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Key West Events

Event calendar courtesy of fla-keys.com - The Tourism & Development Council of the Florida Keys

Events in Key West for January, 2020

Year:  Month: 
January 01,  in Key West
Polar Paddle Plunge
Plunge into a new decade! Blue Moon Kayak is honoring the tradition of cleansing the past year away and getting a refreshing start to 2020. What a better way than cleaning with purifying natural sea salt in the Gulf of Mexico. Start the year off right! $50 per person, departs from Sunset Marina, 5555 College Rd.
January 03 to April 03,  in Key West
First Fridays on Fleming
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.
Contact: 305-304-9001
January 04 to January 05,  in Key West
The Studios of Key West presents ‘Single Occupancies,’ an evening of Contemporary Opera Theatre Monologues
Performed by nationally renowned opera singers, "Single Occupancies" includes two world premiere pieces by Martin Hennessy and Stephen Kitsakos, and one regional premiere by Mark Campbell and Marisa Michelson. Scored for piano, cello, clarinet and double bass, and sung in English, the storylines are riveting, fresh and relevant. Each thirty-minute piece introduces a singularly unique character. Performances start at 8 p.m. Ticket prices range from $100 to $50, with discounts for Studios' members.
Contact: 305-296-0458
January 08 to January 18,  in Key West
Fringe Theater presents: Talley's Folly
WWII is drawing to a close. In an abandoned boathouse, a Jewish immigrant woos a southern belle in this poignant romantic comedy. Can a new start really be found after so much loss? Performance 7 p.m., Back Room at the Key West Theater, 512 Eaton St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
Contact: 305-731-0581
Email: [email protected]
January 09 to January 12,  in Key West
Pole Vault in Paradise
Presented by Key West Track and Field Club, Pole Vault in Paradise is an all-comers pole vault competition with events spread across four days. Youth, College, Elite and Masters divisions. Pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Saturday’s activities are free admission. Enjoy food and drink vendors, and world class competition beginning at 9 a.m. at the beautiful Truman Waterfront Park. Bring your lawn chairs.
Contact: Steve Hanes 512-470-8076
Email: [email protected]
January 09 to January 12,  in Key West
38th Annual Key West Literary Seminar
The 2020 topic is "Reading Between the Lines, Sports & Literature." Literary aficionados from around the world are to gather to focus on writing that examines why sports matter so much and explores the roles sports play in social issues, personal transformation and cultural change.
Contact: 888-293-9291
January 11,  in Key West
Wounded Warrior Project Soldier Ride
This Solder Ride event kicks off the Wounded Warrior Project® (WWP) 2020 Soldier Ride season that will take warriors across the nation, visiting dozens of American cities. Soldier Ride begins at NAS KW at 10:30 a.m. and ends at 11:45 a.m., riding from Boca Chica Field at Naval Air Station, 12 miles to Bayview Park at 1320 Truman Ave., Key West. A welcome ceremony follows. Line the highway into Key West, North Roosevelt Blvd., they will then turn right on White Street, Left on Eaton Street, turn right on Simonton Street, Left on Front Street, Left on Duval Street to Truman Avenue, turning left on Truman ending in Bayview Park. Bring your friends and families, and business along the route have employees outside showing support to the 44 Wounded Warriors participating in this years ride.
January 12,  in Key West
Rams Head Presents Key West: Grace Potter with Devon Gilfillian
An acclaimed songwriter and electrifying performer, Potter has commanded stages around the world. Her voice has paired with Kenny Chesney in hits such as "You and Tequila" and "Wild Child." Sunset Green Event Lawn is a multipurpose event space located between 24 North Hotel and The Gates Hotel. Tickets can be purchased online or visiting the Key West Theater box office at 512 Eaton St.
January 12,  in Key West
Visit the Family-Friendly Sheriff's Animal Farm
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 animals at the farm, including miniature horses, a cow, pigs, goats, bunnies, alligators, tropical birds, Kinkajous, Sloths, a Lemur, Kramer the Emu, a family of Patagonian Cavys, a skunk, an opossum, tortoises and turtles, snakes and many more. 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 the second and fourth Sundays of the month.
Contact: Farmer Jeanne Selander 305-293-7300
January 12,  in Key West
Impromptu Classical Concerts presents: Blake Pouliot
Blake Pouliot, violinist, has quickly become one of Canada’s most celebrated and promising young artists. He was the Grand Prize winner of the 2016 Orchestra Symphonique de Montréal Manulife Competition while featured on a number of television and radio broadcasts across North America including CBC Radio and NPR’s Performance Today. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.
January 12,  in Key West
Key West Artisan Market: Gone to the Dogs! Edition
From 10 am to 2 pm at Clarence H. Higgs Memorial Beach. Meet volunteers of Florida Keys SPCA and maybe a pup or two! Bring your well-behaved four legged friends - the market is always pet friendly and right next to the dog park! Florida Keys SPCA, The Center for Animal Welfare & Education, is dedicated to promoting the humane treatment of all animals through compassionate care, adoption, education, population control and humane law enforcement. Donations toward their mission will be welcome and appreciated. The market is conveniently located close to the free West Martello Tower botanical gardens, White Street Pier and of course, the alluring Atlantic ocean.
January 13,  in Key West
Friends of the Key West Library 2020 Speaker Series
The first speaker in the acclaimed and popular Monday evening lecture series is Rowan Ricardo Phillips, author of The Circuit: A Tennis Odyssey, winner of the 2019 PEN/ESPN Award for Literary Sports Writing. Lecture takes place at the Tropic Cinema on Eaton St. at 6 p.m.  Seating starts at 5:40 on a first come, first served basis. Admission to the lectures is free. 
January 14,  in Key West
Rams Head Presents: Sinbad at Key West Theater
Actor and comedian Sinbad has had audiences laughing for over three decades. His storytelling style of comedy is profound without being profane. Sinbad has recently appeared on Disney’s “Planes,” “Comedy Bang Bang,” “The Eric Andre Show,” FX Television series “It’s Always Sunny in Philadelphia” and NBC’s “Celebrity Apprentice”. Sinbad produced and starred in his own WE TV’s reality show, SINBAD: It’s Just family.” He has done six, one-hour comedy specials in his long comedy career, four on HBO and the last two on Comedy Central…and he’s not stopping anytime soon! Shows at 6:30 p.m. & 9 p.m.
January 15,  in Key West
South Florida Symphony presents Masterworks I: Beethoven, Mahler, Barber
Enjoy two powerful, strikingly beautiful and inspiring musical masterpieces: Bruckner’s dynamic Symphony No. 6, and the U.S Premiere of Borenstein’s glorious Concerto for Violin and Orchestra, featuring accomplished violinist Irmina Trynkos; along with the world premiere of Nardi’s Upon An Ocean. Performance 7:30 p.m., Tennessee Williams Theatre, 5901 College Rd.
January 15 to January 20,  in Key West
22nd Annual Key West Half Marathon & 5k Run
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. 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, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by Competitor.com.
Contact: Barbara Wright 305-240-0727
Email: [email protected]
January 16 to February 01,  in Key West
Waterfront Playhouse presents: Glass
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.
January 16 to January 19,  in Key West
Key West Kingfish Mayhem
Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.
Contact: Jimmy Wickett 954-605-8284
Email: [email protected]
January 16,  in Key West
Studios of Key West presents Carrie Newcomer
Part of TSKW Old Town New Folk Series. Carrie Newcomer is a singer-songwriter, poet and author at the intersection of folk, Americana and progressive spirituality. She’s described as a “prairie mystic” by the Boston Globe and one who asks “all the right questions” by Rolling Stone. Tickets $60 Preferred, $45 General ($10 discount for members - advance only). Showtime 8 p.m., 533 Eaton St.
January 17 to January 18,  in Key West
60th Annual Key West Home Tours
Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $45 each, seating is limited. Tickets without transportation are $35 in advance and $45 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.
Contact: 305-294-9501
Email: [email protected]
January 18 to January 19,  in Key West
15th Annual Florida Keys Seafood Festival
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. - 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.
Email: [email protected]
January 18,  in Key West
Early Music Key West Presents: Dances and Divisions, A Wind Player's Delight
Priscilla and Grant will present a program of medieval and renaissance music that highlights the versatility of the wind player. From lively estampies to virtuosic recorder solos by Jacob van Eyck to Playford dance tunes, we will take a journey through the many styles of solo wind playing. Performance 7 p.m., at The Parish Hall at St. Paul’s Episcopal Church, 401 Duval St. Admission $30, $15 for students in advance, online. At the door, cash only.
January 18,  in Key West
Florida Keys Eco-Discover Center's Discovery Saturday: Forts and Cannons
Kids in kindergarten through fifth grade are invited to join the free, fun-filled Discovery Saturday at the Florida Keys Eco-Discovery Center from 10-11 a.m., hosted by Fort Zachary Taylor State Park, a prime birdwatching location. Children will learn how migrating birds rely on the rich resources of the island chain during their seasonal journeys. Free admission, free parking. Discovery Saturday is held the third Saturday of every month. Pre-registration is recommended. The Florida Keys Eco-Discovery Center is located at 35 East Quay Road on the Truman Annex waterfront in Key West.
January 18,  in Key West
Mile Zero Fights
The Key West boxing tradition that dates back to Ernest Hemingway is to be celebrated, when aficionados can watch 11 fights in an open-air waterfront setting at the island’s East Quay Wall at 301 E. Quay Road. The evening’s anticipated highlights include a three-round boxing match between Scott Diaz and Jude Brogli, a five-round kickboxing challenge pitting Gabriel Alvarez against Chase Brooks and a three-round MMA competition between Oscar Lacayo and Chris Gonzalez.
January 19 to January 25,  in Key West
Tara Mandala Key West presents: Tibetan Monks' 2020 Sacred Arts Tour
Tara Mandala Key West meditation group and St. Paul’s Episcopal Church invite the public to help celebrate at the church’s 401 Duval St. location on the corner of Eaton St. The seven-day Tibetan festival will be led by eight visiting Tibetan monks from the Drepung Gomang Monastery—students of H.H. Dalai Lama— and includes noontime dharma talks, a Tibetan Marketplace, classes in the Tibetan Arts, varying music and dance demonstrations of Tibetan culture, and the monks' week-long creation of a Medicine Buddha sand mandala for world healing. The tour aims to spread the message of peace, loving kindness, wisdom, and compassion while sharing their traditional Tibetan arts and culture.
Email: [email protected]
January 21,  in Key West
Fourth Annual Conch Revival Picnic
The Key West Art & Historical Society, Great Events Catering, and Isle Cook Key West team up to present the fourth annual Conch Revival Picnic, an informal Conch heritage dinner prepared by acclaimed chefs Martha Hubbard and Dave Furman featuring a variety of classic Key West/Conch recipes set to take place, from 6- p.m. on the grounds of the Key West Lighthouse & Keeper’s Quarters. Tickets —$45 for Members, $55 for Non-members, kids under 12 are free.
January 21 to January 27,  in Key West
29th Annual Kelly McGillis Classic International Flag Football Championship
Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate.
Contact: 305-896-8678
Email: [email protected]
January 21 to April 24,  in Key West
LaTeDa presents: Randy Roberts Live!
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.
January 22 to April 28,  in Key West
LaTeDa presents: Christopher Peterson's EyeCons Cabaret
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.
January 22,  in Key West
Tropic Cinema presents 'Kalachakra: The Enlightenment,' a Special Event
A group of Tibetan Monks from the Drepung Gomang Monastery have visited Key West for a stop on the Sacred Art Tour -- public is invited to meet them at the Tropic for a Tibetan Reception and the showing of an inspiring movie of the Tibetan people, their rituals, and their culture. A reception from 6:30-7 p.m. with tea and cookies is followed by a screening of ‘Kalachakra: The Enlightenment’ with a Q&A session with the monks. Admission $20 per person
January 23,  in Key West
Rat Pack Together Again at Key West Theater
A toast to the original Rat Pack, ‘Rat Pack Together Again,’ takes you on a musical journey featuring the greatest hits from the legendary Frank Sinatra, Dean Martin, and Sammy Davis Jr. This production will treat you to Sinatra classics including, ‘Come Fly With Me,’ ‘My Way,’ and ‘New York...’ Dino with great songs like, ‘Everybody Loves Somebody,’ and ‘That's Amore!’ ...and from the dynamic Sammy Davis Jr., ‘Mr. Bojangles’ and Candy Man.’ After watching these performers, you will leave the show feeling as though The Rat Pack is still going strong after all these years. Show Starts 8 p.m., Key West Theater, 512 Eaton St. Tickets available online.
January 25 to January 26,  in Key West
35th Annual Key West Craft Show
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.
Contact: 305-294-1243
Email: [email protected]
January 26,  in Key West
26th Annual Key West Master Chefs Classic
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.
Contact: 305-294-9526, ext 25
January 26 to February 02,  in Key West
Key West Food & Wine Festival
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.
Contact: 800-474-4319
Email: [email protected]
January 26,  in Key West
Visit the Family-Friendly Sheriff's Animal Farm
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!
Contact: Farmer Jeanne Selander 305-293-7300
January 26 to October 08,  in Key West
Impromptu Classical Concerts presents: Trio Gaspard
Trio Gaspard, whose members are from Germany, Greece and the UK, is one of the most sought-after trios of its generation. Jonian Ilias Kadesha (violin), Vashti Hunter (cello) and Nicholas Rimmer (piano) have been invited to perform regularly at major international concert halls like Wigmore Hall and the Berlin Philharmonie. They have been winners of three major international competitions since their inception in 2010. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.
January 26,  in Key West
Cow Key Channel Waterway Clean up
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!
January 26,  in Key West
Key West Artisan Market: Food & Wine Edition
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.
January 28,  in Key West
Tropic Cinema presents: Babette's Feast, with Master Sommelier Doug Frost
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.
January 28 to February 08,  in Key West
The Studios of Key West presents: Prime Time
This new musical follows a female TV executive in the 1970s fighting to keep her variety show afloat, her star husband in check and temptation at bay. Under the direction of Murphy Davis, the script takes off, propelled by commanding performances and a whiff of classic TV nostalgia. Shows Tue-Sat Jan 28-Feb 1 & Feb 4-8, 8 p.m.
January 28 to February 01,  in Key West
Third Annual Mile 0 Fest Key West
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.
January 28,  in Key West
Old Island Restoration Foundation Lecture Series presents: The Architecture of Key West
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.
January 30 to February 01,  in Key West
Cuda Bowl
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.
Contact: Loren Rea 305-360-6969
Email: [email protected]