Ensconce yourself within the ocean-inspired design of our rooms while looking out over the harbor and pools from your private balcony.
Oh, there's no place like Key West for the holidays, and there's no better place to enjoy the festivities than right here in paradise. Holiday happenings across the island include house tours, trolley tours, parades by land and sea, concerts, bike parades, and more! Here is the lineup of events for the 2019 Key West Holiday Season:
The lighting of the Key West “Harbor Walk of Lights”
Wednesday, November 27st at 6 pm
The Holiday Season in Key West kicks off on November 27 at the Historic Seaport Lighting of the Key West "Harbor Walk of Lights." Just steps from our resort at the Harbor Walk, Green and Elizabeth Street, is where you'll view the official lighting of the 2019 Key West Harbor Walk of Lights. Come celebrate the Maritime history of Key West with the lighting of the Fishing Buoy Christmas Tree, a real pine Nautical Christmas Tree, and the Lobster Trap Christmas Tree.
With over 61,000 lights and 58 lighted palm trees, 2019 will be bigger than ever! Stroll down the Harborwalk and enjoy the nautical displays, including ship's anchors, tropical birds, tropical fish, manatees, and animated sea turtles all lit up.
The Harborwalk of Lights is lit every evening through New Year's Eve!
Key West Lighted Bike Ride
Wednesday, December 4th - Bike Ride Begins at 7 pm
Oh, what fun!!! Decorate your bike, dress up, and join us for the Key West Lighted Bike Ride. The streets of Key West will glow as bikes are lit up to help gather needed toys for the struggling, working families of Key West for the holidays. This is a fun family event beginning with registration and check-in at 6 pm - at Bay View Park - and bike ride starting at 7 pm. Registration for the ride is one unwrapped toy for the Key West Holiday Helpers Toy Store.
5:00 pm Check-in at Bayview Park
5:00 – 7:00 pm Helmet Fitting | Picture with Santa | Milk & Cookies
7:00 pm Ride begins
The Bike Parade Ends at Mary Ellen's on Applerouth Lane for a Block Party And all registered Lighted Bike Riders enter FREE – with a wrist band.
There's a new route this year! Learn more about the Lighted Bike Parade by visiting Wesley House Family Services.
Conch Tour Train and Trolley Holiday Lights Tour
This is a must-see and do during the holiday season. All aboard Old Town Trolley's Holiday Lights and Sights Trolley Tour. This is your opportunity to get in the holiday spirit with us see our island all decked out for the holidays. There will be caroling, apple cider and cookies, and complimentary magical viewing glasses. The Conch Tour Train Holiday Lights Tour is 60 minutes long.
Adult (ages 13 and up) : $19.95
Children - 4-12 years old. $10.95
Ages 3 and under ride free
Key West Holiday Parade
Saturday, December 7th - Parade starts at 7 pm
Oh, what fun!!! Join us for the City of Key West Holiday Parade on Saturday, December 7, and find out why this is the best local parade of the year. Marching Bands, floats, school groups, trolleys, cars, bikes, and local businesses gather together to celebrate the holiday season. This is one of our favorite Key West parades fun for everyone. Children sit curbside with open eyes waiting for Santa to make his debut. The parade route proceeds down Truman Ave to Duval, where it takes a right and continues on to Eaton Street.
The best viewing spots are along Duval Street and Truman Avenue.
12th Annual Rudolph Red Nose Run!
Saturday, December 14th - 7 am - 10 am
Run for a good cause at the 12th Annual 5k Rudolph Red Nose Run to benefit for A Positive Step of Monroe County. Enjoy breathtaking views as you run or walk to the Southernmost Point of the United States. Huge Silent auction, raffle, and awards following the race.
RACE Date And Time
Sat, December 14, 2019
7:00 am – 10:00 am EST
Location: Southernmost Beach Cafe, 1405 Duval Street | Key West, FL 33040
Sign up, register, and run with the locals and Rudolph to benefit this good cause!
Learn more about this event.
Photo credit: Schooner Wharf Bar
Schooner Wharf Bar 29th Annual Lighted Boat Parade
Saturday, December 14th - Parade starts at 8 pm
You don't have to go far to enjoy this parade! Right outside our resort, you'll have the best viewing for the 29th Annual Lighted Boat Parade. The Key West Historic Seaport and harbor areas will be lit up as the holiday lights decorate the vessels from rowboats to tall ships. Welcome to the Schooner Wharf Bar Annual Lighted Boat Parade!
The Judges Stand is located at Schooner Wharf Bar, so hang out, grab a drink, enjoy the music, and holiday festivities as the boats pass by in paradise. The parade is scheduled to begin at 8 pm, and there will be festivities starting at 6 pm with live music and holiday happenings all around the Historic Seaport.
Find out more about the 29th Annual Schooner Wharf Bar Annual Lighted Boat Parade!
KWAHS Holiday Concert & Bazaar
December 18th - 5pm - 9pm
The Key West Art & Historical Society invited you to the Fourth Annual Holiday Concert & Bazaar. The Custom House Museum will be the canvas for a spectacular holiday light show while local artisans sell their unique wares and musicians perform with Key West's finest Choirs. There will be plenty of food and festive libations while Santa offers selfies with anyone, regardless of whether they have been naughty or nice. Free Event.
The Custom House is located at 281 Front Street, Key West.
Head over to the Key West Theater on Eaton Street for a truly unique holiday concert and rest assured, this won't be your average Christmas concert!
Get ready for an evening of rocking out to your favorite Christmas classics as well as some unexpected surprises... The Christmas Rocks band will be lead by Joe Tripp & Destiny Montgomery and include our favorite local musicians!
Tickets for this event are $25 to $40. Get Tickets to Christmas Rocks! At the Key West Theater.
The Key West Theater is located at 512 Eaton Street, Key West.
60th Annual Home Tours “Holiday Style”
December 27th & 28th, 3 pm - 7 pm each day
60th Annual Home Tours "Holiday Style" is your opportunity to tour festively dressed Key West homes and gardens. Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3–7 pm each day. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation's museum and programs.
Get Tickets to the 60th Annual Home Tours "Holiday Style"
15th Annual Key West Dachshund Walk
December 31st at NOON
It's a "wiener wonderland" in Key West when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. This is another fun quirky parade with our pups as the stars of the show. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.
November 21, 2023
As the winter holidays approach, Key West embraces the festive season in its own unique way.
October 13, 2023
The excitement is brewing as fall has arrived, and now it's time to get ready for two of our favorite fall festivals and events.
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