The Florida Keys & Key West

Calendar of Events

January 2017: Florida Keys Events

  • Jan. 3, 2017 - Jan. 31, 2017 Location: Key West
  • Randy Roberts Live!
  • Website
  • Female impersonator extraordinaire Randy Roberts brings a one man, all live tribute to some famous and infamous women of stage and screen. A Key West tradition for 18 years. Join Randy for an evening with "Bette Midler", "Cher", and Randy's signature lounge act. Hilarious comedy, gorgeous costumes, and voice that never fails to thrill! Open your eyes and mind and let yourself go with Randy Roberts LIVE! Show dates online.
  • Jan. 3, 2017 Location: Key Largo
  • Orange Bowl Swimming Classic
  • 305- 453-7946 Email Website
  • Some of the best college swimmers - and perhaps future Olympians - in the country compete at Jacobs Aquatic Center, mile marker (MM) 99.6 oceanside, in a competition that is part of the celebration surrounding the annual Orange Bowl college football game in Miami. Spectators are invited to attend this free event, meet the swimmers and coaches. Racing is set to begin at 10 a.m.
  • Jan. 5, 2017 - Jan. 30, 2017 Location: Key West
  • Christopher Peterson's EYECONS
  • 305-296-6706 Website
  • A master of impersonations, both visually and vocally, with impeccable comic timing. The show is all LIVE, no lip-sync. Thrill to his parodies 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, even Lady GaGa. Show dates are online. Show times 9 p.m., at La te da 1125 Duval St.
  • Jan. 6, 2017 - Jan. 8, 2017 Location: Key Largo Category: Fishing
  • Key Largo Sailfish Challenge
  • Tammie Gurgiolo 305-240-9337 Email Website
  • Held at the height of the sailfish season, this event follows a boat-tournament format. Prizes and trophies await first-, second- and third-place teams, and proceeds benefit the Coral Shores High School Band program. NEW THIS YEAR, up to six anglers can form a team to fish the challenge!
  • Jan. 6, 2017 Location: Key West Category: Arts & Culture
  • The Reverend Peyton's Big Damn Band
  • Website
  • The Reverend Peyton's Big Damn Band promises to be a sandal-stomping, scorcher of a debut for these innovators of Americana. A lifelong student of American roots and blues music styles, and a self-proclaimed disciple of country-blues pioneers like Charley Patton and Mississippi Fred McDowell, The Reverend (Josh) Peyton has always been committed to authenticity. The charismatic multi-instrumentalist has innovated a way to plug in and play most anything you can lay hands on. At any time during a show he may produce an instrument built from a cigar box, or an axe handle, or a can of ham. Show time 8 p.m. at Key West Theater, 512 Eaton St.
  • Jan. 6, 2017 - Jan. 7, 2017 Location: Key Largo
  • Brew on the Bay
  • teddreaver@aol.com Email Website
  • Presented by the Rotary Club of Key Largo, this craft beer festival includes a home brew competition and a main event featuring more than 100 craft beers from around the world, showcased in an unlimited tasting with food, music and entertainment along the waterfront at Rowell's Marina, MM 104.5 bayside.
  • Jan. 6, 2017 - Jan. 9, 2017 Location: Marathon Category: Arts & Culture
  • The Florida Keys Celtic Festival
  • Website
  • Some of America's most celebrated Celtic musical masters are to be featured at the Marathon Community Park, MM 49. The festival will also feature Irish and Scottish dancing, Highland athletics, Celtic merchandise, food and beverage booths and children's activities. New this year is a Monday "Hickory Stick Golf Tournament."
  • Jan. 7, 2017 Location: Islamorada
  • Matecumbe Historical Trust presents "29 Points of Interest" Historic Trolley Tour
  • Barbara Edgar 305-393-0940 Website
  • Enjoy an enlightening trolley ride through time. Guided trolley tours depart at 10 a.m., 11 a.m. and noon. from the Islamorada Moose Lodge at 81573 Old Highway in Islamorada.The one-hour, colorful and much acclaimed historical tours feature 29 points of interest on the islands of Islamorada. Tickets may be purchased on site or call in advance. Adults are $15, children six and under are free.
  • Jan. 8, 2017 Location: Key West
  • Visit the Family-Friendly Sheriff's Animal Farm
  • Farmer Jeanne Selander 305-293-7300 Website
  • Looking for a fun place to take the kids? The Sheriff's Animal Farm is open 1 - 3 p.m. Bring the family and come visit the many animals at the farm. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. Open house is held the second and fourth Sundays of the month.
  • Jan. 9, 2017 - Jan. 15, 2017 Location: The Florida Keys
  • Florida Keys Paddle Challenge
  • 352-377-8342 Email Website
  • Enjoy a true island paradise, paddling beside sea turtles and railroad visionary Henry Flagler's 'Eighth Wonder of the World' in the azure waters of the Florida Keys. We'll journey 77 miles beside white sand beaches and mangrove islands, from Long Key State Park to Key West. Register by: Dec. 26, 2016. Limited to 60 paddlers.
  • Jan. 11, 2017 - Jan. 18, 2017 Location: The Florida Keys Category: Arts & Culture
  • Third Annual Paradise Paint Out
  • Email Website
  • The third annual Paradise Paint Out welcomes 21 renowned artists who will paint the Florida Keys "en plein air" (in open air). Artist will create an original series of paintings capturing images of flora, fauna, wildlife, architecture, Florida Bay and iconic locations both on and off the beaten path. Event highlights include Full Moon Nocturnal Painting in Marathon, all are welcome to observe or participate; the Mayor's Ball marks the midway point, with paintings available for purchase before they are moved to the Upper Keys; Florida Bay Day en plein air, a day of painting the Florida Bay. Other event highlights include free daily activities such as artist demonstration nocturnal painting and various receptions for collectors, patrons and visitors.
  • Jan. 11, 2017 Location: Islamorada Category: Arts & Culture
  • Life of Dr. Henry Perrine Subject of Documentary Premiering at Keys History & Discovery Center
  • 305-922-2237 Email Website
  • The Life & Times of Dr. Henry Perrine is the subject of a documentary short that reveals many little known facts about Florida's first visionary botanist/plant explorer. Dr. Henry Perrine was first recognized for his research with Quinine as a medicinal cure for malaria. Later as U.S. Consul to Yucatan in the 1830s, he introduced many beneficial tropical plants to the Florida Keys from Mexico and the Caribbean. Arriving on Indian Key in the Florida Territory on Christmas Day 1838, his Tropical Plant Company would come to an end with Dr. Perrine's untimely death on August 7, 1840 during an Indian attack during the Second Seminole War. The documentary show times are 11 a.m., 2 p.m., 4 p.m. and 6 p.m. Cost of Center members is $5 and $10 for non-members. Reservations are recommended.
  • Jan. 12, 2017 - Jan. 15, 2017 Location: Key West Category: Arts & Culture
  • 35th Annual Key West Literary Seminar
  • 888-293-9291 Website
  • The 2017 topic is "Revealing Power: The Literature of Politics." Literary aficionados from around the world are to gather for readings, discussions and lectures led by some of contemporary literature's most acclaimed writers. Presenters include celebrated biographer Robert Caro, Pulitzer Prize winner Annette Gordon-Reid and noted journalists/authors Gail Collins and Joe Klein. A first-come, first-seated Sunday afternoon session is free and open to the public.
  • Jan. 12, 2017 - Jan. 22, 2017 Location: Key West Category: Arts & Culture
  • Fringe Theater presents: Agnes of God
  • 305-731-0581 Website
  • A novice nun. A dead newborn child. A court-appointed psychiatrist and a mother superior battle for the life of the novice nun, Agnes. Is she gifted in the mysteries of faith or guilty of cold-blooded murder? A psychological war ensues. Performance dates January 12-15 and 19-22, show starts 7 p.m. at The Studios of Key West at 533 Eaton Street.
  • Jan. 13, 2017 - Jan. 14, 2017 Location: Key West
  • 57th Annual Key West House & Garden Tours
  • 305-294-9501 Email Website
  • Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. March tours are offered 10 a.m. to 4 p.m. each day. Transportation between homes is optional, via Conch Train. Tickets are $30. Proceeds help benefit the Old Island Restoration Foundation.
  • Jan. 13, 2017 - Jan. 15, 2017 Location: Islamorada Category: Arts & Culture
  • Fifth Annual Baygrass Bluegrass Festival
  • Robby McClung 305-587-0901 Website
  • Featuring several great Oldgrass, Newgrass and a blend of next generation Bluegrass as well as some tasteful variations of the genre. Tickets to be available in advance online and at the gate. Monies raised help fund music, dance and art scholarships for local students; main event is located at the ICE Amphitheater, MM 87 bayside at Founders Park. Other weekend musical activities are to be planned. Attendees can bring blankets and lawn chairs, but coolers are not permitted. Food and beverages available for purchase.
  • Jan. 14, 2017 Location: Islamorada Category: Arts & Culture
  • 34th Annual Art Under The Oaks
  • 305-360-8556 Email Website
  • Fine art & original crafts, a variety of entertainment, specialty food booths, children's arts & crafts, as well as a raffle of items donated by the artists are part of the annual highlights. San Pedro Church Gardens, 9 a.m. - 4 p.m., Mile Marker 89.5 on Plantation Key in Islamorada. Onsite parking is available for a $5 donation. Free parking is available at Coral Shores High School, with shuttle service to the event.
  • Jan. 14, 2017 - Jan. 15, 2017 Location: The Lower Keys Category: Arts & Culture
  • Nautical Flea Market
  • 305-872-2411 Email Website
  • Admission and parking at this event are free, held at the Lower Keys Chamber of Commerce grounds, MM31, from 8AM to 2PM. Find steals and deals on everything imaginable for boating, fishing, diving and more, from nearly 200 vendors. Crafts, food and beverage, live music and entertainment round out the two-day event.
  • Jan. 15, 2017 Location: Key West
  • Key West Half Marathon & 5k Run
  • Barbara Wright 305-240-0727 Email Website
  • Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. Now in its 19th year, the race typically attracts American and international runners to compete in Key West's balmy January climate. Named as one of the United States' leading winter half marathons in Runner's World, February, 2014; the same magazine included in its list of Best Destination Half Marathons; in April, 2015; Bucket List Best Half Marathons, and most recently in December, 2015 was ranked among 13 must-do U.S. half-marathons by Competitor.com.
  • Jan. 15, 2017 - Jan. 20, 2017 Location: Key West
  • 30th Annual Quantum Key West Race Week 2017
  • Email Website
  • The annual race week challenge features world-class competition and yachting teams from more than 12 countries and 24 American states. More than 100 racing yachts typically compete for class championships in this international regatta. To view the action, fans can book seats on spectator boats ranging from excursion catamarans to historic tall ships or from land at Key West's Atlantic-front restaurants, resorts and beaches.
  • Jan. 16, 2017 Location: Islamorada Category: Arts & Culture
  • Matecumbe Historical Trust presents: A History of Fishing in the Florida Keys
  • 305-393-0940 Website
  • Bob Epstein is a 35-year Tavernier resident and author, fulltime freelance & outdoor writer and photographer. He is to present and audio/visual talk about Florida Keys fishing and "Africa on a Pin & a Prayer." He has authored 12 books including a new release, "The Best Restaurants in the Florida Keys." After the talk he will be available for book signings, and a portion of the evening's book sales benefit the Matecumbe Historical Trust. Lecture is free and open to the public.
  • Jan. 16, 2017 Location: Key West Category: Arts & Culture
  • Friends of Key West Library Speaker Series: Calvin Trillin
  • Website
  • Enjoy distinguished journalist and author Calvin Trillin, whose articles are diverse, both serious and whimsical. They include politics, the cultural importance of Texas barbecue, itinerant chefs with unwanted followings, the effect of New York City water on buffalo mozzarella, and the tic-tac-toe playing chickens of Greenwich Village. Lectures are at the Key West Theater, 512 Eaton St. and admission is free. The talks begin promptly at 6:00 p.m., but seating begins at 5:30 on a first come first serve basis.
  • Jan. 18, 2017 Location: Islamorada Category: Arts & Culture
  • History of Diving Museum's Immerse Yourself! Lecture Series
  • 305-664-9737 Website
  • A free lecture series held at the museum, located at MM 82.9, every third Wednesday of the month at 7 p.m. Adventurers from treasure hunters to aquanauts help tell the story of mankind's attempts to explore, understand and venture under the sea. The evening lectures are informal, informative and provide a valuable educational resource at the museum, an acclaimed facility dedicated to the collection, preservation and display of relics and artifacts related to diving and its heritage.
  • Jan. 21, 2017 Location: Key West Category: Arts & Culture
  • Key West Theater presents: Phil Vassar w. Shastina Chiles
  • 305-985-0433 Email Website
  • Billboard Country Songwriter Of The Year Phil Vassar continues to churn out incisive, soulful lyrics with infectious melodies. Best known for the chart toppers "In A Real Love" and "Just Another Day In Paradise," Phil Vassar also hit the top ten with "Carlene," "Last Day Of My Life," "American Child," "Six-Pack Summer," "That's When I Love You" and "Love Is A Beautiful Thing." Key West resident Shastina Chiles plays her own solo, as well as duo gigs all over the Florida Keys.
  • Jan. 22, 2017 - Feb. 3, 2017 Location: Key West Category: Arts & Culture
  • Conch Republic Cup, Key West Cuba Race Week
  • 305-731-6219 Email Website
  • The CRC is a historic race that started in 1997 with direct race to Varadero then expanded to Havana in 1999. The triangle race as it has been coined is a traditional race to Cuba that allows the racer to complete a triangle between KW and two Cuba cities - Varadero and Havana. The CRC is a non-profit organization with the mission to introduce as many of the US sailing community to Cuba as possible as well as revitalize racing in Cuba.
  • Jan. 24, 2017 - Jan. 28, 2017 Location: Key West Category: Arts & Culture
  • Key-West-to-Cuba Theatrical Exchange
  • (305) 985-0433 Website
  • Key West Theater will present a full production of the Cuban play "Eclipse" by renowned Cuban playwright Jazz Vilá in English with Cuban actors, the first theatrical exchange to take place between America and Cuba in more than 50 years. "Eclipse" is a modern retelling of the classic play "Miss Julie" by August Strindberg, which uses the tool of reality television to contemporize the classic work.
  • Jan. 24, 2017 - Feb. 11, 2017 Location: Key West Category: Arts & Culture
  • Waterfront Playhouse presents: The Trip to Bountiful
  • 305-294-5015 Website
  • American masterpiece about the universal pull that we all feel for "home." Carrie Watts is an elderly widow, trapped in the tiny Houston apartment of her overprotective son and domineering daughter-in-law, who wants to return to her hometown of Bountiful - one last time before she dies. With pension check in hand, she breaks free. Her journey is filled with humor and tenderness that's both touching and life-affirming.
  • Jan. 25, 2017 - Jan. 29, 2017 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.
  • Jan. 25, 2017 - Jan. 26, 2017 Location: Islamorada Category: Fishing
  • IFC Sailfish Tournament
  • Website
  • Presented by the Islamorada Fishing Club, the event is the final leg 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. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.
  • Jan. 26, 2017 Location: Marathon Category: Arts & Culture
  • Marathon Public Library presents: Free Outdoor Concert
  • 305-743-5156
  • The Marathon Branch of Monroe County Public Library is proud to present its first free outdoor concert from 7 p.m. to 9 p.m. Folk-rock duo The Kennedys will be performing under the stars on the library's brand-spanking-new outdoor stage in the back garden. Join us for some fine tunes, excellent companionship and light refreshments (and awesome twinkle lights). In the event of inclement weather, the concert will be moved indoors into the community room. The singer-songwriters are both a band and husband and wife, and have been performing together for 20 years. Their musical influences include the Beatles, Bob Dylan, Buddy Holly, the Everly Brothers and the Byrds. The Marathon Public Library is at 3251 Overseas Highway, oceanside.
  • Jan. 26, 2017 Location: Key West
  • Key West Art & Historical Society Distinguished Speaker Series: Running with the Bulls
  • 305-295-6616, x115 Website
  • In 1926, Ernest Hemingway's novel "The Sun Also Rises" portrayed a dangerous, 875-meter run with bulls in Pamplona, which would subsequently become one of the most famous events in the world because of it. From 6:00 pm - 7:00 pm, John Hemingway, grandson of the legendary author and Key West Art & Historical Society's Distinguished Speaker guest, will appear at the San Carlos Institute to present his own unique experience with the run and the Pamplona Posse affiliated with it. Cost is $25 for members, $35 for nonmembers.
  • Jan. 27, 2017 - Jan. 29, 2017 Location: Key West
  • Fish for Jose!
  • Website
  • Enjoy music, dinners, guest speakers, live auctions and more during this inaugural celebration of Jose Wejebe and his mission of giving back to the Florida Keys fishing community! This three-day event encourages the local community to take time to do something new and/or share a fishing experience with a friend—something that will help continue to spread Jose Wejebe's mission of giving back. Additionally, both the Foundation and the event help carry on Jose's legacy of making fishing dreams come true through organizations like Make-A-Wish Foundation and the Veterans Recreation Department of the Miami VA Hospital.
  • Jan. 28, 2017 Location: Islamorada Category: Fishing
  • Saltwater Sportsman Seminar Series
  • 1-800-448-7360 Website
  • Salt Water Sportsman National Seminar Series provides anglers of all experience levels valuable techniques and tips for fishing. The 9 a.m. to 3 p.m. event is to be staged at the Coral Shores High School's Performing Arts Theater, mile marker 89.9 oceanside. George Poveromo, host of "George Poveromo's World of Saltwater Fishing" on NBC Sports Network and editor-at-large for "Salt Water Sportsman" magazine is to headline the program alongside a series of veteran Florida Keys-based fishing guides. Each seminar location offers chances to win a trip to the Florida Keys!
  • Jan. 29, 2017 Location: Key West
  • 23rd 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 Westin Key West Resort & Marina pier. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens.
  • Jan. 29, 2017 Location: Key West
  • 26th Annual Al Mueller Golf Tournament
  • Register (305) 294-5232 Email
  • Join the Big Pine & Lower Keys Rotary for the 26th Annual Take Stock in Children (Al Mueller Memorial Classic) golf tournament at the Key West Golf Course. The format is a 4-person team best ball scramble. Registration starts at 6:30 a.m. Play starts at 7:30 a.m. Cost is $100 per player. This includes 2 mulligans, 2 red tees and an awards luncheon at the end of the tournament. There will be hole prizes, raffle prizes and 50/50.