Thursday – Sunday
Florida Keys History & Discovery Center
Islamorada: This engaging new attraction encapsulates what living in the “Old Keys” was really like through a series of fascinating exhibits that include the infamous Labor Day Hurricane of 1935, Henry Flagler’s Railroad, the Overseas Highway, legendary anglers and fishing guides and lots more. Open Thursday through Sunday from 10am – 5pm  Located on the property of the Islander Resort, MM 82, Oceanside. Info: 305-922-2237;

Third Thursday
Art Walk
Islamorada: Fine arts, live music and “culinary art” are the hallmark of this festive monthly event which showcases both national and local artisans in galleries along the Morada Way Arts & Cultural District. Takes place from 6 – 9pm on Old Hwy., MM 81.5, Oceanside, Islamorada. Info: 305-393-6012.

August 6
10th Annual Midsummer Night’s Dream & Spectacle
Key West: A wonderland of costumed revelers, interactive art projects, feasting, dancing, and multiple performance stages celebrate the magic of summer and the power of dreams. From 6 – 10pm at Fort East Martello, 3501 S. Roosevelt Blvd, in Key West. Info: 305-394-3804.

August 7
23rd Annual Battle of the Bars
Key West: Unlikely warrriors armed with margarita salt and keg taps, compete to conquer their foes with speed, skill and accuracy in this raucous annual contest that pits local bartenders and servers against one another as they drink, cajole and bribe their way to capture the coveted winning trophy. Takes place from 12:30 – 6:30pm at Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3773;

August 11 – 14
20th Annual Key West Lobsterfest
Key West: It’s a weekend of “Lobstermania” when approximately 10,000 pounds of succulent, locally caught lobster is grilled, sauteed, stuffed and deliciously prepared during to celebrate the bounty of the Keys lobster season. Info: 305-294-2000;

August 11 – 14
Tropical Heat
Key West: This All-Male-All-Adult fever-pitched festival includes more than a dozen intriguingly decadent events ranging from drag shows to themed pool parties and gatherings at island clubs. Not for the faint-hearted! Info: 305-294-4603;

August 20
Anything That Floats Race & Regatta
Key Largo: In this crazy upper Keys Regatta, contestants create “rafts” out of common household materials and compete in a variety of wacky categories. Races begin at 3pm with live music and plenty of on-shore partying. Fireworks at 10pm Takes place at Sundowners Restaurant, MM 104, Bayside, Key Largo. Info: 305-451-4502.

September 1- 5
Seventh Annual Key West Brewfest
Key West: This “tasty” annual event includes  beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the  Signature Tasting Festival Event. Info: 800-354-4455;

September 7 – 11
Key West: This blockbuster four day festival  celebrates freedom and diversity and is a magnet for thousands of women from around the world who come to Key West for non-stop fun including  dance parties, poolside gatherings, sailing and snorkeling, live music, comedy performances and more. Info: 305-294-4603;

September 15 – 18
44th Annual Phil Peterson’s Key West Poker Run
Florida Keys & Key West: Motorcycle enthusiasts from around the U.S. cruise down the Keys’ scenic Overseas Highway from mainland Florida to the Southernmost City to raise money for charity. Stops are arranged throughout the Keys with a final celebration in Key West. Info: 305-235-4023.

September 16 – October 16
WineDine Key West
Key West: Key West’s newest food and wine soiree celebrates affordable fine dining and includes specially priced 3-course prix-fixe menus at some of the Keys’ top restaurants. You can also take advantage of exclusive deals from award-winning spas, luxurious guesthouses, local art galleries and unique boutiques. Info: 800-474-4319;

October 1
Womankind’s Breast Show In Town
Key West: This year Womankind’s signature, high-energy fundraiser features live models in decorated bras and a variety of original artwork depicting breasts in all kinds of different ways. All  proceeds benefit Womankind’s breast cancer screenings and exams. Takes place from 7 – 9pm at The Studios Of Key West, 533 Eaton St., Key West. Info and tickets: 305-294-4004;

October  12 -16
Fourth Annual Humphrey Bogart    Film Festival
Key Largo: A rotating roster of Bogie classics celebrates the life and films of the man who the American Film Institute named “America’s Greatest Male Screen Legend.” Info: 305-451-1414;

October  24 – 31
Wyland Galleries Fantasy Fest      Show Week
Key West: Meet Wyland, the world’s premiere marine life artist and dedicated conservationist, along with many other renowned artists, during this special week-long gallery show that exhibits brilliant original oils and watercolors, magnificent marine life bronzes, fine ocean and environmental art, contemporary works, stunning glass sculptures and more. Takes place at Wyland Galleries, 623 Duval Street. Info: 305-292-4998;

October 21 – 22
Goombay Festival
Key West: Historic Bahama Village transforms itself into party central with non-stop, live entertainment, island-style food, arts and crafts and a “Junkanoo Rush”of costumed marchers through Key West’s downtown at 6pm on Friday and Saturday. Takes place from noon until midnight on Petronia Street. Info: 305-619-8989.

October 21 – 30
37th Annual Fantasy Fest® Celebration: “Political Voodoo & Ballot Box Barbarians”
Key West: This wildly outrageous, world-renowned event celebrates 37 years of fun and debauchery starting with the crowning ceremony of the King and Queen of Fantasy Fest and followed by nine more days of elaborate costume competitions, titillating parties, parades, street festivals and more. Info: 305-296-1817;

October 27
34rd Annual Headdress Ball
Key West: Get out your feathers, glue guns and ribbons for the Key West Business Guild’s annual fundraising extravaganza. This fantastical headdress competition includes “over-the-top” entertainment with a special appearance by world-renowned female illustionist, Christopher Peterson. “Pop-Up” Pre-Party starts at 6:30pm. Showtime: 8 pm. Held rain or shine. Takes place at Truman Waterfront (end of Southard Street). Info: 305-294-4603; Tickets:

November 11
MarrVelous Pet Rescue Spay-ghetti  & No Balls Holiday Gala
Key Largo: This fun annual dinner and auction benefits MarrVelous Pet Rescues which is dedicated to uniting  pets with loving homes and families. Takes place at 6pm at Snook’s Bayside Restaurant & Grand Tiki, MM 99.9 Bayside, Key Largo. Tickets on sale now. Info: 305-453-1315;