Events & Festivals

August – September 2018

Jan. 1, 2018 – Aug. 31, 2018 
Key West Fishing Tournament
Doris Harris 305-923-5934
More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.

Sunday, August 05
Historic Tours of America Locals Day
The first Sunday of every month locals receive free admission into the Key West Aquarium, Shipwreck Treasure Museum, Harry S. Truman Little White House. Old Town Trolley and Conch Tour Train. Families and Individuals Only. Must Show proof of Monroe County (FL) Residency. Contact 305-293-7249 for information

Sunday, August 05, 2018
Schooner Wharf Bar 25th Annual Battle of the Bars
A day of beers, bartenders, margaritas and mayhem helps to dramatically improve the lives of local residents and local causes – only in Key West.
The 25th Annual Battle of the Bars at Schooner Wharf Bar will take place Sunday, August 5th at noon and local “bar squadrons” are preparing for battle and hi-jinks.

Aug. 9, 2018 – Aug. 12, 2018
22nd Annual Key West Lobsterfest: A Crustacean Celebration!
Events include a Thursday night lobster boil, Friday night Duval Crawl, Saturday street fair with lobster-inspired culinary creations and a free concert, and a luscious lobster brunch Sunday. The festive feast celebrates the start of the Florida Keys lobster season.

Aug. 15, 2018 – Aug. 19, 2018 
Tropical Heat
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.

Aug. 18, 2018
HAVANA NIGHTS with Rolando Rojas, Fernando Vargas and Catalina Londono
Join the Havana spirit and Latin rhythms at the Key West Theater, get your tickets for this special night of dancing and listening to the sounds of old Havana. Cuba will provide the Mambo & ChaCha rhythms and the clavé beat. Rolando Rojas, Catalina Londono, and Fernando Vargas will provide the vocal energy. Mario Quintero, Luis Vera, Hiram Garzaro, and the one and only Kenny Fradley will provide the hot Latin music. Doors open 7 p.m., show starts 8 p.m.

Aug. 30, 2018 – Sep. 3, 2018
Ninth Annual Key West Brewfest
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.

Sep. 5, 2018 – Sep. 9, 2018 
Womenfest 2018
Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.

Sep. 7, 2018 – Sep. 9, 2018
Robert James Sales S.L.A.M. Celebrity Tournament
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. A number of celebrities show their support by taking part in the tournament each year. Celebrity competitors have included Major League Baseball Hall of Famer Wade Boggs, former Denver Broncos football player Mark Cooper and former NASA space shuttle astronaut Bruce Melnick.

Sep. 9, 2018 
Rams Head presents: Rick Springfield in Concert
The creator of some of the finest power-pop of the ’80s, a Grammy winning singer, songwriter, and musician who has sold 25 million albums and scored 17 U.S. Top 40 hits, including “Jessie’s Girl,” “Don’t Talk to Strangers,” “An Affair of the Heart,” “I’ve Done Everything for You,” “Love Somebody,” and “Human Touch.” Rick’s latest album, “The Snake King” finds Rick traveling down a dusty dirt road to explore the blues side of his rock ’n roll and marks a definite departure from the power pop he has been known for. Doors open 6:30 p.m., show starts 8 p.m., at Sunset Green Event Lawn, between 24 North Hotel and Gates Hotel.

Sep. 14, 2018 – Sep. 16, 2018
46th Annual Phil Peterson’s Florida Keys Poker Run
Motorcyclists from throughout the United States are to travel one of America’s most scenic highways to raise money for charity. Riders traverse the Overseas Highway (U.S. Highway 1), the 113-mile roadway from mainland to the Lower Florida Keys, that features 42 bridges and long vistas of breathtaking open water. Stops are to include Gilbert’s Resort (MM 108), The Big Chill (MM 104), Robbie’s Marina (MM 77), Island Fish Co. (MM54) and Boondock’s Grille & Ale House (MM27).

Sep. 30, 2018
Rams Head presents: Louie Anderson (Two performances!)
Iconic comedian Louie Anderson, the three¬-time Emmy Award® winner, is one of the country’s most recognized and adored comics? named by Comedy Central as “One of 100 Greatest Stand¬-Up Comedians of All Time.” His career has spanned more than 30 years. He is a best-selling author, star of his own standup specials and sitcoms and he continues to tour the country performing to standing-room-only crowds worldwide. Showtimes 6:30 & 9 p.m.