Maritime merrymakers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Help decorate the tree and participate in a “Best Handmade Ornament” contest for prizes (bring your own hand-decorated ornament). All tree trimmers will be treated to a free holiday cocktail. Participants are invited to bring an unwrapped gift for the Cheryl Cates Memorial Toy Drive for “Angels Just 4 Kids.” Local authors and artists will be on hand, signing and selling original creations for holiday gift giving.

“Messiah” concert, 7:00pm at Key West United Methodist Church, 600 Eaton Street.

City of Key West Tree Lighting Ceremony, 6:00pm at Bayview Park, 1320 Truman Ave.

The ReMARCable Decorated Table Top Tree and Wreath Auction takes place at Opal Key Resort, 245 Front St., presented by First Horizon Foundation. Preview at 5:30pm; live auction at 7:00pm.

The 11th Annual POSH (Paws Often Steal Hearts) Florida Keys SPCA Fundraiser, 6:00pm, a catered gala event at the Audubon House featuring live dance music raffles, and a silent auction.

Pack up Fifi, Fido, and the family and delight in Pet Pictures with Santa at the 16’ nautical Christmas tree at the foot of William Street at the Key West Bight Marina/Harbor Walk of Lights. For a cash donation of $25 you’ll receive a professional high resolution digital image. Benefits the Boys & Girls Club of the Keys.

Dec. 5-15, Nutcracker Key West: Sugarplum fairies trade tutus for sea fans, and the battle between the mice and the soldiers takes on a whole new flavor. Some 200 local children and adults and 16 professional dancers from New York City will join together in 2024 to produce this outstanding historical recreation of Key West's enchanting version of the Nutcracker ballet at the Tennessee Williams Theatre.

Celebrate the holidays with a family friendly party with Santa Claus, music, crafts, food trucks, goodies, games, and rides for the kids, and a festive lighted bike ride through the streets of Key West, which will depart the Amphitheater at 8:00pm and conclude with a “Best Bike” contest. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House Family Services.