The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
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Events in the Florida Keys for May, 2019
Year: Month:  
April 09 to May 03,  in Key West
Arts Council Presents the Connections Project 2019 TOUR
The Florida Keys Council of the Arts' seventh annual Connections Project Keyswide road show features a vibrant 24-foot mosaic mural created by local artists and art lovers. Currently at Royal Furniture in Key West, it moves May 3 to the Gato Building in Key West. Receptions with wine and hors d'oeuvres are open to the public. After connecting with the art, patrons can also collect art by making a $50 donation for one canvas or a $125 donation for three at any reception or online. Once the road show has ended, donors receive a randomly selected piece of the mosaic in the mail. Each work includes an artist statement providing insight into the origin of the work and the artist’s thoughts and inspiration. Proceeds from the Connections Project directly benefit Keys artists and arts organizations.

April 28 to May 02,  in Marathon
Faro Blanco Invitational Tarpon Tournament
This team tournament, with 2-4 anglers per team/boat, allows anglers to fish three nights with three different Captains at three different bridges: Bahia Honda, Long Key and the world-famous Seven Mile Bridge(s) in the heart of tarpon season. A charity tournament, the event's proceeds benefit Ronald McDonald House charities.
Contact: Donna Vankirk 305-393-0699

May 01 to May 03,  in Key West
Fringe Theater presents: Golda's Balcony
This riveting one-woman show examines the life of Golda Meir and her transformative journey from Milwaukee schoolteacher to Prime Minister of Israel. Golda’s Balcony, written by William Gibson, was nominated for a Tony Award and won the Drama Desk Award. It also holds the record as the longest running one-woman show on Broadway. Fringe Theater is a local nonprofit that creates unique opportunities for people to see and do theater. Performances at 7pm with a 5pm performance on May 3 at B-nai Zion Congregation, located at 750 United Street. Tickets available online.
Contact: 305-731-0581

May 03 to May 05,  in Key West
Fourth Annual Papio Kinetic Sculpture Parade
If one man's junk is another man's treasure, then the late Key Largo folk artist Stanley Papio was a treasure 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.
Contact: 305-295-6616

May 03 to May 05,  in Islamorada
Nick Sheahan Dolphin Rodeo
A tournament honoring the memory of Nick Sheahan, a Florida Keys student, funds from this event benefit a namesake community scholarship fund. Hosted at Tavernier Creek Marina, cash prizes and $25,000 to the angler with the dolphin that beats the state record. Hosted at Tavernier Creek Marina, entry fee for adults is $185, $50 for juniors.
Contact: Marcia Panse 305-393-3733

May 03 to May 05,  in Marathon
Marathon Offshore Bull and Cow Dolphin Tournament
A guaranteed grand prize of $10,000 cash is to go to the team that catches the largest bull and cow dolphin fish combined. However, according to organizers, the top prize payout increases as more boats register. With a field of 60-69 boats, the first-place cash award is to be $13,000, increasing incrementally by 10 boats. If a field of 100 boats is reached, the guaranteed first-place cash prize is $25,000. while other prizes are awarded to anglers catching the largest dolphin, wahoo, tuna and tripletail.
Contact: Jack Carlson 305-481-0495

May 04,  in Key West
Key West Paddle Classic
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.
Contact: Sue Cooper 305-304-4259

May 04 to May 09,  in Marathon
Tarponian Tournament
For enthusiastic tarpon anglers, silver kings mean springtime. This high-energy, three-evening tournament mandates that teams fish with a different captain each evening. Teams also rotate among the three major bridge channels in Marathon, so any potential "hot spots" are shared among all anglers.
Contact: Donna Vankirk 305-393-0699

May 04 to May 07,  in Key West
CU In the Keys: Southernmost Fit and Fun Retreat
The focus of the retreat will be aimed at self care, fitness and nutrition, and stress management, all aimed at living a healthier lifestyle. We all get lost in the daily grind of the hustle and bustle. Life is just like that. And you can’t see your way out of the weeds when you are stuck in your current environment… constantly being reminded of all the things you do.  Imagine a place not far away that is warm, tropical, friendly and inviting--where you can join a group of like-minded people for some FUN, FITNESS, and RELAXATION!  Come down to beautiful, sunny Key West for the ULTIMATE reset--to relax, rejuvenate and reset your health and fitness journey!  Register online.
Email: 919-961-6367

May 04,  in Key West
May the Fourth Be With You: A Burlesque Parody
Key West Burlesque presents on of their all time favorite show this May 4th! Star Wars parody burlesque show! May The Fourth Be With You: A Burlesque Parody, is a wild mix of childhood favorites and adult fantasies. Tatah DuJour plays host and narrates this epic take off as the charter "The Force DuJour" while long time Key West Burlesque alumni Moana Amour and Scarlett thrill the audience with their incredible performances as Moana Solo and Chestybawca. Special guest stars and local favorites capture a sexy side of Star Wars with their take on all your favorite classic characters and features the always entertaining Key West Burlesque dancers. Sidebar, 504 Angela Street. Doors open at 7:30PM, show starts at 8PM.

May 08 to May 12,  in Key West
Key West Songwriters' Festival
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.
Contact: Charlie Bauer 305-304-0814

May 09 to May 11,  in Key Largo
13th Annual Mac Arnold and Plate Full O' Blues Cornbread and Collards Festival
Mac Arnold is a legend in the Blues and television world. Mac played bass for BB King, is the last living members of the Muddy Waters Band, did the intro for Sanford & Sons television show, co-produced the Soul Train television show and played with Otis Redding at Leo's Casino the night before he passed away in a plane crash. Mac Arnold is world famous for the great tunes he puts out on his Gasoline Can Guitar built for him by his brother Leroy when they were kids. Bayside Grill at MM 99.5. Shows 7-10 p.m. nightly.

May 09 to May 25,  in Marathon
Marathon Community Theater presents: Making God Laugh
Making God Laugh is a family comedy that takes place in four scenes, each ten years apart and set at various holidays. Beginning in 1980, the newly “launched” kids - a priest, an aspiring actress, and a former star football player - all return home where we learn of their plans as they embark on their adult lives. The “empty nest” parents contend with their own changes as well as old family rituals and dubious recipes are trotted out and ancient tensions flare up.  Show times 8 p.m., Sunday matinee 3 p.m.

May 10 to May 11,  in Marathon
13th Annual Mother's Day Dolphin Tournament
This is a fun and festive one day fishing tournament for the heaviest dolphin. New and seasoned anglers are welcome! Over $8,000 in cash and prizes have been awarded in past events. All registration fees are tax deductible as allowable by law and will be used directly to build four new affordable homes in Marathon. Proceeds benefit Habitat for Humanity of the Middle Keys. The Captain's Meeting is Friday, followed by a day of fishing on Saturday. There are four angler categories: Pro, Weekend Warrior, Ladies, and Junior (16 and under).
Contact: 305-743-9828

May 10,  in Big Pine
Key West Songwriters Festival: Pool Party at the Perry Hotel
Free show, no tickets required. Public is welcome. Live music starting at 3 p.m. featuring Johnny Dibb and John Gurney; enjoy specials from Salty Oyster & Matt's Stock Island Kitchen & Bar, including a back-to-back happy hour from 4-8 p.m, and The Green Pineapple at The Perry Hotel trunk show from 5-8 p.m.; more live music from Ciara Rae, 5-7 p.m.

May 14 to June 01,  in Key West
Waterfront Playhouse presents: Red Speedo
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 16 to May 19,  in Key Largo
Key Largo's Original Music Festival
Enjoy the food, entertainment and ambiance of Key Largo during this singers and songwriters event. Multiple "on the water" venues feature Nashville's hit songwriters and musicians as well as unique local entertainers. Presented by the Upper Keys Business Group.
Contact: 305-394-3736

May 18,  in Key West
Discovery Saturday Educational Series: Sea Turtles
Kids in kindergarten through fifth grade are invited to join the free, fun-filled Discovery Saturday at the Florida Keys Eco-Discovery Center (35 East Quay Road, Key West) from 10-11 a.m., with special guests from Marathon’s Turtle Hospital. Through engaging crafts and activities, children will learn how to reduce the threats to these fascinating sea creatures that nest in the Florida Keys. Free admission, free parking. Discovery Saturday is held the third Saturday of every month. Pre-registration is recommended. The Florida Keys Eco-Discovery Center is located at 35 East Quay Road on the Truman Annex waterfront in Key West.
Contact: 305-809-4750

May 19 to May 22,  in Islamorada
Loop Golden Fly Invitational Tarpon Tournament
Special flies, accurate casts and a bit of luck are the recipe for winning this prestigious challenge, using only a tournament-furnished tippet not greater than 16-pound test. Eligible tarpon must measure at least 48 inches in length to earn release points, and weigh at least 70 pounds for weight points.
Contact: Shandra Rummel 305-587-1460

May 22 to June 01,  in Key West
Studios of Key West presents: Prime Time
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 24,  in Key West
Key West Theater presents: David Crosby & Friends
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.

May 24,  in Key West
Dive the Vandenberg to See 'The Sinking World: Plastic Ocean' Installed
Austrian artist Andreas Franke's newest 24-piece exhibit of The Sinking World, is themed "Plastic Ocean," a subsea “gallery” of fantastical photographic artistry – digitally layered images of people merged with composite shots of the ship. Divers can experience this unique shipwreck and get a peek as specialty divers install the 24 art pieces of "Plastic Ocean" on both sides of Vandenberg’s hull. The Plastic Ocean exhibition is to be displayed underwater from May 25 to August 25, 2019. Book a morning dive with any Key West professional dive operator.

May 25,  in Key West
Key West Blues Festival
Key West Blues Festival has recruited the best of Key West's blues performers to offer you an exclusive concert experience. You can look forward to seeing some of Key West's best blues musicians such as Bill Blue, Caffeine Carl, Ericson Holt, Michelle Dravis, Andy Westcott, Daryl Brooke, Joey Marchiano and Rick Fusco with special guests: Jeff Clark, Wayne Sorbelli and Karri Daley. doors open 7 p.m., show starts 8 p.m.

May 25 to May 26,  in Key West
Key West Lionfish Derby
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
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
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
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
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

The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax

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