Key West Dog Friendly Holiday Events

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Key West Dog Friendly Holiday Events during ‘Bight Before Christmas’

Ahhh… the holiday season in Key West. Our guests are escaping the ice and snow in the north, the island is alive with festivity and cheer (and 75 degree weather), and we’re making memories with our loved ones – both two and four legged.  There’s plenty Key West dog friendly activities in Key West to celebrate this special time of year.

The weekend before Christmas, Santa is vacationing in Old Town Key West, and hopefully, so are you! Get your dog’s picture with Santa at the Historic Bight Marina on December 19th. If not for the cute-ness, for the charity! Photo sales benefit the Boys and Girls Club of Key West.

Key West Dog Friendly

Photo by Rob O’Neal

For a short time on New Year’s Eve, Duval Street is taken over by wiener dogs! That’s right… about 200 short legged, long bodied dachshunds parade through a section of Old Town Key West, showing off funny costumes and other fashionable outfits. Before the adult festivities heat up later that day, enjoy watching this family friendly event street-side, between Faustos on Fleming Street and La Trattoria on Appelrouth Lane.

Take your dog for a 5 minute walk to the Key West dog friendly Historic Seaport where the “Bight before Christmas” Harbor Walk of Lights shines and twinkles in spirited holiday fashion beginning December 4th. A holiday tree made of lobster traps and buoys will don the courtyard at the end of Greene Street and holiday decorations will light up the boardwalk.

Key West Dog Friendly Harbor - Lobster Trap Christmas Tree Key West

Photo by Claudia Miller “Keys Claudia” blog

While the Seaport is shining, the Key West dog friendly restaurants and bars are demanding their own attention with fresh seafood and festive libations.

  • The legendary Schooner Wharf bar offers live music and relaxed fare.
  • Down the boardwalk at the Half Shell Raw Bar, enjoy fresh oysters and cold beer.
  • Also in the area, the Boat House offers a spirited atmosphere and mouthwatering food.
  • Next to Simonton Beach is Shor American Grill, where you and your dog can enjoy an amazing view of the ocean.
  • A block away on Caroline Street, the famous Pepe’s Cafe restaurant is great for brunch or dinner in a very Key West-y, rustic setting.
  • Next door, check out Harpoon Harry’s at brunch-time for the best Bloody Marys in town!
  • A quick walk around the corner next to Mallory Square is Sunset Pier, a perfect pet friendly spot for watching… you guessed it… the famous Key West sunset.
Key West Dog Friendly Restaurants - Sunset Pier

Sunset Pier near Mallory Square in Key West

View more Key West recommendations or go back to our Old Town Manor home page.