Presented by the Key West Art & Historical Society. Info: 305-295-6616. Tickets are online at kwahs.org.
December 15
La Chicharra Story Slam
Key West: This live storytelling competition features a lineup of Key West locals, each with a chance to tell a story based on the theme “One Bad Decision.” No notes are allowed: stories must be told and not read. Takes place at 7 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 15
Earthly Bodies: Two Decades of Nudes
with Eric Anfinson
Key West: Local artist Eric Anfinson’s figurative display of the people who call our
island home, and those who pass through, live on in the faces and figures of his
paintings. A self-trained painter, his work is in collections throughout North America and Europe. Takes place from 5 – 7 pm in the Bumpus Gallery at the Custom House Museum, 281 Front St. Info: 305-295-6616; kwahs.org.
December 17
Historic Architectural Walking Tour
Key West: Celebrate our magnificent island by joining museum curator, Cori
Convertito for an architectural walking tour of Old Town. Learn all about the
historic landmarks, unique architectural styles, significant owners of note, and several uses of homes and buildings since their construction. The 1-1/2 hour tour leaves at 11am from the Armory Building, 600 White St, and ends at The Custom House.
Presented by the Key West Art & Historical Society. Info: 305-295-6616. Tickets are online at kwahs.org.
December 17 – January 9
12th Annual Small Works Juried Exhibit
Key West: Now in its twelfth year, this annual homage to small original works of art has become an artistic tradition in Key West. The juried exhibit includes up to 200 mesmerizing pieces by artists worldwide whose works must not exceed ten inches in any direction. Expect to see everything from crafted mosaics, bold metal sculptures, and artful collages to impressionist paintings — some no larger than a postage stamp. Takes place at Key West’s acclaimed Jag Gallery, 1075 Duval St in Duval Square. Info: 305-407-6202; jaggallery.art.
December 17
Boot Key Harbor Lighted Boat Parade
Marathon: Marathon gets all decked out with their own festive Lighted Boat Parade. It sets sail at 6 pm from the West end of Boot Key Harbor (7 Mile Bridge side) and slowly winds its way east into the harbor towards Sombrero Marina Dockside. The parade continues until 8 pm. Best views include the Marathon Marina, Lazy Days South, Burdines, and Dockside Lounge.
December 17
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 18
Holiday Makers Market
Key West: Get ready for terrific holiday shopping when the Keys’ top artists showcase their unique handcrafted gifts, jewelry, textiles, home accessories, and quality crafts at this annual indoor holiday market. Takes place from 9 am – 2 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 18
Lighting of the Menorah
Key West: Celebrate Chanukah and the Jewish the Feast of Lights with the lighting a huge Menorah. Takes place from 5 – 6 pm at Bayview Park, 1320 Truman Ave. Info: keywestchristmas.org.
December 19
Annual Light Up Key Largo!
Key Largo: For one magical night, you can ice skate in the “Diving Capital of the World” as Key Largo lights Monroe County’s tallest Christmas tree. The celebration includes an Ice Skating Rink, Santa’s Workshop, Carolers, lots of holiday goodies, and more. Tree Lighting at 8 pm. Takes place from 6 – 10 pm at the Murray Nelson Government Center, 102050 Overseas Hwy, MM 102 Bayside. Info: 305-451-1414; keylargochamber.org.
December 20 – January 14
Dear Jack, Dear Louise
Key West: Sparks fly, and love blossoms from a world away when US Army doctor, Jack, begins a correspondence with an aspiring actress, Louise, during WWII. Winner of the Helen Hayes and Charles MacArthur Award for Best New Play of 2020. Takes place at the Red Barn Theatre, 319 Duval St. Info and tickets: 305-296-9911; redbarntheatre.com.
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 28 – 29
63rd 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 28 – 31
Short & Sketchy
Key West: This original play by Carolyn Cooper and Mathias Maloff includes a series of short skits, wacky scenarios, miscommunicated histories, and hilarious sketches. Produced by Fringe at the Armory, 600 White Street. Showtime: 7pm. Tickets: fringetheater.org.
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 7 – 8
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 Sat, January 7, from 10 am — 8 pm and continues on Sun, January 8, from 11 am — 5 pm at Marathon Community Park, MM 49. Tickets and info: 305-743-6412; floridakeyscelticfestival.com.
