Key West Paradise

Mar 06 – Feb 5
Market on the Green
Presented by The Keys Collection of resorts, the versatile Sunset Green Event Lawn, located between sister hotels the Gates Key West and 24 North, transforms into a local artisan market the first Saturday of each month, from 10AM to 2PM. ...More

Nov 04 – Jan 31
Arts Council presents 2021 Members Show ‘Dazzling Horizons’
The Opening Reception will be held Nov. 4, from 5:30 – 7:30 pm at the historic Gato Building, 1100 Simonton St. The exhibition will remain on display through January 2022. Dazzling Horizons - a look forward and a look around - the creativity is inspi...More

Dec 01 – Jul 31
Key West Fishing Tournament
More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish...More

Jan 06 – 27
South of Southernmost by Mark Hedden
Ballast Key is a backcountry island seven miles west of Key West, south of the Southernmost point, once listed for sale for $15.8 million. It was owned and used as a getaway for the influential and the creative by David Wolkowsky, a friend of Tenness...More

Jan 12 – 29
Waterfront Playhouse presents: Matilda, the Musical
Inspired by the twisted genius of Roald Dahl, the Tony Award-winning Roald Dahl’s Matilda The Musical is the captivating masterpiece from the Royal Shakespeare Company that revels in the anarchy of childhood, the power of imagination and the inspirin...More

Jan 15 – May 21
Key West Tropical Forest & Botanical Garden Speaker Series
Interested in learning more about the complex and fascinating environmental world of Key West and the Florida Keys? Then join a Speaker Series the third Saturday of each month this spring. Topics include Jan. 15: 'Then & Now, 85 Years of History of ...More

Jan 17 – 21
The Southernmost Regatta
This event offers five consecutive days of racing on the picturesque blue waters off Key West, and is open to One Design and ORC Racing / Cruising Keelboats. Enjoy a fun, sustainable event that features high-quality racing and social activities! Even...More

Jan 20 – Mar 24
Southernmost Chamber Music Society 2022 Season
Concerts of the season include a January concert featuring music from the baroque period, with composers like Bach, Handel, Soler and others. February welcomes the Classic and Romantic periods, Mozart, Brahms, Schubert, and others. In March, the Fren...More

Jan 21
Opening Reception of Key West Bicentennial Exhibit at Custom House Museum
Key West Art & Historical Society welcomes the public to a special reception from 5-8 p.m. to celebrate the opening of the 'Key West 200' exhibit at the Custom House Museum, 281 Front Street.  This major exhibition commemorates the 200th anniversary ...More

Jan 21 – Dec 11
Key West Bicentennial Exhibit at The Custom House Museum
Key West Art & Historical Society welcomes the public to mark the opening of the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front Street. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key W...More

Jan 22
Historic Key West Cemetery Stroll
Learn first-hand about fascinating people who have given Key West its colorful character! Small groups are escorted to gravesites where interpreters tell the stories of the deceased in brief monologues. Among the gravesites to be visited are those of

Jan 23
Impromptu Classical Concert Series Celebrates 50 Years: Pianist Yekwon Sunwoo
Sunwoo has been hailed for his ‘unfailingly consistent excellence’ by International Piano magazine, and celebrated as ‘a pianist who commands a comprehensive technical arsenal that allows him to thunder without breaking a sweat,’ by the Chicago Tribu...More

Jan 24
Friends of the Key West Library Lecture Series presents: Author S.A. Cosby
The Friends of the Key West Library’s speaker series will present New York Times bestselling author S.A. Cosby, via Zoom presentation. Mr. Cosby is the author of Razorblade Tears and Blacktop Wasteland. A writer from Southeastern Virginia, Cosby’s fi...More

Jan 24 – 31
Kelly McGillis Classic
Women from countries far and wide will be descending upon Key West for flag football competition, fun and learning. It is anticipated this event is to have the most international countries represented, and organizers are expecting teams from USA, Mor...More

Jan 25 – 29
Mile 0 Fest Key West
Mile 0 Fest Key West is a "must see" boutique destination 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 ...More

Jan 28
Keys Concerts by Candlelight Presents: Brit Pop to Rock
A unique musical experience, Keys Concerts by Candlelight allows you to enjoy famous works of music by the ambience of candlelight in various locations. The 2022 season of candlelit concerts will feature a series of contemporary music played by a str...More