Key West Paradise

Nov 01 – Feb 9
Key West Art & Historical Society presents: A Literary History of Key West Exhibit
This exhibit will concentrate on a handful of writers who have found the tranquil and accepting character of Key West a perfect place to pen their novels, tomes, plays and poems.  While the exhibition is enlightening, it is by no means comprehensive....More

Nov 17
Key West Artisan Market: Fill the Pantry
The focus is on fresh, locally sourced food offered by our growers and makers, from 10AM to 2PM. Stock your pantry and fridge with fresh produce, exotic fruits, artisan cheeses, local seafood, honey, pickles, nuts and so much more. Then share the bou...More

Nov 19 – 23
Fringe Theater presents: The Last Flapper
The life of the tragically brilliant Zelda Fitzgerald is told by Zelda herself, and as it turns out, Mrs. F. Scott Fitzgerald has a lot to say on the subject of her husband, her work, and her life.  Performance at Key West Woman's Club, 319 Duval St....More

Nov 20 – 24
Key West Film Festival
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. T...More

Nov 22 – 25
Waterfront Playhouse presents: Hair In Concert
The international musical hit that changed the sound and the face of the Broadway musical. Tickets available online, showtimes TBA....More

Nov 22
Key West Art & Historical Society presents 'Key West Collects: Our Community Treasures'
This exhibit of unusual and wonderful collections of knickknacks, curios, ornaments, trinkets, baubles, tchotchkes, artwork and objects collected by Key West/Florida Keys residents opens with a special reception from 6-7:30 p.m. in the Bumpus Gallery...More

Nov 26
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 throu...More

Nov 27 – Dec 31
Key West Holiday Fest
A merry range of celebrations during Key West's busy holiday season includes lighting of the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. ...More

Nov 27
Lighting of the Bight: Key West Harbor Walk of Lights
Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2019 Key West “Harbor Walk of Lights”with more lights and creative displays than last year, all continuing the “Maritime History of Key West” theme! ...More

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

Dec 01
Key West Artisan Market: Red Ribbon Day Edition
Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge ...More

Dec 04
Key West Lighted Bike Ride
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Entry for the bike ...More

Dec 05
Tennessee Williams Theater presents: Sutton Foster
Sutton Foster is an award-winning actor, singer and dancer who has performed in 11 Broadway shows – most recently the revival of Violet – and originated roles in the Broadway productions of The Drowsy Chaperone, Little Women, Young Frankenstein, Shre...More

Dec 06 – 23
Old Town Trolley Lights & Sights Holiday Tour
The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition. Along with the aweso...More

Dec 07
TRIKW Sprint & Olympic Triathlon
The Key West Triathlon expects up to 1,000 participants and some of the sport's best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic an...More

Dec 07
Key West City Hometown Holiday Parade
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks o...More