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Taste| December 14, in Marathon |
| Marathon Lighted Bike Ride December 14 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 Email: claire.hiller@wesleyhouse.org |
| December 05, in Key West |
| Key West Lighted Bike Ride December 05 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 Email: claire.hiller@wesleyhouse.org |
| December 08 to December 09, in Islamorada |
| Third Annual Islamorada Half Marathon and 10K December 08 to December 09 Join the Friday “Beer Mile” event, which is quite simple: 1 Mile and 4 Beers. Do you have what it takes? Saturday is the main event; there are to be cash prizes for the top 3 finishers for male/female in the half marathon and great awards for the top 3 finishers of the 10K. In addition, prizes for those who place top 3 in their age groups for both races. Register for all events online. Early-bird savings. Contact: Robbie McClung 305-587-0901 Email: islamoradahalf@gmail.com |
| December 31, in Key West |
| New Year’s Eve Shoe Drop Celebration December 31 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. Email: schroedkw@aol.com |
| November 29 to December 02, in Islamorada |
| Islamorada Sailfish Tournament November 29 to December 02 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 Email: ditournaments@aol.com |
| November 21 to December 31, in Key West |
| Key West Holiday Fest November 21 to December 31 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. |
| November 28 to December 01, in Marathon |
| Zonta’s Festival of Trees November 28 to December 01 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. |
| December 06, in Key West |
| Sixth Annual POSH Event December 06 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 |
| December 12, in Marathon |
| Pet Pictures with Santa December 12 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 |
| December 20, in Islamorada |
| Morada Way Arts & Cultural District presents: Third Thursday Art Walk December 20 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. |
| December 07, in Islamorada |
| Islamorada Chamber of Commerce Florida Keys Holiday Festival December 07 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 |
| December 01, in Key West |
| Key West Triathlon and Expo December 01 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. Email: lizlovekw@gmail.com |
| December 07 to December 08, in Big Pine |
| I Love Stock Island Festival December 07 to December 08 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 Email: info@ilovestockisland.org |
| December 15, in Key West |
| Fifth Annual Parade of Paws and Shopping Bazaar December 15 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 |
| December 14, in Key West |
| Holiday Historic Inn Tours December 14 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 |
| December 07 to December 16, in Key West |
| Nutcracker Key West December 07 to December 16 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 |
| December 15, in Islamorada |
| Keys Community Concert Band Holiday Suite Treats Concert December 15 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 Email: keyscommunityconcertband@yahoo.com |
| December 09, in Marathon |
| Key Colony Beach Lighted Boat Parade December 09 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. |
| December 15, in Key West |
| 28th Annual Schooner Wharf Bar Annual Lighted Boat Parade December 15 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 |
| December 31, in Key Largo |
| New Year’s Eve Fireworks on Blackwater Sound December 31 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 |
| December 08, in Key Largo |
| Key Largo Holiday Lighted Boat Parade December 08 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. |
| December 28 to December 29, in Key West |
| 59th Annual Key West Home Tours December 28 to December 29 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 |
| December 31, in Key West |
| New Year’s Eve: Conch Shell Drop at Sloppy Joe’s December 31 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. |
| December 31, in Islamorada |
| New Year’s Eve Celebrations in Islamorada December 31 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 |
| December 31, in Key West |
| New Year’s Eve: Pirate Wench Drop at Schooner Wharf December 31 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. |
| December 01, in Key Largo |
| Ninth Annual Light Up Key Largo December 01 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 |
| December 08, in Key West |
| Key West City Hometown Holiday Parade December 08 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 |
| December 09, in Key West |
| Christmas on the Sheriff’s Animal Farm December 09 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 |
| December 31, in Key West |
| Key West Dachshund Walk December 31 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. |
| December 15, in Key West |
| Florida Keys Eco-Discover Center’s Discovery Saturday: Building a Coral Reef December 15 Discovery Saturday from 10-11 a.m. is hosted by Reef Relief 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 Email: FKEDC@noaa.gov |
| December 07, in Big Pine |
| Stock Island Lighted Boat Parade December 07 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. |
| December 07, in Key West |
| Holiday Historic Inn Tours December 07 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 |
| December 02 to December 30, in Key West |
| Key West Artisan Market December 02 to December 30 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. |
| December 17, in Islamorada |
| History of Diving Museum presents: Immerse Yourself Free Speaker Series December 17 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 |
| December 13 to January 06, in Key West |
| Waterfront Playhouse presents: Peter and the Star Catcher December 13 to January 06 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) Email: Box-Office@waterfrontplayhouse.org |
| December 07, in Key Largo |
| First Friday MM 104 Block Party December 07 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. Email: events@fkrm.com |
| December 27 to December 31, in Key West |
| Fringe Theater presents: Terri White’s Blue Evening December 27 to December 31 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 |
| December 08, in Marathon |
| Christmas By the Sea Boot Key Harbor Lighted Boat Parade December 08 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 |
| December 15, in Key West |
| Rudolph Red Nose Run December 15 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. |
| December 07 to December 22, in Key West |
| Conch Tour Train Holiday Lights Tours December 07 to December 22 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 |
| December 09 to December 22, in Key West |
| Old Town Trolley’s Holiday Lights and Sights Tours December 09 to December 22 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 |
| December 07, in Key West |
| Rams Head Productions presents: Paula Poundstone December 07 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. |
| November 15 to December 08, in Marathon |
| Marathon Community Theater presents: Ken Ludwig’s Leading Ladies November 15 to December 08 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 |
| December 10, in Islamorada |
| Celebrate the Life of Irving R. Eyster, Mr. History December 10 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 |
| December 15, in Key West |
| Maser Gardener Speaker Series at Key West Botanical Garden December 15 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 Stay With US KEYS CARIBBEAN LUXURY RESORT VILLAS & MARINAS You will be glad you did…
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