Key West Christmas Events – 2014

Santa and Indiana Bones at Pet Pictures with Santa at the Bight.
Santa and Indiana Bones at Pet Pictures with Santa at the Bight.

Key West might not be cold and snowy, but Christmas is almost here and Key West residents really get into the holiday spirit! If you are visiting Key West in December, here are a few events that celebrate the holidays. From shopping to song, you will find a slew of things to do and see that will get you ready for Christmas! One of my favorite holiday events is Pet Pictures with Santa; Indiana Bones is a real ham and loves getting his photo taken.

Wednesday, December 3
  • REMARCABLE Keys Federal Table Top Tree Auction – At the Westin Ballroom. Doors open at 5pm and the auction begins at 7pm with Mr. Tom Luna acting as auctioneer. Help a great local cause and attend!
  • Tis the Season at the Pier House – Christmas Benefit Jazz concert and Dinner. 7pm – 10pm. $60 per person plus gratuity. Contact Adele at 305-295-3201 for reservations.
Thursday, December 4

  • The Lighting of the Nautical Harbor Walk of Lights – FREE – 6:00pm – Gather on the Harbor Walk at Green St. to Kick-off the 2014 KW “Bight” Before Christmas Holiday Celebration. The main features will light up this night, including the the Trap Float Christmas Tree, a fresh pine Nautical Christmas Tree and the Lobster Float Christmas Tree. Then stroll the Harbor Walk of Lights for a merry infusion of holiday shopping, water sports gift certificates, great dining and seasonal spirits. The Harbor Walk of Lights is lit every evening through new year’s eve.

Friday, December 5   

  • Upper Duval Street Holiday Stroll – Visit the quieter end of Duval Street and visit shops and galleries. Frangipani featuring Jessica Wilson & Sandy Kaster. Sodu is having a holiday sale.
  • Keys Chorale Holiday Harmonies Concert – This free outdoor concert at Florida Keys Community College starts at 7pm.  Listen to holiday tunes while you enjoy seasonal treats that will be for sale benefitting the college’s residence hall. Feel free to bring chairs, blankets, and snacks.

Saturday, December 6 

  • Southernmost Coconut Castaways Christmas Party! Pincher’s Crab Shack from 1-4pm. Santa will be there at the start too! Bring a new, unwrapped gift for a teen at Wesley House and an ornament too for an ornament exchange. 
  • Key West City Hometown Holiday Parade – FREE – Starts at 7:00pm on Truman Ave. at White St. – Starting at Truman Ave. and White St., then proceeding down Duval St. and ending at Eaton St.  The most charming hometown parade you’ll ever see with holiday floats, and tons of kids of all ages. Of course Santa will make a guest appearance.

Sunday, December 7

  • Annual Celebrate the Season Art Opening Reception – Key West Art Center. From 5-7pm. Call 305-294-1241 for more information.
  • Wine on the Water Holiday Party – Enjoy a sunset sail aboard the Fury catamaran with a five course culinary fare prepared by chef Jose Hernandez of Santiago’s Bodega. There will be live music and a raffle too! registration starts at 4:30pm at the Historic Seaport. $85 per person. Call 305-598-3752 for more information or get tickets online at

Sunday, December 7 & 14 & 21

  • 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.

Wednesday, December 10

  • Lighted Bike Parade – For the Wesley House Toy Drive. Meet at Bayview Park at 5pm. 6:30 is ride start time. You can register online at Bring your bike helmet and a new unwrapped toy for the toy drive.
  • Holiday Wish List Book Bites at he Key West Library. Join us at 5pm with a list of the books that have made an impression on you this year. Contact Allison at 305-292-3595 for more information.

December 10 & 21

  • Holiday Wind & Wine – Join Danger Charters for a festive wine tasting on the water. Featuring fine wine and gourmet appetizers. 6-8:00 pm

Thursday, December 11

  • Christmas Cookie Swap Seminar – $30.00 per person – 5:30pm at the Restaurant Store. Pick your favorite cookie and bake enough to share (6 dozen) along wight he recipe. Wine provided by Premier beverages and bottles will be for sale. Call 305-294-7994 for register. Limited to 25 participants.

Friday, December 12 & 19 

  • Key West Holiday Historic Inn Tour – 6:00 – 8:00pm – Click here for ticket info.  Key West is known for its beautiful historic inns, and the Holiday Historic Inn Tour is the perfect way to visit these magnificent properties decorated for the season, featuring art, fine food from top local restaurants and holiday libations at each stop.

Saturday, December 13 

  • 24th annual Key West Lighted Boat Parade – FREE – Parade starts at 8:00pm. Viewing all along the Harbor Walk of Lights.
  • Sebago Lighted Boat Parade Cruise – Participate in the action aboard Sebago Schooner Appledore II, or cheer from a front row seat on the water. Drinks and appetizers included! 7:30 – 9:30pm. For reservations call 305-292-7212.
  • Catamaran Echo Lighted Boat Parade “Santa Hat Party” – Enjoy front row seats on the water for the Lighted Boat Parade. Free Santa Hats for everyone!  Drinks and appetizers included. 7:30 – 9:30pm. For reservations call 305-292-7212.

December 14

  • Christmas on the Farm – 1 to 3 pm. Bring the family to enjoy animals and activities. And get your picture taken with Santa Clause! Free Event!

December 14 & 18 & 19 & 20 & 21 

  • Nutcracker Key West click for more info. 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.

Tuesday, December 16

  • Happy Christmas showing at the Key West Library at 3:30pm.

Wednesday, December 17

  • Key West Parrot Head Holiday Party. 6:00PM at the Hard Rock Cafe. All welcome!

Friday, December 19 

  • Pet Pictures with Santa TM – Hosted by The All Animal Clinic – FREE to attend. 5:30 – 8:00pm – Look for Santa at the Christmas tree at the foot of William St. on the Harbor Walk of Lights.
  • Snorkeling with Santa – Festive snorkeling trip to the reef. Fundraiser for Wesley House. 5-7:00 pm.

December 19-13

  • Key West Holiday Lights Tour with Old Town Trolley! Tours depart from Mallory Square at 6:00 p.m. December 19th through 23rd! The elves at the Old Town Trolley have scouted the island for the best lights that will put you in the holiday spirit.

Saturday, December 20

  • Santa visits the Key West Library at 1pm, so bring your cameras! Followed by a teen Christmas Party!
  • “Violins in Motion” Holiday Concert by children – 6:30 – 8:00pm – FREE – An uplifting holiday musical performance on the plaza at Green & Elizabeth Streets, under the decorated Lobster Float Tree on the Harbor Walk of Lights.

Sunday, December 21 

  • Holiday Classic Car Show – FREE – 12:00 – 4:00pm – Collecting unwrapped toys for the Domestic Abuse Shelter LOCATION: Main Seaport parking lot – Caroline & Margaret St. Classic cars from every era in competition and decked out for the holidays.  ALL BUSINESSES AROUND THE CAR SHOW AREA ARE OPEN FOR GREAT KEY WEST SHOPPING, FOOD AND LIBATIONS!      
  • St.Paul’s Episcopal Church Annual Christmas Concert – $20 – Starts at 7:30pm. For tickets call 305-296-5142.
  • Bring your kids by Turtle Kraals for pictures with Santa from 12:30-3:00pm!  

Tuesday, December 23

  • Merry Friggen Christmas is showing at the Key West Library at 3:30pm.

See what else is happening on the island during your visit by checking out our Key West Events Calendar, and for other things to do and see in our island city, go to our Key West Web Site.

Before making your reservations for Christmas dinner check out our restaurant reviews!

Feel free to Email Me if you have any questions about Key West!!
Island Genn
Key West Concierge

About the author: Island Genn

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