The Lighting of the 2024 “Harbor Walk of Lights” – Wednesday, Nov. 27 – Free

Come participate in the main Harbor Walk Lighting at the 2024 “Fishing Buoy Christmas Tree”! Lights come on at 6:00pm and holiday music starts at 5:00pm at Greene and Elizabeth St. Plaza. Santa and Mrs. Claus will be making a NICE list and passing out treats!

**SECOND lighting of the 2024 “Lobster Trap Christmas Tree” – Lights come on at 7:00pm, holiday music starts at 6:00pm – Margaret St. Plaza (Old Lands End Village).

There will be holiday cookies and candy canes for the children! The Harbor Walk of Lights is on every night from Thanksgiving eve through New Year’s eve!

The lighting of the Harbor Walk will also kick off the “Cheryl Cates Toy Drive.” Bring a toy, or toys will be available at the “Imagination Station” table to purchase and donate a toy. ALSO, be there for a special announcement from the Cheryl Cates Toy Drive!

Private Holiday Charter on Catamaran Echo!

Available from December 1 – January 15

Private 2 hour Sail – Morning or Afternoon cruise. 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

Join the Conch Tour 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™ – Thurs, Dec. 5, 6:00pm-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.

2024 Tree Trimming Party and Toy Drive at Schooner Wharf! Sun, Dec. 1

Starting at 6:00PM – LOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St.

Maritime merry makers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Great PRIZES for the Best Handmade Ornaments that are:

• Most Original
• Most Nautical
• Most Popular with the holiday crowd

All tree trimmers will be treated to a free holiday cocktail — eggnog, hot apple jack or Swedish Glogg.

Then step into Santa’s southernmost workshop at Schooner Wharf. Share the holiday spirit, as local artists and authors sign and sell ORIGINAL WORKS for HOLIDAY GIFT GIVING.

Bring a donation for the “Cheryl Cates Memorial Toy Drive” by Angles Just 4 Kids! Each of Santa’s helpers who donates an unwrapped gift will also receive a free holiday drink from Schooner Wharf Bar.

Some favorite local musicians will be playing Holiday Tunes, Reggae, and Calypso with the island sound of Steel Drums to round out the festivities.

Schooner Wharf Bar and Absolute Vodka’s Annual Key West Lighted Boat Parade 2024 – Sat, Dec. 14

Saturday, December 14 – 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!

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!

2024 Holiday Classic Car Show at Conch Republic Seafood Co. – Sun, Dec. 15 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 Key West Historic 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 www.KeyWestChristmas.org!

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

Key West Historic Seaport and Key West Bight Marina:

Your Gateway to Everything Key West!