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Event calendar courtesy of — The Tourism & Development council of the Florida Keys

Calendar of Events for December, 2018


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Marathon / November 15 to December 08
Marathon Community Theater presents: Ken Ludwig's Leading Ladies
The play is set in the late 1950's in and around York, PA. Leo Clark and Jack Gable, two down on their luck British actors performing their tired mash-up of "Scenes from Shakespeare", have been booed off the Elk and Moose Lodge circuit and are down to their last dollar. As they ride the train out of town, they read about a dying, elderly woman living nearby, who has been searching for her long-lost sister's children, Max and Steve, who have been raised in England, in hopes of leaving them her multi-million inheritance. Leo and Jack concoct a scheme to pass themselves off as her British nephews, and are surprised to learn that Max and Steve are actually Maxine and Stephanie! Forging ahead with their plans, they rapidly swap their men's attire for ladies' stylish finery. Tickets are $25 pp.
Contact: 305-743-0994 Box Office

Key West / November 21 to December 31
Key West Holiday Fest
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.

Marathon / November 28 to December 01
Zonta’s Festival of Trees
The annual Festival of Trees is to take place at the Florida Keys Country Club. Holiday trees are festively displayed, and decorated by members of the Zonta Club of Marathon, a humanitarian service organization. Visitors and residents can view and bid to purchase the decorated trees between 5-9 p.m., and Saturday, Dec. 1 from 9:30 a.m. to noon.

Islamorada / November 29 to December 02
Islamorada Sailfish Tournament
The first leg of the triple-crown Florida Keys Gold Cup Championship series is the only tournament in the series to offer a junior division for anglers age 16 and younger. Unlimited anglers are allowed per vessel. Kick off is Nov. 29; fish dates Nov. 30, Dec 1 and 2. Awards ceremony Dec 2.
Contact: Dianne Harbaugh 305-522-4868

Key West / December 01
Key West Triathlon and Expo
The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport's best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

Key Largo / December 01
Ninth Annual Light Up Key Largo
Sponsored by the Key Largo Chamber of Commerce, holiday happenings with live music, decorations, food and drinks are to spark the holiday spirit, from 5-9 p.m. The annual tree lighting is to be at 8:30 p.m., events held at the Murray E. Nelson Government and Cultural Center, MM 102. Eggnog, caroling, holiday cookies and ornament making for stocking stuffers are guaranteed to get everyone in the festive mood.
Contact: 305-451-1414

Key West / December 02 to December 30
Key West Artisan Market
Browse among culinary, textile, jewelry, wood, artists & crafters, curiosities, live music, craft beer, wine and art and food concessions. From 10 a.m. to 2 p.m., every three weeks (except Easter), at a NEW location this year, at Higgs Beach. Bring your own bags. A fantastic, family-friendly, free event. Dates: Dec. 2, 16 & 30.

Key West / December 05
Key West Lighted Bike Ride
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration/checkin at 6 p.m. with the Lighted Bike Ride beginning at 7:00 p.m. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Key West Holiday Store. Register online.
Contact: Claire Hiller at 305-809-5000

Key West / December 06
Sixth Annual POSH Event
The Paws Often Steal Hearts, or POSH, party is to be held at the Audubon House & Tropical Gardens, 205 Whitehead St., from 6-9 p.m., to benefit the Florida Keys Society for the Prevention of Cruelty to Animals. Attendees are encouraged to wear island-style formal attire and "fascinator" hats. General admission tickets are $40 pre-purchased and $45 at the door, per person.
Contact: 305-304-1232

Big Pine & the Lower Keys / December 07 to December 08
I Love Stock Island Festival
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 & Little Mr. & Miss contest, and more.
Contact: Jill Snodgrass 573-680-5468

Islamorada / December 07
Islamorada Chamber of Commerce Florida Keys Holiday Festival
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.
Contact: 305-664-4503

Key West / December 07 to December 16
Nutcracker Key West
Inspired by the unique and colorful environment of the Florida Keys, Clara and her young Prince encounter enchanted landscapes complete with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea-Star Fairy, and "underwater" sequences of almost unimaginable beauty. Local children, adults and community leaders are cast alongside a nationally-cast corps de ballet in this spectacularly crafted semi-annual production of a beloved classic. Shows held at the Tennessee Williams Theatre.
Contact: Box office 305-295-7676

Big Pine & the Lower Keys / December 07
Stock Island Lighted Boat Parade
Stock Island Lighted Boat Parade is a free event. Activities begin at 5 p.m., with the parade scheduled for 7 p.m., and an after-party at 9 p.m. Guests will delight in seeing the bright lights on everything from tri-masted schooners to dinghies to the shrimp boats that call Stock Island home. The boat parade is presented by Sunset Watersports with free viewing events at Stock Island Marina Village and Safe Harbor.

Key West / December 07
Holiday Historic Inn Tours
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.
Contact: 305-296-4959

Key Largo / December 07
First Friday MM 104 Block Party
Join Key Largo's new monthly, free-admission block party along the Overseas Highway at mile marker 104 in Key Largo, presented by the Upper Keys Merchants Assoc. Held the first Friday of each month, rain or shine, from 6-10 p.m., stroll among artists, street bites, gifts, eateries and more. Park at any of the MM104 businesses and walk along the bayside bike pathway.

Key West / December 07
Rams Head Productions presents: Paula Poundstone
With smart, observational humor and a legendary spontaneous interaction with the crowd, Paula Poundstone is one of our country's pre-eminent comedians. She improvises with a crowd like a Jazz musician, swinging in unexpected directions without a plan, without a net. There's a disarming ease in her craft, an immediate sense that she's so quick on her feet you need never worry about the possibility of something going wrong. Doors open 7 p.m., show starts 8 p.m., at Key West Theater, 512 Eaton St.

Key West / December 07 to December 22
Conch Tour Train Holiday Lights Tours
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. TOUR DATES: Dec. 7, 15, 19, 21 and 22
Contact: 305-294-5161

Marathon / December 08
Christmas By the Sea Boot Key Harbor Lighted Boat Parade
From dinghies to yachts, both power and sail boats welcome! Parade starts at 6 p.m. from the west end of Boot Key Harbor and slowly wind its way east into the harbor toward Sombrero Marina Dockside, back through the harbor and ending at Lazy Days South at Marathon Marina for a post-parade award party at approximately 8:30 p.m. Best viewing spots include Lazy Days South, Burdines Waterfront/Panchos Fuel Dock, Marathon Marina and Sombrero Marina Dockside. Prizes for best boat in each division.
Contact: 305-743-6575

Key West / December 08
Key West City Hometown Holiday Parade
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 non-motorized floats and lively community participation. The parade kicks off at Bayview Park's Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.
Contact: 305-809-3881

Key Largo / December 08
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.

Islamorada / December 08 to December 09
Fourth Annual Islamorada Half Marathon and 10K
Winter distance runners in the Florida Keys can welcome warmer climes and the return of Islamorada's annual Half Marathon, 10k and the run-for-fun Beach N' Beer Mile. The subtropical road race is open to bucket list runners or newbies of all ages and skill levels. Registration is open for the half-marathon and 10k events from 11 a.m. to 3 p.m. Saturday, Dec. 8. At noon the fun-while-you-run Beach N' Beer Mile kicks off from the iconic Robbie's Marina, mile marker 77.5 bayside. The main half-marathon and 10k events Sunday also begin at Robbie's Marina.
Contact: Robbie McClung 305-587-0901

Marathon / December 09
Key Colony Beach Lighted Boat Parade
Christmas lights on outriggers, Santa's elves and brightly lit deck displays highlight the beautiful festivities during the Key Colony Beach Boat Parade. Set to begin at the 7th Street canal, the parade is open to all boats, and the route visits canals and cuts, and passes city hall three times. Great viewing spots include Sadowski Causeway at MM 53.5 and the dock area behind city hall and the post office. The public is welcome.

Key West / December 09
Christmas on the Sheriff's Animal Farm
From 1-3 p.m., kids 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 situated at the county's detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff's Animal Farm is open the second and fourth Sundays of the month.
Contact: 305-293-7300

Key West / December 09 to December 22
Old Town Trolley’s Holiday Lights and Sights Tours
The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best decorated historic neighborhoods, buildings and homes. TOUR DATES: Dec. 9, 15, 19, 21 and 22
Contact: 305-296-6688

Islamorada / December 10
Celebrate the Life of Irving R. Eyster, Mr. History
The posthumous celebration of the late Irving R. Eyster will be held at the Islamorada Moose Lodge. Hors d'oeuvres will be served starting at 5:30 p.m. followed by an audio visual presentation of Mr. Eyster's life, who would have been 100 years young on this day. A presentation is to show some of the most unusual and fascinating items ever found on our islands, and Eyster, a well-known historian and archaeologist, collected items and preserved them for future generations for over 60 years. Known as Mr. History, his knowledge was extensive. He excavated Indian Key in the 1970's, was the foremost authority on the island and was known as Mr. Indian Key. Presentation will include items from the early Indians, shipwrecks, diving, Flagler's Railway, Indian Key, lighthouses, maps, documents, and some rare and unusual items. Donation of $30 per person to honor and share the life of Mr. Eyster also helps the MHT. The evening will end with birthday cake to finish off the celebration.
Contact: Barbara Edgar at 305-393-0940

Marathon / December 12
Pet Pictures with Santa
Hosted by Keys Animal Hospital. Santa is to pose for photos with pets from 4-7 p.m. 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 welcomed.
Contact: 305-743-DOGS

Key West / December 13 to January 06
Waterfront Playhouse presents: Peter and the Star Catcher
Who doesn't love the magic of the story of Peter Pan? Peter and the Starcatcher is the Tony Award-winning smash that is packed with theatrical razzle dazzle. This play with music is a prequel to Peter Pan, as we learn how a young orphan boy becomes The Boy Who Won't Grow Up. Based on the best-selling novels of Dave Barry and Ridley Pearson, Peter... uses ingenious stagecraft to bring the adventures of Peter to life.  See website for show dates. Showtimes 8 p.m.
Contact: Box-Office (305-294-5015)

Marathon / December 14
Marathon Lighted Bike Ride
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Marathon for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration/checkin at 6 p.m. with the Lighted Bike Ride beginning at 7 p.m. at the Marathon Airport. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Marathon Holiday Store. Register online.
Contact: Claire Hiller at 305-809-5000

Key West / December 14
Holiday Historic Inn Tours
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.
Contact: 305-296-4959

Key West / December 14 to December 21
Chief Peachy-Poo’s Holiday Revue
Deck the halls and jingle your balls, it's time for Chief Peachy-Poo's Holiday Revue! Key West's smallest strongman and drag-tastic super star, Chief Peach, hosts two evenings of holiday cheer. Peach is joined by the Conch Republic's Queen of Burlesque, Tatah DuJour, along with Nick Mazza, and the Key West Burlesque Dancers to celebrate the season. The show will feature festive weekly guest performers including Sofia Luna, Aurora Natrix, and Cheeky Derrière. Doors open at 7:30 p.m., show starts at 8 p.m. Show nights Dec. 14 & 21 at the Backroom at Sidebar 504 Angela St.
Contact: Tickets 305.294.0555

Key West / December 15
Rudolph Red Nose Run
Don your festive holiday running attire, affix your ruby-red nose, and join in the 11th Annual 5K Rudolph Red Nose Run, Saturday Dec. 15, starting and ending at the Southernmost Beach Café. Race day check-in starts at 7 a.m. with an 8 a.m. start. After the race, enjoy refreshments, fun, prizes and a huge silent auction.

Key West / December 15
Maser Gardener Speaker Series at Key West Botanical Garden
The Key West Botanical Garden Society presents Master Gardener, Michelle Leonard-Mularz to begin its 6-month Speaker Series. Held at 1:30 p.m. in the Toppino Nature Chapel. Michelle will speak on "Gardening in the Keys and the Master Gardener Program." Admission is free for members, $5 for non-members. All proceeds directly benefit the Garden's conservation program. The Garden is located at 5210 College Road, Stock Island.
Contact: 305-296-1504

Key West / December 15
Fifth Annual Parade of Paws and Shopping Bazaar
Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet's photo! Shopping Bazaar inside the dog park features entertainment, food vendors, a Kissing Booth, holiday gifts for that special snuggle bug and more! A unique opportunity to support the lifesaving mission caring for the Keys' community's homeless animals, the event supports the Florida Keys SPCA. Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends to meet reigning King and Queen, Tigger and Cat!
Contact: 305-294-4857

Key West / December 15
28th Annual Schooner Wharf Bar Annual Lighted Boat Parade
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.
Contact: 305-292-3302

Islamorada / December 15
Keys Community Concert Band Holiday Suite Treats Concert
The family-friendly free-admission event, themed "Holiday Suite Treats," offers traditional and pops music performed by the Keys Community Concert Band, sing-alongs, stories and Santa as well as a children's ballet troupe performance and handbell ringers. Concert is to be held at 4 p.m., at the ICE Amphitheater at Founders Park, mile marker 87 bayside.
Contact: Donna Heiner 305-853-7294

Key West / December 15
Florida Keys Eco-Discover Center's Discovery Saturday: Building a Coral Reef
Discovery Saturday from 10-11 a.m. is hosted by Mote Marine and includes a lesson for children to learn how corals grow and they will make their own reef using clay, pipe cleaners and beads. 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.
Contact: Register at 305-809-4750

Islamorada / December 17
History of Diving Museum presents: Immerse Yourself Free Speaker Series
The History of Diving Museum presents the annual presentation series that spotlights a new topic the third Wednesday of each month, at 7 p.m. Exhibits and museum store stay open late (normal museum admission applies).
Contact: 305-664-9737

Islamorada / December 20
Morada Way Arts & Cultural District presents: Third Thursday Art Walk
Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82, as well as "culinary art" and live music from 6-9 p.m. A great pre-holiday celebration. Free admission. Art Walk is held the third Thursday of each month.

Key West / December 27 to December 31
Fringe Theater presents: Terri White’s Blue Evening
Broadway star Terri White shares her personal journey to Broadway and back again. The evening intersperses personal stories and show tunes, triumphs and challenges. Accompanied by Pianist Megan Clay. Little Room Jazz Club, 821 Duval Street. Show starts 7 p.m.
Contact: Rebecca Tomlinson 305-587-8961

Key West / December 28 to December 29
59th Annual Key West Home Tours
Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-6 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $35 in advance, $40 day-of-tour. Proceeds benefit the foundation's museum and programs.
Contact: 305-294-9501

Key West / December 31
New Year's Eve: Conch Shell Drop at Sloppy Joe's
The arrival of 2019 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. and featuring dancing in the street and a countdown to midnight recorded on a huge clock.

Islamorada / December 31
New Year's Eve Celebrations in Islamorada
Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the beach at Morada Bay Beach Café at MM 81.6 bayside, who is to host a colorful large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.
Contact: 305-664-0604

Key West / December 31
New Year's Eve: Pirate Wench Drop at Schooner Wharf
For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2018. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

Key West / December 31
Key West Dachshund Walk
Frost-free Key West becomes a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.

Key West / December 31
New Year's Eve Shoe Drop Celebration
The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

Key Largo / December 31
New Year's Eve Fireworks on Blackwater Sound
The back bay is the setting for the annual New Year's Eve fireworks extravaganza hosted by Sundowners, Jimmy Johnson's Big Chill, Senor Frijoles, Cactus Jacks, Gus' Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, MM 103-104. Check website for details.
Contact: 305-451-4502