Lots to Do Over the Holidays in the Florida Keys!


Dec. 15, 2017 – Dec. 17, 2017
Islamorada Junior Sailfish Tournament
Tammie Gurgiolo 305-240-9337
Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates to tie a bimini or rig ballyhoo. One weekend each year anglers aged 16 and younger can apply such lessons in this competition. A maximum of six anglers is allowed per boat. Proceeds aid the Montessori Island School.

Dec. 15, 2017
Reef Environmental Education Foundation presents: Lionfish Jewelry Workshop
Want to learn abut lionfish while making jewelry? Enjoy a 7 p.m. lecture from REEF about the background of the invasion, biology/ecology of lion fish, its impacts, current research findings, collecting tools and techniques and more. Jewelry created at the workshop will be ready to take home that evening. Fee is $30 per person, includes materials, food/beverages.
Dec. 16, 2017
RESCHEDULED: Key Largo Holiday Lighted Boat Parade
Blackwater Sound is to shimmer as decorated boats parade along the shoreline in celebration of the holiday season; 55-foot yachts to single-person kayaks are to set sail at 7:30 p.m. The best viewing and libations are to be found at Sundowners, Jimmy Johnson’s Big Chill, Senor Frijoles, the Marriott Key Largo Bay Resort and Caribbean Club, MM 103-104. Awards after-party at Sundowners, at 10 p.m.

Dec. 17, 2017
Santa Claus & His Carolers Come to Town!
From 5:30 p.m. to 9:19 p.m., Santa is en route with Season’s Greetings between Lower Matecumbe and Plantation Shores! Bring new unwrapped toys to the parade for a donation to Toys for Tots.


Dec. 15, 2017 – Dec. 16, 2017
Marathon Community Theater presents Annual Holiday Show
Jenn 305-394-1588 Website
Each 7 p.m. show includes a variety of skits, dancing and holiday sing-a-longs. Both productions are offered for a donation at the door, first-come first-served with no reserved seating only, as the Theater continues its rebuilding process.


Nov. 22, 2017 – Dec. 31, 2017
Key West Holiday Fest  Website
Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.


Dec. 14, 2017 – Dec. 16, 2017
Sugar Rum Cherry: A Burlesque Nutcracker
Christa Hunt 305.619.2862 Website
Put on your stockings and pull out your sugarplums for Key West Burlesque’s “Sugar Rum Cherry: A Burlesque Nutcracker.” This naughty holiday 2-act reverie features your favorite local performers, international burlesque superstars, and amazing aerial acrobats as they visit the land of libations. Doors open at 7:30 p.m., show starts at 8:00 p.m. Performance at Key West Theatre, 512 Eaton Street.

Dec. 14, 2017 – Jan. 6, 2018
Waterfront Playhouse presents: Inspecting Carol
305-294-5015 Website
Grab a large helping of holiday cheer with this hilarious, madcap comedy! It’s a cross between A Christmas Carol and Noises Off. Behind the scenes of a struggling theatre’s annual slapdash production of A Christmas Carol, rehearsals are at a standstill. Tim is no longer Tiny, Scrooge wants to do the play in Spanish (Feliz Navidad), and their funding is on hold pending an inspection. This laugh out loud spoof makes for a night at the theatre that is anything but show business as usual. “Inspecting Carol” is a delightful mix of “A Christmas Carol,” “Noises Off,” “Waiting for Guffman.”

Dec. 14, 2017
South Florida Symphony presents a Soiree at Hemingway House
Join the Symphony to commemorate its 20th season at the historical and beautiful Hemingway House. Immerse yourself in the writings of Hemingway as the Symphony brings to life four of his beloved stories in the four movements of the Tales of Hemingway concerto. From 6-8 p.m., at 907 Whitehead Street. Meet Grammy Award winners cellist Zuill Bailey and composer Michael Daugherty and the lead dancers of the Siudy Flamenco Dance Theater. Tickets $100 pp. Purchase tickets online.

Dec. 15, 2017
Holiday Historic Inn Tours
305-296-4959 Website
Enjoy an enchanted evening to 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.

Dec. 15, 2017
RESCHEDULED: Schooner Wharf Bar Annual Lighted Boat Parade
305-292-3302 Website
Lighted and decorated vessels from rowboats to tall ships proceed around Key West’s Historic Seaport and harbor areas. Festivities are to begin at 6 p.m. with the children of Gerald Adams Elementary Steel Your Heart Band! Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport as vessels of all shapes and sizes dazzle the crowd.

Dec. 16, 2017
Florida Keys Eco-Discover Center’s Discovery Saturday: Dolphins in the Florida Keys
Register at 305-809-4750
Discovery Saturday from 10-11 a.m. features guests from the Dolphin Research Center teaching children about the friendly and fascinating ocean mammal often seen in the waters of the Florida Keys. Space is limited. The Florida Keys Eco-Discover Center, operated by Florida Keys National Marine Sanctuary, hosts Discovery Saturday for children in kindergarten through fifth grade on the third Saturday of each month. Located in NOAA’s Dr. Nancy Foster Florida Keys Environmental Complex on the Truman Annex waterfront in Key West, the Eco-Discovery Center features more than 6,000 square feet of interactive exhibits, which interpret the resources and management efforts of Florida Keys National Marine Sanctuary, two national parks, and four national wildlife refuges.

Dec. 16, 2017
South Florida Symphony presents: Mozart Meets Hemingway & Siudy Flamenco Concert
305-295-7676 Website
Zuill Bailey, cellist extraordinaire, returns to commemorate the 20th Anniversary of the South Florida Symphony Orchestra led by Founder|Music Director Sebrina Maria Alfonso. Bailey’s rare combination of celebrated artistry, technical wizardry, and engaging personality has secured his place as one of the most sought after and active cellists today. Bailey performs the wondrous Tales of Hemingway concerto for cello and orchestra for which he won the Best Classical Instrument Solo Grammy Award in 2017. Pre-concert chat 7 p.m., performance at 7:30 p.m., Key West High School Auditorium, 2100 Flagler Avenue. Tickets available online.

Dec. 17, 2017
Keys Love Festival
Elmira Leto 305-434-6564  Website
Featuring a wide variety of talented local favorites on the City of Key West Amphitheater stage, at the Truman Waterfront from 12 noon-6pm, an all-star lineup of local musical icons includes Howard Livingston, Caffeine Carl & the Buzz, Clayton Lopez, Coffee Butler and many other well-known musicians takes the stage to make this a special day and an authentic Florida Keys event. Laid back, relaxed and in true island style, you’re asked to bring your lawn chairs and blankets for seating on the lawn. Soak up the sun for the afternoon, with final performances taking the stage under our glorious Key West sunset. Admission is free with donations of any amount greatly appreciated upon entrance, being made to support the children, families and individuals of the Florida Keys through KeysStrong.org. The funds raised will provide much needed aide and support to individuals throughout Monroe County who have been affected by Hurricane Irma.The concert will be broadcast live on Facebook Live at KeysStrong.org’s official Facebook page.

Dec. 17, 2017
Monthly Artisan Market, A Holiday “Shop Local” Edition
Browse the vibrant open-air bazaar filled with Keys artists, authors, chef-made cuisine, craftspeople and performers. Admission is free and the market is open to the public from 10 a.m. to 2 p.m. every third Sunday of each month. Bring your own bags.

Dec. 21, 2017 – Dec. 31, 2017
Fringe Theater presents: An Evening with Lillian Baxter- ALL NEW!
305-731-0581 Website
Back by popular demand! John Vessels and Jay Schwandt bring Lillian Baxter back to Key West in this all-new “one woman” show. Lillian Baxter is sweet, funny, and capable of knocking your socks off when she belts out a song! Cabaret comedy with beautiful renditions of the American songbook. Enjoy an upbeat show about life just left of the spotlight. Limited Seating. Shows 12/21-24, 12/26-31 at Little Room Jazz Club. 821 Duval Street. House opens at 6 p.m. Show at 7 p.m.

Dec. 21, 2017
Second Annual Holiday Concert & Bazaar at Custom House Museum
305-295-6616 Website
Key West Art & Historical Society is to host this second annual event, from 5-9 p.m. at the historic Custom House Museum, to feature Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show. 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. Open and free to the public.
When in the Florida Keys, we are your home away from home


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