A Key West Christmas: Top Recommendations

Want a break from the cold this Christmas? Want to go to a town where real people live? Where you’ll be greeted on the street-often with a huge smile and the comment, “another perfect day in paradise”?

Yes, total strangers will say this to you in Key West.

Key West is quirky and cozy. It offers music, art, theatre, and history. It also offers a Saturday night feel every night of the week on Duval Street. Throughout the month of December there are seasonal celebrations to make a Key West Christmas special. Events like the lighting of the Harbor Walk of Lights, tours of historic decorated inns, and a holiday parade. And there’s more…

Duval Street in the early morning.

Six recommendations for a festive Key West Christmas

1) Key West Holiday Parade-Dec. 5

It’s the annual hometown parade complete with marching groups and floats presented by churches, civic organizations, businesses, and neighborhood and school groups.

2) Hot Pink Holidays-Dec. 3-6

LGBT Hot Pink Holidays is full of festive activities and special retail opportunities on the island. Events include holiday lights tours, a hometown holiday parade experience, and Christmas caroling.

3) Schooner Wharf Bar & Galley Lighted Boat Parade-Dec. 12

Festively decorated kayaks, fishing and pleasure craft, small yachts, and schooners glitter Key West’s Historic Seaport during the Annual Schooner Wharf Bar Lighted Boat Parade. Spectators can view the dozens of participating vessels from Schooner Wharf as well as resorts, bars, and restaurants in and around the Historic Seaport.

4) House & garden Christmas tour-Dec. 27-28

The Annual Key West House & Garden Tour showcases festively dressed Key West homes and gardens. Tickets are $30 and proceeds benefit the Old Island Restoration Foundation’s museums, collection, and education, grant, and scholarship programs.

5) A Weiner Wonderland – Dec. 31

The Annual Key West Dachshund Walk involves about 200 dachshunds and their owners taking a noontime New Year’s Eve stroll through the island’s picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.

Christmas with orchids growing wild everywhere. There’s so much to love about Key West.

6) A Key West New Years

There are many ways to celebrate New Year’s Eve in Key West.

• “Conch Shell Drop” at Sloppy Joe’s Bar, 201 Duval Street
• The descent of a super-sized red high-heeled shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex, 724 Duval Street
• The lowering of a pirate wench from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William Street
• “Splashdown” of a Key lime wedge into a giant margarita glass at Ocean Key Resort and Spa, 0 Duval Street.

What would you like to do in Key West?