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2018 Key West Holiday Fest

Presented By 


First State Bank, Historic Tours of America, Margaritaville Key West Resort & Marina, Ocean Key Resort, The Lodging Association of the Florida Keys and Key West & the Monroe County Tourist Development Council


1 Boat Parade C Tedesco KW Holiday Fest 5Q0A7829-2


November 21, 2018 "Lighting of the Key West “Harbor Walk of Lights”

Kick off the season! Lighting of the Key West “Harbor Walk of Lights” FREE 6:00p.m.

Gather on the Harbor Walk at Greene and Elizabeth St. to see the best official lighting of the ... 2018
Key West “Harbor Walk of Lights”. The main features will light up the night, including the "Fishing Buoy Christmas Tree", a fresh pine "Nautical Christmas Tree" and the "Lobster Trap Christmas Tree" 
all honoring the Maritime History of Key West. The Harbor Walk is lit nightly through New Year’s Eve.

November 24, 2018 Studios of Key West's Holiday Artisan Market

Make holiday shopping fun! Enjoy cookies and coffee as you stroll through a friendly, festive indoor market. Over 20 artisans present unique and locally produced gifts: jewelry, textiles, home accessories and quality crafts. From 9 a.m. to 2 p.m., 533 Eaton Street.


Dec. 2 Old Stone Church’s “Messiah.”
Key West. Key West United Methodist Church, known as the historic “Old Stone Church,” hosts its
Christmas “Messiah” concert at 7 p.m., with organ, piano, timpani and soloists. Complimentary admission. Visit or call 305-296-2392.

Dec. 2, 16 and 30 Artisan Market. Key West
A “shop local” holiday tradition, the open-air bazaar, this year at Higgs Beach, 100 Atlantic Blvd., from 10 a.m. to 2 p.m., is filled with Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit or call 573-619-2200.

December 2, 2018 Lighting of the Menorah

On December 2nd, the community will gather back at Bayview Park for the Lighting of the Menorah at 5:00 p.m. Rabbi Shimon Dudai from Congregation B’Nai Zion and Rabbi Jacob Zucker from Chabad of the Florida Keys will say the blessings.


December 3, 2018 Schooner Wharf Tree Trimming Party

Make our tree yours and bring a handmade ornament for the 8-foot live Christmas tree. Ornaments will be entered in a contest and prizes will be awarded for the Most Original, Most Nautical and Most Popular with the holiday crowd. All tree trimmers will be treated to a free holiday cocktail. For the 19th year in a row, the Schooner Wharf “Breakfast Club” is heading up a Toy Drive on Tree Trimming Day, benefiting Toys for Tots and Angels – Just 4 Kids. Each of Santa’s helpers who donates a gift to this worthwhile cause will also receive a free holiday drink. Visit or call 305-292-3302.


December 5, 2018 Lighted Bike Parade

The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for
the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride
is a family event beginning with a registration/check-in at 6 p.m. with the Lighted Bike Ride beginning at
7:00 p.m. Families and individuals with lighted and decorated bikes ride through the streets for the
community to see. Registration for the ride is one unwrapped toy for the Key West Holiday Store.
Register online at
Lighted Bike Parade .

December 6, 2018 6th Annual POSH - Paws Often Steal Hearts

Benefiting Florida Keys SPCA! Benefit is located at the Audubon House & Tropical Garden from 6p.m. – 9p.m. There will be live music, silent auction, Tapas-style appetizers, complementary specialty welcome drink and local priced cash bar! Tickets in advance $40 and $45 at the door, available at FKSPCA POSH Tickets. Purchase a fascinator from the Mad Hatter and you will receive a $5 discount code off your POSH ticket!


December 6 - 23, 2018 Conch Tour Train - Holiday Lights Tour

Join the Conch Tour Train for their annual holiday lights tour of the island. To get things started we will serve up some holiday cheer with cider and cookies. Then it is all aboard for an hour tour that takes you to all the island's most elaborately decorated houses, buildings and neighborhoods and caroling. Visit; or call 305-294-5161 for reservations and information.


December 6 - 23, 2018 Old Town Trolley Holiday Lights and Sights Tour

Celebrate the season aboard Old Town Trolley on their Holiday Lights and Sights Trolley. There won't be a white Christmas in Key West, but that doesn't stop the island from decking the halls with lights and decorations. Visit or call 305-296-6688 for reservations and information.


December 7, 2018 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 The Gardens Hotel, Island City House Hotel, Amsterdam's Curry Mansion Inn, The Weather Station Inn and Key West Butterfly & Nature Conservatory. Tickets may be purchased by calling The Lodging Association office at 305- 296-4959 or on th
e any day prior to the tour each night.


December 7, 2018 Pet Pictures with Santa

Key West. All Animal Clinic sponsors photos with Santa, scheduled 6-8 p.m., allowing families to enjoy Santa, pets and kids, with treats. Photos are priced at $20, with proceeds to benefit Key West Boys Club. Santa is to be at the nautical Christmas tree, at the foot of William Street. Visit 

December 8, 2018 Key West City "Hometown Holiday Parade"
Parade begins at 7p.m. Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. Catching the tossed candy is a highlight for kids. The route begins at Bayview Park and the best viewing spots are along Duval Street and Truman Avenue.


December 8-16, 2018 Nutcracker Key West

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 or call 305-295-7676.

December 9, 2018 Christmas on the Sheriff's Animal Farm

From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff’s Office Animal Farm is situated at the county’s detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff’s Animal Farm is open the second and fourth Sundays of the month. Call 305-293-7300.


December 13, 2018 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, 2018 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 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” on Thursday, December 14 through Saturday, December 16 at Key West Theater, 512 Eaton Street. 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 7:30p.m., show starts at 8:00p.m. Sponsored in part by the Monroe County Tourist Develop.ment Council. Tickets available at or call 305.985.0433.


December 15, 2018 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 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends. Visit or call 305-294-4857.


December 15, 2018 The Schooner Wharf Bar 28th Annual Key West Lighted Boat Parade
Key West. In the Keys’ largest lighted boat parade around Key West’s Historic Seaport and harbor areas at 8 p.m., more than $20,500 in prizes is to be awarded to 12 top vessels during this  28th annual event. Boats creatively “deck their hulls.” There’s a free raffle for all participants. An awards ceremony is Dec.16 at 8 p.m. Visit or call 305-292-3302.


December 15, 2018 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, 2018 Sebago Lighted Boat Parade Cruise
Participate in the action aboard Sebago Schooner Appledore II, or cheer from a front row seat on the water. 7:30-9:30 p.m.


December 16, 2018 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 11:00 a.m. - 3:00 p.m. 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, 2018 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 or call 305-295-6616. Open and free to the public.

December 23, 2018 Holiday Jazz in the Gardens
Free .Festive outdoor jazz performance at the Gardens Hotel. Cash bar & large wine selection. 5:30 to 7:30 p.m. 

December 28 & 29, 2018 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 or call 305-294-9501.


December 31, 2018 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, 2018 Key West New Year's Eve Celebrations

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





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