Key West Hannukah and Christmas Holidays 2022

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 Hannukah and Christmas holidays full of sun and artistic events, Key West is the perfect place.

11/23/2022 to 12/28/2022

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 2022 Christmas and holiday events.

Wednesday, November 23, 2022 – Lighting up the Waterfront!!

Lighting of the “Harbor Walk of Lights”
Lights come on at 6:00pm, holiday music starts at 5:00pm – FREE

LOCATION: The 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. Light sculptures of ship’s anchors, tropical birds, tropical fish, a flock of pink flamingos, jolly pelicans, merry manatees, animated sea turtles and dancing dolphins, and even a festive moray eel.

Monday, November 28, 2022 -Christmas Tree Lighting – FREE

At 6pm the Monday after Thanksgiving — Monday, Nov. 28, — the city will hold the tree lighting ceremony. Always a family favorite, this ceremony will feature the Horace O’Bryant School Jazz Band, and culminate with the arrival of Santa.  

LOCATION:  Bayview Park, 1320 Truman Avenue

Tuesday, November 29, 2022 – Menorah Lighting – FREE

At 5:30 p.m. on Tuesday, Nov. 29, Rabbis Shimon Dudai and Jacob Zucker will perform the Lighting of the Menorah.

LOCATION:  Bayview Park, 1320 Truman Avenue

Saturday, December 3, 2022 – Key West City “Hometown Holiday Parade”

Starts at 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!

Sunday, December 4, 2022 – 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!

12/03/2022 thru 12/22/2022 – Old Town Trolley Holiday Lights & Sights Tours – $

No need to gas-up the snowblower 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 

Friday, December 9, 2022 – 5th Annual Holiday Concert & Bazaar – from 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.

Saturday, December 10, 2022 – 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. 

Saturday, December 17, 2022 – A Positive Step 5K Rudolph Red Nose Run – the PJ Edition – 7am check-in/ 8am start time – 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.

12/18 & 26/2022 – Key West Artisan Market “Shop Local for the Holidays” – FREE

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,

Tuesday, December 27 & Wednesday the 28, 2022 – Key West Holiday Home Tours from – 10 am to 4 pm – $

The annual Key West Home Tours are one of the longest running tours in America and have been conducted by the Old Island Restoration Foundation since 1960. Each tour features 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 truly a wonderful time of year to visit our special island. We hope to see you on Key West for the Holiday Season 2022 and to ring in 2023!