When it comes to celebrating the holidays in Key West, there’s never a dull moment! One of our all-time favorite events, coming up on Friday, December 14, is the Holiday Historic Inn Tour where you can tour five festive properties and enjoy special treats and libations.
Here’s a list of a lot more fun holiday happenings:
Now – December 16
Nutcracker Key West
Florida Keys children, adults and community leaders appear with a nationally cast corps de ballet in a stunning Keys-themed adaption of the beloved holiday classic. There’s a wicked Rooster-King, an exquisite Sea-Star Fairy and gorgeous “underwater” sequences. Key West’s Joyce Stahl, executive producer and artistic director, is a former performer with New Jersey’s American Repertory Ballet. Multiple afternoon and evening performances with tropically colored and specially designed costumes are held at Tennessee Williams Theatre. Visit nutcrackerkeywest.com or call 305-295-7676.
December 13
Sail with Santa on Fury Water Adventures
Festive trip to the reef including Holiday Music, Appetizers, Treats, Hot Chocolate, Beer, Wine, Champagne, Soda, Water & SANTA!!! Call 305-292-4600.
December 14
Holiday Historic Inn Tours
Tour five festive properties decorated for the holidays and a sampling of holiday treats and holiday cheer. The Inns for this night are Hemingway Rum Co. Distillery, Old Town Manor, Wicker House, The Mermaid & The Alligator, Suite Dreams Inn and Santa Maria Suites Resort. Tickets may be purchased by calling The Lodging Association office at 305- 296-4959 or on the Keystix.com any day prior to the tour each night.
December 14 -16
“Sugar Rum Cherry: A Burlesque Nutcracker”
Put on your stockings and pull out your sugarplums for Key West Burlesque’s “Sugar Rum Cherry: A Burlesque Nutcracker.” This naughty holiday two-act reverie features your favorite local performers, international burlesque superstars, and amazing aerial acrobats as they visit the land of libations. Doors open at 7:30pm; show starts at 8:00pm. Takes place at Key West Theater, 512 Eaton St. Sponsored in part by the Monroe County Tourist Development Council. Tickets available at thekeywesttheater.com or call 305.985.0433.
December 15
2nd Annual Parade of Paws & Holiday Bazaar
Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet’s photo! Holiday Bazaar inside the dog park features entertainment, food vendors, photos with Santa, gifts for that special person on your list and more! A unique opportunity to support the lifesaving mission caring for the Keys’ community’s homeless animals, the event supports the Florida Keys SPCA. Check in is 9am Event is from 10am to 2pm at the Higgs Dog Park. Bring four-legged friends. Visit fkspca.org or call 305-294-4857.
December 15
The Schooner Wharf Bar 28th Annual Key West Lighted Boat Parade
The Keys’ largest lighted boat parade takes place at the Key West’s Historic Seaport at 8pm. More than $20,500 in prizes will be awarded to 12 top vessels during this dazzling annual display where boats creatively “deck their hulls.” There’s a free raffle for all participants. An awards ceremony is Dec16 at 8 p.m. Visit schoonerwharf.com or call 305-292-3302.
December 15
Catamaran Echo Lighted Boat Parade Watch “Santa Hat Champagne Party”
Enjoy front row seats near the reviewing stand area on the smooth water for the Lighted Boat Parade. Free Santa Hats for everyone! Drinks & Appetizers included. 7:30-9:30 p.m. 14 adults max.
December 15
Sebago Lighted Boat Parade Cruise
Participate in the action aboard Sebago Schooner Appledore II, or cheer from a front row seat on the water. 7:30-9:30pm.
December 16
Conch Republic Seafood “Holiday Classic Car Show”
Classic cars from every era at the Harbor Walk Plaza located at Greene & Elizabeth Streets. Admission is Free, and the Classic Car Show runs from 11am – 3pm. Collection of unwrapped toys for Monroe County’s Domestic Abuse Shelter. Awards for: “People’s Choice”, BEST Engine, Interior, Original & Custom, and Best in Show. Enjoy holiday specials, classic holiday music, and classic cars from every era decked out for the holidays! Florida Keys Southernmost Car Club – Non-member cars may enter!
December 19
Third Annual Custom House Holiday Concert & Bazaar
The Key West Art & Historical Society hosts the third annual event, 5-9 p.m., at the historic Custom House Museum, 281 Front St. Highlights are to include performances by musicians and choirs, local artisans showcasing their wares, a light show and “selfies” with Santa. Visit kwahs.org or call 305-295-6616. Open and free to the public.
December 23
Holiday Jazz in the Gardens
Free .Festive outdoor jazz performance at the Gardens Hotel. Cash bar & large wine selection. 5:30 to 7:30pm
December 28 & 29
59th Annual Key West House and Garden Tour
Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-7 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation’s museum and programs. Visit oirf.org or call 305-294-9501.
December 31
Annual Key West Dachshund Walk
Frost-free Key West becomes a “wiener wonderland” when about 200 dachshunds and their owners take a noontime New Year’s Eve stroll through the island’s picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.
December 31
Key West New Year’s Eve Celebrations
There is so much going on in Key West for New Year’s Eve that you’ll be hard pressed to know where to go!
•Conch Shell Drop at Sloppy Joes, 305.296.2388.
•Red High Heal with Drag Queen Drop at Bourbon St. Pub, 305.293.9800
•New Year’s Eve Dockside Bash on the Shooner America 2.0
•Pirate Wench Drop at Historic Seaport, 305.292.3302
Key Lime Wedge in Margarita Glass at the Ocean Key Resort, 305.296.7701
