Starting Thanksgiving week and lasting all the way through the new year, with over 60,000 twinkling lights and lit palm trees, come visit the Key West Historic Seaportfor a fantastic holiday season where you can eat, drink, be merry, and make memories to last a lifetime!
The Lighting of the “Harbor Walk of Lights” – Wed, November 22
The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree. Lights come on at 6:00pm, holiday music starts at 5:00pm, and this year, it’s going to be an extra special lighting, with a heartfelt tribute to Jimmy Buffett and other surprises in store!
LOCATION: The Harbor Walk plaza at Greene & Elizabeth St. for best view.
Private Holiday Charter on Catamaran Echo!
Available from December 1 – January 15
Sailing every day starting as early as 9:00am, or wherever they have room in their schedule. Enjoy free-flowing Chandon Champagne, a world class 8 wine list, ice cold Beers, White Claws and savory holiday party food – all included with your reservation. Plus, all ages welcome! Enjoy a private charter holiday party for up to 14 guests with premium drinks, mimosas, Christmas cookies & choice of holiday food. Register here!
Key West Express – Holiday Gifting the Whole Year Through!
Escape, enjoy, and explore Key West with a gift that keeps on giving! KW Express Travel vouchers are the perfect gift for any occasion! PURCHASE ONE TODAY and SAVE $66.00 roundtrip during this limited time holiday promotion!
Conch Tour Train Holiday Lights Tours – December 8-23, 2023
Join the Conch Train for their annual holiday lights tour of the island. Take a one-hour tour of the city’s best lights, elaborately decorated houses and businesses with special holiday lights glasses! Call 305-294-5161 or visit their website to purchase tickets!
Pet Pictures with Santa™ – Fri, Dec. 1, 6:00-8:00pm
Hosted by The All Animal Clinic at the 16’ Nautical Christmas Tree at William St. Pictures by photographer Rob O’Neal are $25 (cash only) & benefit the local Boys & Girls Club! See photos here.
2023 Tree Trimming Party and Toy Drive at Schooner Wharf! – Sun, Dec. 3, 6:00 PM
Maritime merry makers will deck the halls & make dreams come true at the popular waterfront winter wonderland. Great PRIZES for the Best Handmade Ornaments! Click here for more details.
Schooner Wharf Bar & Galley and Absolute Vodka’s 32nd Annual Key West Lighted Boat Parade 2023
Saturday, December 9 – FREE. Music starts at 6:00pm and the parade starts at 8! Watch the parade all along the “Harbor Walk of Lights” at the Historic Seaport. Come early for live holiday music performances, dinner and drinks and to see the decked out holiday boats still in dock! Click here for more information and see how to enter your boat!
Be a participant in the 2023 The Lighted Parade aboard the Schooner Appledore II Parde Boat! The trip Includes: Premium beer, boutique wines, wines and soft drinks. Very Limited Seating!
Christmas Day Brunch Sail Aboard Schooner America 2.0 – Mon, Dec. 25 10:00am – 12:30pm
Enjoy Christmas morning the Key West way – sailing! This two-hour Christmas Day Brunch Sail features complimentary mimosas, Bloody Marys, wine, beer, soft drinks, and water. Brunch is provided, including spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudités, and other delicious Christmas day treats! Click here to register today!
2023 Holiday Classic Car Show at Conch Republic Seafood Co. – Sun, Dec. 17 FREE – 11am-3pm
LOCATION: Conch Republic Seafood Company – on the Harbor Walk of Lights at Greene St. Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter. VOTE for the “Peoples Choice” award for: BEST sports car, pick up, engine, interior, original & custom, pre & post 1950, 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!
New Years Eve Lowering of the Pirate Wench at Midnight at Schooner Wharf Bar!
Great Food, Holiday Drinks and LIVE Music! The party starts early in the day with 3 Local and National Acts. Party Favors – Champagne & Fun – The Unique Schooner Wharf Bar’s Seaport Tradition! LOCATED: The Harbor Walk of Lights at William St.