FLORIDA KEYS — Colorful history, artistic culture, quirky ambiance and celebrations of the Florida Keys island chain’s underwater paradise, outdoor adventures and tasty cuisine provide visitors with year-round entertainment, festivals and special events.
While this calendar lists top events and festivities for summer 2018 through the year’s end, a more detailed schedule of only-in-the-Keys events can be found at fla-keys.com/calendar.
Battle in the Bay Dragon Boat Festival (June 2; battleinthebaydragonboat.com) transforms the waters off Marathon’s Sombrero Beach into a course for dragon boat racing. Attractions include the pristine setting and direct-from-the-beach launches of sleek 40-foot-long race boats.
Key West Pride (June 6-10; keywestpride.org) includes five days of fun for Key West’s LGBT visitors and allies. Events typically include pool parties, late-night soirees, the finale of a North American cocktail competition, a street fair, a lively parade and pageants to select Mr., Miss and Ms. Key West Pride.
Stock Island Film Festival (June 7-9; stockislandfilmfestival.com) on Stock Island at The Perry Hotel and Coast, a space for makers, features Billy Corben, director of “Cocaine Cowboys” and “The U,” and local filmmaker Quincy Perkins. Short award-winning films about smuggling, fishing, drugs, falling in love and other topics are scheduled.
Coralpalooza: Plant a Coral, Restore a Reef (June 8-9; coralrestoration.org/
The Florida Keys Guitar Festival’s Guitar Summit (June 15-17; floridakeysguitarfestival.com) features virtuoso Florida Keys guitarists Mateo Jampol, David Feder and Rolando Rojas entertaining audiences in classical, contemporary and Latin genres. Performances are scheduled in Islamorada, Marathon and Key West.
The FKCC Swim Around Key West (June 30; swimaroundkeywest.org) is an epic 12.5-mile open-water swim around the island of Key West for solo participants and relay teams. It’s the only sanctioned, insured and U.S. Coast Guard permitted race around Key West. Swimmers also can participate in shorter challenges, and a USA Swimming–sanctioned swim meet is planned July 1.
Key West’s Key Lime Festival (June 30–July 4; keylimefestival.com) draws fans of Key lime pie to salute the tiny tart fruit that inspired the Florida Keys’ signature dessert. Tasty events include a Key lime pie–eating contest, lime lovers’ cocktail stroll, Key Lime Pie Drop and Key Lime Pie Hop.
The Underwater Music Festival (July 7; lowerkeyschamber.com/festival.
Key West’s Hemingway Days (July 17-22; hemingwaydays.net) celebrates legendary author Ernest Hemingway, who lived and wrote on the island during the 1930s. Highlights include the Hemingway Look-Alike Contest for stocky bearded men, prose and poetry readings, the wacky “Running of the Bulls,” presentations on the writer’s influence and a three-day marlin tournament recalling his passion for deep-sea angling.
Tropical Heat (Aug. 15-19; tropicalheatkw.com) is an all-male celebration presented by the Key West Business Guild that typically includes pool and dance parties and themed gatherings.
The annual Key West BrewFest (Aug. 30-Sept. 3; keywestbrewfest.com) marks Labor Day weekend, highlighted by a Sept. 1 signature tasting festival with close to 200 beers and microbrews on tap. Proceeds benefit the Key West Sunrise Rotary Club of the Conch Republic.
Heroes Salute Weekend (Aug. 31-Sept. 2; floridakeysheroes.com) features three days of patriotic Middle Keys fun with moving tributes, all-American fireworks, a 5k run and walk, and a barbecue at Hawks Cay Resort on Duck Key. The annual event honors military, fire and rescue, law enforcement and medical personnel.
Womenfest (Sept. 5-9; womenfest.com) lures singles, couples and groups of women to Key West for one of North America’s largest gathering of lesbians and their friends. Attractions typically include festivities, flag football, pool parties and musical and comedy performances.
REEF Lionfish Derby for Divers (Sept. 14-16; reef.org) at Key Largo’s John Pennekamp Coral Reef State Park is a weekend of derby events to collect lionfish, an invasive species becoming popular as a food fish for its light, mild flavor. Educational seminars teach safe collecting and handling techniques.
During the Swim for Alligator Lighthouse (Sept. 15; swimalligatorlight.com), distance swimmers can test their endurance in an 8-mile roundtrip race from the shores of Islamorada to the Alligator Lighthouse and back. Solo and relay swimmers can participate. Proceeds help provide scholarship opportunities and preserve treasured historic lighthouses on Florida’s coastal waterways.
Key Largo’s REEF Fest (Sept. 20-23; reef.org) celebrates marine conservation with educational seminars, social gatherings, diving and eco-adventures with prestigious leaders in diving and marine conservation.
The Southernmost Marathon, Half Marathon & 5K (Oct. 6; multirace.com) includes 26.2-, 13.1- and 3.1-mile challenges featuring Atlantic Ocean and Gulf of Mexico views and iconic Key West landmarks. Athletes can test their speed and stamina on flat, fast courses that start and end at Lagerheads, 0 Simonton St.
Bahama Village Goombay Festival (Oct. 19-20; fantasyfest.com), a lively family-friendly event in Key West’s historic Bahama Village neighborhood, celebrates island-style food, arts and crafts, live entertainment and dancing in the streets. It’s held noon to midnight both days on the first weekend of Fantasy Fest.
Ladies Let’s Go Fishing! Keys Saltwater Weekend Seminar (Oct. 19-21; ladiesletsgofishing.com) enables female anglers to learn or polish their skills during a fun, lively weekend seminar. Held in the Upper Keys, the popular weekend event spotlights techniques for offshore, bottom, inshore and fly-fishing.
Key West’s annual Fantasy Fest (Oct. 19-28; fantasyfest.com) gives masquerade madness the center stage. This year themed “Oh…The Games We Play!,” the outrageous 10-day costuming and masking festival is recognized around the world. Highlights include a costume competition for pets, headdress ball, street fairs, madcap march and lavish parade with dazzling motorized floats, elaborately garbed walking groups and dancers in bright feathered costumes.
The Key West Super Boat World Championship (Nov. 4-11; superboat.com) features high-speed offshore powerboats in an adrenaline-fueled event known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph.
The Key West Film Festival (Nov. 14-18; kwfilmfest.com), themed “Passion Meets Paradise,” showcases films highlighting creativity, diversity, sustainability and beauty. The program typically includes films from multiple genres and categories as well as social events with filmmakers, actors and special guests.
The International Sand Art Competition (Nov. 21-25; justsandandwater.com/isac) is held in Key West at the Casa Marina, A Waldorf Astoria Resort, overlooking the Atlantic Ocean. World-renowned sand sculptors compete to create the best large-scale masterpiece, using only sand and water, as Thanksgiving visitors watch the creations take shape.
The annual Big Pine & The Lower Keys Island Art Festival (Nov. 24;lowerkeyschamber.com/art_fair.
The Key West Holiday Fest (Dec. 1-31; keywestholidayfest.com) spotlights seasonal celebrations including the illumination of the Harbor Walk of Lights, a hometown holiday parade, tours of decorated historic inns, a lighted boat parade and lively New Year’s Eve celebrations.
The Florida Keys Holiday Festival (Dec. 7; islamoradachamber.com) is a magical seasonal gathering in Islamorada — complete with a 30-ton snow mountain, holiday parade, community tree lighting and visit from Santa.
The I Love Stock Island Festival (Dec. 7-9; ilovestockisland.org) has music, food, history and art studio tours, watersports and straight-off-the-boat seafood. The family-friendly festival salutes Stock Island’s seafaring traditions and culinary riches in an eclectic working waterfront. The signature Taste of Stock Island is Dec. 7.
Nutcracker Key West (Dec. 8-16; nutcrackerkeywest.com) at Tennessee Williams Theatre is a uniquely crafted semiannual holiday production flavored with characters and sets depicting Key West’s colorful history, vibrant coral reef environment and even free-roaming local roosters. Renowned professional dancers perform alongside local children and adults in a stunning subtropical version of the classic ballet.
New Year’s Eve Fireworks on Blackwater Sound (Dec. 31; keylargofireworks.com) features a back bay setting for a fireworks extravaganza hosted by top Key Largo restaurants and resorts at mile markers 103 and 104.
New Year's Eve “Drops” in Key West (Dec. 31; sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, oceankey.com) ring in 2019 with a “conch shell drop” at Sloppy Joe's Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.; and the lowering of a pirate wench from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St. At the Ocean Key Resort & Spa, a huge replica of a Key lime wedge splashes down into a larger-than-life margarita glass.
Florida Keys calendar of events: fla-keys.com/calendar
Florida Keys visitor information: fla-keys.com or 1-800-FLA-KEYS