Posted: Nov 28, 2019
Christmas in Key West

​Ahhh - Key West for Christmas.  No galoshes. No gloves.  No wool hats yanked hard down ‘round red ears, shoulders pinched together and pointed into a bracing wind. Our breeze carries the scent of the sea, not shards of ice.  Riding a bike through the hidden alleys and lanes of Old Town to my favorite neighborhood haunts and eateries makes me happy and hungry just thinking about it. A Key West Christmas has festivities for kids and for grownups. On land and at sea. Free and for fee. But what festivities will there be, where and when?  You have a hotel or guesthouse to stay in but now what.  Ahhh - what indeed!

MARC House Christmas Tree


When it comes to Christmas Trees, Key West couldn't be farther from the source.  Many Key Westers decorate their palm trees, poinciana and other outdoor trees.  But what about inside?  A great place to buy Christmas Trees, plants and wreaths is the MARC House of Key West.


December 10 - If you're more interested in a table top tree, then the annual Keys Federal ReMARCable Table Top Christmas Tree auction on Tuesday, December 10th at 7PM is best.  Twenty beautiful trees, completely decorated, wrapped and ready to go will be auctioned beginning at 7PM at the Margueritaville Key West Resort and Marina.  Its a  Great time.  The Monroe Association for ReMARCable Citizens is a non-profit agency that serves adults within Monroe County who have developmental disabilities.  All purchases are tax deductibe.




Christmas in Paradise


December 4 - The Key West Lighted Bike Parade benefits Wesley House Family Services and begins and ends at Bayview Park. The Ride starts at 7pm.  FREE with donation of unwrapped child’s gift. Holiday all a-glow!!


December 7 - Feel like burning some serious calories before your Chirstmas feasting?! Try the Mack Cycle Key West Triathlon. TRIKW is proud to be in its 8th year. TRIKW has become the token season closer for many triathletes. With a maximum of 1,000 participants, its a big race on a little island


December 7 - Nothing says Christmas like a parade!  Every year the Key West Christmas Parade glides through Key West beginning at Bayview Park down Truman Avenue to Duval Street.  Music, floats, school bands with majorettes and sports cars aglow with lights and Christmas cheer!  City streets are lined with friends, families and well-wishers tossing candy and munching treats.  Small town fun for everyone.



December 6 & 13  - In its 17th year, the Holiday Historic Fest Inn Tour features twelve Old Town guesthouses; six different inns on each evening, from 6 - 8 pm. Tickets are required and can be purchased by calling the Lodging office at 305.296.4959 or purchased the night of the tour at the first property on the tour or at Trolley transportation is provided and food and drink will be at each Inn.  Of note, you can begin your tour at any guesthouse as the trolley runs continuously from guesthouse to guesthouse.


  1. Dec 6 - Hemingway Rum Co. Distillery* (201 Simonton St. - enter on Greene St.), Amsterdam's Curry Mansion Inn, The Weatherstation Inn, The Gardens Hotel and the Island City House Hotel.
  2. Dec 13 - Avalon Bed & Breakfast* (1317 Duval Street), Wicker Guesthouse, The Mermaid & The Alligator, Santa Maria Suites Resort and the Key West Butterfly & Nature Conservatory


This an Excellent opportunity to see some of the best Guesthouses and B&B's in Key West.



Boat Parade Schooner Wharf


December 14 - the 29th Annual Schooner Wharf Bar & Galley Lighted Boat Parade will be held on Saturday, December 14th at 8:00 p.m. in the Key West Bight and Harbor.  Kayaks, the US Coast Guard and mighty sailing ships vye for $25,000 in prizes and unlimited bragging rights.  Arrrgggh me mateys!

And if the hair of the dog still beckons, prizes will be given to the winners the following evening, Sunday, December 15th.

At 6 p.m. the world famous Bahama Village Music Program “House of Pan” steel band chimes in with Caribbean and calypso Christmas carols in the Harbor Walk area. Delightful.


B'nai Zion Key West



December 22 - Hanukkah.  Key West is home to one of Florida’s oldest Jewish communities – with Jews settling here when the City was incorporated in 1832. The first Key West Congregation, B’nai Zion was founded in 1887 and is located at 750 United St.  A a large menorah is lit in front of the synagogue each night of the holiday, with Rabbi and congregants gathering for the “festival of lights”.  Also, a latke and salmon feast is held on December 22 at 6PM - YUM!



St. Mary Star of the Sea




December 25 - Christmas is here!  Gifts and food and drink and joy to the world.  But hey! What are we really celebrating?! There are many beautiful churches in Key West, many dating to the turn of the (last) century.  Find one. Give thanks and wish a stranger a Merry Christmas. 


My church is a 160+ year old cornerstone of Catholic faith - Pre-K to 8th Grade education, food pantry and meal preparation services and charity in Key West - the Basilica of St. Mary Star of the Sea.  Please call 305.294.1018, #1 for a schedule of Masses.





Old Island Restoration Foundation



December 27 & 28 - The Old Island Restoration Foundation will be hosting its 60th Annual House Tour.  Each tour consists of 4 or 5 different houses with other tour dates also in January, February and March 2020. This is a great chance to see behind the walls of some of Key West's great homes and conch cottages and view the ecletic treasures captured by the travels, lifestyles and imaginations of Key Westers.


Tickets can be purchased here. Take this opportunity to see unique and personalized treasures not found in mass media magazines and obnoxious TV real estate shows.



If I was a Doberman, I'd make you wear t...


December 31 - Nope, not done yet.  One more parade, the Pooches Promenade, aka the 14th Annual Key West Dachshund Walk.  Its a weiner wonderland!!  Beginning around noon at the corner of Whitehead and Fleming streets in front of the Courthouse in Key West's historic downtown, there'll be a "short" walk from the 400 block of Fleming Street, along the 500 block of Duval Street along the entire one-block length of Appelrouth Lane.


Proof positive dogs are a ga-gillion dollar industry.


Rockets red glare



December 31 - OK Now.  Three places to blow out New Years Eve


First,  the lowering of the pirate wench from the mast of a tall ship at the Schooner Wharf Bar.

Second, the lowering of a giant manmade conch from the top of Sloppy Joe's Bar. 

And Third, female impersonator Sushi is lowered from the top of the New Orleans/Bourbon St. Pub. 


Not sure if fireworks will rocket from White St. pier.  Hopefully so.  Have a good time. 


Remember the Navy pilots creed when partying hardy - always party with a Buddy.  Otherwise - solo, loaded and late into the early morn could turn your good time into shine-ola.


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