Crowds gathered at the Key West Historic Seaport on Nov. 22, 2023, for the lighting of the seaport’s trees, ships, shops and restaurants. CAROL TEDESCO/

Bright and “belighted” subtropical holidays in the Florida Keys and Key West are filled with warmth and good cheer throughout the island chain. The 2023 holiday season features spirited events such as lighted boat parades, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.

A number of December’s holiday events in Key West and the Lower Keys are listed below. Additional events can be found at

Friday, Dec. 1

  • Wesley House Family Services Holiday Village and BeLighted Bike Ride. Key West. The family-friendly Holiday Village is set for 4-8 p.m. with community vendor booths, holiday-themed inflatable obstacle courses for kids, rides, food trucks, a “best bike” contest and photos with Santa. Visit or call 305-809-5000.

Saturday, Dec. 2

  • Key West Hometown Holiday Parade. Key West. The parade kicks off at Bayview Park’s White Street and Truman Avenue location at 7 p.m. 

Thursday, Dec. 7

  • I Love Stock Island’s Taste of Stock Island Trolley Tour with a Holiday Twist. Stock Island. Board a trolley for an early-evening culinary tour of favorite Stock Island restaurants. Visit

Dec. 8 and 15

  • Holiday Historic Inn Tours. Key West. Friday evenings from 6-8 p.m. tours offer a glimpse at lavish decorations and unique architecture.

Dec. 8-12 and 15-23

  • Conch Tour Train’s Holiday Sights & Festive Nights Tours. Key West. Tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 7:30, 8 and 8:30 p.m. Visit or call 305-707-5775 or 305-296-6688.
People enjoy the sparking lights of the City of Key West's Christmas tree at Bayview Park on Nov. 27, 2023, at the city’s annual tree lighting ceremony.

Dec. 8-23

  • Old Town Trolley’s Holiday Sights & Festive Nights Tours. Key West. Trolleys showcase Key West’s best-decorated neighborhoods, buildings and homes. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m.CAROL TEDESCO/

Friday, Dec. 8

  • Key West Art & Historical Society Holiday Concert & Bazaar. Key West. Takes place on the porch and walkway of the Custom House Museum at 281 Front St.  from  5-9 p.m. 
  • Stock Island Lighted Boat Parade. Visit

Saturday, Dec. 9

  • Schooner Wharf Bar Lighted Boat Parade. Visit
  • Pet Pictures with the Key West Grinch. Key West. Hard Rock Café, 313 Duval St., noon to 3 p.m. $20 donation supports the senior dog sanctuary River’s Wish. Contact [email protected] for information.

Sunday, Dec. 10

  • Christmas on the Sheriff’s Animal Farm. Stock Island. 5501 College Road, 1 to 3 p.m.  
  • Eaton Street Christmas Stroll. Key West. Wander the blocks between Whitehead and Simonton between 3:30 and 7 p.m., stopping at venues like St. Paul’s Episcopal Church at 401 Duval St. for a traditional Christmas concert, and Tropic Cinema at 416 Eaton St. for some classic cartoons. The Studios of Key West hosts an open house at 533 Eaton St. during the event. Visit 
Zamaria Smith, 10, left, shares a Christmas wish with Santa Claus, while her sister Laneice, 2, checks out a candy cane during the lighting of the City of Key West's Christmas tree event at Bayview Park on Nov. 27, 2023. CAROL TEDESCO/
Zamaria Smith, 10, left, shares a Christmas wish with Santa Claus while her sister Laneice, 2, checks out a candy cane at the lighting of the City of Key West Christmas tree event at Bayview Park on Nov. 27, 2023. CAROL TEDESCO/

Tuesday, Dec. 12

  • Pet photos with the Grinch. Big Pine Key. 5-7 p.m. at 30085 Overseas Hwy. Visit or call 305-743-4800.

Dec. 15-30

  • Key West Waterfront Winter Wonderland. Key West. A family-friendly holiday experience including light displays, an ice-skating rink, games, rides, attractions, music and more. Visit

Dec. 29-30

  • Home Tours ‘Holiday Style.’ Key West. The Old Island Restoration Foundation’s Key West Home Tours are among America’s longest-running home tours. Visit for tickets or call 305-294-9501.

Sunday, Dec. 31

New Year’s Eve ‘Drops’ in Key West. Ring in 2024 with a “conch shell drop” at Sloppy Joe’s Bar, 201 Duval St.; a super-sized red high-heel shoe carrying a drag queen at the Bourbon St. 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 a huge replica of a Key lime wedge splashing down into a larger-than-life margarita glass at Ocean Key Resort & Spa, 0 Duval St. Revelers can also witness the “flight” of a uniformed “stewardess” in a section of a replica aircraft and enjoy a ticketed Gatsby-style party at First Flight Island Restaurant & Brewery, 301 Whitehead St.