Always a unique getaway, the Keys always know how to celebrate each day with their own festive vibe. The spirit of the holiday season comes alive in the Florida Keys & Key West with celebratory events and functions spreading cheer in the island chain’s subtropical climate. From Key Largo to Key West, the calendar is packed with events designed to celebrate the holiday spirit. Listed here are some highlights, all spiced with a traditional Keys flair.


Nov. 25 – Dec. 20: Key West Holiday Fest. Key West. A wide range of seasonal celebrations include the Nov. 25 lighting of the Harbor Walk of Lights along the Historic Seaport at the Key West Bight, tours of historic decorated inns, a lighted parade and more. Events are to be hosted by the Lodging Association of the Florida Keys & Key West. For a complete schedule of events, visit www.keywestholidayfest.com.

Dec. 12: Pops in the Park Jingle Bells Rock Concert. Islamorada. A special holiday concert is to be held at the ICE amphitheater at Founders Park, MM 87 bayside. The family-friendly concert features traditional music of the season. Presented by Keys Community Concert Band, the event starts at 4 p.m. and admission is free. All seats are outdoors and attendees are encouraged to bring chairs and blankets. Details: Click Here, or call Donna Heiner at 305-853-7294.

Dec. 12, 13 & 19: Lighted Boat Parades. Throughout the Florida Keys. Decorated and lighted boats are to cruise through Keys waters Dec. 12 on Key Largo’s Blackwater Sound and in Key West Harbor and Marathon’s Boot Key Harbor; Dec. 13 at Key Colony Beach and Dec. 19 at the Lower Keys’ Pine Channel Causeway. Details: Key Largo Holiday Boat Parade (305-394-3736); Key West Lighted Boat Parade (305-292-3302); Key Colony Beach lighted Boat Parade (305-743-7214); Boot Key Harbor Lighted Boat Parade (305-849-0285); Lower Keys Lighted Boat Parade (305-923-5370).

Dec. 13: Christmas on the Sheriff’s Animal Farm. Stock Island. Kids and adults can visit the furry, fluffy and feathered residents of the animal farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff’s Office Animal Farm is located at the county’s detention center at 5501 College Road. Admission is free and the farm is open to the public the second and fourth Sundays of each month. Details: Click Here, or call 305-293-7300.

Dec. 19: A Holiday Concert at Marathon Community Theater. Marathon. Shows are slated to ring in the holiday cheer at 5 p.m. and 8 p.m. Tickets are $5 for adults and $2 for children. Details: Click Here, or call 305-743-0994.

Dec. 20: Monthly Artisan Market, A Holiday “Shop Local” Edition. Key West. Browse the vibrant open-air bazaar filled with Keys artists, authors, chef-made cuisine, craftspeople and performers. Admission is free and the market is open to the public from 10 a.m. to 2 p.m. the first Sunday of each month. Details: Click Here.

Dec. 26-27: 56th Annual Key West House & Garden Tours. Key West. Presented by the Old Island Restoration Foundation, the annual self-guided tours showcase festively dressed Key West homes and gardens. Advance tickets are $30 and proceeds benefit the Old Island Restoration Foundation’s museums, collection and education, grant and scholarship programs. Details: Click Here, or call 305-294-9501.

Dec. 27: Florida Keys Craft Beer & Bubbly Fest. Marathon. From noon to 7 p.m., enjoy tastings of craft beers, wines and champagnes along with live entertainment and delicious food at Marathon Community Park, MM 49 Oceanside. Admission is free. Details: Click Here.

Dec. 31: Annual Key West Dachshund Walk. Key West. Frost-free Key West becomes a “wiener wonderland” when about 200 dachshunds and their owners take 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. Email keywestdachshundwalk@gmail.com.

Dec. 31: New Year’s Eve Fireworks on Blackwater Sound. Key Largo. The backcountry bay is the setting for the annual New Year’s Eve fireworks extravaganza hosted by Sundowners, Jimmy Johnson’s Big Chill, Señor Frijoles, Cactus Jack’s, Gus’s Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, all located around MMs 103-104. Details: Click Here.

Dec 31: New Year’s Eve Midnight Fireworks in Islamorada. Cheeca Lodge & Spa, MM 82 Oceanside, is to offer a gourmet dinner, live music, dancing on the beach and a midnight fireworks display. Visit www.cheeca.com or call 305-517-4580. Morada Bay Beach Café at MM 81.6 Bayside is to host a large beach party with live music, a specially planned beach barbecue, signature cocktails, performers and fireworks. Details: Click Here.

Dec. 31: New Year’s Eve Celebrations in the Southernmost City. Key West. The Southernmost City typically celebrates with a “conch shell drop” at Sloppy Joe’s Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St.; the lowering of a pirate wench from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St.; and at the Ocean Key Resort & Spa, at 0 Duval St., plans call for a huge replica of a Key lime wedge to splash down into a larger-than-life margarita glass on the property’s Sunset Pier.


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