2023 Holiday Happenings in Key West
There’s just something about an island Christmas.
Yes, it’s 80 degrees and most of the time too hot to wear the typical holiday attire but one thing about Key West is they really know how to show up when it comes to the holiday spirit and there is always room to sparkle & shine!
Check out this list (courtesy of our friends at Island 106.9 Radio!) of holiday happenings this year in Key West :
✨Nov 22 – Dec 31: Harbor Walk of Lights
✨Dec 1: 3rd Annual Holiday Village & BeLighted Bike Ride
Takes off at 8 p.m. from the Truman Coffee Butler Amphitheater
✨Fri, Dec 1 & Sat, Dec 2: Free Santa Photos & Goodie Bags
The Key West Butterfly & Nature Conservatory
6pm - 8pm
✨Sat, Dec 2: Pet Pictures with the Grinch
Hank’s Hair of the Dog Saloon
11am – 2pm
✨Sat, Dec 2: Key West Hometown Holiday Parade
The parade begins at 7 p.m. at Truman Avenue and White Street, right next to Bayview Park, and then winds its way down Duval Street before concluding at Eaton Street.
✨Sun, Dec 3: Eaton Street Christmas Stroll
Stroll begins at St Paul’s Episcopal Church, 401 Duval Street at 4 pm.
A family-friendly holiday event! Keys Choral Arts presents a short program of sacred & secular music for this festive season.
✨Sun, Dec 3: “Holiday Classic Car Show”
Conch Republic Seafood
FREE 11:00am – 3:00pm
✨Fri, Dec 8: Annual Holiday Concert & Bazaar
Custom House Museum
5 pm to 9 pm – FREE
✨Fri, Dec 8: Stock Island Lighted Boat Parade
✨Sat, Dec 9: Key West Lighted Boat Parade
✨Sun, Dec 10: Christmas on the Farm
Monroe County Sheriff’s Office Animal Farm
1pm - 3pm
✨Fri, Dec 15: Shots and Photo Shots with Bad Santa
The Marker Key West Harbor Resort
6:00 pm - 8:00 pm
✨Dec 15-30: Winter Wonderland in Paradise
@Coffee Butler Amphitheater
Guests can glide on a custom ice skating rink, complemented by festive music and twinkling lights.
✨Sat, Dec 16: SantaCon Key West Pub Crawl
2pm - 9pm
✨Fri & Sat, Dec 15 & 16
Key West Burlesque Presents
The 12 Days of Stripmas
Key West Theater @ 7pm
✨Sat, Dec 16: A Positive Step 5K Rudolph Red Nose Run
8 am start
✨Sun, Dec 17: Menorah Lighting
Bayview Park @ 5:00pm
✨Dec 17 & 26: Key West Artisan Market
“Shop Local for the Holidays”
Higgs Beach, Indigenous Park
10am - 3pm
✨Dec, 25: Christmas Day Brunch Sail Aboard Schooner America 2.0
10am - 12pm
✨Dec 25: Holiday Jazz in the Gardens
The Gardens Hotel offers a festive poolside jazz performance
5pm - 7pm
