Illuminating the Season: The Key West Historic Seaport Bight Before Christmas!

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 Seaport for a fantastic holiday season where you can eat, drink, be merry, and make memories to last a lifetime!

key west harborwalk of lights


The Lighting of the 2023 “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 and Elizabeth St. for the 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!

Echo Catamaran

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!

Key West Express

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!

santa and girl with pet

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.

Schooner Appledore Lighted Boat Parade Party – Sat, Dec. 9 – 7:30-9:30pm

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!

Holiday Boat Parade Image. Boat is covered in holiday lights that resemble a train.

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!

Schooner Wharf Bar Tree Trimming Party Logo


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!

2023 Holiday Classic Car Show at Conch Republic Seafood Company – Sun, Dec. 17 FREE – 11:00am-3:00pm

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!

two people standing outside of a red car in a car show.

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.

Finally, for more information on all of the exciting holiday festivities taking place during this most wonderful time of year, visit our website and!

‘Twas the Bight before Christmas, and we look forward to celebrating with you all season long!

lit palm trees kwhs harborwalk of lights

Key West Historic Seaport and Key West Bight Marina:

Your Gateway to Everything Key West!

key west historic seaport logo