Key West Events Calendar

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.
Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

There is never a shortage of activity on Key West. A new year is here and the events keep on coming. Culinary delights start off the year here in the Keys; with events like the Seafood Festival and the Food and Wine Festival foodies are in heaven!  There are also many marathons and other physical events like flag football and SUP for those athletic types. And let’s not forget about the art scene; concerts, art openings, seminars and plays are abundant throughout the year, starting off with the Annual Literary Seminar in January. So no matter when you visit our island Paradise, you will find as much action and entertainment or relaxation as you are looking for.

2020

January 1, 2020

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 4 – 5, 2020

THE STUDIOS OF KEY WEST PRESENTS ‘SINGLE OCCUPANCIES,’ AN EVENING OF CONTEMPORARY OPERA THEATRE MONOLOGUES – 305-296-0458 – 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 8 – 18, 2020 

FRINGE THEATER PRESENTS: TALLEY’S FOLLY – 305-731-0581 – 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 9 – 12, 2020 

POLE VAULT IN PARADISE – Steve Hanes: 512-470-8076 – 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.

January 9 – 12, 2020 

38TH ANNUAL KEY WEST LITERARY SEMINAR – 888-293-9291 – 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 12, 2020

VISIT THE FAMILY-FRIENDLY SHERIFF’S ANIMAL FARM – Farmer Jeanne Selander: 305-293-7300 – 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, 2020

RAMS HEAD PROMOTIONS PRESENTS: GRACE POTTERAn acclaimed songwriter and electrifying performer, Potter has commanded stages around the world. 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, 2020

Impromptu Classical Concert at St. Paul’s Episcopal Church – 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 14, 2020

RAMS HEAD PRODUCTION 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! Show starts 9 p.m.

January 15 – 20, 2020 

22ND ANNUAL KEY WEST HALF MARATHON & 5K RUN – Barbara Wright: 305-240-0727 – 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 15, 2020

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 16, 2020

Carrie Newcomer: Old Town New Folk Series – 8pm show. $60 Preferred, $45 General ($10 discount for members – advance only)
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.

January 16 – Feb 1, 2020

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 – 19, 2020 

KEY WEST KINGFISH MAYHEM – Jimmy Wickett: 954-605-8284 – Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.

January 17 – 18, 2020

60TH ANNUAL KEY WEST HOME TOURS305-294-9501 – 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

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.

January 21 – 27, 2020 

29TH ANNUAL KELLY MCGILLIS CLASSIC INTERNATIONAL FLAG FOOTBALL CHAMPIONSHIP – 305-896-8678 – 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.

January 23, 2020

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 26 – October 8, 2020

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, 2020

VISIT THE FAMILY-FRIENDLY SHERIFF’S ANIMAL FARM – Farmer Jeanne Selander 305-293-7300 – 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, 2020

26TH ANNUAL KEY WEST MASTER CHEFS CLASSIC –305-294-9526, ext 25 – 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 2, 2020 

KEY WEST FOOD & WINE FESTIVAL – 800-474-4319 – 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 28 – February 1, 2020

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, 2020

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 28 – February 1, 2020

Prime Timewritten by Blake Hunter, directed by Murphy Davis 8pm show. $100 Tier A, $60 Tier B, $45 General ($10 discount for members – advance only). 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.

January 30 – February 1, 2020 

CUDA BOWL – Loren Rea: 305-360-6969 – 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 4 – 8, 2020

Prime Timewritten by Blake Hunter, directed by Murphy Davis 8pm show – $100 Tier A, $60 Tier B, $45 General ($10 discount for members – advance only). 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.

February 6 – 7, 2020 

FRINGE THEATER PRESENTS: MA RAINEY’S BLACK BOTTOM, A READING WITH MUSIC – 305-731-0581 – 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 9, 2020

IMPROMPTU CLASSICAL CONCERTS PRESENTS: CANELLAKIS-BROWN DUO – 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 9, 2020

SOUTH FLORIDA SYMPHONY PRESENTS BEETHOVEN 250TH ANNIVERSARY CELEBRATION – 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 12 – 15, 2020 

WATERFRONT PLAYHOUSE PRESENTS: LADY DAY AT EMERSON’S BAR AND GRILL– 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, 2020

Johnsmith: Old Town New Folk Series – 8pm show. $55 Preferred, $40 General ($10 discount for members – advance only). 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.

February 14, 2020

TENNESSEE WILLIAMS THEATER PRESENTS: MANDY PATINKIN– 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 – 15, 2020

60TH ANNUAL KEY WEST HOME TOURS – 305-294-9501 – 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 17, 2020

WILLIE NELSON AT KEY WEST AMPHITHEATER – 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. Tickets available online starting Friday, Nov. 22.

February 19 – 22, 2020

Anna in the Tropicswritten by Nilo Cruz, directed by Dennis Zacek – 8pm show; $100 Tier A, $60 Tier B, $45 General ($10 discount for members – advance only). 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.

February 19 – 23, 2020 

FRINGE THEATER PRESENTS: DESDEMONA– 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, 2020

RAMS HEAD PRODUCTION PRESENTS: KOOL & THE GANG, WITH THE VILLAGE PEOPLE – 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 on sale Aug. 23, available online.

February 23, 2020

IMPROMPTU CLASSICAL CONCERTS PRESENTS: THE RASCHER SAXOPHONE QUARTET – 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 26 – 29, 2020

Anna in the Tropicswritten by Nilo Cruz, directed by Dennis Zacek – 8pm show; $100 Tier A, $60 Tier B, $45 General ($10 discount for members – advance only). 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.

February 27 – March 1, 2020

Bill Mack & Gary Welton to Appear in Key West –An impressive collection of artwork and extraordinary sculpture by world-renowned artists Bill Mack and Gary Welton will be on exhibition and available for acquisition at Key West Gallery in Key West. The limited-engagement exhibition begins Thursday, February 27, 2020 and extends through Sunday, March 1, 2020. The Artists will be making special Appearances at the gallery on Friday, February 28 and Saturday, February 29 from 7:00pm – 11:00pm. The gallery is open every day from 10:00am – 11:00pm. RSVPs for the Artist Appearances are suggested at 305-923-1696 or info@keywestgallery.com.Visit www.keywestgallery.com for more info.

March 1, 2020

RAMS HEAD PRODUCTION PRESENTS: JOHN TESH AT KEY WEST THEATER – 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 starting 6/26/19.

March 3, 2020

Tom Rush: Old Town New Folk Series – 8pm show. $55 Preferred, $40 General ($10 discount for members – advance only). 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.

March 5 – 28, 2020

WATERFRONT PLAYHOUSE PRESENTS: PRISCILLA QUEEN OF THE DESERT, THE MUSICAL – Based on the smash-hit movie; a heartwarming, uplifting adventure of three friends, Tick, Bernadette and Adam, played by Christopher Peterson, Dave Bootle and Connor Cook, searching for love and friendship and end up finding more than they ever could have ever dreamed of. With a hit parade of dance floor favorites including “It’s Raining Men,” “I Will Survive,” “Hot Stuff,” “Boogie Wonderland,” “Go West,” “Girls Just Wanna Have Fun,” and “I Love The Nightlife,” this wildly fresh and funny musical is a journey to the heart of FABULOUS! Showtimes 8 p.m.

March 7, 2020

58TH ANNUAL CONCH SHELL BLOWING CONTEST – 305-294-9501 – 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 7, 2020

Artist Studio Tours – 11am-3pm, $30 Door, $25 General ($20 members)
One of our most popular annual events, the Studio Tours return to Old Town this season with a carefully curated collection of creative work spaces. Spend the afternoon peeking into the homes and studios of some of the island’s most fascinating artists. See website for details.

March 8, 2020

SOUTH FLORIDA SYMPHONY PRESENTS MASTERWORKS III: MENDELSSOHN, BEETHOVEN, ZWILICH (WORLD PREMIERE)– 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 8, 2020

IMPROMPTU CLASSICAL CONCERTS PRESENTS: NATALIA KAZARYAN – 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 8, 2020

GEORGE THOROGOOD & THE DESTROYERS – 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 12, 2020

Repair: Work in Progress written and directed by Mike Marrero – 8pm show; ticket holders may attend one or both shows$35 General ($10 discount for members – advance only). Witness the evolution of a script by one of Key West’s singular talents. Writer/Director Mike Marrero, whose provocative comedy Alligator Alley premiered at The Studios last year, presents a public table reading of his latest script, and then a lightly produced show a week later.

March 9 – 12, 2020

MARCH MERKIN INVITATIONAL PERMIT TOURNAMENT – 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

TENNESSEE WILLIAMS THEATER PRESENTS: THE COLOR OF PURPLE, THE MUSICAL –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 

60TH ANNUAL KEY WEST HOME TOURS – 305-294-9501 – 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, 2020

WATERFRONT PLAYHOUSE PRESENTS: TRUNK MATERIAL 2 – 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.

March 17 – 18, 2020

FRINGE THEATER PRESENTS: BLOOMSDAY – A James Joyce professor journeys to Dublin to find his “almost love of a lifetime” from 35 years ago. A shift in time provides him more than just an opportunity to reminisce. If you could go back, would you? Performance 7 p.m. at BCG at Bayview Park. Fringe Theater is Key West’s community-focused theater providing unique opportunities for people to see and do theater. 

March 19, 2020

Repair: Work in Progress written and directed by Mike Marrero – 8pm show; ticket holders may attend one or both shows$35 General ($10 discount for members – advance only). Witness the evolution of a script by one of Key West’s singular talents. Writer/Director Mike Marrero, whose provocative comedy Alligator Alley premiered at The Studios last year, presents a public table reading of his latest script, and then a lightly produced show a week later.

March 21, 2020

TENNESSEE WILLIAMS THEATER PRESENTS: THE CHOIR OF MAN – It’s a party. It’s a concert. It’s a pint-filled good time set in a working pub (free beer anyone?) that combines hair-raising harmonies, high-energy dance, and live percussion with foot-stomping choreography. Showtime 8 p.m., Tennessee Williams Theater, 5901 College Rd.

March 22, 2020

IMPROMPTU CLASSICAL CONCERTS PRESENTS: THE CALIDORE STRING QUARTET – The Calidore String Quartet’s “deep reserves of virtuosity and irrepressible dramatic instinct” (New York Times) and “balance of intellect and expression” (Los Angeles Times) have won them accolades across the globe and firmly established them as one of the finest chamber music ensembles performing today. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.

March 28, 2020

MOTE MARINE LABORATORY’S ANNUAL OCEAN FEST: A COMMUNITY CELEBRATION – From 10 a.m. – 6 p.m. at NOAA’s Florida Keys Eco-Discovery Center and Truman Waterfront. Underwater and outdoor enthusiasts, eco-travelers and families are encouraged to celebrate the marine environment as we explore conservation exhibits, view and purchase wares from local artists and vendors, experience touch tanks, and listen to live music all while raising funds for coral reef research and restoration.

April 1 – 3, 2020

Dignity, Always Dignity: A Post-Apocalyptic Cabaretdecided by Zachary Fine and Bryce Pinkham – 8pm show. $100 Tier A, $60 Tier B, $45 General ($10 discount for members – advance only) Following an apocalyptic event in 2022, Tony-nominated Broadway star Bryce Pinkham finds himself stranded, coming to terms with his fate and the fate of humanity. Bryce passes the time attempting to perform the entirety of Singin in the Rain, determined to ‘make em laugh’ all the way to the end.

April 5, 2020

RAMS HEAD PRODUCTION PRESENTS: THE TEMPTATIONS – No matter the change in personnel within the band, The Temptations have remained true to The Tempta-tions tradition. The Temps began their musical life in Detroit in the early sixties. It wasn’t until 1964 however, that the Smokey Robinson written-and-produced “The Way You Do the Things You Do” turned the guys into stars. Make your way to Sunset Green Event Lawn situated between 24 North and The Gates ho-tel’s on North Roosevelt Blvd. to catch one of the country’s most legendary bands to come out of the hopping Motown era. Tickets available online. Doors open 5:30 p.m., show starts 7 p.m.

April 9, 2020

Cary Morin: Old Town New Folk Series – 8pm show. $35 General ($10 discount for members – advance only). Described as “one of the best acoustic pickers on the scene today,” Morin plays with a deft finger style and melodic vocals that veer from elation to gritty world-weariness. Morin’s inimitable style is often characterized as acoustic Native Americana, blending qualities of blues, bluegrass, jazz, jam, reggae, and dance.

April 17, 2020

SOUTH FLORIDA SYMPHONY PRESENTS MASTERWORKS IV: STRAVINSKY, DELIUS, BEETHOVEN – The spectacular season concludes with Stravinsky’s mythical and rarely performed full ballet score of The Firebird; renowned British composer Frederick Delius’ only Piano Concerto, featuring internationally acclaimed pianist Mark Bebbington; and Beethoven’s spirited Coriolan Overture. Performance 7:30 p.m., Tennessee Williams Theatre, 5901 College Rd.

April 17 – 26, 2020

38TH ANNUAL CONCH REPUBLIC INDEPENDENCE CELEBRATION – 305-296-0213 – With activities such as a lighthearted sea battle featuring tall ships, the Conch Republic’s 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys.

April 21 – 25, 2020 

FRINGE THEATER PRESENTS: THE COMPLETE WORKS OF SHAKESPEARE (ABRIDGED) – 305-731-0581 – 37 plays in 97 minutes! It’s irreverent. It’s fast paced. It’s laugh out loud funny. Shakespeare? Exactly. Performance 7 p.m. at TBA location. Fringe Theater is Key West’s community-focused theater providing unique opportunities for people to see and do theater. 

April 30 – May 3, 2020

KEY WEST PADDLE CLASSIC – Sue Cooper: 305-304-4259 – Presented by Lazy Dog Adventures, the challenge includes a 12-mile Elite Race around the island and a 4-mile open race. Other events include a kick-off registration party, paddleboard clinics and races for kids.

May 6 – 10, 2020 

KEY WEST SONGWRITERS’ FESTIVAL – Charlie Bauer: 305-304-0814 – The annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. The largest festival of its kind in the world celebrates 24 years as both a tourist attraction and favorite of island locals. The festival revolves around five days and nights of big stars in intimate settings, introducing audiences to the faces, voices and stories behind the songs.

May 14 – 16, 2020

The Pickpocket’s Daughterwritten by Neal Ruchman, directed by Murphy Davis – 8pm show. $100 Tier A, $60 Tier B, $45 General ($10 discount for members – advance only). Unless Matzy Moses successfully navigates the corruption and gang warfare of 1930’s New York City, she will lose everything. Based on the life and times of the playwright’s mother, audiences call The Pickpocket’s Daughter, “A first class thriller with loads of laughs.”

May 21 – 23, 2020

The Pickpocket’s Daughterwritten by Neal Ruchman, directed by Murphy Davis – 8pm show. $100 Tier A, $60 Tier B, $45 General ($10 discount for members – advance only). Unless Matzy Moses successfully navigates the corruption and gang warfare of 1930’s New York City, she will lose everything. Based on the life and times of the playwright’s mother, audiences call The Pickpocket’s Daughter, “A first class thriller with loads of laughs.”

June 2 – 6, 2020 

FRINGE THEATER PRESENTS: FIVE LESBIANS EATING A QUICHE – 305-731-0581 – It’s 1956, and the Susan B. Anthony Society for the Sisters of Gertrude Stein are meeting for their annual quiche breakfast. Will they be able to keep their cool when a Communist attack threatens their idyllic way of life? Performance 7 p.m. at Key West Armory, 600 white St. Fringe Theater is Key West’s community-focused theater providing unique opportunities for people to see and do theater. 

June 3 – 7, 2020

KEY WEST PRIDE – Matt Hon: 305-294-4603 – Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, and pageants to select Mr., Miss and Ms. Key West Pride.

June 20, 2020

FKCC SWIM AROUND KEY WEST – Lori Bosco: 305-809-3562 – The officially sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach.

June 25 – 28, 2020

MANGO FEST KEY WEST 2020 – Mango Fest of Key West features all things mango including mango tasting, mango trees and mango daiquiris. The culinary competitions between local chefs and residents alike showcases the colorful abilities of what the mango, also known as the king of fruit, has to offer. The Vendor Village gives art collectors and foodies the experience of a festival atmosphere. Music is provided along with live radio broadcasts. From 10AM to 3PM, Bayview Park, 1400 Truman Ave.

June 26 – 28, 2020 

MYSTERY FEST KEY WEST – Renowned mystery writers, aspiring authors, true crime experts and fans meet in America’s southernmost city. The Fest features a who’s-who of award-winning and bestselling mystery/suspense authors and true crime experts, Mystery Fest Key West is a fun and fascinating meet-and-greet where writers can catch up with old friends and readers can meet leading authors, collect signed books and participate in workshops, panels, and presentations where the most devious of minds explain why—and how—they do it.

July 2 – 6, 2020 

EIGHTH ANNUAL KEY LIME FESTIVAL – A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop.

July 18, 2020

28TH ANNUAL HEMINGWAY 5K SUNSET RUN/WALK & PADDLEBOARD RACE – Barb Wright: 305-240-0727 – This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details.

July 18 – 21, 2020 

DEL BROWN PERMIT TOURNAMENT – Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.

July 22 – 25, 2020

STOCK ISLAND MARINA VILLAGE KEY WEST MARLIN TOURNAMENT – Tim Greene: 305-304-0317 – 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 12 – 16, 2020 

TROPICAL HEAT – 305-294-4603 – The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization.

September 2 – 6, 2020

WOMENFEST 2020 – 305-294-4603 – Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.

September 3 – 7, 2020

KEY WEST BREWFEST – During a festival “crafted” for Labor Day weekend, attendees can sample nearly 200 beers and ales while also discovering the flavors of the continental United States’ southernmost city. The annual Key West BrewFest is highlighted by a lavish oceanside tasting festival, beer-focused brunches, pool parties featuring specialty beers, daytime tap takeovers and dinners pairing each course with brews that complement the cuisine.

October 16 – 25, 2020

FANTASY FEST – This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. The 2020 festival theme is “Roaring 2020’s & Future Fictions.”