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2016 Key West Holiday Fest

Presented by:

The Westin Key West Resort & Marina, The Ocean Key Resort & Spa, Historic Tours of America, The Lodging Association of the Florida Keys and Key West & the Monroe County Tourist Development Council


November 23, 2016  
Lighting of the Harbor Walk of Lights
Kick-off the holidays in Key West with the lighting of the Harbor Walk of Lights at the Key West Bight. 6:00 pm. Free.

November 27, 2016  Old Stone Concert Series presents: Messiah 
Organ, Piano and Timpani combine for a memorable performance to include several soloists. Starts 7 p.m., at Key West United Methodist Church, 600 Eaton St. Free admission.

December 7, 2016 
5th Annual POSH - Paws Often Steal Hearts

At the Audubon House 6:30 p.m. 305-797-1232

Decmber 2, 2016   
Holiday Harmonies
FKCC Keys Chorale, comprised of students in the Mixed Community Chorus class, will perform a free "Holiday Harmonies Under the Sky" concert at 7 p.m. at the Key West Campus.

December 3, 2016  
Key West Holiday Parade
City of Key West annual family-friendly parade. Starts at Bayview Park. Watch the parade from Truman Avenue or Duval Street. 7:00 pm. Free.

December 7, 2016 
Lighted Bike Parade

For Wesley House Toy Drive, 5:00 p.m. Bayview Park 305-809-5000

December 9, 2016 
Holiday Historic Inn Tour
Tour five festive properties decorated for the holidays and a sampling of holiday treats and holiday cheer. Tour includes trolley transportation. 6-8:00 pm. The Inns for tonight are The Mermaid & The Alligator, The Le Mer Hotel, The Dewey House, The Wicker Guesthouse and  The Alan Maltz Gallery. Tickets may be purchased by calling The Lodging office (305) 296-4959 or on the website any day prior to the tour each night.

December 9, 2016
  Pet Pictures with Santa hosted by All Animal Clinic
Look for Santa at the Christmas Tree at the foot of William Street. 6:00-8:00 pm.

December 10 - 18, 2016  
Nutcracker Key West

Set to the enchanting music of Tchaikovsky, the production tells the story of The Nutcracker with a Key West twist. Features original costumes and set.

December 10, 2016  
2nd Annual Parade of Paws & Holiday Bazaar 

Higgs Dog Park 10:00 a.m. - 2:00 p.m. 305-294-4857

** Change** December 14, 2016 
The Schooner Wharf Bar 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.

(Due to high winds, the date for the 26th annual Schooner Wharf Bar & Galley Lighted Boat Parade has been moved from Saturday, December 10 to Wednesday, December 14. The boats will begin parading at 8 p.m., but come early to enjoy the magical beauty of the Key West Harbor Walk of Lights with its array of shops, restaurants and watering-holes, charmingly decorated for the holidays. From 6-8 p.m., catch the House of Pan kids steel drum band as they perform holiday tunes on the Schooner Wharf stage, followed by more live holiday music by Raven Cooper and Friends)  



** Change** December 14, 2016  Sunset Watersports Lighted Boat Parade Watch

Ride with the Sunset Watersports for the parade on their beautifully decorated boat. There will be a live DJ and Free light appetizers, mixed well drinks, draft beer, wine, champagne, and soft drinks. 7:30 - 10:00  $59 adults $39 kids under 12. Call (305) 296-2554

** Change** December 14, 2016 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.

** Change** December 14, 2016 
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


** Change** December 14, 2016 Danger Charters Lighted Boat Parade Cruise

Ride in the parade boat or view form the water on a boat. Drinks and snacks ar provided. For more information please call 251-209-7469.


December 11, 2016 Cool Yule

St. Paul's Episcopal Church 401 Duval St. Featuring the Music Room Students and Guest Artists Skipper Kripitz, Joe Dallas, Othello Molineaux & Laura Thompson Free

December 16, 2016 
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 16, 2016 Holiday Historic Inn Tour
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 Westwinds Inn, The Island City House Hotel, The Southwinds Motel 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.


Returning in 2017  Violins in Motion 
An uplifting holiday musical performance at the plaza at Green and Elizabeth. 6:30-8:00 pm. Free.

December 18, 2016   Holiday Classic Car Show

Classic cars from every era on the Harbor Walk plaza at Greene & Elizabeth Streets. Noon-4:00 pm. Free. Collecting toys for children at the Monroe County Domesric Abuse Shelter.


December 18, 2016 Holiday Concert on the Beach

Enjoy holiday music by Joal rush and Chris Thomas on South Beach 5:30-7:30 pm. Free

December 25, 2016
  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

December 31, 2016 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 
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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