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Calendar of Events for the Florida Keys

Event calendar courtesy of - The Tourism & Development Councel of the Florida Keys

Calendar of Events for May
Year:   Month:   Location:  
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January 01 to August 31,  in Key West
Key West Fishing Tournament
January 01 to August 31
Anglers of all ages and abilities can target more than 40 species of fish in the Key West Fishing Tournament, a free-entry multidivision challenge that takes place Jan. 1 to Aug. 31, 2019. The tournament features divisions for men, women, junior anglers ages 10 to 15 and Pee Wees under 10 years old — making it ideal for extended families and multigenerational groups who want to share the angling experience.
Contact: Doris Harris 305-923-5934

May 14 to June 01,  in Key West
Waterfront Playhouse presents: Red Speedo
May 14 to June 01
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. See website for show dates. Show times 8 p.m.
Contact: Box-Office (305-294-5015)

May 22 to June 01,  in Key West
Studios of Key West presents: Prime Time
May 22 to June 01
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.

May 25 to May 26,  in Key West
Key West Lionfish Derby
May 25 to May 26
This derby is organized to commemorate the 10th anniversary of the sinking of the USNS General Hoyt S. Vandenberg. A Captain's Meeting is mandatory for the team captains, at Turtle Kraals located along the historic Key West Seaport. All team members are encouraged to attend. The team captain must be one of the four participants in the derby, but does not need to be the captain of the boat. Sanctioned by Key Largo’s Reef Environmental Education Foundation (REEF), derby rules and safe collecting and handling techniques are to be reviewed. Team registration is $125 for four teammates. A portion of the derby proceeds will benefit the History of Diving Museum in Islamorada.
Contact: Tyler Mahler 305-457-3519

May 26 ,  in Islamorada
Afro Roots Fest, 2
May 26
The festival’s events take place within Islamorada’s colorful Morada Way Arts & Cultural District between mile markers 81 and 82. Attendees at the Memorial Day weekend event, headquartered at the Florida Keys Brewing Co. at 151 Morada Way, can expect music, stellar brews and a chance to browse intriguing arts and crafts.The Spam Allstars are to highlight the musical portion of the day, presenting their trademark fusion of Latin rhythms, electronica, Afro-Cuban sounds and hip-hop. The eclectic talent lineup also includes Grupo Barrio Abajo, known for Colombian-Caribbean folkloric music; Morikeba Kouyate with master guitarist David Feder, FABI World Music, Venezonix, a project by Andres Ponce of Elastic Bond and AGPA DJ Selector. Admission is free but a $10 per person donation is suggested.

May 26 ,  in Key West
28th Annual Schooner Wharf Minimal Regatta
May 26
To compete in the wacky challenge, each six-member team must construct a craft out of the most minimal supplies: a single sheet of 4-by-8-foot plywood, two 8-foot-long 2-by-4s, a pound of fasteners and a trusty roll of duct tape.Regatta rules even forbid the use of caulking or adhesives, though epoxy paint is permitted. The "sink or swim" challenge is a tradition in the Florida Keys, with Sunday's fun scheduled to begin at 11 a.m. when teams can register at the Schooner Wharf Bar, 202 William St.

May 27 ,  in Islamorada
Memorial Day Service
May 27
The Matecumbe Historical Trust will hold their annual Memorial Day Service at 9 a.m. at the Islamorada Hurricane Monument, Mile Marker (MM) 81.8 Overseas Highway. (IN EVENT OF RAIN, service is to be held at the Islamorada Fire Station) The monument was dedicated in 1937 to honor the Veterans and civilians killed in the Labor Day Hurricane of 1935. Barbara Edgar, President of the Matecumbe Historical Trust will make the introductory welcome presentation followed by the invocation, Presentation of Colors, the National Anthem, guest speakers, a brief history of the Hurricane Monument, the laying of the memorial wreath, Taps, and God Bless the USA sung by country artist Dan Furmanik. The service is open to the public. Residents and visitors are encouraged to attend in observance of Memorial Day.
Contact: Barbara Edgar 305-393-0940

May 31 to June 02,  in Key Largo
Fifth Annual Skippers Dolphin Tournament
May 31 to June 02
This tournament is headquartered at Skippers Dockside Restaurant, behind the Holiday Inn. Anyone, including captains and mates, are eligible to participate. Junior anglers must be under the age of 16 on the first day of the tournament. First-place team is awarded $20,000 cash. Prize monies are given the top six teams, including $10,000 to second place, $5,000 for third place, daily-angler, lady-angler, junior-angler cash prizes and more.
Contact: Dianne Harbaugh 305-522-4868

Calendar of Events for May
Year:   Month:   Location:  
Review other months or locations!

All events are subject to change. Contact the event coordinators for the most current dates and times.

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