The Florida Keys & Key West

Calendar of Events

Current Key West 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 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 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 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 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 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.
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.
  • 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.
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