The Florida Keys & Key West

Calendar of Events

Current Florida Keys Events

Image for First Fridays on Fleming
  • Jan 3, 2020 - Apr 3, 2020 Location: Key West Category: Arts & Culture
  • First Fridays on Fleming
  • 305-304-9001 Website
  • Key West boutique owners in “The Fabulous 500 Block of Fleming Street” have kicked off a monthly First Fridays on Fleming 6-9 p.m. block party to encourage local buying. First Fridays on Fleming showcase boutiques, galleries and eateries in the 500 block of Fleming Street with events such as jewelry trunk shows, art openings, book signings, tastings and libations. Participants include The Roost Bar and Liquor Store, La Rubia Authentic Panama Hats, Key West Island Books, Key West Local Luxe Jewelry, Amanda Johnson Fine Art, Sea Store Antiques, Assortments Menswear, Island Antiques, Duck & Dolphin Antiques, Clemente’s Trolley Pizzaria, La Petite Grignote French Bakery, Thirsty Mermaid Seafood and Jean Pierre Klifa Resort Wear. First Fridays are scheduled Jan. 3, Feb. 7, March 6 and April 3.
Image for 2020 Upper Keys Members Art Show: Small Works, Flora and Fauna
  • Jan 11, 2020 - Jan 29, 2020 Location: Key Largo Category: Arts & Culture
  • 2020 Upper Keys Members Art Show: Small Works, Flora and Fauna
  • An opening reception will be held Saturday, Jan. 11, from 1–4 p.m. at the Key Largo Library, 101485 Overseas Hwy. The public is invited, refreshments will be served, and there is ample free parking. This Upper Keys Arts Council Member's Show at Key Largo Library supports the Art in Public Buildings program which offers an alternate space for artists to display their work. The exhibition will remain on display through January 29, 2020.
Image for Stock Island Arts District's Second Saturday Art Stroll
  • Jan 11, 2020 - Apr 11, 2020 Location: The Lower Keys Category: Arts & Culture
  • Stock Island Arts District's Second Saturday Art Stroll
  • Website
  • A new Stock Island Arts District encompasses Collections Key West at Safe Harbor Marina, The Art Shack at 6404 Front St., The Shops at the Perry Hotel, The Studios at Stock Island Marina Village and Washed Up Studios. Each spot 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 along with several retail and gallery buying opportunities. There's a few stand-alone studios that will be open for viewing, as well, including Yodanis Studios. ‘Stroll' at leisure from 11AM to 4PM between the studios. Some artists will offer drawings for great prizes and delicious food & beverages. It's free to attend and free to park. Guests can look for the bright pink 'Arts District' banners flying proud at each location and follow the route on the mobile map 
Image for History of Diving Museum NEW Featured Exhibit: Dive Into Art, The Beauty of Recycling
Image for Waterfront Playhouse presents: Glass
  • Jan 16, 2020 - Feb 1, 2020 Location: Key West Category: Arts & Culture
  • Waterfront Playhouse presents: Glass
  • Website
  • Two legendary figures of the American Theatre, Tennessee Williams and actress Laurette Taylor, meet backstage before the opening night of The Glass Menagerie in Chicago to exchange best wishes. When an unopened bottle of scotch is discovered in her dressing room, sparks ignite as they are both challenged to face down a common demon. Showtimes 8 p.m.
Image for Marathon Community Theater presents: Four Old Broads
  • Jan 16, 2020 - Feb 8, 2020 Location: Marathon Category: Arts & Culture
  • Marathon Community Theater presents: Four Old Broads
  • Website
  • In this laugh-out-loud comedy, retired burlesque queen Beatrice Shelton desperately needs a vacation--and a Sassy Seniors Cruise may be just the ticket if she can convince her best friend, Eaddy Mae Clayton, to stop praying and join her. Unfortunately, things haven’t been pleasant at Magnolia Place Assisted Living since Nurse Pat Jones was hired. A mystery unfolds, hilarity ensues at a Miss Magnolia Senior Citizen Pageant. Will the four old broads make it to their cruise ship? Show dates online; showtimes 8 p.m.; Sunday matinee 3 p.m.
Image for LaTeDa presents: Randy Roberts Live!
  • Jan 21, 2020 - Apr 24, 2020 Location: Key West Category: Arts & Culture
  • LaTeDa presents: 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. His roster of famous and infamous ladies also includes: Mae West (a perennial favorite), Joan Crawford, Carol Channing, Ann Miller, Phyllis Diller and a bevy of original ladies. He closes every show with a mini-lounge act, allowing him the chance to get up close and personal with his audience. Showtimes and tickets online.
Image for LaTeDa presents: Christopher Peterson's EyeCons Cabaret
  • Jan 22, 2020 - Apr 28, 2020 Location: Key West Category: Arts & Culture
  • LaTeDa presents: Christopher Peterson's EyeCons Cabaret
  • 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 even Lady GaGa. Christopher transforms himself from icon to icon right in front of your eyes aided by his magic closet on stage. Showtimes and tickets online.
  • Jan 24, 2020 - Jan 26, 2020 Location: Marathon Category: Arts & Culture
  • Island Boat Show & Festival
  • Bob Phelps 239-691-3290 Website
  • Come enjoy a great show with loads of the top boat brands , auction items, food, vendors featuring a variety of merchandise, great fishing seminars presented by local captains... all at a very reasonable $10 admission. The show is to take place 1-5 p.m. Friday, 10 a.m. to 5 p.m. Saturday and 10 a.m. to 3 p.m. Sunday. Venue at Hawks Cay Resort.
  • Jan 24, 2020 - Jan 26, 2020 Location: Islamorada Category: Fishing
  • Cheeca Lodge Presidential Sailfish Tournament
  • Lisa Thornhill 305-517-4512 Email Website
  • Second in the Gold Cup series. Anglers put 20-pound line and light-tackle skills to the test during the two-day challenge against the high-flying acrobatic fish, known for tail-walking the waves. Only circle hooks can be used. "The Presidential" typically awards sophisticated sculpture trophies to top anglers who release the most sailfish.
  • Jan 25, 2020 - Jan 26, 2020 Location: Key West Category: Arts & Culture
  • 35th Annual Key West Craft Show
  • 305-294-1243 Email Website
  • The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.
  • Jan 26, 2020 Location: Key West Category: Arts & Culture
  • 26th Annual Key West Master Chefs Classic
  • 305-294-9526, ext 25 Website
  • Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens.
Image for Key West Food & Wine Festival
  • Jan 26, 2020 - Feb 2, 2020 Location: Key West Category: Arts & Culture
  • Key West Food & Wine Festival
  • 800-474-4319 Email Website
  • Top chefs and restaurateurs display culinary creativity and the Keys' indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively "Old Town Uncorked," neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.
Image for Visit the Family-Friendly Sheriff's Animal Farm
  • Jan 26, 2020 Location: Key West
  • Visit the Family-Friendly Sheriff's Animal Farm
  • Farmer Jeanne Selander 305-293-7300 Website
  • Open between 1 - 3 p.m., the Sheriff's Animal Farm invites you to bring the family and visit the animals at the farm, including horses, a cow, pigs, goats, bunnies, alligators, tropical birds, a Kinkajou, Sloths, a Lemur, Kramer the Emu, a family of Patagonian Cavys, tortoises and turtles, snakes and many more. The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. The Animal Farm is open every second and fourth Sundays of the month. The Animal Farm is always free, but donations are appreciated!
Image for Banana Bay Bazaar
  • Jan 26, 2020 Location: Marathon
  • Banana Bay Bazaar
  • Website
  • The Banana Bay Bazaar is a premier art and culture event held the last Sunday of every month at the infamous sunset bar, The Pointe. This outdoor, fully immersive experience will showcase diverse arts and local vendors bringing together some of the best attractions to give attendees a wonderful taste of The Florida Keys. Celebrate the afternoon with live local music, food trucks and drinks offered at The Pointe, from noon to 5 p.m., inside Banana Bay Resort, mile marker 45.9 bayside.  
Image for Cow Key Channel Waterway Clean up
  • Jan 26, 2020 Location: Key West
  • Cow Key Channel Waterway Clean up
  • Website
  • Paddle with a purpose! Join the Blue Moon Crew from 3-5 p.m., helping beautify the Keys’ waterways. Blue Moon Kayak Key West has adopted Cow Key Channel and encourages volunteers to help keep the waters crystal clear. Make an impact on your vacation by looking closely in the water, in the mangroves and on the beaches. Everyone can make a difference by picking up one, two, three or more pieces of plastic. Participants are educated on the different types of debris, how long each takes to decompose in the Keys’ natural environment and what impacts they have on local flora and fauna. Free kayak rentals for the first 10 signups!
Image for Key West Artisan Market: Food & Wine Edition
  • Jan 26, 2020 Location: Key West
  • Key West Artisan Market: Food & Wine Edition
  • Website
  • Enjoy wine and spirit sampling and bottle and case pricing to stock your cellar. Enjoy a full bar, multiple food trucks and stalls and shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Listen to awesome local musicians, from 10 am to 2 pm at Clarence H. Higgs Memorial Beach. The market is conveniently located close to the free West Martello Tower botanical gardens, White Street Pier and of course, the alluring Atlantic ocean.
Image for Tibetan Monks' 2020 Sacred Arts Tour, Upper Keys
  • Jan 27, 2020 - Jan 30, 2020 Location: Islamorada
  • Tibetan Monks' 2020 Sacred Arts Tour, Upper Keys
  • Tibetan Buddhist monks from the Drepung Gomang Monastery return to the Upper Keys to share their ancient cultural teachings, artistic expressions and unique vocal chants with sacred instruments. A series of events include a Tibetan marketplace with handcrafted items.
Image for Florida Keys Concert Association presents: Rising Star Concert
  • Jan 27, 2020 Location: Marathon Category: Arts & Culture
  • Florida Keys Concert Association presents: Rising Star Concert
  • (305) 289-1110 or (216) 408-6546 Website
  • Each year the Florida Keys Concert Association presents a “Rising Star” in the classical music field.  Meet Pianist Youlan Ji, born in 1999 in Beijing, China.  At the age of four, she began studying the piano with her mother, and between the ages of nine and twelve, continued her piano studies with Professor Yuan Ling at the Affiliated Middle School of Central Conservatory of Music at Beijing.  In 2012, Youlan moved to New York to attend the Juilliard School’s Pre-College Division, where she continues to study with Yoheved Kaplinsky. Performance at Marathon High School Performing Arts Center. Performance 7:30 p.m. Tickets online.
Image for Third Annual Mile 0 Fest Key West
  • Jan 28, 2020 - Feb 1, 2020 Location: Key West Category: Arts & Culture
  • Third Annual Mile 0 Fest Key West
  • Website
  • Mile 0 Fest Key West is a "must see" music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.
Image for Old Island Restoration Foundation Lecture Series presents: The Architecture of Key West
  • Jan 28, 2020 Location: Key West Category: Arts & Culture
  • Old Island Restoration Foundation Lecture Series presents: The Architecture of Key West
  • Website
  • Key West is the largest historical district of wooden structures on the US Department of the Interior’s National Register of Historic Places. The charm of Old Town can be attributed to the eclectic mix of over 3,000 wooden buildings constructed throughout the 19-Century; some of which were built in the Bahamas and brought to Key West. In her presentation, art historian Snow Philip will discuss the wide variety of styles and influences that led to Key West’s unique architectural fusion. Snow lives between Key West and Venice, Italy and currently gives presentations to Road Scholar tours on the subject of Architecture. Gates open at 6:00 PM. Admission: $25, OIRF members $15. Water and soft drinks will be available for sale. Held at The Garden at the Oldest House Museum, 322 Duval St. Tickets available online.
Image for Florida Keys Concert Association presents: Rising Star Concert
  • Jan 28, 2020 Location: Islamorada Category: Arts & Culture
  • Florida Keys Concert Association presents: Rising Star Concert
  • Website
  • Each year the Florida Keys Concert Association presents a “Rising Star” in the classical music field.  Meet Pianist Youlan Ji, born in 1999 in Beijing, China.  At the age of four, she began studying the piano with her mother, and between the ages of nine and twelve, continued her piano studies with Professor Yuan Ling at the Affiliated Middle School of Central Conservatory of Music at Beijing.  In 2012, Youlan moved to New York to attend the Juilliard School’s Pre-College Division, where she continues to study with Yoheved Kaplinsky. Performance at Island Community Church. Performance 7:30 p.m. Tickets online.
Image for Tropic Cinema presents: Babette's Feast, with Master Sommelier Doug Frost
  • Jan 28, 2020 Location: Key West Category: Arts & Culture
  • Tropic Cinema presents: Babette's Feast, with Master Sommelier Doug Frost
  • Website
  • Meet Doug Frost, one of only three people in the world to have achieved Master Sommelier and Master of Wine distinctions, for a special screening of Gabriel Axel’s Oscar-winning 1987 masterpiece, ‘Babette’s Feast.’ The film is lauded as one of the most sumptuous all-time cinematic celebrations of food and wine. Doug will introduce the event and discuss the featured wines and their context. And, throughout the screening, attendees have the opportunity to taste similar wines to those being featured on screen. Tickets online.
  • Jan 29, 2020 - Jan 30, 2020 Location: Islamorada Category: Fishing
  • IFC Sailfish Tournament
  • Website
  • Presented by the Islamorada Fishing Club, the event is the last leg this year of the three-pronged Florida Keys Gold Cup Championship series and typically draws a field of up to 30 boat teams of elite sport fishermen. Kickoff is 1/29 and fishing day is 1/30. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.
  • Jan 30, 2020 - Feb 1, 2020 Location: Key West Category: Fishing
  • Cuda Bowl
  • Loren Rea 305-360-6969 Email Website
  • Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.
Image for Pop and Pour, at the Perry Hotel
  • Jan 31, 2020 - Feb 1, 2020 Location: Islamorada Category: Fishing
  • Swamp Guides Ball
  • Website
  • Sponsored by the Florida Keys Fishing Guides Association, this all-release event offers team and individual awards to anglers for bonefish, redfish and snook. Anglers fish the shallows of the Florida Keys and the saltwater fringes of the Everglades. Social events are to be headquartered at the Lorelei Restaurant & Cabana Bar.
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