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Santa, Sweets, and Holiday Tree Lighting

Key West Womans Club 319 Duval Street, Key West, Fl, United States

Celebrate the season with the Key West Woman’s Club and Mayor Teri Johnston at the beautiful historic Hellings Curry Museum at 319 Duval St. Guests can enjoy appetizers, deserts, Amsterdam eggnog and holiday music performed by the Bahama Village Children’s Choir and the Key West Community Orchestra. Donations of unwrapped, new clothing items for students K-12 appreciated.

Schooner Wharf Tree Trimming Party and Toy Drive

Schooner Wharf 202 William Street, Key West, FL, United States

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.”

“Messiah” Concert

Key West United Methodist Church 600 Eaton Street, Key West, FL, United States

Sunday, Dec. 3, 7:00pm, “Messiah” concert at Key West United Methodist Church, 600 Eaton Street.

Holiday Village and BeLighted Bike Ride

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 illuminated pedaling party through the streets of Key West

Annual POSH (Paws Often Steal Hearts)

Audubon House 205 Whitehead Street, Key West, FL, United States

Annual POSH (Paws Often Steal Hearts) Florida Keys SPCA Fundraiser at the Audubon House, a catered gala event featuring live dance music by Phat Hat, raffles, and a silent auction.

6th Annual Holiday Concert & Bazaar

Custom House 281 Front St, Key West, FL, United States

6th Annual Holiday Concert & Bazaar at the Key West Museum of Art & History at the Custom House: This festive free party features some of Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show. 281 Front Street.

Annual Parade of Paws & Holiday Bazaar at Higgs Beach

Higgs Beach Dog Park White Street & Atlantic Blvd, Key West, FL, United States

Annual Parade of Paws & Holiday Bazaar at Higgs Beach / Higgs Dog Park: Benefits the Florida Keys SPCA. Costumes encouraged!

Pet Pictures with The Grinch at the Hard Rock Cafe

Hard Rock Cafe 313 Duval St., Key West, FL, United States

Bring your critters for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a 501(c)(3) non-profit senior dog sanctuary.

Schooner Wharf Annual Lighted Boat Parade

Schooner Wharf 202 William Street, Key West, FL, United States

Schooner Wharf Annual Key West Lighted Boat Parade: A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights.

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