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Events in Key West

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Key West for 2020

  • January 01 Key West
  • Polar Paddle Plunge
  • Website
  • 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 04 - 05, 2020 Key West
  • The Studios of Key West presents ‘Single Occupancies,’ an evening of Contemporary Opera Theatre Monologues
  • 305-296-0458 Website
  • 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.
  • January 08 - 18, 2020 Key West
  • Fringe Theater presents: Talley's Folly
  • 305-731-0581 Email Website
  • 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. 
  • January 09 - 12, 2020 Key West
  • Pole Vault in Paradise
  • Steve Hanes 512-470-8076 Email Website
  • 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.
  • January 09 - 12, 2020 Key West
  • 38th Annual Key West Literary Seminar
  • 888-293-9291 Website
  • 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.
  • January 11 Key West
  • Wounded Warrior Project Soldier Ride
  • Website
  • 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 Key West
  • Rams Head Presents Key West: Grace Potter with Devon Gilfillian
  • Website
  • 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 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 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.
  • January 12 Key West
  • Impromptu Classical Concerts presents: Blake Pouliot
  • Website
  • 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 Key West
  • Key West Artisan Market: Gone to the Dogs! Edition
  • Website
  • 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 Key West
  • Friends of the Key West Library 2020 Speaker Series
  • Website
  • 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 Key West
  • Rams Head Presents: Sinbad at Key West Theater
  • Website
  • 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 Key West
  • South Florida Symphony presents Masterworks I: Beethoven, Mahler, Barber
  • Website
  • 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 - 20, 2020 Key West
  • 22nd Annual 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. 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.
  • January 16 - Feb 01, 2020 Key West
  • 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.
  • January 16 - 19, 2020 Key West
  • Key West Kingfish Mayhem
  • Jimmy Wickett 954-605-8284 Email Website
  • 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.
  • January 16 Key West
  • Studios of Key West presents Carrie Newcomer
  • Website
  • 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 - 18, 2020 Key West
  • 60th Annual Key West Home Tours
  • 305-294-9501 Email Website
  • 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.
  • January 18 - 19, 2020 Key West
  • 15th Annual Florida Keys Seafood Festival
  • Email Website
  • 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.
  • January 18 Key West
  • Early Music Key West Presents: Dances and Divisions, A Wind Player's Delight
  • Website
  • 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 Key West
  • Florida Keys Eco-Discover Center's Discovery Saturday: Forts and Cannons
  • Website
  • 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 Key West
  • Mile Zero Fights
  • Website
  • 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 - 25, 2020 Key West
  • Tara Mandala Key West presents: Tibetan Monks' 2020 Sacred Arts Tour
  • Email Website
  • 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.
  • January 21 Key West
  • Fourth Annual Conch Revival Picnic
  • Website
  • 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 22 Key West
  • Tropic Cinema presents 'Kalachakra: The Enlightenment,' a Special Event
  • Website
  • 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 Key West
  • Rat Pack Together Again at Key West Theater
  • Website
  • 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 - 26, 2020 Key West
  • 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.
  • January 26 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!
  • January 26 Key West
  • 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.
  • January 26 - Feb 02, 2020 Key West
  • 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.
  • January 26 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!
  • January 26 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.
  • January 26 - Oct 08, 2019 Key West
  • Impromptu Classical Concerts presents: Trio Gaspard
  • Website
  • 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 28 Key West
  • 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.
  • January 28 - Feb 08, 2020 Key West
  • The Studios of Key West presents: Prime Time
  • Website
  • 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 Key West
  • 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.
  • January 28 - Feb 01, 2020 Key West
  • 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.
  • January 30 - Feb 01, 2020 Key West
  • 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.
  • February 03 - 08, 2020 Key West
  • Elizabeth Bishop Birthday Celebration
  • Website
  • The celebration honors the life and work of Elizabeth Bishop, a former U.S. Poet Laureate, and features the first public viewing of the Key West home she owned from 1938 to 1946. Among attractions are lectures, discussions, a documentary film screening and readings by speakers including Thomas Travisano, author of “Love Unknown: The Life and Worlds of Elizabeth Bishop.” Saturday, Feb. 8, is the 109th anniversary of Bishop's birth.
  • February 06 Key West
  • Tropic Cinema's Cinematheque Series
  • Website
  • The Tropic's Cinematheque Series brings the finest in international, independent, arthouse and documentary cinema to the island of Key West every Thursday night. Screenings are at 6:30 p.m.
  • February 06 - 07, 2020 Key West
  • Fringe Theater presents: Ma Rainey's Black Bottom, A Reading with Music
  • 305-731-0581 Email Website
  • Ambition and music collide when legendary blues singer, Ma Rainey, brings her band together for a recording session.  An American Masterpiece. 1984 NY Drama Critics' Circle Award winner. Performance 7 p.m., VFW Post 168, 803 Emma St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
  • February 09 Key West
  • Impromptu Classical Concerts presents: Canellakis-Brown Duo
  • Website
  • Canellakis-Brown Duo. Pianist and composer Michael Brown and cellist Nicholas Canellakis have been hailed as “a pair of adventurous young talents” by Time Out New York and lavishly praised by the New York Times as ‘two outstanding musicians who are captivating audiences with innovative programs that combine masterpieces from the standard repertoire with original compositions and arrangements.” The two highly acclaimed artists continue to pursue solo careers with performances in such venues as the Lincoln Center and Alice Tully Hall. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.
  • February 09 Key West
  • Key West Artisan Market: Love is in the Air Edition
  • Website
  • Find everything you need for your sweeties including wine & champagne by the bottle, beautiful jewelry, gifts and all the makings for a romantic dinner. Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers; fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. 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.
  • February 09 Key West
  • South Florida Symphony presents Beethoven 250th Anniversary Celebration
  • Website
  • In honor of the 250th anniversary of Beethoven’s birth is this special presentation of his epic Symphony No. 9, with a full choir and the famous Ode to Joy finale. Also on the bill is Schumann’s beloved Piano Concerto, featuring audience favorite, Svetlana Smolina on piano. Performance 6:30 p.m., Glynn R. Archer Center for the Performing Arts.
  • February 10 Key West
  • Monday Night Movie Classics: Unlikely Love Stories
  • Website
  • The February series of Monday Night Classics is highlighting unlikely love stories — and John Huston’s iconic riverboat adventure is one of the all-time greats. “The African Queen” stars Humphrey Bogart in his Oscar-winning portrayal of Charlie Allnut, the slovenly, gin-swilling captain of a tramp steamer called the African Queen, which ships supplies to small East African villages during World War I. Katharine Hepburn plays Rose Sayer, the maiden-lady sister of a prim British missionary, Rev. Samuel Sayer (Robert Morley). When Germans invade and Samuel dies, Allnut offers to take Rose back to civilization. She can’t tolerate his drinking or bad manners; he isn’t crazy about her imperious, judgmental attitude — but it does not take long before their passionate dislike turns to love, even as they’re devising a plan to destroy an invading German gunboat. Showtime 6:30 p.m. at Tropic Cinema, 416 Eaton St.
  • February 12 - 15, 2020 Key West
  • Waterfront Playhouse presents: Lady Day at Emerson's Bar and Grill
  • Website
  • The time is 1959. The place is a seedy bar in Philadelphia. The audience is about to witness one of Billie Holiday’s last performances, given four months before her death. More than a dozen musical numbers are interlaced with salty, often humorous reminiscences to project a riveting portrait of the lady and her music. Showtimes 7 p.m.
  • February 13 Key West
  • The Studios of Key West presents: Johnsmith
  • Website
  • Part of TSKW Old Town New Folk Series. For thirty-plus years, Johnsmith has shared his music across America and abroad. With faded jeans, blue eyes, and an infectious smile, audiences get the sense of a man who simply loves life, his family and friends, and sharing songs and stories. Showtime 8 p.m., 533 Eaton St. Tickets $55 Preferred, $40 General ($10 discount for members - advance only)
  • February 14 Key West
  • Tennessee Williams Theater presents: Mandy Patinkin
  • Website
  • Mandy Patinkin in Concert: DIARIES, presents the acclaimed actor / singer / storyteller in his most electrifying role: concert performer. “Mandy Patinkin is in the business of showstopping,” raves The New Yorker, and that’s exactly what he does in this powerful, passionate evening of song. DIARIES is a marriage of many of Mandy’s favorite Broadway and classic American tunes, along with selections from his newest recordings on Nonesuch Records, Mandy Patinkin Diary January 2018 and Mandy Patinkin Diary April/May 2018. From Randy Newman to Stephen Sondheim, from Harry Chapin to Rufus Wainwright, Mandy Patinkin takes you on a dazzling musical journey you’ll never forget. Showtime 8 p.m., Tennessee Williams Theater, 5901 College Rd.
  • February 14 Key West
  • Oh My Gods and Goddesses: A Heavenly Burlesque Show
  • Website
  • Key West Burlesauqe presents a burlesque show of epic proportion! This ”one night only” production will transport you out the earthly realm and into the kingdom of celestial and supreme beings. Key west burlesque favorites Tatah DuJour and Moana Amour are joined by a cast of local and nationally touring burlesque and variety performers who portray immortal deities with a wink and a smile! Doors open 7:30 p.m., show start 8 p.m., at the Key West Theater, 513 Eaton St.
  • February 14 - 15, 2020 Key West
  • 60th Annual Key West Home 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 interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $35 in advance and $45 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.
  • February 15 Key West
  • Discovery Saturday Educational Series: Love is in the Air (and Water)
  • Website
  • 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 the Key West Aquarium. This month’s children’s program will include lessons and activities about marine species reproduction. 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.
  • February 16 Key West
  • Key West Artisan Market: For the Birds Edition
  • Website
  • Meet the volunteers of the Key West Wildlife Center and discover how you can support this organization. Donations help fund wildlife rescue and rehabilitation programs. 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. Enjoy live music, a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-in or take-away. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. 
  • February 17 Key West
  • Willie Nelson At Key West Amphitheater
  • Website
  • With a six-decade career and 200 plus albums, this iconic Texan is the creative genius behind the historic recordings of Crazy, Red Headed Stranger, and Stardust. Willie Nelson has earned every conceivable award as a musician and amassed reputable credentials as an author, actor, and activist. He continues to thrive as a relevant and progressive musical and cultural force. Doors open 5:30 p.m., show starts 7 p.m. SOLD OUT!
  • February 19 - 29, 2020 Key West
  • The Studios of Key West presents: Anna in the Tropics
  • Website
  • In Nilo Cruz’s Pulitzer Prize winning script, Juan Julian is hired to read to cigar factory workers as they hand roll cigars in Ybor City in the early 1900s. He introduces the cigar workers to Tolstoy’s Anna Karenina, sparking romance and its inherent madness. Anna celebrates the cultural history of Cuban immigrants, and an era of sultry tropical nights shrouded in cigar smoke. Shows Wed-Sat Feb 19-22 & Feb 26-29, 8 p.m.
  • February 19 - 23, 2020 Key West
  • Fringe Theater presents: Desdemona
  • Website
  • Nobel Prize-winning novelist, Tony Morrison, has given voice to Desdemona, one of Shakespeare’s most mysterious women, in this inventive retelling of her murder by Othello. Music and movement will create a unique evening of performance theater. Performance at Aqua Side Bar, 504 Angela St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
  • February 21 Key West
  • Rams Head Production presents: Kool & the Gang, with The Village People
  • Website
  • From Nairobi to Newark, Kool & the Gang has performed continuously longer than any R&B group in history and their bulletproof funk and jazzy arrangements have also made them the most sampled R&B band of all time. Village People is considered the greatest disco group in the world, their music part of the international songbook. Victor Willis who was Village People before Village People even existed returned with a fresh re-boot of the group. Doors open 5:30 p.m. at Key West Amphitheater, 21 Quay Rd. showtime 7 p.m. Tickets available online.
  • February 22 - 23, 2020 Key West
  • 55th Annual Old Island Days Art Festival
  • 304-294-1243 Website
  • The 55th annual juried outdoor fine art festival features over 70 local and national artists who are to grace the streets with fine art ranging from jewelry, paintings, photography and sculpture. Bring the kids to create an art piece at the children’s art booth. Staged from 10 a.m. - 5 p.m. at Whitehead and Caroline Streets in Old Town Key West.
  • February 23 Key West
  • Impromptu Classical Concerts presents: The Rascher Saxophone Quartet
  • Website
  • The Raschèr Saxophone Quartet appears regularly at major concert halls in Europe, Asia and the U.S. The Vienna Zeitung hailed the quartet as the “Uncrowned Kings of the Saxophone” and a critic from Die Welt claimed, “If there were an Olympic discipline for virtuoso wind playing, the Raschèr Quartet would definitely receive a gold medal.” Although founded in the United States in 1969 the quartet was relocated in Germany several years later and has been based there ever since. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.
  • February 23 Key West
  • 35th Annual Schooner Wharf Bar Annual Wrecker's Cup Race Series
  • Website
  • This all-in-fun race series recalls the tradition of the wreckers in the Key West of the 1800’s. Racers compete in different classes; Classic, Schooner, Multihull, Monohull over 40 feet, Monohull 30 – 39 feet, Monohull 29' and Under, other categories may apply depending on entries. The Wrecker's fleet consists of 16' Hobie Cat's to 105' Schooners! All sailing vessels, local sailors and visiting yachtsmen are welcome to join the regatta.
  • February 23 Key West
  • It's For the Birds Fundraiser to Benefit Key West Wildlife Center
  • Website
  • Set for 3 p.m. to 5:30 p.m. at the West Martello Towers, 1100 Atlantic Blvd., this annual event offers fabulous food, an amazing Silent Auction and raffles generously donated from a variety of local resorts, businesses and restaurants. In addition, there will be a separate Super Silent Auction featuring private home dinner parties, five-course full moon dinner cruises, and more entertaining events. The Key West Wildlife Center, located at 1801 White Street, is a non-profit organization providing rescue and rehabilitative care to wildlife from mile marker 0-30 in the Florida Keys. They are a rescue and rehabilitation facility operating as a trauma clinic and field hospital. Their main focus is rescuing and rehabilitating sick, injured or orphaned native wildlife and returning them to the wild. 
  • February 27 - Mar 01, 2020 Key West
  • Celebrity Artist Bill Mack to Appear in Key West
  • 305-923-1696  Email Website
  • An impressive collection of artwork and extraordinary sculpture by world-renowned artists Bill Mack and Gary Welton will be on exhibition, through March 1 at Key West Gallery, 601 Duval St. Bill Mack, artist of Presidents, Celebrities and Luminaries, premiers his Hollywood Collection. Mack will be making very special appearances at the gallery on Friday, Feb. 28 and Saturday, February 29 from 7:00pm – 11 p.m. The gallery is open every day from 10 a.m. – 11 p.m. RSVPs for the Artist Appearances are suggested.
  • February 29 Key West
  • Sixth Annual Cow Key Channel Bridge Run
  • Website
  • Feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? From 10AM to 2PM, join zany-dressed participants for the world's only Zero K across one of the shortest bridges in the Keys. The event is free to watch.
  • March 01 Key West
  • Rams Head Production presents: John Tesh at Key West Theater
  • Website
  • Whether at the solo piano, with a 12-piece 'big band' or an 80 piece orchestra, Tesh’s ability to create a unique journey for concert fans with music and storytelling has taken him from the Red Rocks Amphitheater and the Coliseum in Rome to Carnegie Hall and The Kennedy Center. John’s live television concerts, including the seminal ‘Live at Red Rocks,’ have raised more than 20 million dollars for Public Television. Doors open 7 p.m., show starts 8 p.m. Tickets available online.
  • March 01 Key West
  • Key West Artisan Market: Car-Free Key West Edition
  • Website
  • Come learn about the benefits of reducing our carbon footprint and becoming more sustainable in our community. Please ride your bike and BYOB (bring your own bag). Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. 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. 
  • March 03 Key West
  • The Studios of Key West presents: Tom Rush
  • Part of TSKW Old Town New Folk Series. Tom Rush’s shows are filled with the rib-aching laughter of terrific storytelling, the sweet melancholy of ballads and the passion of gritty blues. Although he’s known for his live performances, Rush’s albums are also legendary; The Circle Game, according to Rolling Stone, ushered in the singer/songwriter era. Showtime 8 p.m., 533 Eaton St. Tickets $55 Preferred, $40 General ($10 discount for members - advance only).
  • March 07 Key West
  • 58th Annual Conch Shell Blowing Contest
  • 305-294-9501 Email Website
  • An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make "music" with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 a.m., contest starts at noon.
  • March 08 Key West
  • South Florida Symphony presents Masterworks III: Mendelssohn, Beethoven, Zwilich (World Premiere)
  • Website
  • Masterworks III boldly integrates the old classical music and the new, bringing together in one evening two preeminent composers of different eras: Ellen Zwilich’s world premiere Concerto for Cello and Orchestra, featuring renowned GRAMMY® Award-winning cellist Zuill Bailey; and Mendelssohn’s Symphony No. 5, known as the “Reformation.” The 250th Anniversary of Ludwig van Beethoven’s birth continues with his The Consecration of the House Overture, commissioned to celebrate the opening of a Vienna theater. Performance 7:30 p.m., Tenessee Williams Theater, 5901 College Rd.
  • March 08 Key West
  • George Thorogood & the Destroyers
  • Website
  • Make your way to Sunset Green Event Lawn for what is sure to be an epic night of live music with a rock legend! Enjoy a good old-fashioned lunch-bucket rock & roll show that includes signature hits like “Get A Haircut”, “I Drink Alone”, “One Bourbon, One Scotch, One Beer”, “Move It On Over”, “Who Do You Love” and the definitive badass anthem “Bad To The Bone,” among others. Sunset Green is situated between 24 North Hotel and The Gates Hotel. Gates open 5:30 p.m., show starts 7 p.m.
  • March 08 Key West
  • Impromptu Classical Concerts presents: Natalia Kazaryan
  • Website
  • Natalia Kazaryan, pianist and Impromptu’s 2020 “Rising Star”, has performed at a number of prestigious venues across Europe. She has received top prizes from the Eastman Young Artists International, Kosciuszko Foundation Chopin, and the New York piano competitions as well as the Concours FLAME and Concours international de piano d’Ile de France. She studied at The Juilliard School and recently completed her doctoral studies at the University of Michigan. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.
  • March 08 Key West
  • Key West Artisan Market: Spring Forward! Edition
  • Website
  • Key West Artisan Market reminds you to 'Spring Forward', set your clocks and don't miss the market, conveniently located close to the free West Martello Tower botanical gardens, White Street Pier and of course, the alluring Atlantic ocean.  Please ride your bike and BYOB (bring your own bag). Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. From 10 am to 2 pm at Clarence H. Higgs Memorial Beach. 
  • March 09 - 12, 2020 Key West
  • March Merkin Invitational Permit Tournament
  • Email Website
  • A charity flats-and-fly-only tournament with a twist - in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Yacht Harbor Marina on Stock Island.
  • March 12 - 13, 2020 Key West
  • Tennessee Williams Theater presents: The Color of Purple, The Musical
  • Website
  • The Tony Award®-winning revival that exhilarated Broadway is now on tour across North America. With a soul-raising, Grammy-winning® score of jazz, gospel, ragtime and blues, The Color Purple is an unforgettable and intensely moving revival of an American classic. Showtimes 8 p.m., Tennessee Williams Theater, 5901 College Rd.
  • March 13 - 14, 2020 Key West
  • 60th Annual Key West Home 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 interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. This is a walking or biking tour. Tickets are $35 in advance and $45 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.
  • March 15 Key West
  • Waterfront Playhouse presents: Trunk Material 2
  • Website
  • It’s back! A Fabulous evening, featuring the cast of Pricilla Queen of the Desert, pulling their favorite songs out of a trunk and sharing them with you! Showtime 7 p.m., Waterfront Playhouse, 407 Wall St., Mallory Square.
  • March 15 Key West
  • Key West Artisan Market: Let's Get Hoppy! Edition
  • Website
  • Come do some sampling of some tasty Keys-based products and a full selection at the bar. If beer's not your thing we've got bloody’s, mimosas along with a full bar and multiple food trucks and stalls offering eat-here or take-away.  Please ride your bike and BYOB (bring your own bag). Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. 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. 
  • June 01 - Jul 31, 2020 Key West
  • Key West Art in the Garden
  • Website
  • The 10th annual Key West ART in the GARDEN opens June 1 at the Key West Tropical Forest & Botanical Garden with artistic expressions emphasizing harmony with nature. These works are earth-friendly in the selection of materials (including recycled and natural material) and themes. Sculptures by local artists accent the natural beauty of the conservation site on Stock Island through July 31, 2020, 10am-4pm seven days a week.
  • June 17 Key West
  • Key West Songwriters Festival One-Night-Only Streaming Event
  • Website
  • Music fans around the world can tune in to a one-night-only streaming “taste” of the annual Key West Songwriters Festival to hear tunes and tales from some of America’s top country and pop music hitmakers. Set for 8 p.m. EDT at Facebook.com/KeyWestSongwritersFest, the performance is to be hosted by radio and television personality Storme Warren and feature a special performance by country superstar Toby Keith.
  • June 21 Key West
  • Key West Artisan Market - Father's Day Edition
  • Website
  • Father's day will offer a special afternoon of classical guitar and vocals live! From 10AM to 2PM at Clarence H. Higgs Memorial Beach, Key West. The Key West Artisan Market will team up with The Key West International Guitar Festival to present a Guitar Summit Concert Series featuring father-daughter duo Mateo and Belle. Enjoy Bloody Mary’s and mimosas, specialty coffees, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Guests are encouraged to bring a lawn chair or make a donation to Little Pink Houses of Hope to sit in the pink chairs (socially distanced, of course). The market is conveniently located close to the Higgs Beach Dog Park, free West Martello Tower botanical gardens, Key West White Street Pier and of course, the alluring Atlantic ocean across the street at Higgs Beach. Free entry, free parking. Please BYOB (bring your own bags). Hand sanitizer stations provided using Key West First Legal Rum Distillery 60 proof ruminizer and social distancing protocols, as per Monroe County orders, will apply.
  • June 22 - 28, 2020 Key West
  • Fourth Annual Mango Fest Key West Goes Virtual
  • Website
  • Mango Fest Key West features all things Mango. The culinary videos presented by local chefs and residents alike showcases the colorful abilities of what the mango, also known as the king of fruit, has to offer. A Virtual Vendor Village gives any & all businesses the experience of a virtual festival atmosphere. Music is provided virtually along with live radio broadcasts. Proceeds to benefit Key West Police Athletic League.
  • July 21 - 26, 2020 Key West
  • Hemingway Days
  • Website
  • Writers, anglers and fans of the late author Ernest Hemingway’s work are to converge on Key West for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Scheduled highlights include a virtual symposium with presenters including Ernest’s grandson John Hemingway.
  • July 22 - 25, 2020 Key West
  • Stock Island Marina Village Key West Marlin Tournament
  • Tim Greene 305-304-0317 Email Website
  • Anglers ply the waters once fished by writer Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West's annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.
  • August 06 Key West
  • Keys Guitar Concerts presents: Mateo Jampol
  • Website
  • Keys Guitar Concerts, as part of the Key West International Guitar Festival, teams up with the Key West Truman Waterfront Farmers Market to present classical guitar master Mateo Jampol live for sunset. The Market is open 3 pm to sunset with Mateo playing from 5-8 p.m. The concert and admission to the Market are free. Please bring your own seating and social distancing will apply. Masks must be worn unless eating and drinking while seated. Lots of convenient parking. Rain date: Aug. 13.
  • August 08 Key West
  • Key West LobsterFest Lobster Boil
  • Website
  • Join the Key West LobsterFest Lobster Boil on the roof top at the Waterfront Brewery from 5pm to 9pm for the annual seafood lobster boil, a tradition that includes andouille sausage, jumbo shrimp, fresh lobster, corn on the cob, fresh baked jalapeño corn bread and dirty rice. Enjoy a beautiful Key West sunset full bar, music and delicious food. Waterfront Brewery is located at 201 William St.
  • August 09 Key West
  • Key West LobsterFest Brunch
  • Website
  • Savor a decadent lobster-filled brunch that can't be missed. Held within the tropical gardens of the First Flight Grill & Brewery. 301 Whitehead Street. Brunch is served from 10am until 2pm and reservations are required. Seating limited.
  • October 03 Key West
  • NEW DATE: Key West Paddle Classic
  • Sue Cooper 305-304-4259 Email Website
  • Watersports enthusiasts on paddleboards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration.
  • October 07 - 11, 2020 Key West
  • Key West Songwriters Festival
  • Website
  • Audiences can rock, sway and sing along to some of America’s hottest contemporary hits and classics at the annual Key West Songwriters Festival, the largest festival of its kind. Since 1997 BMI has been a presenting sponsor of the festival and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.
  • November 06 Key West
  • 13th Annual Florida Keys SPCA Spring Social
  • Website
  • Join the Florida Keys SPCA to benefit the homeless animals of the Lower Keys!  Their biggest celebration of the year is at the Key West Golf Course that includes dinner, a live & silent auction, entertainment, complimentary wine & beer with cash liquor bar.  VIP tickets include a Champagne Reception starting at 5:30pm before the main event, passed appetizers, a sneak peek at one of the largest silent auctions on the island, reserved seating and VIP food stations.  The VIP Reception begins at 5:30pm and General Admission entry is at 6:30pm. Tickets are available online.
  • November 18 - 22, 2020 Key West
  • Key West Film Festival
  • Brooke Christian (202) 841-9898 Website
  • Showcasing films that exhibit excellence in storytelling, the festival's lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.
  • November 27 - Dec 06, 2020 Key West
  • NEW DATES: Conch Republic Independence Celebration
  • Website
  • Every year visitors join Florida Keys residents for the Conch Republic Independence Celebration, a quirky event honoring the birth of the republic and its place in Keys history. The republic was founded in April 1982 to protest the installation of a U.S. Border Patrol checkpoint that stopped traffic at the top of the Florida Keys Overseas Highway, the only road in and out of the Keys.

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