Holiday Events in Key West - 2015

Holiday Events in Key West

Christmas in Key West may not mean hot coco, sleighs and snow, but that doesn’t stop this island from spreading holiday cheer. Here are a list of events happening throughout the 2015 holiday season in Key West.   
International Sand Sculpting Competition

The Casa Marina understands that when you celebrate Christmas in Key West, the beach is a must. That’s why they’re hosting this sandy spectacular! For four days, six internationally-renowned sculptors will compete for the best sand sculpture of the season. Mark this one in your calendars, as you’ll not want to miss this holiday extravaganza.

When: Wednesday, Nov. 25 (8-5:30pm) – Saturday, Nov. 28 (8-1pm)
Where: Casa Marina

Sunset Watersports Thanksgiving Sunset Dinner Cruise

Enjoy Thanksgiving dinner a little different this year. Set sail with Sunset Watersports and feast on a traditional turkey buffet while experiencing the best view of Key West’s famous sunset. Dance to live music and enjoy unlimited mixed drinks, draft beer, wine and champagne. For more information call (305) 296-2554.

Thanksgiving dinner cruise 2015 #

Schooner Wharf Bar’s Annual Lighted Boat Parade in Key West

Head down to William Street for the best light show on water of the season. All boats, big and small, are welcome to join the evening cruise for a small fee. Sunset Watersports is offering a lighted boat parade cruise, so you can be a part of this Key west occasion. The cruise will go from 6:30-9:30pm – $59 per person/$39 ages 6-12. Free draft beer, wine, champagne and soft drinks will be available. Including, a full liquor cash bar and festive finger foods.  For more information call (305) 296-2554.

When: Sunday, Dec. 12; 8pm
Where: Schooner Wharf Bar – 202 William Street

Lighted boat parade flyer #.pdf.2015

Holiday Parade Downtown

Join the locals as they stroll down Duval for this hometown, festive parade. Make sure you grab a spot on the route early, as this holiday event has become a community favorite for the last 15 years.

When: Saturday, Dec. 5; 7pm
Where: Route starts at the corner of Truman and White, down White to Duval, then Duval to Eaton.

Harbor Walk of Lights

A stroll along Key West Bight is beautiful on any evening, but add lights and holiday decorations and you’ve got yourself a special treat. The bright holiday lights make this boardwalk and its waterfront view absolutely picturesque.

When: Dec. 5 – Jan. 1
Where: Key West Bight – past Greene St., William St. and Margaret Street.

Holiday Historic Inn Tour

For something a little different, join the Key West Innkeepers Association for their annual evening tour of Key West’s favorite Victorian homes and historic estates, as they are decked out with holiday lights and decorations.

When: Dec. 12th or Dec. 19th
Where: Tickets and information about tours available at

9th Annual Gingerbread House Making Party

For the last 8 years, local law firm – The Smith Law Firm – hosts a gingerbread house making party open to families and kids of all ages. With an endless supply of yummy yuletide treats, everyone is welcome to build their own edible merry mansion.

When: Saturday, Dec. 19; (TBD – previous years 11-3pm)
Where: Garden of the Oldest House – 322 Duval Street

Holiday Events Key West - 2015 Season

16142496186_8fa05533c6_oNo, Key West doesn’t have a ball drop for New Years…. but we do drop a conch shell, high-heel and a pirate (explained more below):

Conch Shell Drop at Sloppy Joe’s Bar – 201 Duval St.

High-heel Shoe Drop from Bourbon Street Pub – 724 Duval St.

Pirate Leap from Schooner America 2.0 at Schooner Wharf – When the clock strikes midnight, watch pirate Evalena leap from the top of Schooner America 2.0’s 75-foot mast! – 202 William St.


Sunset Watersports – Key West’s Premier Activities, Attractions and Watersports Company
Key West Bight * Smathers Beach * Parrot Key Resort * Hurricane Hole Marina
Key West, FL 33040 (305) 296-2554


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