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2018 Key West Holiday Fest

Presented by: Margaritaville Key West Resort & Marina, Historic Tours of America, The Lodging Association of the Florida Keys and Key West & the Monroe County Tourist Development Council




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  6:00pm  

Gather on the Harbor Walk at Greene and Elizabeth St. to best see the official lighting of the ... 2018 Key West “Harbor Walk of Lights”. The main features will light up the night, including the 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.    


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 also Angels – Just 4 Kids. Each of you Santa’s helpers who donates a gift to this worthwhile cause will also receive a free holiday drink.


December 7, 2018  Pet Pictures with Santa hosted by All Animal Clinic
Bring the pets and kids to get your holiday photo! 6:00 - 8:00 PM at the "Nautical Christmas Tree" at the foot William St. on the "Harbor Walk of Lights". Benefiting the Key West Boys Club!

December 8, 2018  
Key West City "Hometown Holiday Parade"
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.


TBA 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/checkin 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. 


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

 Join the Conch Tour Train for thier 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 of the island's most elaborately decorated houses, buildings and neighborhoods and caroling.  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. Call 305-296-6688 for reservations and information.

TBA  Holiday Historic Inn Tours 


TBA  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.


TBA  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.


December 15, 2018  The Schooner Wharf Bar & Galley 28th Annual Key West Lighted Boat Parade
Popular annual event features lighted boats at the Historic Key West Bight. Visitors can watch or become part of the parade on board a decorated boat. 8:00 pm. Free. LOCATION: Viewing all along the Harbor Walk of Lights at the Historic Seaport. Reviewing stand is at the Schooner Wharf Bar and Galley. Come early for great shopping, holiday music, dinner and drinks.  

December 15, 2018  
Catamaran Echo Lighted Boat Parade Watch "Santa Hat Champagne Party"

Enjoy front row seats near the reviewing stand areaon the smooth water for the Lighted Boat Parade. Free Santa Hats for everyone! Drinks & Appetizers included. 7:30-9:30. 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 pm


TBA  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.


TBA  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.


TBA  Lighting of the Menorah

On Thursday, December 14th, the community will gather back at Bayview Park for the Lighting of the Menorah at 5:30. Rabbi Shimon Dudai from Congregation B’Nai Zion and Rabbi Jacob Zucker from Chabad of the Florida Keys will say the blessings


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, December16 at Key West Theater,512 Eaton Street.This naughty holiday 2-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. Sponsored in part by the Monroe County Tourist Development Council. Tickets: or call 305.985.0433


TBA   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 Avalon Bed & Breakfast, The Mermaid & The Alligator, The Gardens Hotel, The Island City House and The Key West Butterfly & Nature Conservatory. Tickets may be purchased by calling The Lodging office (305) 296-4959or on the website any day prior to the tour each night.


December 16, 2018  Conch Republic Seafood "Holiday Classic Car Show"

Classic cars from every era on the Harbor Walk plaza at Greene & Elizabeth Streets. 11:00 - 3:00 pm. Free. Collecting unwrapped toys for Monroe Cnty. Domestic Abuse Shelter Awards for: “Peoples Choice”, BEST engine, interior, original & custom, Best in Show Enjoy holiday specials - Classic Holiday music See classic cars from every era decked out for the holidays! Florida Keys Southernmost Car Club - Non-member cars may enter!



TBA   Monthly Artisan Market, A Holiday "Shop Local " Edition

Browse the vibrant open-air bazaar filled with Keys artists, authors, chef-made cuisine, craftspeople and performers. Admission is free and the market is open to the public from 10 a.m. to 2 p.m. every third Sunday of each month. Bring your own bags.


TBA  Second Annual Holiday Concert and Bazaar at the Custom House Museum

Key West Art & Historical Society is to host this second annual event, from 5-9 p.m. at the historic Custom House Museum, to feature Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show. Highlights of the evening gathering are to include performances by musicians and choirs, local artisans showcasing their wares, a light show and “selfies” with Santa. Open and free to the public.

TBA  Holiday Jazz in the Gardens
Festive outdoor jazz performance at the Gardens Hotel. Cash bar & large wine selection. 5:30 to 8:00 pm. Free


TBA  58th 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.


TBA  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, 2017  Key West New Year's Eve Celebrations   
Conch Shell Dropat 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 Schooner 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