Key West Hanukkah and Christmas Holidays 2023

Enjoy the Warmth of the Holidays in Key West

Key West is a special place to enjoy the holiday season. During the holidays, Key West lights up with fun festivities and offers a unique atmosphere to celebrate this exciting time of year. If you’re looking to escape the cold and enjoy the Hanukkah and Christmas holidays full of sun and artistic events; Key West is the perfect place for you and yours to gather and create very special holiday memories!

11/22/2023 to 12/30/2023

Over the past 20+ years, we’ve created hundreds of Holiday Season Vacations in Key West. We love sharing this special time of year with our guests. On this page, we highlight some of Key West’s best 2023 Christmas and holiday events.

Wed, Nov 22 through New Year’s Eve

Lighting up the Waterfront!!

Lighting of the “Harbor Walk of Lights”
Lights come on at 6 pm

LOCATION: Start anywhere along the harbor, but don’t miss Harbor Walk plaza at Greene and Elizabeth St. for the best view. Enjoy creative holiday displays and thousands of lights honoring the “Maritime History of Key West”. 

The Key West “Harbor Walk of Lights” main features include:  20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree.  Walk along the water’s edge for a merry infusion of colorful lights and nautical holiday displays.

Fri, Dec 1  4 pm to 8 pm

Holiday Village and BeLighted Bike Ride

Wesley House Family Services Holiday Village and BeLighted Bike Ride at the Coffee Butler Amphitheater at the Truman Waterfront Park. It starts with a family-friendly party with Santa Claus, music, crafts, games, food trucks, treats for the kids, and a “Best BeLighted Bike” contest. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House Family Services. Belighted Bike Ride through the streets of Key West departs at 8 pm.

Fri, Dec 1 & Sat, Dec 2 – 6 pm to 8 pm

The Key West Butterfly &

Nature Conservatory Presents

Free Santa Photos & Goodie Bags

LOCATION:  1316 Duval St

Sat, Dec 2

11 am – 2 pm

The ORIGINAL Pet Pictures

with the Grinch!

Presented by Bone Island Dog Spa


Hank’s Hair of the Dog Saloon

Help raise funds for River’s Wish Senior Dog Sanctuary.  Enjoy our silent auction, cocktails, mocktails and great food from Garbo’s Grill! The first 40 attendees get a free doggie gift bag!

All proceeds go to River’s Wish nonprofit. Help sweet senior dogs while you get a festive picture with the grinch and your pet. 

LOCATION: Hank’s Hair Of The Dog Saloon, 409 Caroline St

Sat, Dec 2

Key West City “Hometown Holiday Parade”

7:00pm – FREE

LOCATION: Parade starts on Truman Ave (at White St) then proceeds to Duval St, then down Duval St ending at Eaton St. The most charming hometown parade you’ll ever see with holiday floats, and throngs of children of all ages. Of course, Santa will make a guest appearance!

Dec 2 through Dec 21

Old Town Trolley

Holiday Lights & Sights Tours

No need to gas-up the snow blower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Lights & Sights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition.6:30pm & 7:15pm, No tours offered December 5, 2021*
Phone 305-296-6688 

Sun, Dec 3 at 4PM

Eaton Street Christmas Stroll

A family friendly holiday event! Keys Choral Arts presents a short program of sacred & secular music for this festive season. Admission is FREE. You may reserve tickets for guaranteed seating online at or at the box office.

LOCATION: Stroll begins at St Paul’s Episcopal Church, 401 Duval Street at 4pm.

Sun, Dec 3

Conch Republic Seafood

“Holiday Classic Car Show”

FREE • 11:00am – 3:00pm

LOCATION: Conch Republic Seafood Company – on the Harbor Walk of Lights at Greene St.

TOY DRIVE: Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter.

VOTE for the “People’s Choice” award for: BEST engine, interior, original & custom, Best in Show.  See classic cars from every era decked out for the holidays!  Run by the Florida Keys Southernmost Car Club.  Non-member cars may enter same day FREE with an unwrapped toy!

Taste of Stock Island – Holiday Edition!

Thurs, Dec 7

4 pm – 7:30 pm

Our Signature Stock Island Event- With a Holiday Twist!

Board the Old Town Trolley for a culinary tour of Stock Island favorite restaurants. At each stop you will enjoy a specially selected small plate and beverage paring.

Stops Include: Matt’s Sock Island Kitchen, Sloppy Joe’s Dockside, Salty Oyster, El Mocho, Roostica, Hogfish Bar & Grill, Fishbusterz, The Docks, Yellowfin @ Oceans Edge and the newly opened Cayo Hueso Brewing Company

Fri, Dec 8

5th Annual Holiday Concert & Bazaar

5pm to 9pm – FREE

Join the Key West Art & Historical Society on the sweeping historic porch and walkway of the Custom House Museum.  The celebration will feature some of Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show of magical vector projections on the face of the Museum.  Browse hundreds of unique gift options while enjoying the music and refreshments on and around the island’s architectural crown jewel. 

305-295-6615 ext. 114

Sat, Dec 9

32nd Annual Key West Lighted Boat Parade FREE

Schooner Wharf Bar & Galley and Absolute Vodka Present this annual popular event.   

Music starts at 6:00pm, Parade starts at 8:00pm.

LOCATION: Viewing all along the “Harbor Walk of Lights” at the Historic Seaport. Reviewing stand is at the Schooner Wharf Bar and Galley.  Arrive early for live holiday music performances, dinner and drinks. 

For more information contact Schooner Wharf Bar, 305-292-3302 

Sun, Dec 10

1 to 3 pm

Christmas on the Farm

Monroe County Sheriff’s Office Animal Farm invites everyone to its annual Christmas on the Farm. 5501 College Road, Stock Island. Donations welcomed.

Tue, Dec 12th at 7pm

Keys Choral Arts presents the Hodie, Hodie!

Hodie, Hodie! Key Choral Arts Christmas Concert for 2023, in collaboration with the Southernmost Chamber Music Society, will be on Tuesday, December 12, 2023 at 7pm at St. Pauls’ Episcopal Church in Key West. Tickets may be purchased at the door or online at!

Fri, Dec 15

Holiday Historic Inn Tours – Night 2,

6 pm to 8 pm

Visit and tour four decorated island locales: Hemingway’s Library at Papa’s Pilar Distillery, the Marquesa Hotel, The Gardens Hotel, and Island City House.

Fri, Dec 15

6:00 pm to 8:00 pm

Shots and Photo Shots with Bad Santa!

Bad Santa encourages an early Christmas celebration at The Marker Key West Harbor Resort! $5 shots include a pro photographer’s shot with Bad Santa!  A portion of the proceeds will benefit the Highgate Charitable Foundation; Aga Khan Foundation | Save The Children.

LOCATION:  The Marker Key West Harbor Resort, 200 William St

Sat, Dec 16 – 2 pm to 9 pm

SantaCon Key West Pub Crawl

The official, ticketed pub crawl is sold out, but everyone is encouraged to fill the island’s streets with Santa’s! Join the Merriest Event of the year as we turn Key West into the Southernmost North Pole. We want the whitest beards and reddest suits. This is going to be the best winter crawl you have ever attended, strap on your boots (slip on your flip-flops) and grab your sleighs (bikes, motorized ice chests, etc.) and be your jolliest elf self!

Fri & Sat, Dec 15 & 16

Doors Open 7 pm – 8 pm Curtain

Key West Burlesque Presents

The 12 Days of Stripmas

Enter a world of flirtatious, festive fun as Key West Burlesque brings the classic holiday song, The 12 Days of Christmas, to life! The Victorian style extravaganza combines the talents of world class burlesque performers with tongue-in-cheek comedy to create an extraordinary show! The highly interactive production features a cast that is sure to dazzle and delight every audience member while stripping bare and spreading holiday cheer! Questions? Please email

LOCATION: Key West Theater, 512 Eaton Street

Sat, Dec 16

A Positive Step 5K Rudolph Red Nose Run

The PJ Edition – 7am check-in/ 8am start

Minimum Donation $ – FREE to Cheer on Participants

 Don your festive holiday jammies for this annual walk/ run starting and ending at the Southernmost Beach Café, 1405 Duval Street.  Runners and walkers of all ages and abilities are welcome to participate; first 100 registrants receive a free t-shirt. Presented by A Positive Step of Monroe County, a 501(c)(3) non-profit organization serving Monroe County’s highest risk kids and their families since 1999 and the Key West Southernmost Runners Club.  After the “race”, enjoy refreshments, prizes and a fabulous silent auction.  Cheer on participants along the route:  Race begins at Southernmost Beach Café, right on South Street, to Casa Marina, past Higgs Beach and White Street Pier to a turnaround point and back.  305-304-0091

Sun, Dec 17

Menorah Lighting – FREE

At 5:00 pm, Rabbis Shimon Dudai and Jacob Zucker will perform the Lighting of the Menorah.

LOCATION: Bayview Park, 1320 Truman Avenue

December 17 & 26, 2023

Key West Artisan Market

“Shop Local for the Holidays”

Higgs Beach, Indigenous Park from 10am to 3pm The show will be stocked with keys-made items perfect for gift giving this holiday season. Free entry, free parking. Please BYOB (bring your own bags). Contact: Sean Krikorian, T: 305-294-7994,

Dec, 25 – 10 am to 4 pm

Key West Christmas Ultimate Adventure H2.0

I’m Dreaming of an Aqua Blue Christmas… Get ready to set sail on one of Fury’s spacious catamarans offering a Holiday Menu, Complimentary Beverages, Snorkeling North America’s Only Living Coral Reef, Parasailing, Jet Skiing (Double Rider), Banana Boat Riding and enjoying Key West’s Largest Ocean Water Park with Over 3,500 sq. ft. of connected inflatable water toys, the Action Tower, Monkey Bars, Water Slide & more!

LOCATION: Fury Water Adventures Key West, 631 Greene Street

Dec, 25 – 10 am to 12 pm

Christmas Day Brunch Sail Aboard Schooner America 2.0

Enjoy Christmas morning the Key West way – sailing!  Enjoy complimentary mimosas, Bloody Marys, wine, beer, soft drinks, spiraled ham, bagels, pastries, meats, cheeses, smoked salmon, crudités, and other delicious Christmas day treats!

Mon, Dec 25 – 5 pm to 7 pm

Holiday Jazz in the Gardens

The Gardens Hotel offers a festive poolside jazz performance. Free Admission & Cash Bar

Tues, Dec 26 &

Wed, Dec 27

Key West Holiday Home Tours

10 am to 4 pm

The annual Key West Home Tours feature lovely homes and gardens reflecting the varied tastes and originality of their owners.  You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more.  305-294-9501 for information and tickets or visit

the Oldest House Museum Store, 322 Duval Street.

Thanks for your interest in Key West during the Holidays. This is a wonderful time of year to visit our special island. We hope to see you on Key West for the Holiday Season 2023 and to ring in 2024!

Visit HERE for our list of some of the best

New Year’s Celebrations on the island!