Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total., Contact: Tim Greene 305-304-0317, Email: [email protected], Islamorada /7/21/2016, Morada Way Arts & Cultural District presents: Third Thursday Art Walk, 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., Key West /7/21/2016, Key West Theater presents: Leon Russell, Leon Russell is a music legend and perhaps the most accomplished and versatile musician in the history of rock ‘n roll. Leon has played on pop, rock, blues, country, bluegrass, standards, gospel, and surf records. As a session musician, arranger, producer, singer, songwriter, pianist, guitarist, record company owner, bandleader, and touring musician, he has collaborated with hundreds of artists from Joe Cocker, Frank Sinatra, Eric Clapton, Bob Dylan and scores more., Contact: 305-985-0433, Email: [email protected], Key West /7/23/2016, Hemingway 5K Sunset Run & Paddleboard Race, This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details., Contact: Barb Wright at 305-240-0727, Email: [email protected]
The 36th annual celebration of the legendary author’s work and lifestyle features literary readings, Running of the Bulls, short story competition, fishing tournament, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s 7/21st birthday., Contact: (305) 296-2388 (Look-Alike); 797-0579 (literary)
The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization., Contact: 305-294-4603, Key Largo /8/20/2016, Anything that Floats Race, Grab your oars and anything that floats and enjoy this family-fun event – an on-the-water race of vessels crafted from items around the house – on Blackwater Sound, mile marker 104 bayside. Waterfront bars and restaurants offer excellent viewing areas for observing the race and enjoying a Keys sunset, with live music and more fun to follow., Contact: 305-451-4502, Email: [email protected]
More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the offered activities., Contact: 800-354-4455, Email: [email protected]
Each fall, Hawks Cay Resort on Duck Key hosts an annual Heroes Salute program to honor military, fire and rescue, law enforcement and medical personnel; a special Labor Day Weekend event is planned to include an All-American barbecue, heroes tribute, country music concert and fireworks show., Contact: 1-877-484-9342, Email: [email protected]
Thousands of singles, couples and groups of women flock to Key West each year for this renowned celebration for lesbians and their friends. Activities generally include dance parties, poolside gatherings, sailing and snorkeling, live music, comedy performances and more., Contact: 305-294-4603
In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis., Contact: Susan Ellis 305-664-2002, Email: [email protected], Key Largo /9/10/2016, Lionfish Derby for Divers, Teams of up to four divers compete for cash and prizes. Derby divers who successfully remove invasive lionfish from sanctuary waters can win for most, largest and smallest lionfish. The Upper Keys derby is held at John Pennekamp Coral Reef State Park. Visit REEF website to register; teams of up to four people can join. Divers can participate in a derby from their own private vessel or join a professional dive operator’s charter., Contact: REEF 305-852-0030, Email: [email protected]
It’s an All-American event as motorcycle enthusiasts from around the U.S. travel the Keys’ scenic Overseas Highway – designated Florida’s only All-American Road – from mainland Florida to Key West to raise money for charity. Winner takes all, and can win a new Harley-Davidson Motorcycle or cash. Stops are arranged throughout the Keys with a final celebration in Key West. Keys-wide events are planned., Contact: Drew Peterson 305-235-4023, Email: [email protected]
Named after the man known affectionately as “Mr. Everglades,” the event is headquartered at the Islander Resort, A Guy Harvey Outpost. Anglers are challenged to target fish in multiple species only in the boundaries of Everglades National Park, fishing areas that Lucerne favored., Email: [email protected], Islamorada /9/17/2016, Fourth Annual Islamorada Swim for Alligator Lighthouse, In the event’s fourth year, swimmers participate in a 9-mile roundtrip race from Islamorada to the Alligator Lighthouse and back. Proceeds benefit the Friends of the Pool in Islamorada, helping provide scholarship opportunities to those in need, and preserve treasured historic lighthouses on Florida’s coastal waterways., Contact: Rob Dixon 305-664-7149, Email: [email protected]
This 17th annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. A popular Sunday evening dinner and auction showcase is open to the public. Proceeds support local vocational scholarships for all ages, and Take Stock in Children scholarships for financially challenged Upper Keys students., Email: [email protected]
Join an on-the-water wacky weekend charity golf tournament that brings together four-person teams to enjoy a game of nine holes by boat, to “drive” biodegradable golf balls toward floating greens – without any sand traps. A live or silent auction as well as a 50/50 cash raffle also are planned. Proceeds benefit local Keys charities., Email: [email protected]
This challenge recognizes individual and team champions scoring the largest bonefish and permit, and the top anglers in fly and grand slam divisions (for the top spin or fly angler who releases the largest bonefish, permit and tarpon “slam”). The event is one of the few tournaments where anglers can fish without a professional guide., Contact: Barb 305-304-8682, Email: [email protected]
Join Reef Environmental Education Foundation (REEF) in a celebration of marine conservation. Morning activities include ocean adventures of kayaking, snorkeling and diving, all alongside marine life experts. Afternoons feature free seminars from renowned experts in topics like Marine Mammals, Shark Behavior, Deep Sea Exploration and Emerging Ocean Issues. Evenings boast food, drinks and fun with friends old and new. All events are open to the public., Contact: 305-852-0030, Email: [email protected]
Presented by Pat Croce’s Rum Barrel, this event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County., Contact: 305-766-5284, Email: [email protected]
A host of elite Nashville songwriters are to liven up three Key Largo stages during this Columbus Day weekend festival that features music in genres including jazz, blues, rock and roll, country and contemporary pop. In addition, music lovers can enjoy the stories behind yesterday’s favorites and today’s popular hits., Contact: Robert DiGiorgio 305-619-0172, Email: [email protected]
For the first time in 25 years, the second tournament in the Redbone Trilogy moves to Islamorada, and targets permit and bonefish to raise money for cystic fibrosis research. Past participants include legendary angler Stu Apte, former Denver Bronco and Tampa Bay Buccaneer Mark Cooper and Major League Baseball Hall of Famer Wade Boggs., Contact: 305-664-2002, Email: [email protected]
Known locally as the “Fall All-Tackle,” the three-day fishing challenge attracts energized newcomers to face seasoned veterans, in a competitive format since 1970. Up to 25 participants can fish in the tournament; festivities kick off Oct. 9, fishing Oct. 10-12. One angler per boat pairs with a licensed captain to vie for division winners’ trophies. The three largest bonefish and three largest permit are to be scored by length, not weight., Contact: Betsy Bullard 305-587-1460, Email: [email protected]
The fourth annual Humphrey Bogart Film Festival is to screen a rotating selection of Bogie classics and a group of movies celebrating the life and films of the man the American Film Institute named “America’s greatest male screen legend.” The festival, hosted by the screen legend’s son, Stephen Bogart, is the only event of its kind, and is backed by the Bogart Estate.
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars 3/ing groups, island-style bands and lavish floats. The/2016 festival theme is “Political Voodoo and Ballot-Box Barbarians.”, Contact: 305-296-1817, Email: [email protected], Key West /10/23/2016, Key West Halloween Half Marathon and 5K Run, Competitors are encouraged to dress in their favorite costumes for this Halloween-themed running event., Email: [email protected]
Held in Key West’s historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West’s Bahamian heritage.