Key West Events Calendar

37th Annual Conch Republic Independence Celebration 

April 19 - 28, 2019, in Key West

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.

Fourth Annual Papio Kinetic Sculpture Parade 

May 3 - 5, 2019 | Key West


If one man's junk is another man's treasure, then the late Key Largo folk artist Stanley Papio was atreasure hunter extraordinaire. Fans of "outsider art" can celebrate the renegade metal sculptor's legacy with a people-powered parade of mobile sculptures crafted in the spirit of his extraordinary creations. The Papio Kinetic Sculpture Parade features colorful sculptural floats, tricycles with exotically costumed riders, fantastically decorated bicycles and other moving works of art — all powered by human effort alone — and are to follow a route along the length of Key West's Duval Street. 

key west paddle classic

Key West Paddle Classic 

May 4, 2019 | Key West

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.

Key West Songwriters' Festival 

May 8 - 12, 2019 | Key West

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.

Waterfront Playhouse Presents: Red Speedo 

May 14 - Jun 1, 2019 | Key West

Would you do anything to win an Olympic medal? What is the line in the high stakes world of modern sports? This is the dilemma posed in Red Speedo, a razor-sharp play about whether doping is acceptable in the pursuit of that elusive medal - and more importantly, when commercial endorsements are at stake.

Studios of Key West Presents: Prime Time 

May 22 - Jun 1, 2019 | Key West

Blake Hunter has penned a new musical following a female TV Executive in the 1970s who fights 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. Tickets $60 Preferred, $44, $35 mbrs. May 22–26 (Wed-Sun) and May 28–Jun 1 (Tue-Sat), 8pm showtime; at Studios of Key West, 533 Eaton St. 

Key West Theater Presents: David Crosby & Friends 

May 24, 2019 | Key West

Two-time Rock and Roll Hall of Famer and co-founder of the Byrds and Crosby, Stills & Nash, David Crosby is heading out on tour in May and June. Joining him will be five musical friends, collectively and affectionately known as the ‘Skytrails Band’. James Raymond, David Crosby’s son, on keys, Mai Agan on bass, Steve DiStanislao on drums, Jeff Pevar on guitar and Michelle Willis on keyboards and vocals. Crosby is in the midst of an incredibly creative and powerful period, showcasing his skills as the brilliant songwriter that he is. On this tour, he will be performing some of his best loved songs and greatest hits from right across his illustrious career, alongside material from the Sky Trails album, plus a few surprises as well. Doors open 7 p.m., show starts 8 p.m., Key West Theater, 512 Eaton St.

June 01, in Key West43rd Annual Swim Around Key West 
The Annual Swim Around Key West is a 12.5-mile endurance swim clockwise around the entire island of Key West, started by founder Anna Fugina in 1977. The Annual Swim Around Key West is an independent and insured swim, permitted by the U.S. Coast Guard. There are three categories: solo swimmer, two-person relay team and three-person relay team. Presented by Key West Athletics Association.    Reserve a beautiful cottage or condo from our collection and dive right in!
June 05 - 09, 2019, in Key WestKey West Pride 
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, a 10k relay for tutu-wearing runners and walkers, and pageants to select Mr., Miss and Ms. Key West Pride.    Resere a beautiful cottage or condo from our collection and celebrae your pride!
June 09, in Key WestKey West Concerts presents: Slightly Stoopid 
The Ocean Beach, California-based band formed by multi-instrumentalists Kyle McDonald and Miles Doughty has matured into a versatile musical ensemble consisting of drummer Ryan “Rymo” Moran; percussionist Oguer “OG” Ocon; saxophonist Daniel “Dela” Delacruz; keyboardist Paul Wolstencroft; trumpet and trombone player Andy Geib, and an arsenal of guests that frequent the stage, most notably Karl Denson (Rolling Stones/Greyboy Allstars), Don Carlos, Chali 2na (Jurassic 5) and Rashawn Ross (Dave Matthews Band). Special guests include Matisyahu, Tribal Seeds and Hirie. Gates open 3:30 p.m., show states 4:30 p.m., Key West Amphitheater.   Reserve a beautiful cottage or condo from our collection and enjoy the show!
June 10, in Key WestStudios of Key West presents: Twice Told Tales 
The hit of Summer Stage returns for a third round of dueling mono- logues! Can the same words mean more than one thing? Twice Told Tales provides a fresh twist on a theatrical staple. Each monologue is presented by one director, but two actors, giving two wildly different takes on the material. Showtime 8 p.m., 533 Eaton St.    Reserve a beautiful cottage or condo from our collection and enjoy this tale!
June 15, in Key WestFKCC Swim Around Key West 
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. 
Contact: Lori Bosco 305-809-3562
Email:;  Reserve a beautiful cottage or condo from our collection and dive right in!
June 15, in Key WestSeventh Annual VFW Fishing Tournament 
Sponsored by the Southernmost VFW Post 3911, this family oriented inshore and offshore tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee, senior angler and active service member. The heaviest Dolphin: 1st-$3000.00; 2nd-$1000.00; and 3rd $500.00. Weigh-in at Murray Marine. All proceeds benefit VFW Relief Fund for Monroe County veterans, and local charities.
Contact: Pete Thomas 610 304 2392
Email:  Reel in a great deal on a cottage or condo from our collection!
June 20, in Key WestKey West Theater presents: Brian Imbus, Mentalist 
Brian Imbus is an internationally recognized Mentalist that has performed for thousands of audiences for over 20 years. Brian has performed at over 3,000 professional engagements, has Hypnotized over 100,000 people. ‘Miracles of the Mind’ includes a unique blend of humor, psychological illusion, and hypnosis. Predic-tions will be made, minds will be read and one impossible finale will add an exclamation point to this award winning performance! Doors open 7 p.m., show starts 8 p.m.    Reserve a beautiful cottage or condo from our collection and enjoy this show!
June 21 - 23, 2019, in Key WestKey West International Guitar Festival: Bridges to Paradise 
The festival features a fusion of master guitarists performing classical, jazz, Latin, blues, folk & contemporary music in historic venues throughout the island, in a series of world-class concerts. Food and wine events are to be paired with music throughout the island offering a culinary and cultural experience highlighted by a special event, “Virtuoso Chefs of Key West.” Featured artists include Mateo, Belle, Rolando Rojas and Larry Baeder. Tickets on sale April 6, online.
Contact: Mateo 305-304-1437
Email:  Pick out a beautiful cottage or condo from our collection and strum along!
June 21 - 23, 2019, in Key WestMystery 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.   It's no mystery that you need a beautiful cottage or condo from our collection!
June 29, in Key WestKey West Mango Fest 2019 
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.   We're celebrating our mangos, so reserve a beautiful cottage or condo from our collection and celebrate with us!