Florida Keys
Calendar of Events for May  
Year:   Month:  Location:  
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May 22,  in Key West
Visit the Family-Friendly Sheriff's Animal Farm
May 22
Looking for a fun place to take the kids? The Sheriff's Animal Farm is open 1 - 3 p.m. Bring the family and come visit the many animals at the farm. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. Open the second and fourth Sundays of the month.
Contact: Farmer Jeanne Selander 305-293-7300


May 12 to May 14,  in Key Largo
10th Annual Mac Arnold and Plate Full O' Blues Festival
May 12 to May 14
Mac Arnold is a legend in the Blues and television world. Mac played bass for BB King, is one of 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. Show start at 7 p.m. nightly.


May 14,  in Islamorada
Invasive Lionfish Awareness & Removal Day
May 14
Designated an annual event (the first Saturday after Mother's Day each year), this weekend is to be dedicated to statewide lionfish removal and awareness activities. Coastal counties around the state will be harvesting lionfish in an attempt to remove as many of the invasive critters as possible. The Florida Fish & Wildlife Conservation Commission (FWC) is encouraging all divers to remove as many lionfish on the weekend of May 14-15, no matter where they are in Florida. Join Key Dives for aa morning lionfish dive. The morning dive will cost $85 ($70 if you are a REEF member!) Check in is at 8 a.m.
Contact: Key Dives 305-664-2211; REEF 305-852-0030


October 02 to May 20,  in Key West
Key West Outdoor Movies
October 02 to May 20
Enjoy free-admission outdoor movies at Bayview Park every first and third Friday through May 20th. Starts at dusk. Bring lawn chair, snack and refreshments. Check website for upcoming movie events.
Contact: Jason 305-791-4375


April 28 to May 08,  in Marathon
Marathon Community Theater presents: Taking My Turn
April 28 to May 08
Taking My Turn is the award-winning, critically acclaimed musical by the same team that collaborated on the hit show The Me Nobody Knows. Taking My Turn was one of the first musicals to deal with aging. The spoken words were collected from interviews with people "in their prime," which became the basis for the non-linear book. Visit website for show times and matinees.
Contact: 305-743-0994
Email: gm@marathontheater.org

May 21,  in Key West
Discovery Saturday Educational Series: Sea Turtles Hit the Beach!
May 21
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. Learn about sea turtles! May is the beginning of turtle nesting season and it is important for everyone to learn how they can help hatchlings survive. The Turtle Hospital will be bringing a live sea turtle and there will be other games and hands on activities. 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
Email: rachel.pawlitz@noaa.gov

May 29,  in Key West
25th Annual Schooner Wharf Minimal Regatta
May 29
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 Memorial Day Weekend 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.


April 22 to May 01,  in Key West
34th Annual Conch Republic Independence Celebration
April 22 to May 01
With activities ranging from wacky bed race to 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.
Contact: 305-296-0213


May 06 to May 08,  in Islamorada
Nick Sheahan Dolphin Rodeo
May 06 to May 08
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
Email: mpmanate@bellsouth.net

May 22 to May 25,  in Islamorada
Loop Golden Fly Invitational Tarpon Tournament
May 22 to May 25
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: Betsy Bullard 305-587-1460
Email: fishnfever@bellsouth.net

May 12 to May 15,  in Key Largo
Key Largo's Original Music Festival
May 12 to May 15
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 06 to May 07,  in Marathon
10th Annual Mother's Day Dolphin Tournament
May 06 to May 07
This is a fun and festive one day fishing tournament for the heaviest dolphin. Over $8,000 in cash and prizes. Three entry levels: Pro, Weekend Warrior and Jr. Divisions. Come join us and "Fish for a Cause." All registration fees are tax deductible as allowable by law and will be used directly to build four new affordable homes in Marathon. Tournament proceeds benefit Habitat for Humanity of the Middle Keys.
Contact: 305-743-9828
Email: execdirector@habitatmiddlekeys.org

May 04 to May 08,  in Key West
Key West Songwriters' Festival
May 04 to May 08
The 21st annual showcase of musical magic features America's foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings.
Contact: Charlie Bauer 305-304-0814
Email: kwswf@aol.com

April 28 to May 01,  in Key West
Key West Paddle Classic
April 28 to May 01
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
Email: sue@lazydog.com

May 21,  in Key West
Key West Ladies' Dolphin Championship
May 21
Cash and prizes totaling $10,000 are to be shared by the tournament's winning boat team and top five individual anglers. The angler who catches the heaviest dolphin during the daylong tournament earns a $3,000 cash prize. The second-place angler is to receive $1,500 cash, while $500 awaits the third-place finisher and prizes await the fourth- and fifth-place participants. In addition, $1,000 is to be awarded for the largest wahoo caught.
Contact: Lee Murray 305-296-0364
Email: lee@murraymarine.com

May 30,  in Islamorada
Memorial Day Service
May 30
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. The monument was dedicated in 1937 to honor the Veterans and civilians killed in the Labor Day Hurricane of 1935. The ceremony will begin with an introductory presentation, followed by the invocation by Pastor Tony Hammon of Island Community Church, Presentation of Colors, the National Anthem, a brief history of the Hurricane Monument, the laying of the memorial wreath and a benediction. 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 01 to May 04,  in Marathon
Tarponian Tournament
May 01 to May 04
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: David Breznicky at 215-542-1492
Email: dbreznicky@breznickyassociates.com

April 30 to May 01,  in Marathon
Marathon Offshore Bull and Cow Dolphin Tournament
April 30 to May 01
Over $30,000 is cash and prizes awaits the top anglers with the largest bull and cow combined, while other prizes are awarded to anglers catching the largest dolphin, wahoo, tuna and tripletail.
Contact: Jack Carlson 305-481-0495
Email: bigtimetackle@comcast.net

May 13 to May 15,  in Florida Keys
Florida Keys Dolphin Championship
May 13 to May 15
This Keys-wide dolphin challenge allows anglers to fish one tournament from Key Largo to Key West, and weigh in at five locations. An unlimited number of anglers can join a team, in this boat/team event. Visit website for more details.
Contact: Mike Weinhofer 305-395-3474
Email: fishnkw@aol.com

May 08,  in Key West
Visit the Family-Friendly Sheriff's Animal Farm!
May 08
Looking for a fun place to take the kids? The Sheriff's Animal Farm is open 1 - 3 p.m. Bring the family and come visit the many animals at the farm. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. Open the second and fourth Sundays of the month.
Contact: Farmer Jeanne Selander 305-293-7300


May 14,  in Marathon
Battle in the Bay Dragon Boat Festival
May 14
The waters off Sombrero Beach are to be transformed into a swift racecourse for a day of dragon boat racing that involves 20 paddlers moving in unison a combination of strength and teamwork. Sombrero Beach provides a pristine setting and unique, direct-from-the-beach launch for the sleek, 40-foot-long race boats. The festival is free and open to the public. Food, beverages, merchandise and a variety of entertainment are to be available shoreside.
Contact: Christine Canevari 813-426-3544
Email: christine@highfivedragonboat.com

May 12,  in Key West
Key West Theater presents: Tinsley Ellis
May 12
Southern blues-rocker Ellis easily ranks as one of today's most electrifying blues-rock guitarists and vocalists. He approaches his music with rock power and blues feeling, in the same tradition as his Deep South musical heroes Duane Allman and Freddie King and his old friends Derek Trucks and Warren Haynes. Show time 8 p.m.
Contact: 305-985-0433
Email: keywesttheater@gmail.com

May 04,  in Key West
The Sexy Side of Star Wars: A Burlesque Parody
May 04
Key West Burlesque's ensemble cast takes on the cherished Star Wars universe like you have never seen them before in this not to be missed production. Tatah DuJour plays host and narrates this epic take off as the charter "The Force DuJour". Show at The Studios of Key West. Doors open at 7:30 p.m., show time 8 p.m. Tickets are available at keystix.com for $25, $35 and $50.


May 07,  in Big Pine
Lower Keys Chamber of Commerce presents: Business Walkabout & Auctions
May 07
Open to the public, the event showcases the Lower Keys, from eclectic to adventurous and artistic, in a fun expo atmosphere. From 9 a.m. to 2 p.m., browse a large silent auction, participate in an exciting live auction, as well as beer and wine tastings. Catch the event action live on US1 radio. Admission is free, event held at Boondocks Grille & Draft House, MM 27.5, Ramrod Key.
Contact: 305-872-2411


May 29,  in Islamorada
Memorial Day Weekend Beach Barbecue at Cheeca Lodge & Spa
May 29
Staged at the north end of the private beach for traditional American fare with a "Keys" twist. Kids (and parents) can enjoy activities including face painting and seasonal crafts from 5-7pm on the beach. Activities are complimentary for all kids. Starting at 7:30pm watch a patriotic favorite movie beneath the stars, "National Treasure". This event is complimentary for all attendees and will feature a concession station offering popcorn, candy and other light refreshments for your viewing pleasure. Barbecue price: Adults $30, Veterans (retired and active personnel) $15, Kids $15. This year, 10% of proceeds from the Beach BBQ will be donated to The Long Walk Home, a Keys-based organization helping Veterans make the transition from military life to civilian life.


May 19,  in Islamorada
Morada Way Arts & Cultural District presents: Third Thursday Art Walk
May 19
Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82 - formerly named Industrial Road - as well as "culinary art" and live music from 6-9 p.m. Free admission. Art Walk is held the third Thursday of each month.


May 01,  in Islamorada
ICE presents: Sultans of String Jazz
May 01
The acclaimed group from Toronto brings its unusual combination of Spanish Flamenco, Arabic folk, Cuban rhythms and French Manouche Gypsy-jazz to the stage.


April 26 to May 14,  in Key West
Red Barn Theatre presents: The Cripple of Inishmaan
April 26 to May 14
The people of Inishmann learn that a Hollywood director is coming to a neighboring island to film a documentary. No one is more excited than Cripple Billy, an unloved boy whose chief occupation has been gazing at cows and yearning for a girl who wants no part of him.
Contact: 305-296-9911


May 08 to May 10,  in Key West
Red Barn Theatre presents: The Story Goes On
May 08 to May 10
A Mother and Daughter's Musical Journey Starring Camille Russo Toler and Erica Money Butters. From blues to showtunes to rock'n'roll to opera!
Contact: 305-296-9911


May 11 to May 28,  in Key West
Waterfront Playhouse presents: Die, Mommie, Die!
May 11 to May 28
This outrageous comic melodrama from Charles Busch evokes the movie thrillers from the early 60's that featured cinematic icons like Bette Davis, Joan Crawford and Lana Turner. A faded pop singer tries to escape her corrosive marriage and find happiness with a younger lover. Bad acid trips, a resentful daughter, a weird son and a poisoned suppository all play a part in this outrageous comedy. Tickets available online.
Contact: 305-294-5015 Box Office


May 13 to May 15,  in Key West
Papio Kinetic Sculpture Parade
May 13 to May 15
The Key West Art & Historical Society presents this inaugural, family-friendly exhibition event that is also an art-inspired float parade powered by humans on bicycles. People of all ages can celebrate the creative, funky and wild designs on display.


May 21 to May 22,  in Key Largo
The Long Walk Home's Inaugural Fishing Tournament
May 21 to May 22
Headquartered at Key Largo Fisheries, events include a Pirate's Treasure Raffle, music, silent auction, two days of fishing, and awards dinner. Cash and trophy prizes are to be awarded. Proceeds benefit the Long Walk Home Veterans Charity Community Outreach.
Contact: 305-504-3795
Email: thelongwalkhomeinc@gmail.com

April 30 to May 01,  in Islamorada
History of Diving Museum presents: Bob Croft, Father of Freediving
April 30 to May 01
"Testing the Waters: My Career as an Underwater Research Subject" will be presented and will focus on Croft's career as a test subject and collaborative investigator for the US Navy. Croft, who is considered to be the father of American freediving, was the first person to dive beyond 200 feet while breath holding. He is credited with perfecting "air-packing," a technique that is commonly used by modern free divers. Presentation April 30 is 2-3 p.m., with a 3-5 p.m. book signing; Sunday, all-day book signing. Museum is located at 82990 Overseas Highway, mile marker (MM) 83.
Contact: 305-664-9737


May 29,  in Key West
Key West Theater presents: The Ramble
May 29
Key West musicians come together to perform in this exclusive concert experience: a celebratory night of live music featuring the best talent this island has to offer! All shows feature the Rambler Band which includes Nick Norman, Jeff Clark, Caffeine Carl, Ericson Holt, Claire Finley, James Whitehead, Robyn Whitehead, Daryl Brook, Randy Morrow, Derik Reay and Joey Marchiano. Show starts 8 p.m.
Contact: 305-985-0433
Email: keywesttheater@gmail.com

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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Captain Jim Sharpe, Captain Michael Vaughn

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