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.
Image for Key West Holiday Fest
Image for Zonta’s Festival of Trees
  • Nov. 28, 2018 - Dec. 1, 2018 Location: Marathon Category: Arts & Culture
  • Zonta’s Festival of Trees
  • Website
  • 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.
  • Nov. 29, 2018 - Dec. 2, 2018 Location: Islamorada Category: Fishing
  • Islamorada Sailfish Tournament
  • Dianne Harbaugh 305-522-4868 Email Website
  • 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.
Image for Key West Triathlon and Expo
  • 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 Key West Artisan Market
  • Dec. 2, 2018 - 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., 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.
Image for Key West Lighted Bike Ride
  • Dec. 5, 2018 Location: Key West
  • Key West Lighted Bike Ride
  • Claire Hiller at 305-809-5000 Email Website
  • 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.
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 I Love Stock Island Festival
  • Dec. 7, 2018 - Dec. 8, 2018 Location: The Lower Keys Category: Arts & Culture
  • I Love Stock Island Festival
  • Jill Snodgrass 573-680-5468 Email Website
  • 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.
Image for Islamorada Chamber of Commerce Florida Keys Holiday Festival
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 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.
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.
  • 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 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.
  • Dec. 8, 2018 Location: Key West
  • Key West City Hometown Holiday Parade
  • 305-809-3881 Website
  • 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.
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 Fourth Annual Islamorada Half Marathon and 10K
  • Dec. 8, 2018 - Dec. 9, 2018 Location: Islamorada
  • Fourth Annual Islamorada Half Marathon and 10K
  • Robbie McClung 305-587-0901 Email Website
  • 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.
Image for Key Colony Beach Lighted Boat Parade
  • Dec. 9, 2018 Location: Marathon
  • Key Colony Beach Lighted Boat Parade
  • Website
  • 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.
Image for Christmas on the Sheriff's Animal Farm
  • Dec. 9, 2018 Location: Key West
  • Christmas on the Sheriff's Animal Farm
  • 305-293-7300 Website
  • 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.
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.
Image for Waterfront Playhouse presents: Peter and the Star Catcher
  • Dec. 13, 2018 - Jan. 6, 2019 Location: Key West Category: Arts & Culture
  • Waterfront Playhouse presents: Peter and the Star Catcher
  • Box-Office (305-294-5015) Email Website
  • 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.
Image for Marathon Lighted Bike Ride
  • Dec. 14, 2018 Location: Marathon
  • Marathon Lighted Bike Ride
  • Claire Hiller at 305-809-5000 Email Website
  • 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.
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.
  • 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 Rudolph Red Nose Run
  • 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.
  • 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.
Image for Fifth Annual Parade of Paws and Shopping Bazaar
  • Dec. 15, 2018 Location: Key West
  • Fifth Annual Parade of Paws and Shopping Bazaar
  • 305-294-4857 Website
  • 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!
Image for 28th Annual Schooner Wharf Bar Annual Lighted Boat Parade
  • Dec. 15, 2018 Location: Key West
  • 28th Annual 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.
Image for Keys Community Concert Band Holiday Suite Treats Concert
Image for Florida Keys Eco-Discover Center's Discovery Saturday: Building a Coral Reef
  • Dec. 15, 2018 Location: Key West
  • Florida Keys Eco-Discover Center's Discovery Saturday: Building a Coral Reef
  • Register at 305-809-4750 Email Website
  • 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.
Image for History of Diving Museum presents: Immerse Yourself Free Speaker Series
Image for Fringe Theater presents: Terri White’s Blue Evening
Image for 59th Annual Key West Home Tours
  • Dec. 28, 2018 - Dec. 29, 2018 Location: Key West
  • 59th Annual Key West Home Tours
  • 305-294-9501 Website
  • 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.
Image for New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Dec. 31, 2018 Location: Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • 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.
  • Dec. 31, 2018 Location: Islamorada
  • New Year's Eve Celebrations in Islamorada
  • 305-664-0604 Website
  • 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.
Image for New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Dec. 31, 2018 Location: Key West
  • New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Website
  • 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.
Image for Key West Dachshund Walk
  • Dec. 31, 2018 Location: Key West
  • Key West Dachshund Walk
  • Website
  • 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.
Image for New Year's Eve Shoe Drop Celebration
  • Dec. 31, 2018 Location: Key West
  • New Year's Eve Shoe Drop Celebration
  • Email Website
  • 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.
Image for New Year's Eve Fireworks on Blackwater Sound
  • Dec. 31, 2018 Location: Key Largo
  • New Year's Eve Fireworks on Blackwater Sound
  • 305-451-4502 Website
  • 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.
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