Spice up the holiday season with Florida Keys flair by exploring the following highlight events — and check out the Keys’ complete calendar at fla-keys.com/calendar for even more options.
Nov. 22 – Dec. 31: Key West Holiday Fest. Key West. Each year during the holiday season, a wide range of celebrations takes place throughout Key West. Highlights include the lighting of the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade. For event details and updates, visit keywestholidayfest.com.
Nov. 22: Lighting of the Key West “Harbor Walk of Lights.” Key West. The eagerly awaited pre-Thanksgiving event is to begin at 6 p.m. at Greene and Elizabeth streets, with the lighting of a holiday tree made from plastic foam trap floats, a nautically decorated fresh pine Christmas tree and a lobster trap tree along the Key West Historic Seaport’s Harbor Walk. The Harbor Walk is lit nightly through New Year’s Eve. Visit keywestchristmas.org.
Nov. 25: Big Pine & Lower Keys Island Art Festival. Big Pine Key. Held outdoors in a relaxed natural setting, the event features a creative range of holiday and Keys crafts. The art fair takes place from 9 a.m. to 2 p.m. on the grounds of the Lower Keys Chamber of Commerce at mile marker 31 oceanside. Visit lowerkeyschamber.com or call 305-872-2411.
Nov. 29 – Dec. 2: Zonta’s Festival of Trees. Marathon. The annual Festival of Trees is to take place at the Florida Keys Country Club at 4000 Sombrero Blvd. Holiday trees are festively decorated and displayed by members of the Zonta Club of Marathon, a humanitarian service organization. Visitors and residents can bid to purchase the decorated trees. Visit zontaclubofmarathon.org or call Charlotte Quinn at 305-393-9501.
Dec. 1: Florida Keys Holiday Festival. Islamorada. Frolic in a 30-ton magical mountain of snow at Founders Park at mile marker 87 from 4-10 p.m., watch the ceremonial lighting of a 35-foot-tall tree or bid on a one-of-a-kind Keys-designed creation during the popular ornament auction. Inspired by the Burl Ives song, “Silver and Gold,” a themed parade is to usher in Santa Claus amid food, drink, music and kids’ activities. A Santa Paws canine competition for dogs and owners awards the best doggone holiday attire. Visit islamoradachamber.com or call 305-664-4503.
Dec. 2: Light Up Key Largo. Key Largo. Sponsored by the Key Largo Chamber of Commerce, holiday happenings with live music, decorations, food and drinks are to spark the seasonal spirit. The annual tree lighting and related activities are to be held at the Murray E. Nelson Government Center and Key Largo Cultural Center, mile marker 102, from 5-9 p.m. Eggnog, caroling and an appearance by Santa and Mrs. Claus are virtually guaranteed to put everyone in a festive mood. Visit keylargochamber.org or call 305-451-1414.
Dec. 2: Key West City Hometown Holiday Parade. Key West. Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and nonmotorized floats and lively community participation. Catching tossed candy is a highlight for kids. The route begins at Bayview Park and the best viewing spots are along Duval Street and Truman Avenue. Call 305-809-3881.
Dec. 6: Pet Photos with Santa. Marathon. Scheduled from 4-8 p.m. at Keys Animal Hospital, the event supports the medical and special needs for the shelter animals at Florida Keys SPCA campus in Marathon. Cost of photos is free, although contributions of pet food, toys, beds or financial donations are welcome. Call 305-743-DOGS (6250).
Dec. 6, 9 and 10: Lighted Bike Rides. In Key West (Dec. 6), Key Largo (Dec. 9) and Marathon (Dec. 10). Three lighted bike rides are held in the Keys to benefit Wesley House, a family service organization, and its toy drive. Families and individuals decorate and light their bikes for the evening rides. Registration is one new unwrapped toy. Email email@example.com or call 305-809-5000.
Dec. 8-10: Inaugural Southernmost Spirits Festival. Key West. Enjoy a cocktail, culinary and cultural extravaganza celebrated in Key West. Appealing to industry insiders, consumer cocktail and culinary lovers alike, the event is to encompass product innovation, education and a good time filled with entertainment, camaraderie, tastings, celebrity bartender competitions and fun. Visit southernmostspiritsfest.com.
Dec. 8-10: I Love Stock Island. Stock Island. The family-friendly festival is to blend culinary events, live music, history and art studio tours, a lively community party, watersports offerings and other immersive experiences that showcase the island and its eclectic working waterfront. A boat parade, “Taste of Stock Island,” “Discover Stock Island” excursions, “StockFest,” the Stock Rock & Roll Bike Ride and more highlight the area’s seafaring tradition, culinary riches and vibrant creative enterprises. Visit ilovestockisland.org.
Dec. 8 and 15: Holiday Historic Inn Tours. Key West. Two evenings of tours include trolley transportation between several participating inns, each decorated for the holidays. Treats and libations are offered at each inn. Event-goers also can provide their own transportation or bicycle to the inns. Contact the Lodging Association of the Florida Keys and Key West to purchase tickets, priced at $30 per person. Visit keywestholidayfest.com or call 305-296-4959.
Dec. 9: Keys Community Concert Band Holiday Concert. Key Largo. The family-friendly free-admission event, themed “Not So Frozen,” offers traditional and pops music performed by the Keys Community Concert Band, singalongs, stories and Santa as well as a children’s ballet troupe performance. The concert is to be held at the Murray Nelson Government & Cultural Center, mile marker 102. Visit keyscommunityconcertband.org.
Dec. 9: Fourth Annual Parade of Paws and Holiday Bazaar. Key West. The pet parade at Higgs Beach Dog Park supports the Florida Keys SPCA’s animal care fund. Pets’ humans gather funding pledges from family and friends. Top earners win bragging rights for the titles of king, queen, prince, princess, duke or duchess for their treasured companions. Four-legged creatures and owners can mingle, take photos with Santa and enjoy entertainment, food and crafts from 10 a.m. to 2 p.m. Visit fkspca.org or call 305-294-4857.
Dec. 8, 9 & 10: Lighted Boat Parades. Stock Island, Key West, Key Largo & Key Colony Beach. Decorated and lighted boats are to cruise Florida Keys waters. For details about the Stock Island Lighted Boat Parade (Dec. 8) through community marinas, visit ilovestockisland.org. For more on the Schooner Wharf Lighted Boat Parade (Dec. 9) that travels around Key West’s Historic Seaport and harbor areas, visit schoonerwharf.com. For the Key Largo Boat Parade (Dec. 9) on Blackwater Sound around mile marker 104, visit keylargoboatparade.com. For the Key Colony Beach Boat Parade (Dec. 10) visit kcbca.org/boatparade.htm.
Dec. 10: Christmas on the Sheriff’s Animal Farm. Key West. Children and adults can visit the furry, fluffy and feathered residents of the animal farm and petting zoo and 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. 15 & 16: A Holiday Concert at Marathon Community Theatre. Marathon. Shows are slated to ring in the holiday cheer at 7 p.m. both evenings at the theater, located at 5101 Overseas Highway. Tickets are on sale online at marathontheater.org or call 305-743-0994.
Dec. 17: Artisan Market, A Holiday “Shop Local” Edition. Key West. Browse the vibrant open-air bazaar filled with Keys artists, authors, chef-made cuisine, craftspeople and performers. Admission is free and the market, located at 1111 Eaton St., is open to the public from 10 a.m. to 2 p.m. Visit facebook.com/KeyWestArtisanMarket.
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 who are showcased in galleries at Morada Way between mile markers 81 and 82, as well as beer tastings and live music, from 6-9 p.m. Admission is free to this great pre-holiday celebration. Art Walk is held the third Thursday of each month. Visit moradaway.org.
Dec. 21: Second Annual Custom House Holiday Concert & Bazaar. Key West. The Key West Art & Historical Society is to host this second annual event at the historic Custom House Museum, 281 Front St. Highlights of the evening gathering 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. 27-28: 58th Annual Key West House Tours. Key West. Self-guided tours of unique Key West homes and gardens, festively dressed for the holidays, are to be presented by the Old Island Restoration Foundation. Tickets are $35 each. 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. As many as 200 dachshunds, many of them costumed, participate in this noontime “wiener wonderland” stroll. Canines and their people meander through the island’s picturesque downtown during the beloved, much photographed walk. Spectators can watch the fun and 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 a “conch shell drop” at Sloppy Joe's Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying 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. For more information on the respective events, 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, Jimmy Johnson’s Big Chill, Señor Frijoles, Cactus Jack’s, Gus’s Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, all located around mile markers 103-104. 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 large beach party with live music, a beach barbecue, signature cocktails, performers and fireworks. Visit moradabay.com/full-moon-party/.
Florida Keys events calendar: fla-keys.com/calendarofevents/
Florida Keys visitor information: fla-keys.com or 1-800-FLA-KEYS (1-800-352-5397)
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