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Calendar of Events

December 2020: Florida Keys Events

Due to the coronavirus crisis, most near-term Florida Keys special events have been or are likely to be canceled. If you see an event listed, please check the event’s website or call its organizer for more details.

Image for History of Diving Museum Featured Exhibit: In Depth - 15 Years of the Diving Museum
  • Dec 1, 2020 - Jul 31, 2021 Key West Fishing
  • Key West Fishing Tournament
  • Website
  • More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.
Image for Randy Roberts Live!
  • Dec 1, 2020 - Dec 30, 2020 Key West
  • Randy Roberts Live!
  • Website
  • The Randy Roberts Show is an all live, multi-media tribute to some of the world’s most loved performers. Randy’s uncanny impersonations of Cher and Bette Midler have kept him in the spotlight for the past twenty years. Performances at LaTeDa Cabaret and Piano Bar, 1125 Duval St. LaTeDa practices social distancing. Face coverings must be worn to enter property and while standing or walking, face coverings can only be removed while seated for eating or drinking. Showtimes, dates and tickets available online.
Image for Zonta’s Festival of Trees
  • Dec 3, 2020 - Dec 12, 2020 Marathon Arts & Culture
  • Zonta’s Festival of Trees
  • Website
  • The annual Festival of Trees is to take place at the Marathon Community Theater, 5101 Overseas Highway. 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 during open hours. Sunday, Dec. 6, from 11 a.m. to 2 p.m., kids can enjoy cookies and photos with Santa. Masks are required to wear inside the theater.
Image for Islamorada Sailfish Tournament
  • Dec 3, 2020 - Dec 6, 2020 Islamorada Fishing
  • Islamorada Sailfish Tournament
  • Email Website
  • For over 50 years, the Islamorada Sailfish Tournament has opened the renowned triple-crown Florida Keys Gold Cup Sailfish Championship series. This first leg of the series is the only tournament in the series to offer a junior division for anglers ages 16 and younger. The all-release tournament is a primary fundraiser for the Islamorada Charter Boat Association.
Image for Holiday Lights & Sights Tours with Old Town Trolley Tours
Image for Conch Tour Train Holiday Light Tours
  • Dec 4, 2020 - Dec 23, 2020 Key West
  • Conch Tour Train Holiday Light Tours
  • 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 6:30 p.m. and 7:15 p.m. with departures from Key West High School, 2100 Flagler Ave. Capacity is limited. COVID-19 safety protocols in place.
Image for Islamorada Chamber of Commerce presents Holiday Ornaments Auction
  • Dec 4, 2020 - Dec 13, 2020 Islamorada
  • Islamorada Chamber of Commerce presents Holiday Ornaments Auction
  • Website
  • Due to recent COVID-19 safety protocols, and in order to keep everyone safe and healthy during the holiday season and beyond, the Islamorada Chamber of Commerce has cancelled their popular Holiday Festival & Parade. However, one of the fest’s most popular features, the Holiday Ornaments Auction, is being held online. The auction is open through Sunday , Dec.13, 2020 at 3 p.m. Winners are to be announced on Monday, Dec. 14, 2020 on the chamber’s Facebook page.
  • Dec 4, 2020 - Dec 6, 2020 Islamorada
  • Islamorada Half Marathon, 10K and Beer N' Beach Mile
  • Robbie McClung 305-587-0901 Email Website
  • Run the half, a 10K or a 5K! You choose, and you can even participate virtually, from your hometown and still get cool swag. The "Beer Mile" event, that is quite simple: 1 Mile and 4 Beers. Do you have what it takes? 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. Earlybird savings, and COVID-19 safety protocols are to be in place.
Image for Christopher Peterson's EYECONS
  • Dec 5, 2020 - Dec 31, 2020 Key West
  • Christopher Peterson's EYECONS
  • Website
  • Christopher Peterson is a master of impersonations, both visually and vocally, and his comic timing is impeccable. The show is All Live, no lip-sync, and audiences will be thrilled with his characterizations of Marilyn Monroe, Carol Channing, Madonna, Joan Rivers, Reba McEntire, Bette Midler, Tina Turner, Julie Andrews, Barbra Streisand, Liza Minnelli, Judy Garland, Eartha Kitt, Cher, Bette Davis, Lucille Ball and now even Lady GaGa. LaTeDa Cabaret and Piano Bar, 1125 Duval St., practices social distancing. Face coverings must be worn to enter property and while standing or walking, face coverings can only be removed while seated for eating or drinking. Showtimes, dates and tickets available online.
Image for Marathon Community Theater's Annual Holiday Show
  • Dec 5, 2020 Marathon
  • Marathon Community Theater's Annual Holiday Show
  • Website
  • Get in the spirit with the MCT Annual Holiday Show (8:30 pm showtime) - to immediately follow Zonta's Festival of Trees (5-8 pm). Please note that this is a socially distanced, indoor production in MCT's Main Auditorium. Temperature Check at front door. Face masks will be required to enter, move about the building and during the stage production. There are a limited amount of seats and will be sold in groups of two (2) and four (4). Tickets available online.
Image for Holiday Artisan Market with The Studios of Key West
  • Dec 8, 2020 - Dec 24, 2020 Key West
  • Holiday Artisan Market with The Studios of Key West
  • Website
  • Kick off the holiday season with The Studios of Key West by supporting community artists and small businesses. This season, TSKW is temporarily transitioning to an online platform, helping you find the perfect gifts. Their online shop will be available to browse through Christmas Eve. It will still be a one-stop-shopping experience with links to 25 unique local artisans who create jewelry, textiles, home accessories and more.
Image for 'Art. Wherever You Are.' Winter Members’ Exhibition
  • Dec 8, 2020 - Dec 31, 2020 Key West
  • 'Art. Wherever You Are.' Winter Members’ Exhibition
  • Website
  • If being mostly housebound over the last year has taught us anything, it’s been new ways of connecting. We’ve explored the world virtually, scheduled screen chats with loved ones, and opened our eyes to old injustices and hidden treasures that were around us all along. Our ties to our neighbors – both across the street and across the globe – have never felt more real, and the physical places where we find ourselves seem to matter more than ever, and not at all. For our winter members’ exhibition, we invite artwork about wherever you are – whether it’s the view from your window, or from your mind’s eye.?
Image for Celebrate 60 Years of John Pennekamp Coral Reef State Park
  • Dec 10, 2020 Key Largo
  • Celebrate 60 Years of John Pennekamp Coral Reef State Park
  • Website
  • Join a milestone birthday celebration as John Pennekamp Coral Reef State Park, America’s first underwater preserve, turns 60 years old. The park was dedicated Dec. 10, 1960, capping efforts by the late “Miami Herald” editor John Pennekamp to create the Florida Keys jewel that lies just 90 minutes’ drive from Miami. Today, the park named for Pennekamp draws more than one million visitors annually to explore its nature trails and beaches and observe the abundant underwater wildlife that inhabits its 70 nautical miles. Register to join the Zoom presentation; virtual program from 7-8 p.m..
Image for Islamorada Junior Sailfish Tournament
  • Dec 11, 2020 - Dec 13, 2020 Islamorada Fishing
  • Islamorada Junior Sailfish Tournament
  • Tammy Gurgiolo 305-240-9337 Email
  • The Florida Keys’ oldest sailfish tournament for kids age 16 and under, this event has been held since 1964. It is designed to teach teens fishing skills they can apply in competition.
Image for Artist Showcase at the Green Pineapple at The Perry
  • Dec 11, 2020 The Lower Keys
  • Artist Showcase at the Green Pineapple at The Perry
  • Website
  • Join a special Holiday Edition of the Green Pineapple Artist Showcase in the lobby of the beautiful Perry Hotel! From 5:30-7:30 p.m., share the evening with incredible local artists plus back-to-back happy hour at Salty Oyster and The Barrel House, followed by dinner at Matt’s Stock Island.
Image for Stock Island Art Stroll
  • Dec 12, 2020 The Lower Keys
  • Stock Island Art Stroll
  • Website
  • From 11am to 5pm, stroll the Stock Island Arts District. Each location offers a variety of eclectic shops and working studios with multiple artists and disciplines from sculptures to woodworking, mosaics to screen printing, soaps to fabric art. Please maintain social distancing and wear a mask when indoors and outdoors when social distancing isn't possible. Stay safe and have fun!
  • Dec 12, 2020 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 the parade's host location, Jimmy Johnson's Big Chill, and other waterfront venues between, MM 103-104. Free to enter, $2,000 in cash and prizes.
Image for Marathon Community Theater's Annual Holiday Show
  • Dec 12, 2020 Marathon
  • Marathon Community Theater's Annual Holiday Show
  • Website
  • Get in the spirit with the MCT Annual Holiday Show (8:30 pm showtime) - to immediately follow Zonta's Festival of Trees (5-8 pm). Please note that this is a socially distanced, indoor production in MCT's Main Auditorium. Temperature Check at front door. Face masks will be required to enter, move about the building and during the stage production. There are a limited amount of seats and will be sold in groups of two (2) and four (4). Tickets available online.
Image for Key West Artisan Market Holiday Mart
  • Dec 12, 2020 Key West
  • Key West Artisan Market Holiday Mart
  • Website
  • Enjoy the Holiday Mart: Shop Local Edition at the unique Sunset Green Event Lawn, 12,000 square feet of lush, open air tropical landscaping located at the Gates Hotel and 24 North Hotel. Twenty five artists and makers are to showcase stunning handcrafted items perfect for holiday gift giving. The Artisan Market will temporarily move from its Higgs Beach location to facilitate this show. The hotel will offer coffee, full bar and snacks for purchase to nourish guests while they shop this curated market. Stringent safety measures and precautions will be in place to guard attendees and the vendors who serve them. Masks will be required, booths spaced out, social distance signage posted and the number of guests per stall limited. Hand sanitizing stations will be at the entrances.  The Market offers free entry and ample free parking. Guests are encouraged to ride bikes, BYOB (bring your own bags) and WYM (wear your mask).  
Image for Cocktails and Carols, Key Choral Arts' Virtual Concert
  • Dec 13, 2020 - Dec 27, 2020 Key West
  • Cocktails and Carols, Key Choral Arts' Virtual Concert
  • Website
  • Singing for in-person audiences this holiday season is not possible. Instead, Keys Choral Arts has prepared a virtual concert, their only fundraiser of the year, to premier on December 13, at 4PM. The hour-long concert is to include several musical pieces performed by 40 regular KCA performers in virtual choir fashion.  Enjoy solos, duets and small groups of singers from the KCA performers. Performances online for 14 days. Tickets $20/viewer.
Image for Immerse Yourself: Famed Wreck Diver John Chatterton
  • Dec 16, 2020 Islamorada
  • Immerse Yourself: Famed Wreck Diver John Chatterton
  • Website
  • Hosted by the History of Diving Museum as part of its monthly free lecture series. Join film actor and famed wreck diver John Chatterton as he tells guests about his explorations to some of the challenging sites in the underwater world. Presentation is virtual; starts 7 p.m.
Image for LIVE From the Lawn: Patrick & the Swayzees at The Perry
  • Dec 18, 2020 The Lower Keys
  • LIVE From the Lawn: Patrick & the Swayzees at The Perry
  • Website
  • Enjoy an exclusive concert outdoors on The Perry Hotel’s event lawn, starting at 8 p.m. This exclusive performance will be limited to 100 guests - please reserve chair or blanket space on the lawn for up to 4 guests. In the interest of social distancing, reservations are required and tickets must be purchased in advance.
Image for Key West Holiday Movie Challenge
  • Dec 19, 2020 Key West
  • Key West Holiday Movie Challenge
  • Website
  • What would Love Actually sound like with a Conch accent? What if It’s a Wonderful Life’s George Bailey grew up in Key West instead of Bedford Falls? Participants have one long weekend to reimagine their favorite Christmas movies with a Key West twist. The challenge is open to filmmakers of all levels—even first timers. People’s Choice awards will be given in two categories: short film and mini challenge.
Image for 61st Annual Key West Home Tours
  • Dec 29, 2020 - Dec 30, 2020 Key West
  • 61st Annual Key West Home Tours
  • 305-294-9501 Email Website
  • Presented by the Old Island Restoration Foundation, the annual tours from 1-5 p.m. each day showcase festively dressed Key West homes and gardens. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in the Key West local community fulfilling OIRF’s mission of “Celebrating and sustaining Key West’s unique architecture, culture and history.”  The number of visitors allowed inside each home will be limited, masks will be required and hand sanitizers will be provided. Reservations for tour time slots are required and tickets must be purchased in advance.
Image for Marathon Community Theater presents: The Vagina Monologues
  • Jan 7, 2021 - Dec 23, 2020 Marathon Arts & Culture
  • Marathon Community Theater presents: The Vagina Monologues
  • Website
  • An Obie Award-winning whirlwind tour of a forbidden zone. THE VAGINA MONOLOGUES by Eve Ensler, introduces a wildly divergent gathering of female voices, including a six-year-old girl, a septuagenarian New Yorker, a vagina workshop participant, a woman who witnessed her best friend give birth, a Bosnian survivor of rape, and a feminist happy to have found a man who “liked to look at it.” Performances Thursday, Friday and Saturday evening shows at 8:00 pm with a 3:00 pm matinee offered on Sunday, January 17. Tickets $25 pp.
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