Top 5 Things to do at the Historic Seaport this Holiday Season

Header Image Photo Credit: Rob O’Neal (Left & Middle) –Schooner Wharf Bar (Right)

And just like that, 2018 is coming to an end! It’s time to roll out the colorful lights, stock up on gifts for everyone on your list and prepare for the holiday season. Key West and the Historic Seaport have its own holiday traditions. One of those traditions is kicking off the season with an official welcome of all the festivities in a family-fun way with the Harborwalk of Lights.

The Historic Seaport came alive on November 21, 2018 for the annual lighting of the Key West “Harborwalk of Lights.” Every evening, the harborwalk will shine with lights through New Year’s eve. The Historic Seaport backdrops itself into a truly magical winter wonderland. With over 61,000 lights, 58 lighted palm trees and an array of nautical displays, the harborwalk is sure to get you into the holiday spirit. Check out the top 5 things to do this month at the Historic Seaport and start planning your next trip down to Key West.

1. Tree Trimming Party

     Where: Schooner Wharf Bar

     When: December 2, 2018 at 5PM

Bring a handmade ornament to the tree trimming party and receive a free holiday drink. Ornaments will be added to Schooner Wharf Bar’s 8-foot tree and entered into a contest where you could win for Most Original, Most Nautical and Most Popular among the holiday crowd. Prizes will be awarded to winners. Please consider bringing a toy for Schooner Wharf’s annual toy drive that will be benefiting Toys for Tots and Angels – Just 4 Kids and receive a free holiday drink!

2. Pet Pictures with Santa

     Where: At the Nautical Christmas Tree at the end of William Street

     When: December 7, 2018 from 6PM-8PM

Santa is coming back to the Historic Seaport this year! Show your pet some love and bring them over to see Santa in front of the Nautical Christmas Tree at the end of William Street along the Harborwalk of Lights. The All Animal Clinic is hosting this event and all photo sales will benefit Boys and Girls Club of The Keys Area.

Photo Credit: Rob O’Neal

3. 28th Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade

     Where: Marina behind Schooner Wharf Bar

     When: December 15, 2018 at 6PM

Parade floats through the streets are fun and entertaining but are also pretty common. Key West and the Historic Seaport take parades to the next level with its tropical tribute to the season. Get the best view of the parade at the Historic Seaport and watch vessels ranging from kayaks, schooners, catamarans and fishing boats decked out in lights and other decorations. Begin the evening with holiday tunes and drinks at Schooner Wharf Bar and then experience the festive parade.

Photo Credit: Schooner Wharf Bar

4. Holiday Classic Car Show

     Where: Conch Republic Seafood Company

     When: December 16, 2018 from 11AM-3PM

Stop by the Holiday Classic Car Show  to see classic cars from every era decorated for the holidays. There will be awards given for Best Engine, Best Interior, Best Original & Custom, Best in Show and People’s Choice. Please bring an unwrapped toy for the Monroe County Domestic Abuse Shelter.

Photo Credit:

Schooner Wharf Bar Lowering of the Pirate Wench

5. “Lowering of the Pirate Wench” New Year’s Eve Celebration 

    Where: Schooner Wharf Bar

     When: December 21, 2018

The “Lowering of the Pirate Wench” is an annual Schooner Wharf

 Bar event where the co-owner (Evalena Worthington) descends dramatically from the towering mast of the tall ship America 2.0. Head on down to Key West for the best New Year’s celebration. This bash was rated by AOL as the #2 New Year’s party in the nation – second to Times Square in New York City. Be part of the tradition and enjoy live music, party favors and drink specials to ring in the New Year!

Photo Credit: Rob O’Neal

Now that you know what the top 5 things to do at the Historic Seaport are during this holiday season, all that’s left to do is book your holiday gateway! With affordable accommodations just steps from the Historic Seaport, the magic of the Seaport this time of year is that much closer.

Key West Historic Seaport: Your Gateway to Everything Key West!

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