Florida Keys Holidays to Sparkle with Lights and Subtropical Warmth

FLORIDA KEYS — Bright and beautifully “belighted” subtropical holidays in the Florida Keys & Key West are filled with warmth, inspiring good cheer throughout the 125-mile-long island chain. From Key Largo to Key West, the 2023 holiday season features spirited events such as lighted boat parades, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.

Select Keys holiday events are outlined below, while additional Florida Keys & Key West events can be found at fla-keys.com/calendar. 

Nov. 22 - Dec. 31: Harbor Walk of Lights. Key West. The Harbor Walk of Lights at the Key West Historic Seaport stretches along the harbor past Greene, William and Margaret streets to the Key West Ferry Terminal. Stroll the waterfront to see the ocean-themed, illuminated decor, including a 20-foot-tall Fishing Buoy tree, a 16-foot-tall Nautical Christmas tree and a Key West Lobster Trap tree. The lighted displays continue nightly through Dec. 31. Visit keywestchristmas.org.

Nov. 28 – Dec. 2: Zonta’s Festival of Trees. Marathon. The Zonta Club of Marathon, a women’s service organization, 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 5-8 p.m. Tuesday through Thursday, 3:30-10 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  zontaclubofmarathon.com or call 305-289-1221.

Dec. 1: Wesley House Family Services Holiday Village and BeLighted Bike Ride. Key West. The annual 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. 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 wesleyhouse.org/events/belighted2023 or call 305-809-5000.

Dec. 1: Holiday Fest. Islamorada. Kids can frolic on a 30-ton snow mountain during the 19th annual Holiday Fest set for 4-10 p.m. on the Great Lawn at Founders Park, mile marker 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, this year themed “Happy Holidays and Best Fishes!” is to kick off at 7:30 p.m. with Santa, antique cars, bands and floats. Visit islamoradachamber.com/holiday-fest or call 305-664-4503.

Dec. 2: Key West Hometown Holiday Parade. Key West. Local holiday spirit abounds in this eagerly awaited 7 p.m. parade that features marching bands, school groups, creatively styled 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.

Dec. 2: 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. The market is held at 94040 Overseas Highway. Visit ganclubupperkeys.org. 

Dec. 3, Dec. 17, Dec. 31: Artisan Market. Key West. A Key West holiday shopping tradition filled with one-of-a-kind gifts, the open-air bazaar takes place every other Sunday from 10 a.m. to 2 p.m. at Indigenous Park at Higgs Beach, 1801 White St. Markets feature Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit facebook.com/KeyWestArtisanMarket or call 305-509-3385.

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. Attractions include a small plate and beverage pairing at each stop as well as insights from the chef, owner, sommelier and/or brew master. For participating restaurants, tickets and trolley schedule, visit ilovestockisland.org.

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 sweeping porch and walkway of the historic Custom House Museum at 281 Front St. The 5-9 p.m. free-admission event features a holiday light show produced by Key West High School’s Conch 5 Studios, unique gifts crafted by local artisans, musicians, choirs, food, libations and photos with Santa. Visit kwahs.org/education/bazaar.

Dec. 8: 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. The furry fun is set for 4:30-6:30 p.m. at 9141 Overseas Highway. Visit fkspca.org or call 305-743-4800. 

Dec. 8-12 and 15-23: Conch Tour Train's Holiday Sights & Festive Nights Tours. Key West. Lively Conch Tour Train 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 conchtourtrain.com/key-west-christmas-holiday-tours or call 305-707-5775 or 305-296-6688.

Dec. 8-23: Old Town Trolley's Holiday Sights & Festive Nights Tours. Key West. The popular green and orange trolleys, festively 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 trolleytours.com/key-west/christmas-holiday-tours or call 855-623-8289 or 305-296-6688.

Dec 8, 9, 10, 16: Lighted Boat Parades. Stock Island, Key Largo, Key West, Marathon, Key Colony Beach, Little Torch Key. Lighted and festively decorated boats are to cruise waters surrounding the Florida Keys. For details about the Holiday Lighted Boat Parade on Stock Island (Dec. 8), visit keywestrotary.com. For the Key Largo Boat Parade on Blackwater Sound, themed “Christmas Around the World” (Dec. 9), visit keylargoboatparade.com. For the Schooner Wharf Bar Lighted Boat Parade (Dec. 9) around the Key West Historic Seaport and harbor, visit schoonerwharf.com. For details on the Boot Key Harbor Christmas Boat Parade (Dec. 9), visit bootkeyharbor.com. 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 facebook.com/events/1311932189541310.

Dec. 8 and 15: Holiday Historic Inn Tours. Key West. Old Town Key West is filled with lovely historic inns, and two Friday evenings of 6-8 p.m. tours offer a chance to glimpse lavish decorations, discover unique architecture, and experience holiday cheer and treats at featured properties. Visit keywestholidayfest.com for information and ticketing.

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 jeanne@riverswishinc.org for information.

Dec. 10: Christmas on the Sheriff’s Animal Farm. Stock Island. Children and adults love visiting the unique Monroe County Sheriff’s Office Animal Farm, just northeast of Key West at 5501 College Road. The farm opens from 1-3 p.m. for a special holiday open house to include photos with Santa, crafts, live vocal music and a free gift for each child that attends. Holiday donations to the farm are encouraged. Call 305-293-7300.

Dec. 10: Eaton Street Christmas Stroll. Key West. Eaton Street becomes a southernmost North Pole Sunday, Dec. 10. 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 tskw.org.  

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 fkspca.org 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 thekeywestamp.com/events/detail/waterfront-winter-wonderland.

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 cranepoint.net or call 305-743-9100.

Dec. 16: Pops in the Park Concert “Ice Cream Suites.” Islamorada. The family-friendly, free-admission 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. The Burton Bell Ringers are to be special guests, along with Santa. An Ugly Christmas Sweater contest and free ice cream round out the fun. Attendees can bring chairs and blankets to the 4-5 p.m. outdoor concert at the Founders Park amphitheater, mile marker 87 bayside. Visit keyscommunityconcertband.org or call 305-451-4530.

Dec. 21: Third Thursday Art Walk. Islamorada. Showcasing the area’s fine arts, music and culinary nuances, the Morada Way Arts & Cultural District features national and local artisans whose work is showcased in galleries along Morada Way between mile markers 81 and 82. Art Walks are held on the third Thursday of each month — and this 6-9 p.m. holiday edition features live music, beer tastings and other seasonal cheer. Admission is free. Visit moradaway.org or call 305-664-2471.

Dec. 29-30: Home Tours “Holiday Style.” Key West. The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 64th series features self-guided tours of several Key West homes and gardens, each festively dressed for the holidays. Three additional tour weekends are scheduled in 2024, with dates set for Jan. 12-13, Feb. 16-17 and March 15-16. Visit oirf.org for tickets or call 305-294-9501.

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.; the descent of 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 at midnight 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., known as the birthplace of Pan American Airways. At Hard Rock Cafe, 313 Duval St., ticketed attendees can watch a guitar drop at midnight at the music-themed establishment. Visit sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest/, firstflightkw.com and hardrockcafe.com/location/key-west/.

Florida Keys events calendar: fla-keys.com/calendar/