From Key Largo to Key West, the 2023 holiday season features lighted boat parades, frivolity, waterfront celebrations and other island festivities.

Nov. 28-Dec. 2: Zonta’s Festival of Trees. Marathon. The Zonta Club of Marathon offers a free-admission display of decorated trees at its 13th annual Festival of Trees at Marathon Garden Club, 5270 Overseas Highway. View and bid to purchase the decorated trees from 5 to 8 p.m. Tuesday through Thursday, 3:30 to 10 p.m. Friday and 10 a.m. to 8 p.m. Saturday. Kids can enjoy cookies with Santa and the Grinch Saturday from 10 a.m. to noon. Raffle tickets can be purchased for a chance to win a favorite tree, with a drawing for all trees set for 8 p.m. Dec. 2. Visit or call 305-289-1221.

Nov. 28-Jan. 7: Florida Keys Sea of Trees. Islamorada. The Florida Keys Sea of Trees is the Keys’ newest event showing more than 100 uniquely-themed trees. Select nights will include Santa’s Village. The holiday events supports Dolphins Plus Marine Mammal Responder’s new hospital, The Protect Center, MM 82, bayside. Visit nightly, 6-9 p.m. through Jan. 7.

Friday, Dec. 1

  •  Wesley House Family Services Holiday Village and BeLighted Bike Ride. Key West. The annual family-friendly Holiday Village is set from 4 to 8 p.m. with vendor booths, holiday-themed inflatable obstacle courses for kids, rides, food trucks, a “best bike” contest and photos with Santa. The bike ride, featuring a parade of bicycles decorated with holiday lights, leaves at 8 p.m. from the Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Road. Tickets are $20 each for those age 4 and up (four tickets for $70). Kids age 3 and under are admitted free. Visit or call 305-809-5000.
  • Holiday Fest. Islamorada. Kids can frolic on a 30-ton snow mountain during the 19th annual Holiday Fest set from 4 to 10 p.m. on the Great Lawn at Founders Park, MM 87 bayside. Families can view the 6 p.m. lighting of a 35-foot-tall tree with snow blowing through its branches, enjoy holiday treats from Santa’s Sweet Shoppe, bid on Keys-crafted ornaments by 50 local artists during an online auction, shop at the Holiday Gift Bazaar and enjoy live stage performances. The holiday parade, “Happy Holidays and Best Fishes!” will kick off at 7:30 p.m. with Santa, antique cars, bands and floats. Visit or call 305-664-4503.

Saturday, Dec. 2

  • Key West Hometown Holiday Parade. Key West. 7 p.m. parade features marching bands, school groups, floats and community participation. The parade kicks off at Bayview Park’s White Street and Truman Avenue location. Seeing Santa is a highlight for kids. Call 305-809-3881.
  • Garden Club of the Upper Keys Holiday Market. Key Largo. Browse and shop from 9 a.m. to 4 p.m. in the club’s Holiday Garden filled with artists, artisans, plants and more. 94040 Overseas Highway. Visit

Friday, Dec. 8

  • Key West Art & Historical Society Holiday Concert & Bazaar. Key West. The Key West Art & Historical Society hosts its annual concert and holiday shopping event on the porch and walkway of the Custom House Museum at 281 Front St. from 5 to 9 p.m. Free event features a holiday light show produced by Key West High School’s Conch 5 Studios, gifts crafted by local artisans, musicians, choirs, food, libations and photos with Santa. Visit
  • Pet photos with the Grinch. Marathon. Strike a pose with your pet and the Grinch to create a Who-tastic holiday picture in exchange for a donation to the Florida Keys SPCA. Pets should be on a leash or in a carrier. From 4:30 to 6:30 p.m. at 9141 Overseas Highway. Visit or call 305-743-4800.

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. Included are holiday lights glasses as keepsake items. The one-hour tour takes riders past the island’s most elaborately decorated houses, buildings and neighborhoods, with holiday caroling. Visit or call 305-707-5775 or 305-296-6688.

Dec. 8-23

  • Old Town Trolley’s Holiday Sights & Festive Nights Tours. Key West. The green and orange trolleys, adorned with holiday lights, showcase Key West’s best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m. Visit or call 855-623-8289 or 305-296-6688.

Dec 8, 9, 10, 16 

  • Lighted boat parades. Stock Island, Key Largo, Key West, Key Colony Beach, Little Torch Key. Lighted and decorated boats will cruise waters surrounding the Florida Keys. For details about the Holiday Lighted Boat Parade on Stock Island (Dec. 8), visit For the Key Largo Boat Parade on Blackwater Sound, themed “Christmas Around the World” (Dec. 9), visit For the Schooner Wharf Bar Lighted Boat Parade (Dec. 9) around the Key West Historic Seaport and harbor, visit For the Key Colony Beach Christmas Boat Parade (Dec. 10), call 518-859-5662. For the Kiki’s Sandbar Lighted Boat Parade on Little Torch Key (Dec. 16), visit

Saturday, Dec. 9

  • Pet Pictures with the Key West Grinch. Key West. Bring pets in their holiday best to Hard Rock Café, 313 Duval St., for photos with the Key West Grinch from noon to 3 p.m. for a $20 donation to support the senior dog sanctuary River’s Wish. Contact [email protected] for information.

Sunday, Dec. 10

  • Christmas on the Sheriff’s Animal Farm. Stock Island. The Monroe County Sheriff’s Office Animal Farm, just northeast of Key West at 5501 College Road, holds an open house from 1 to 3 p.m., including photos with Santa, crafts, live vocal music and a free gift for each child who attends. Holiday donations to the farm are encouraged. Call 305-293-7300.
  • Eaton Street Christmas Stroll. Key West. Eaton Street becomes the southernmost North Pole. Wander the blocks between Whitehead and Simonton streets 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

Tuesday, Dec. 12

  • Pet photos with the Grinch. Big Pine Key. Strike a pose with your pet and the Grinch to create a Who-tastic holiday picture in exchange for a donation to the Florida Keys SPCA. Pets should be on a leash or in a carrier. The animal antics are set for 5-7 p.m. at 30085 Overseas Highway. Visit or call 305-743-4800.

Dec. 15-30

  • Key West Waterfront Winter Wonderland. Key West. The Coffee Butler Amphitheater at Truman Waterfront Park becomes the Key West Waterfront Winter Wonderland for a family-friendly holiday experience including stunning light displays, an ice-skating rink, games, rides, attractions, music and more. The amphitheater’s vendor village is to offer a variety of food options and wares by local artisans – perfect for holiday shopping. Visit

Saturday, Dec. 16

  • Winter Wonderland at Crane Point. Marathon. At Crane Point Hammock Museum & Nature Trails, 5550 Overseas Highway, families can enjoy an evening winter wonderland from 4:30 to 8 p.m. Attractions are to include reindeer ponies, Santa and Mrs. Claus, performers from Marathon Community Theatre, sleigh rides, holiday decorations, a chocolate fountain, other seasonal treats and alcoholic drinks for purchase – plus a forecast of snow! Visit or call 305-743-9100.
  • Pops in the Park Concert. The free holiday concert themed “Ice Cream Suites” offers traditional and pops music by the Florida Keys Community Concert Band as well as sing-alongs of holiday favorites. An Ugly Christmas Sweater contest and free ice cream round out the fun. Attendees can bring chairs and blankets to the outdoor concert from 4 to 5 p.m. at the Founders Park amphitheater, MM 87 bayside. Visit or call 305-451-4530.