The Florida Keys & Key West

Calendar of Events

December 2018: Florida Keys Events

Image for Marathon Community Theater presents: Ken Ludwig's Leading Ladies
  • Nov 15, 2018 - Dec 8, 2018 Location: Marathon Category: Arts & Culture
  • Marathon Community Theater presents: Ken Ludwig's Leading Ladies
  • 305-743-0994 Box Office Website
  • 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.
  • Dec 1, 2018 Location: Key Largo Category: Arts & Culture
  • Ninth Annual Light Up Key Largo
  • 305-451-1414 Website
  • 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.
Image for Sixth Annual POSH Event
  • Dec 6, 2018 Location: Key West
  • Sixth Annual POSH Event
  • 305-304-1232 Website
  • 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.
Image for Stock Island Lighted Boat Parade
  • Dec 7, 2018 Location: The Lower Keys
  • 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.
Image for Holiday Historic Inn Tours
  • Dec 7, 2018 Location: Key West
  • 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.
  • Dec 7, 2018 - Dec 22, 2018 Location: Key West
  • Conch Tour Train Holiday Lights Tours
  • 305-294-5161 Website
  • 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
Image for Nutcracker Key West
  • Dec 7, 2018 - Dec 16, 2018 Location: Key West Category: Arts & Culture
  • Nutcracker Key West
  • Box office 305-295-7676 Website
  • 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.
Image for First Friday MM 104 Block Party
  • Dec 7, 2018 Location: Key Largo
  • First Friday MM 104 Block Party
  • Email Website
  • 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.
Image for Rams Head Productions presents: Paula Poundstone
  • Dec 7, 2018 Location: Key West Category: Arts & Culture
  • Rams Head Productions presents: Paula Poundstone
  • Website
  • 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.
Image for Christmas By the Sea Boot Key Harbor Lighted Boat Parade
  • Dec 8, 2018 Location: Marathon
  • Christmas By the Sea Boot Key Harbor Lighted Boat Parade
  • 305-743-6575
  • 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.
Image for Key Largo Holiday Lighted Boat Parade
  • Dec 8, 2018 Location: Key Largo
  • Key Largo Holiday Lighted Boat Parade
  • Website
  • 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.
Image for Celebrate the Life of Irving R. Eyster, Mr. History
  • Dec 10, 2018 Location: Islamorada Category: Arts & Culture
  • Celebrate the Life of Irving R. Eyster, Mr. History
  • Barbara Edgar at 305-393-0940
  • 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.
Image for Pet Pictures with Santa
  • Dec 12, 2018 Location: Marathon
  • Pet Pictures with Santa
  • 305-743-DOGS Website
  • 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.
  • Dec 14, 2018 - Dec 21, 2018 Location: Key West
  • Chief Peachy-Poo’s Holiday Revue
  • Tickets 305.294.0555 Website
  • 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.
Image for Holiday Historic Inn Tours
  • Dec 14, 2018 Location: Key West
  • 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.
Image for Keys Community Concert Band Holiday Suite Treats Concert
  • Dec 15, 2018 Location: Key West
  • Maser Gardener Speaker Series at Key West Botanical Garden
  • 305-296-1504 Website
  • 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.
  • Dec 15, 2018 Location: Key West
  • Rudolph Red Nose Run
  • Website
  • 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.
Image for History of Diving Museum presents: Immerse Yourself Free Speaker Series
Image for Fringe Theater presents: Terri White’s Blue Evening
Image for JJ Grey Returns to Key West with Full Band, JJ Grey & Mofro
  • Dec 29, 2018 Location: Key West Category: Arts & Culture
  • JJ Grey Returns to Key West with Full Band, JJ Grey & Mofro
  • Email Website
  • From the days of playing greasy local juke joints to headlining major festivals, JJ Grey remains an unfet-tered, blissful performer, singing with a blue-collared spirit over the bone-deep grooves of his composi-tions. His presence before an audience is something startling and immediate, at times a funk rave-up, other times a sort of mass-absolution for the mortal weaknesses that make him and his audience human. When you see JJ Grey and his band Mofro live—and you truly, absolutely must—the man is fearless.
Image for GLO on the Beach
  • Dec 30, 2018 Location: Key West
  • GLO on the Beach
  • Starting at 6 p.m., a free event with DJ music, food and beverages available for purchase; complimentary "glo" items and face painting for kids; stay for the fireworks show that starts at 9 p.m. Held at Marriott Beachside Hotel 3841 N. Roosevelt Blvd.
Image for Key West Artisan Market
  • Dec 30, 2018 Location: Key West
  • Key West Artisan Market
  • Website
  • 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.,  at a NEW location this year, at Higgs Beach. Bring your own bags. A fantastic, family-friendly, free event. 
Image for Great Gatsby NYE 2019
  • Dec 31, 2018 Location: Key West
  • Great Gatsby NYE 2019
  • Website
  • Dress to impress in your best Gatsby-era outfits! Enjoy bottomless champagne, live music and DJ performances, passed hors d'oeuvres and chef-manned food stations; tickets are $99 per person. From 8 p.m. to 1 a.m., at First Flight Brewery, 301 Whitehead St.
Image for TEST EVENT
Image for New Year's Eve Rock the Tuna Celebration
  • Dec 31, 2018 Location: Key West
  • New Year's Eve Rock the Tuna Celebration
  • Ring in the New Year at Smokin' Tuna Saloon, 4 Charles St. A $10 cover includes champagne and party favors at midnight, live entertainment and the Tuna drops at midnight.
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