Key West Paradise

Dec 01 – Jul 31
Key West Fishing Tournament
Anglers of all ages and abilities can target more than 40 species of fish in the Key West Fishing Tournament, a free-entry multi-division challenge that takes place Dec. 1 to July. 31, 2020. The tournament features divisions for men, women, junior an...More

Jan 21 – Apr 24
LaTeDa presents: Randy Roberts Live!
The Randy Roberts Show is an all live, multi-media tribute to some of the world’s most loved performers. Randy’s uncanny impersonations of Cher and Bette Midler have kept him in the spotlight for the past twenty years. His roster of famous and infamo...More

Jan 22 – Apr 28
LaTeDa presents: Christopher Peterson's EyeCons Cabaret
Christopher Peterson is a master of impersonations, both visually and vocally, and his comic timing is impeccable. The show is all live, no lip-sync, and audiences will be thrilled with his characterizations of Marilyn Monroe, Carol Channing, Madonna...More

Feb 06 – Dec 31
Tropic Cinema's Cinematheque Series
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. ...More

Feb 07 – Apr 3
First Fridays on Fleming
Key West boutique owners in “The Fabulous 500 Block of Fleming Street” have kicked off a monthly First Fridays on Fleming 6-9 p.m. block party to encourage local buying. First Fridays on Fleming showcase boutiques, galleries and eateries in the 500 b...More

Feb 19 – 29
The Studios of Key West presents: Anna in the Tropics
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 inheren...More

Feb 19 – 23
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. Perfo...More

Feb 21
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 grea...More

Feb 22 – 23
55th Annual Old Island Days Art Festival
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’...More

Feb 23
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 discipli...More

Feb 23
35th Annual Schooner Wharf Bar Annual Wrecker's Cup Race Series
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...More

Feb 29
Sixth Annual Cow Key Channel Bridge Run
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...More

Mar 01
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 ...More

Mar 01
Key West Artisan Market: Car-Free Key West Edition
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 truck...More

Mar 03
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 ar

Mar 05 – 28
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...More