Meet Me at the Key West Historic Seaport! 

November 27th officially kicked off the 2019 Key West Historic Seaport Holiday Season with the Lighting of the Harborwalk as part of the Key West Holiday Festival and the “Bight” Before Christmas!

Locals and visitors gathered at the Key West Historic Seaport’s famous Harborwalk Waterfront to watch the lighting of the Key West “Harborwalk of Lights.” With over 61,000 twinkling lights and 58 decorated palm trees, the 2019 Lighting of the Harborwalk was a true testament of what’s to come this holiday season! 

For a detailed list of all the amazing upcoming events happening at the Historic Seaport, please see below. 

  • Schooner Wharf Bar & Galley Tree Trimming Party 

The rules are simple — Bring in one nautical Christmas ornament to Schooner Wharf’s Annual Tree Trimming party in exchange for eggnog with rum! Each ornament that is brought in will automatically be entered to win the prize for most original, most nautical AND most popular! From live music to refreshing cocktails and some of the best seafood at the Historic Seaport, you do not want to miss this amazing event! Receive a free holiday beverage by bringing in a toy for Toys For Tots & Angels or Just For Kids. Click here for more information >> Schooner Wharf Tree Trimming Party 

  • Pet Pictures with Santa Claus

Benefiting the Key West Boys and Girls Club, come out on December 6th for the Historic Seaport’s Annual Pet Pictures with Santa! Starting at 6 PM come get your very own professional, furry, family photo under the “Nautical Christmas Tree” on William Street. Your holiday furry holiday photo awaits you! Click here for more information >> Pet Pictures with Santa

  • Hometown Holiday Parade 

Starting at 7 PM on December 7th, come celebrate Key West’s Annual Hometown Holiday Parade! The parade will start on Truman Avenue, proceed down Duval Street and end on Eaton Street.  This is one of the most charming hometown parades you’ll ever see with holiday floats and a ton of fun for kids of all ages! Of course, Santa will be making a guest appearance! Click here for more information >> Hometown Holiday Parade

  • Key West Lighted Boat Parade 

It is no secret that Key West and the Historic Seaport can throw a good party! With the 29th Annual Key West Lighted Boat Parade being no different, come and let us show you what our little island is made of by joining us for this historic event starting on December 14th at 8 PM! Whether you feel like entering your own vessel, chartering your private front-row seat or sitting alongside our famous Harborwalk Waterfront, it is safe to say the Historic Seaport has all your viewing pleasure covered! 

  • Conch Republic Seafood Company Holiday Classic Car Show 

The Conch Republic Seafood Companies Annual Holiday Classic Car Show is set for December 15th! Visitors and locals are welcomed to come and see numerous classic cars from every era decked out for the holidays starting at 11 AM. Come join for a good cause and bring an unwrapped toy for the Domestic Abuse Shelter of the Florida Keys. Click here for more information >> Conch Republic Holiday Classic Car Show.

  • Violins in Motion 

On the Harborwalk of Lights, under the “Fishing Buoy Christmas Tree”, come and listen to amazing Children’s Group performing your favorite holiday classics at 6:30 PM. Come listen to their annual Violins in Motion performed by aspiring musicians ages 6 to 18 years old. There truly is no sweeter way to get into the Christmas spirit! Click here for more information >> Violins in Motion.

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