Holiday Events Sparkle Throughout the Florida Keys & Key West

FLORIDA KEYS — Sunny holidays bring warmth and good cheer to the Florida Keys & Key West throughout the 125-mile-long island chain. From Key Largo to Key West, the 2019 holiday season — filled with spirited events such as lighted boat parades, historic inn tours, only-in-the Keys frivolity and waterfront celebrations — sparkles with island festivities. Major holiday events are detailed below, with a more complete Florida Keys & Key West calendar at fla-keys.com/calendar.

Nov. 27–Dec. 31: Key West Holiday Fest. Key West. Seasonal celebrations begin at the Key West Historic Seaport with the Lighting of the Harborwalk Nov. 27 at 6 p.m. The harborwalk area from Greene to Grinnell streets is to glimmer with maritime-themed holiday displays and offer unique events throughout the season. Other festival highlights include tours of historic lighted inns and a boat parade with decorated vessels and good cheer. Visit keywestholidayfest.com. 

Nov. 30: Big Pine & Lower Keys Island Art Festival. Big Pine Key. Find distinctive gifts and celebrate the holiday spirit from 9 a.m. to 3 p.m. on the grounds of the Lower Keys Chamber of Commerce, mile marker 31 oceanside. Exhibits and booths showcase handcrafted art, jewelry and creative wares by local artisans. Visit lowerkeyschamber.com or call 305-872-2411.

Dec. 4 and Dec. 6: Lighted Bike Rides. Key West (Dec. 4) and Marathon (Dec. 6). The popular lighted bike rides, held annually, benefit the Wesley House family service organization and its holiday toy drive. Photos with Santa, cookies and milk are included. Registration is an unwrapped toy or monetary donation. Visit wesleyhouse.org/event/lighted-bike-parade-key-west/ and wesleyhouse.org/event/lighted-bike-parade-marathon/ or call 305-809-5060.

Dec. 4-7: Zonta’s Festival of Trees. Marathon. The Zonta Club of Marathon, a women’s service organization, displays its annually decorated trees at the Festival of Trees at the Florida Keys Country Club, 4000 Sombrero Blvd. This year’s theme is “Putting on the Glitz.” Tickets are sold for admission. Visit zontaclubofmarathon.com.

Dec. 6: Florida Keys Holiday Festival. Islamorada. Kids can frolic on a 30-ton snow mountain during the annual event from 4-10 p.m. at Founders Park, mile marker 87 bayside. Families attending the plastic-free festival can applaud the 6 p.m. lighting of a 35-foot-tall community tree, bid on ornaments created by Keys artists during a silent auction, shop for gifts, enjoy musical and dance performances, view a holiday parade and more. A $5 donation is to be collected for on-site parking. Visit islamoradachamber.com/holiday-fest or call 305-664-4503.

Dec. 6, 12-14, 16-19, 21-23: Old Town Trolley’s Holiday Lights and Sights Tours. Key West. The popular green and orange trolleys, festively adorned with holiday lights, showcase “Christmas Chill” in Key West’s best-decorated historic neighborhoods, buildings and homes in fun-filled 60-minute excursions. Tours depart from Mallory Square; treats include cookies and hot cider. Visit trolleytours.com or call 305-296-6688.

Dec. 6 and 13: Holiday Historic Inn Tours. Key West. Old Town Key West is filled with unique historic inns, and two Friday evenings of 6-8 p.m. tours offer a chance to glimpse lavish decorations and experience holiday cheer, treats at bed-and-breakfast properties and two popular Key West attractions. Visit keywestholidayfest.com or call 305-296-4959.

Dec. 7: Key West City Hometown Holiday Parade. Key West. Charming spirit abounds in the popular 7 p.m. event in the southernmost city in the continental United States. The parade kicks off at Bayview Park’s Truman Avenue and White Street entrance, rolls down Duval Street and ends at Eaton Street. Local flavor — infused with tossed candy and Santa’s participation — prevails with marching bands, floats and community and school groups. keywesthistoricseaport.com/event/key-west-hometown-holiday-parade/. Call 305-809-3881.

Dec. 7: Lighting of the Lighthouse & Boat Parade. Marathon. The second annual lighting of the iconic Middle Keys lighthouse, hosted by Faro Blanco Resort & Yacht Club, 1996 Overseas Highway, is slated for 4-9 p.m. Attendees can enjoy food, music, performances, an appearance by Santa and holiday shopping, with the boat parade to begin at 7 p.m. Visit facebook.com/events/648065525696234/ or call 305-434-9035.

Dec. 8, 13 and 14: Lighted Boat Parades. Key Colony Beach, Stock Island and Key West. Lighted and festively decorated boats are to cruise waters surrounding the Florida Keys. For details about the Tucker Degraw Memorial Christmas Boat Parade (Dec. 8) in Key Colony Beach, visit kcbca.org/boatparade.htm. For the I Love Stock Island Lighted Boat Parade (Dec. 13), visit ilovestockisland.org. For the Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade (Dec. 14) around the Key West Historic Seaport and harbor, visit schoonerwharf.com.

Dec. 14: Parade of Paws and Holiday Bazaar. Key West. The sixth annual pet parade at Higgs Beach Dog Park at Atlantic Boulevard and White Street supports the Florida Keys SPCA animal care fund. Attractions at the 10 a.m. to 2 p.m. event include photos with Santa, wares by local vendors, entertainment and a “Smooch a Pooch” booth. Visit fkspca.org/events-and-news/upcoming-events/ or call 305-294-4857.

Dec. 14: Pops in the Park Concert: “Suite Dreams.” Islamorada. The family-friendly holiday concert, themed “Suite Dreams,” offers free-admission traditional and pops music by the Florida Keys Community Concert Band. Attendees can bring chairs and blankets to the 4 p.m. outdoor concert at Founders Park’s ICE amphitheater, mile marker 87 bayside. Visit keyscommunityconcertband.org or call 305-451-4530.

Dec. 15: Christmas on the Sheriff’s Animal Farm. Stock Island. Children and adults love visiting the Monroe County Sheriff’s Office Animal Farm, just northeast of Key West at 5501 College Road. The farm, open 1-3 p.m. on the second and fourth Sundays of each month, is a unique and educational haven for feathered, furry and fluffy creatures that are cared for by jail inmates. Holiday highlights include photos with Santa. Call 305-293-7300.

Dec. 18: Custom House Holiday Concert and Bazaar. Key West. The Key West Art & Historical Society hosts its 4th annual event on the sweeping porch and walkway of the historic Custom House Museum at 281Front St. The 5-9 p.m. event features unique gift options created by local artisans as well as musicians, choirs, food and libations, a large-scale light show, photos with Santa and free admission to the museum. Visit kwahs.org or call 305-295-6616.

Dec. 19, 20 and 21: Sugar Rum Cherry: A Burlesque Nutcracker. Key West. Inspired by the holiday classic “Nutcracker” ballet, this spirited and naughty two-act “reverie” is presented by Key West Burlesque. Clara, a young ingénue, celebrates the season with sugar rum cherry cocktails and is transported in a dream to the “Land of Libations.” The performance is staged at 8 p.m. at the Key West Theater, 512 Eaton St., with doors opening at 7:30 p.m. Visit thekeywesttheater.com or call 305-985-0433.

Dec. 21: Key Largo Boat Parade. Blackwater Sound will shimmer as decorated boats parade along the shoreline in celebration of the holiday season. The best viewing and libations are to be found at Jimmy Johnson’s Big Chill, Sundowner’s Restaurant and the Caribbean Club, MM 103-104 Bayside. The parade is free to enter; one grand prize winner and one randomly selected lucky boat are to receive $500 each. Hosted by The Rotary Club of Key Largo Sunset, the parade starts at 7:30 p.m. Visit keylargoboatparade.com.

Dec. 27 and 28: 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 back to 1960. This 60th annual series features self-guided tours of five Key West homes and gardens, all festively dressed for the holidays, plus a “bonus” stop at a historic inn or hotel with complimentary drinks and nibbles. Visit keywesthometours.com/60th-season-home-tours or call 305-294-9501.

Dec. 31: Annual Key West Dachshund Walk. Key West. Spectators can meet and greet as many as 200 dachshunds — many of them costumed — in a “wiener wonderland” on Fleming Street between Whitehead and Duval streets. Starting at noon, canines and proud owners stroll through a portion of the island’s picturesque downtown during this much photographed event. Visit facebook.com/Key-West-Dachshund-Walk-161327957238019/.

Dec. 31: New Year’s Eve Fireworks on Blackwater Sound. Key Largo. The back bay is the setting for the annual midnight New Year's Eve fireworks extravaganza hosted by Sundowners, mile marker 104 bayside, with live music to accompany the festivities. For details and to reserve seats for a special New Year’s Eve dinner, visit sundownerskeylargo.com/event/new-years-eve-at-sundowners/.

Dec. 31: New Year’s Eve at Cheeca Lodge & Spa. Islamorada. Cheeca Lodge & Spa, located at mile marker 82 oceanside and known for its scenic beachside location and cuisine, is to host a midnight fireworks display over the Atlantic Ocean with live music. Visit cheeca.com/experience/holidays-at-cheeca/ or call 305-664-4651. 

Dec. 31: New Year’s Eve Celebrations. Islamorada. Revelers in the Upper Keys can ring in the New Year with midnight fireworks on the beach at Morada Bay Beach Cafe, located at mile marker 81.6 bayside, and hosting a large full moon beach party with live music, beach barbecue, cocktails, performers and fireworks. Visit moradabay.com/full-moon-party/ or call 305-664-3225.

Dec. 31: Old Island Restoration Foundation 1860s or 1960s Costume Gala. Key West. The Old Island Restoration Foundation’s 60th anniversary celebration includes a New Year’s Eve party themed “MadMen MadWomen,” to be held at the Oldest House Museum, 322 Duval St. The venue opens at 6 p.m. with dinner at 8:15 p.m. in the garden, a chance to watch revelers promenade on Duval Street and a countdown to midnight. Visit thegardenattheoldesthouse.org/60th-anniversary-celebration or call 305-294-9501.

Dec. 31: New Year's Eve “Drops” in Key West. Ring in 2020 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 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 at First Flight Island Restaurant & Brewery, 301 Whitehead St., the building known as the birthplace of Pan Am, and the “tuna drop” at the Smokin’ Tuna Saloon, 4 Charles St. Visit sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest/, firstflightkw.com and smokintunasaloon.com. 

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