With so many fun happenings for the holidays and New Year, its a fun ride in paradise!
Now – January 4
EXHIBITION: Human Interest —
Jack Baron
Key West: This amazing collection of luminescent needlepoint tapestries and acrylic paintings represents a 20-year commitment by beloved folk artist, Jack Baron. Inspired by his Key West friends, neighbors, conch houses, roosters, and cats, each piece reflects his uniquely whimsical and effervescent style. On view daily from 9:30 am — 4:30 pm at the Custom House Museum, 281 Front St. Info: 305-850-8343; kwahs.org.
Now – December 31
EXHIBITION: Celebrating 20 Years!
History of Diving Museum
Islamorada: This special, limited-time exhibit examines how the world’s largest collection of diving equipment on public display was created and how diving has evolved since the Museum opened. You’ll also have an opportunity to see unique artifacts that have never been displayed before. On view daily from 10 am – 5 pm at The History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Info: 305-664-9737; divingmuseum.org.
Now – December 31
Key West Holiday Fest
Key West: A merry range of celebrations during Key West’s busy holiday season includes the Lighting of the Key West Bight, the Harbor Walk of Lights, Holiday Historic Inn Tours, a spectacular lighted boat parade, and lots of good cheer. Other events that you won’t want to miss: the annual hometown holiday parade, festive island lights tours on 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: keywestinns.com/holiday-fest/.
Now – December 31
Key West Harbor Walk of Lights
Key West: This festive annual celebration 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. For more holiday happenings in Key West, hit up keywestinns.com/holiday-fest/.
December 2
The ReMARCable Decorated Table Top Tree & Wreath Auction
Key West: This annual Bid on beautifully decorated Christmas Trees and Wreaths to benefit MARC. Preview begins at 5:30 pm with auction at 7 pm at Opal Key West, 245 Front St. Info: 305-294-9526; marchouse.og.
December 2 – 7
15th Annual Festival of Trees
Marathon: The Middle Keys’ most creative display of eclectic Christmas trees! View and bid on your favorite from 5 – 8 pm on Tu – Th; from 3:30 – 9 pm on F; and from 10 am – 8 pm on Sa, when you can enjoy a raffle and cookies with Santa and the Grinch until noon. Takes place at the Marathon Garden Club, 5270 Overseas Hwy. Info: 305-743-4971; marathongardenclub.org.
December 3 – February 15
EXHIBITION: Shadow & Light: Island Contrast
A Juried Exhibition
Key West: This juried exhibition showcases a variety of artists living and creating
in the Florida Keys. Capturing natural light and its interaction with everyday objects, these featured artists create original plein air works that evoke contemplation, wonder, and introspection. Opening reception on Friday, December 3 from 5 – 8 pm;
On view daily from 9:30 am – 4:30 pm at the the Key West Art & Historical Society’s Custom House Museum, Custom House Museum, 281 Front St. Info: 305-850-8343; kwahs.org.
December 4
20th Annual Pet Pictures With Santa
Key West: Pack up Fido and the family and delight in Pet Pictures with
Santa with your. Takes place from 6 – 8 pm next to the 16’ Nautical Christmas
Tree on the Harbor Walk of Lights at the foot of William St.
December 4
The 12th Annual POSH (Paws Often Steal Hearts)
Florida Keys SPCA Fundraiser
Key West: This fun annual catered gala event for a good cause includes live music, dancing, raffles, and a silent auction. Takes place from 6:30 – 9:30 pm at the historic Audubon House, 205 Whitehead St. Info & tickets: 305-294-4857; poshkeywest.com.
December 4 – 20
Some Enchanted Evening
Key West: A stunning revue of Rodgers & Hammerstein’s most treasured songs, this elegant theatrical presentation brings five performers into a world of timeless music — from backstage intimacy to full-stage splendor. Showtime: 7:30 pm with a 2 pm matinee on Sa, Dec 13 at the Waterfront Playhouse, 407 Wall St in Mallory Square. Info & tickets 305-294-5015; waterfrontplayhouse.org.
December 4 – 30
Winter Member’s Show
Key West: A perpetual crowd favorite, this annual kickoff event celebrates the launch of The Studios of Key West’s upcoming season. The special exhibition features over 100 outstanding artworks in all mediums. Opens on Th, Dec 4 from 6 — 8 pm and continues every Tu — Su from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 5
21st Annual Islamorada Holiday Festival
Islamorada: A 35-foot holiday tree blows magical snow at this spirited night of holiday fun, which includes a snow mountain, a festive parade, community tree lighting, caroling, a 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, 87000 Overseas Hwy, MM 87, Bayside. Info: 305-664-4503; islamoradachamber.com.
December 5
4th Annual Wesley House Holiday Village & BeLighted Bike Ride
Key West: This fun annual “pre-party” kicks off Key West’s annual BeLighted Bike Ride. The magical Holiday Village includes photos with Santa, rides, games, crafts, food vendors, music, local performances, and more! This year’s event also features large, holiday-themed inflatable obstacle courses for the kids! Takes place from 5 — 9 pm with the festively creative “Best Bike Contest” at 7:30 pm. The BeLighted Bike Ride follows at 8 pm. Takes place at Truman Waterfront Park, 21 E Quay Rd. & info: 305-809-5000; wesleyhouse.org.
December 6
Key West Woman’s Club European-Style
Holiday Market
Key West: Shop ’til you drop as you revel in this unique open-air European-style holiday shopping experience. Takes place from Noon – 4 pm at the historic
Curry Museum, 319 Duval St. Info: 305-294-2039.
December 6
Duval 300 Block Party
Key West: Get into the holiday spirit and “go-a-wassailing” at this festive pre-parade party that celebrates the season. Takes place from 10 am – 6 pm at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; OIRF.org.
December 6
Key West Hometown Holiday Parade
Key West: The most charming hometown parade you’ll ever see, with lots of holiday floats and tons of kids of all ages. Festivities kick off at 7 pm on Truman Ave at White St. The parade then proceeds down Duval and ends
at Eaton. Info: 305-809-3881; keywesthistoricseaport.com.
December 6
Christmas Parade Porch Party
Key West: Party on the historic porch overlooking the happiest parade in Key West. Kicks off at 6 pm after the Duval 300 Block Party at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; OIRF.org.
December 6
7 Mile SantaCon
Marathon: Dress up in your most festive holiday garb for this fun Holiday Poker Run that celebrates our holiday season with drinks, poker, good cheer, and cash prizes for winning hands and best dressed. Poker Run takes place from noon — 5 pm at some of Marathon’s favorite hot spots. Awards announced at 6 pm. For more info and a complete list of participating locations, contact 305-743-5417; info@floridakeysmarathon.com.
December 6 – January 5
San Pablo Church’s Christmas Lights
Marathon: Stroll through the beautiful gardens and experience one of The Keys’ most iconic signs of the season. The amazing lighted outdoor display inspires a sense of peace, love, and reflection. Takes place nightly from dusk to 9:30 pm at San Pablo Catholic Church, 550 122 St, MM 53.5 oceanside. Info: 305-289-0636; sanpablomarathon.org.
December 7
Holiday Open House at The Studios of Key West
Key West: Enjoy a lively and festive Holiday Open House, where you can sip on Christmas cocktails on the rooftop of Hugh’s View and do some holiday shopping at the special Member’s Show. Takes place from 3:30 pm – 7:30 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 7
Schooner Wharf Bar’s Annual
Tree Trimming Party & Toy Drive
Key West: Enjoy a complimentary holiday cocktail when you bring a nautical ornament for tree trimming or an unwrapped kids’ gift for this fun annual Toy Drive. Prizes for the most original, most nautical, and most popular outfit. FYI: Be sure to visit Santa’s Southernmost Schooner Workshop, where local artists and authors sign and sell original works for holiday gift giving. Benefits a variety of children’s organizations. Takes place at 6 pm at the Schooner Wharf Bar at the foot of Williams St in the Historic Seaport. Info: 305-292-3773; schoonerwharf.com.
December 7
Annual Holiday Tree Lighting
Key Colony Beach: Wear your ugliest Christmas sweater and high tail it over to the annual lighting of a giant Christmas Tree “Under the Tiki.” Make a donation to “Presents in Paradise” and add an ornament to the tree.
There is plenty of eggnog and hot chocolate to get you into the spirit, live music, a 50/50 raffle, food, drinks, and a visit from Santa. Kicks off at 5 pm with a tree lighting at 7 pm at Havana Jack’s Oceanside, 401 E Ocean Dr. Info: 305-743-4849; HavanaJacksOceanside.com.
December 7 – 15
Annual Festival of Trees
Key West: Crafted and decorated by local students, a festive forest of holiday trees takes center stage on the porch of Key West’s historic Custom House before being donated to families through the Housing Authority of Key West. Takes place daily from 10 am – 5 pm at the Key West Museum of Art & History, 281 Front St.
Info: 305-295-6616; kwahs.org.
December 12 & 19
Holiday Historic Inn Tours
Key West: This enchanted self-guided tour takes you to five gorgeously decorated inns for a sneak peek of what’s inside, as well as a sampling of holiday treats and cheer at each property. Takes place on Friday, Dec 8 and Dec 15, from 6 – 8 pm. Info & tickets: 305-296-4959; keywestinns.com.
December 9 – January
3
Scrooge Macbeth
Key West: It’s a hilarious mash-up of Dickens and Shakespeare when a theater company must come up with a replacement show when all of the actors call in sick. On stage Tu – Sa at 7:30 pm (no performances on Christmas Eve or New Year’s Eve) at the Red Barn Theatre, 319 Duval St. Info & tickets: 305-296-9911; redbarntheatre.com.
December 12
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 and handcrafted items. 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 & tickets: 305-295-6616; kwahs.org.
December 12
December Duo Holiday Concert: Irie Monte & Crispin Campbell
Key West: Prepared to be enchanted when violinist Irie Monte and cellist Crispin Campbell team up for a night of beautiful string music. Showtime: 5:30 pm on Hugh’s View Rooftop at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 13
Historic Pigeon Key Holiday Spectacular
Marathon: This historic 5-acre island, which lies beneath the Old 7 Mile Bridge, is not to be missed during the holiday season when festive decorations transform it into a magical tropical paradise. You can spend a whole day enjoying marine science activities, holiday food and drinks, guided tours, holiday-themed movies on the big screen, Santa encounters, and even snow!. Access the island by walking or biking along the 7 Mile Bridge ramp, or simply hop on the island launch, which departs at 10 am, Noon, and 2 pm from the Visitors Center, located at 2010 Overseas Hwy. FYI: On Sa, a special “Polar Express” will make runs to the island starting at 1 pm and continuing throughout the day and into the evening. Info: 305-743-5999; pigeonkey.net.
December 14
Pops in the Park: Holiday Harmony
Islamorada: Enjoy this free bayside outdoor concert with holiday favorites and
sing-alongs by the Keys Community Concert Band. Also includes SnowBall Games, a visit by Santa, and the Burton Bell Ringers. Bring your chairs and blankets. Showtime: 4 pm at Founders Park, 87000 Overseas Hwy, MM 87, Bayside. Info: 305-853-7294; keyscommunityconcertband.com.
December 17
Dolphin Sunset Celebration
Marathon: What’s better than a margarita at sunset? How about sharing a non-alcoholic Jello shot with a dolphin! This totally unique Sunset experience is your opportunity to interact with dolphins, chat with experts, and discover what it means to build meaningful relationships with these special animals. As the sky turns gold, you can raise your glass of champagne to the setting sun, surrounded by playful dolphins, an ocean breeze, and unforgettable island beauty. Space is limited, so reserve asap! Takes place at 4 pm at the Dolphin Research Center, 58901 Overseas Hwy (MM 59 Gulfside) on Grassy Key. Info: 305-289-1121; dolphins.org.
December 19 – 20
Personal Affects
Key West: This World Premiere of Chris Moore’s new play explores what happens when siblings arrive in Key West to sort through the personal effects of their estranged and now deceased father. Produced by Art House, Fringe. Showtime: 7pm at the Armory, 600 White St. Info & reserved tickets: 305-295-7676; keystix.com.
December 24
Christmas Eve Parade With Santa
Marathon/Key Colony Beach: Santa puts the “Ho, Ho, Ho” into The Night Before Christmas with his annual holiday trek through the streets of Marathon and Key Colony Beach, making several stops along the way.
Look for his honking Fire Engine starting at dusk.
December 25
Christmas Day Brunch Sail
Key West: Dreaming of a crystal clear, blue Christmas? Then hop on board The Schooner America 2.0 for a two-hour brunch sail that includes a fully catered brunch with complimentary Mimosas, Bloody Marys, or champagne. Departs from the dock behind the Schooner Wharf Bar, located at the foot of William St in the Historic Seaport. Info & tickets: 305-293-7245; sail-keywest.com.
December 26 – 27
Annual Key West Home Tours
Key West: Festively dressed Key West homes and gardens are the stars of the show during this highly anticipated annual event. The self-guided tour showcases exquisite restorations, creative renovations, and delightful interiors and exteriors of some of the island’s most stunning homes. Takes place from 1 – 4 pm and benefits the Old Island Restoration Foundation. Info & tickets: 305-294-9501; OIRF.org.
December 29 – 31 & January 1
Camp blends art and music with storytelling and science, which gives kids a unique opportunity to explore their own creativity.
Takes place from 9 am — 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
December 31
New Year’s Eve Celebrations in Key West
Key West: Ring in 2026 with a “Conch Shell Drop” at Sloppy Joe’s Bar (201 Duval St); a big blow out bash at the Schooner Wharf Bar, which culminates with the descent of a pirate wench from the mast of a majestic schooner (202 William St); Bourbon Street Pub’s world-renowned descent of a super-sized red high-heel shoe, commandeered by an outrageous drag queen, (724 Duval St); and the splash down of a massive Key lime wedge into a larger-than-life margarita glass at Ocean Key Resort & Spa (0 Duval St). Too wild for words!
December 31
Dockside New Year’s Eve Party
On Schooner America 2.0
Key West: This wild dockside 21+ event aboard Key West’s most spectacular schooner backdrops a night of non-stop revelry. The celebration includes VIP access to the “Lowering of the Pirate Wench” — a midnight countdown marked by the wench’s descent down the rig of Schooner America 2.0! Kicks off at 9 pm on
deck of the Schooner America 2.0, behind the Schooner Wharf Bar, at the foot of William St in the Historic Seaport. Info & tickets: 305-293-7245; sail-keywest.com.
December 31
New Year’s Eve Soirée
at Cheeca Lodge & Spa
Islamorada: This ultra-chic beachside resort kicks off the New Year with a luxe annual Soirée that includes dinner, dancing, and a dazzling midnight fireworks display. The celebration begins at 5 pm at Cheeca Lodge & Spa, located at 81801 Overseas Hwy (MM 82, Oceanside). Info: 305-664-4651; cheeca.com.
December 31
New Year’s Eve Fireworks on Blackwater Sound
Key Largo: The Back Bay is the setting for the annual New Year’s Eve midnight fireworks extravaganza, set to live music performed at Sundowners, 103900 Overseas Hwy (MM 104 Bayside). Info: 305-664-4651; sundownerskeylargo.com.
January 8 – 29
EXHIBITION: Worm — A Cuban American Odyssey
by Edel Rodriguez
Key West: Edel Rodriguez, one of the most prominent political artists of our time,
traces his journey from Cold War Cuba to international acclaim in a riveting show
that brings the story behind his acclaimed graphic memoir, WORM, to life. Opens
on Th, Jan 8 from 6 — 8 pm and continues every Tu – Sa from 10 am – 4 pm
at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
January 8 – 29
EXHIBITION: Oceans Not Mars
by Barbara Boissevain
Key West: Photographer and environmental artist, Barbara Boissevain, explores the fragile beauty and regenerative power of the Florida Keys coral reef, using both photography and mixed media. Opens on Th, Jan 8 from 6 – 8 pm and continues
every Tu – Sa from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
January 8 — 29
EXHIBITION: Saltwater Diaries
by Barbara Hann
Key West: Barbara Hann’s collection of plein air oil paintings was painted on location in real time. Her intimate body of work is a living diary of standing in wind, chasing light, and honoring the raw, evolving beauty of the Keys. Opens on Th, Jan 8 from 6 – 8 pm and continues every Tu – Sa from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
January 8 – 29
EXHIBITION: It Always Grows
by Ian J Wech
Key West: Through printmaking, drawings, and handmade paper incorporating
materials gathered from the landscapes, Welch’s work documents landscapes in
flux. From lush ecosystems to sites altered by human boundaries, his art reflects
the tension between human intervention. Opens on Th, Jan 8 from 6 – 8 pm and continues every Tu – Sa from 10 am- 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
January 9 – February 15
EXHIBITION: Analogous —
Old Cameras. New Work
Key West: This experiment in analog photography, by artists Michael Marrero and Mark Hedden, explores new works using pre-digital photographic techniques: ones that rely on chemicals reacting to light. On view daily from 9:30 am – 4:30 pm at the Custom House Museum, 281 Front St. Info: 305-850-8343; kwahs.org.
January 10 – 11
Annual Florida Keys Celtic Festival
Marathon: Enjoy top acts by international Celtic bands, Celtic food, and beer, Highland Athletics, a Children’s Glen and a Celtic Marketplace. Open from 10 am – 7 pm on Sa; and from 11 am – 5 pm on Su at Marathon Community Park, 200 Ocean & 200 36th St (MM 49 Oceanside). Info: 305-743-6412; floridakeyscelticfestival.com.
January 12
EXHIBITION: First Pitch —
Key West Baseball Heritage
Key West: See original artifacts from Key West’s storied baseball history, along with some amazing baseball art, including original works by acclaimed Cuban artist Julia Arroyo. Takes place from 10 am – 4 pm at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; OIRF.org.
January 17
42nd Art Under the Oaks
Tavernier: This annual outdoor fine arts and crafts show is literally held “under the oaks” with a variety of live music, a bake sale, raffles, and refreshments. Takes place from 9 am – 4 pm at the San Pedro Church Gardens, 89500 Overseas Hwy. Info: 305-852-5372; artundertheoaks.com.
January 17 – 18
Living History Weekend
Key West: Experience what life was like in a coastal fortification during the 1860s through reenactments, exhibits, displays, demonstrations, and more. Takes place from 10 am – 2 pm inside the fort at the parade grounds of Fort Zachary Taylor Historic State Park. 601 Howard England Way. Info: 305-292-6713; fortzacharytaylor.com.
January 23 – 24
66th Annual Key West Home Tours
Key West: One of America’s oldest and longest-running home tours showcases five lovely homes and gardens on each day’s self-guided tour. Each stop reflects the varied tastes and originality of its owners. Takes place from 1 – 4 pm. Info &tickets: 305-294-9501; OIRF.org.
January 24 – 25
22nd Annual Big Pine & Lower Keys Nautical Expo
Big Pine: Get great deals on all things nautical, as well as on local arts & crafts, clothing, and jewelry. Live music, food, and beverages, too! Open from 8 am – 4 pm on Sa; and from 8 am — 2 pm on Su. Takes place on the grounds of the Lower Keys Chamber of Commerce, 31020 Overseas Hwy, (MM31) Oceanside. Info: 305-872-2411; lowerkeyschamber.com.
January 23 – 24
66th Annual Key West Home Tours
Key West: One of America’s oldest and longest-running home tours showcases five lovely homes and gardens on each day’s self-guided tour. Each stop reflects the varied tastes and originality of its owners. Takes place from 1 – 4 pm. Info &tickets: 305-294-9501; OIRF.org.
January 25
Schooner Wharf Wrecker’s Cup Race
Key West: This is the first leg of the spirited 7-mile race to Sand Key, where bragging rights are the top prize. The race kicks off at 1pm with an Awards Ceremony at 7 pm. Takes place at Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.
January 25
Wrecker’s Cup Race
Aboard Schooner America 2.0
Key West: If you really want to enjoy the thrill of the Wrecker’s Cup Race, then climb aboard the fastest schooner in Key West: Schooner America 2.0. The fun starts at 1 pm with the firing of the cannon. Tickets include a round of beer, wine, champagne, and a boxed lunch. Info & tickets: 305-292-7245; sail-keywest.com.
January 28 – February 1
17th Annual Key West Food & Wine Festival
Key West: Voted one of the Best Food & Wine Festivals in the US, this creative series of wine and food events showcases a diverse range of wines and inventive cuisine at a variety of iconic Island locations. Over 20 unique events, including waterfront tastings, Winemaker/Chef collaborations, and funky events, present an authentic taste of Key West. This year’s theme, “Experience the Pacific,” celebrates the wine and culture of the Pacific Coast. Info & tickets: keywestfoodandwinefestival.com.
January 30
Petals & Pearls Gala
Key West: Celebrate 90 years of enchantment at this swanky anniversary gala that includes an open bar, elegant dinner, and dancing under the stars with Skipper & Friends. Kicks off at 6 pm at the Key West Tropical Forest & Botanical Garden, 5210 College Rd on Stock Island. Info & tickets: 305-296-1504; keywest.garden.
January 31
EXHIBITION: Bronson Arroyo Band Concert &
Baseball Art Show
Key West: This benefit concert for Key West Baseball and the Oldest House Museum also includes nostalgia and art showcasing major league retired players from Key West. Takes place from 10 am – 4 pm at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; OIRF.org.
COMING SOON
February 5 – 26
SPECIAL PREVIEW: Annual Ann McKee Fine Art Auction
Key West: This highly acclaimed annual art auction is the one night when a considerable measure of the cream of the Keys’ crop will be on display. Get a sneak peek of the beautiful works coming up for bid on February 27 during this special preview. Opens on Th, February 5 from 6 – 8 pm and continues every Tu – Sa from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org or mckeefund.org.
February 13 –14;
March 13 –14
66th Annual Key West Home Tours
Key West: One of America’s oldest and longest-running home tours showcases five lovely homes and gardens on each day’s self-guided tour. Each stop reflects the varied tastes and originality of its owners. Takes place from 1 – 4 pm. Info &tickets: 305-294-9501; OIRF.org.
February 21 – 2
2
61st Annual Key West Art & Craft Festival
Key West: This nationally recognized juried fine art show attracts over 100 fine and skilled artists from across the country and includes painters, sculptors, photographers, collage artists, and other non-functional fine arts. Takes place from 10 am – 5 pm at Truman Waterfront Park, 21 E Quay Rd. Info: 305-294-1243;
keywestartcenter.com.
Photos: Courtesy Carol Tedesco
