FLORIDA KEYS — A free-spirited holiday season comes alive in the Florida Keys & Key West, with subtropical warmth and festive cheer throughout the 125-mile-long island chain. From Key Largo to Key West, visitors can find plenty of only-in-the-Keys activities designed to celebrate the seasonal spirit.
Major holiday events are highlighted below, with a more complete Florida Keys & Key West calendar at fla-keys.com/calendar.
Nov. 21 – Dec. 31: Key West Holiday Fest. Key West. A merry range of celebrations during Key West’s busy holiday season includes lighting of the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Visit keywestholidayfest.com.
Dec. 2, 16 and 30: Artisan Market. Key West. A “shop local” holiday tradition, the open-air bazaar is held from 10 a.m. to 2 p.m. at Higgs Beach, 100 Atlantic Blvd., with Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit facebook.com/KeyWestArtisanMarket or call 573-619-2200.
Dec. 5 and 14: Lighted Bike Rides. Key West (Dec. 5) and Marathon (Dec. 14). Lighted bike rides are to be held to benefit the family service organization Wesley House and its holiday toy drive. This year, photos with Santa, milk and cookies and a block party are included in the family-fun bike rides. Cost to register is a new unwrapped toy. Email email@example.com or call 305-809-5000.
Dec. 7, 15, 19, 21 and 22: Conch Tour Train Holiday Lights Tours. Key West. During its annual holiday lights tours of the southernmost island in the continental United States, the Conch Train travels past decorated historic homes, buildings and neighborhoods. Tours are offered at multiple times with departures from Key West High School, 2100 Flagler Ave. Visit conchtourtrain.com or call 305-294-5161.
Dec. 7: Islamorada Chamber of Commerce Holiday Festival. Islamorada. Kids can frolic in a magical 30-ton snow mountain during the event at Founders Park, mile marker 87, and watch the lighting of a 35-foot-tall community tree. Parents can bid on one-of-a-kind Keys-designed ornaments during a silent auction and explore a gift bazaar. Other activities include caroling and a holiday parade. Visit islamoradachamber.com or call 305-664-4503.
Dec. 7, 8, 9 and 15: Lighted Boat Parades. Stock Island, Key Largo, Key Colony Beach and Key West. Decorated and lighted boats are to cruise Florida Keys waters. For details about the Stock Island Lighted Boat Parade (Dec. 7) through community marinas, visit ilovestockisland.org. For the Key Largo Boat Parade (Dec. 8) on Blackwater Sound around mile marker 104, visit keylargoboatparade.com. For the Key Colony Beach Christmas Boat Parade (Dec. 9), visit kcbca.org/boatparade.htm. For the Schooner Wharf Bar/Absolute Vodka Lighted Boat Parade (Dec. 15), traveling around the Key West Historic Seaport and harbor areas, visit schoonerwharf.com.
Dec. 7 and 14: Holiday Historic Inn Tours. Key West. Two evenings of tours include trolley transportation between participating inns, each decorated for the holidays. Seasonal treats are offered. Event-goers also can bicycle or walk to the inns. To purchase tickets, contact the Lodging Association of the Florida Keys and Key West. Visit keywestholidayfest.com or call 305-296-4959.
Dec. 7-8: I Love Stock Island Festival. Stock Island. Celebrate Stock Island’s culture and heritage with culinary offerings featuring fresh-off-the-boat seafood, wine and beer tastings, history and art studio tours, live music and other elements that showcase the eclectic island and its working waterfront. Highlights include a lighted boat parade from Stock Island Marina Village; kid’s activities, a Little Mr. & Miss contest and more. Visit ilovestockisland.org.
Dec. 7-16: Nutcracker Key West. Key West. Florida Keys children and adults appear with 15 professional dancers from around the world in a stunning Keys-themed adaptation of the classic holiday ballet. There’s a wicked Rooster King, an exquisite Sea-Star Fairy and gorgeous “underwater” sequences. Multiple afternoon and evening performances are scheduled at Tennessee Williams Theatre, 5901 College Road. Visit nutcrackerkeywest.com.
Dec. 8: Key West City Hometown Holiday Parade. Key West. Local holiday spirit abounds in this annual 7 p.m. parade that features marching bands, school groups, creatively styled floats and community participation from all ages. The parade kicks off at Bayview Park’s Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids. Call 305-809-3881.
Dec. 9, 15, 19, 21 and 22: Old Town Trolley’s Holiday Lights and Sights Tours. Key West. The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West’s best decorated historic neighborhoods, buildings and homes. Visit trolleytours.com or call 305-296-6688.
Dec. 9: Christmas on the Sheriff’s Animal Farm. Key West. Children and adults can visit furry, fluffy and feathered residents of the animal farm and petting zoo from 1-3 p.m. and even get a photo taken with Santa. The Monroe County Sheriff's Office Animal Farm is located at the county's detention center just northeast of Key West at 5501 College Road. It’s open on the second and fourth Sundays of each month. Call 305-293-7300.
Dec. 12: Pet Photos with Santa. Marathon. Santa is to take photos with furry friends, with holidays goodies for all, during this 4-7 p.m. gathering at Keys Animal Hospital. The event supports medical and special needs for shelter animals at Marathon’s Florida Keys SPCA campus. The event is free, although contributions of pet food, toys, beds or monetary donations are welcome. Visit keysanimalhospital.com or call 305-743-DOGS (6250).
Dec. 15: Keys Community Concert Band Holiday Concert. Islamorada. The family-friendly free-admission Holiday Suite Treats event, themed “Stories and Santa,” offers traditional and pops music performed by the Keys Community Concert Band. Other attractions include a singalong, stories and Santa and a children’s ballet troupe performance. The concert takes place at the ICE Amphitheater at Founders Park, mile marker 87 bayside. Visit keyscommunityconcertband.org.
Dec. 15: A Holiday Concert at Marathon Community Theatre. Marathon. Two holiday performances are scheduled at 5 p.m. and 8 p.m. at the theater at 5101 Overseas Highway. Tickets are on sale online at marathontheater.org or call 305-743-0994.
Dec. 19: Third Annual Custom House Holiday Concert & Bazaar. Key West. The Key West Art & Historical Society hosts the 5-9 p.m. event at the historic Custom House Museum, 281 Front St. Highlights are to include performances by musicians and choirs, local artisans showcasing their wares, a light show and “selfies” with Santa. Visit kwahs.org or call 305-295-6616.
Dec. 20: Third Thursday Art Walk. Islamorada. Showcasing the area’s fine arts, music and cuisine, the Morada Way Arts & Cultural District features national and local artisans in galleries at Morada Way between mile markers 81 and 82 as well as beer tastings, food trucks and live music from 6-9 p.m. Admission is free to the preholiday event. Visit moradaway.org.
Dec. 28-29: 59th Annual Key West Home Tours. Key West. Self-guided tours of unique Key West homes and gardens, festively dressed for the holiday, are presented by the Old Island Restoration Foundation from 3-6 p.m. Tickets are $35 in advance or $40 on tour days. Proceeds benefit the foundation’s museum and programs. Visit oirf.org or call 305-294-9501.
Dec. 31: Annual Key West Dachshund Walk. Key West. Scores of dachshunds, many of them costumed, participate in the popular annual “wiener wonderland” stroll kicking off at noon. Canines and their people amble through the island’s picturesque downtown during the highly photographed walk. Spectators can “meet” the canine participants on Fleming Street between Whitehead and Duval streets. Visit facebook.com/Key-West-Dachshund-Walk-161327957238019/.
Dec. 31: New Year's Eve “Drops” in the Southernmost City. Key West. Ring in the new year with the 26th annual “conch shell drop” at Sloppy Joe's Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying world-famous drag queen Sushi 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.; or at the Ocean Key Resort & Spa at 0 Duval St., watch as a huge replica of a Key lime wedge splashes down into a larger-than-life margarita glass. Visit sloppyjoes.com, bourbonstpub.com, schoonerwharf.com or facebook.com/SunsetPierKeyWest/.
Dec. 31: New Year's Eve Fireworks on Blackwater Sound. Key Largo. The backcountry bay is the setting for the annual New Year's Eve fireworks extravaganza hosted by Sundowners, Key Largo Bay Marriott Beach Resort, Jimmy Johnson’s Big Chill, the Caribbean Club and other popular Key Largo venues, each located around mile markers 103 and 104. Visit keylargofireworks.com.
Dec 31: New Year’s Eve Midnight Fireworks in Islamorada. Morada Bay Beach Café at mile marker 81.6 bayside is to host a colorful beach party with live music, a beach barbecue, signature cocktails, performers and fireworks. Visit moradabay.com or call 305-664-0604.
Florida Keys events calendar: fla-keys.com/calendarofevents/
Florida Keys visitor information: fla-keys.com or 1-800-FLA-KEYS (1-800-352-5397)