While this calendar lists selected highlights for 2018, a full and frequently updated schedule of only-in-the-Keys events can be found at fla-keys.com/calendar.
Uncorked: The Key Largo and Islamorada Food and Wine Festival (Jan 4-14; floridakeysuncorked.com) is a culinary, wine and spirits celebration that boasts scores of tantalizing events showcasing the flavors of the two Upper Keys regions. The highlight is a Jan. 13 Grand Tasting at Islamorada’s Keys History & Discovery Center at Islander Resort.
The Florida Keys Celtic Festival (Jan. 6-7; floridakeyscelticfestival.com) at Marathon Community Park features some of America’s most celebrated Celtic musical groups, Irish and Scottish dancing, Highland athletics, Celtic merchandise, food and beverage booths, and children’s activities.
The Key West Literary Seminar (Jan. 11-14; kwls.org), headquartered at Key West’s San Carlos Institute, has explored a different annual literary theme since 1983. This year’s “Writers of the Caribbean” features readings, discussions and lectures with some of that region’s most acclaimed writers.
The 14th annual Big Pine & Lower Keys Nautical Expo (Jan. 13-14; lowerkeyschamber.com) attracts water enthusiasts with nautical gear galore sold at the “pop-up” outfitter of supplies. Proceeds benefit the Lower Keys Chamber of Commerce.
In Key West, the 13th annual Florida Keys Seafood Festival (Jan. 13-14; floridakeysseafoodfestival.com) is held at Bayview Park spotlighting the Keys’ world-renowned fresh seafood and the commercial fishermen who harvest it. The family-friendly feast is presented by the Florida Keys Commercial Fishermen’s Association.
The Key West Half Marathon & 5k (Jan. 14; keywesthalfmarathon.com/) attracts several thousand runners and walkers eager to experience a 13.1-mile flat, scenic course in subtropical Key West. Now in its 20th year, the race has been acclaimed as one of the United States’ leading winter half-marathons.
During the Kelly McGillis Classic International Flag Football Championship (Jan. 22-29; iwffa.com), more than two dozen teams of women and girls from the U.S. and other countries meet in Key West for flag football action. The championship is named for and endorsed by the “Top Gun” actress, a former Key West resident.
Another Key West event, with “flip flops required,” is the Key West Food and Wine Festival (Jan. 24-28; keywestfoodandwinefestival.com). Attendees can enjoy gourmet galas and tastings, cuisine seminars and only–in–Key West experiences that spotlight the region’s lively culinary scene.
Key West’s Master Chefs Classic (Jan. 28; masterchefsclassic.com) blends a culinary competition for local chefs with a tasting of entries in the appetizer, entrée and dessert categories for 450 lucky attendees.
The 24th annual Pigeon Key Art Festival (Feb. 2-3; pigeonkeyartfestival.com) at Marathon Community Park attracts scores of art lovers to view exemplary artwork in the mediums of pottery, painting, glass, sculpture, photography, jewelry and more. Event proceeds benefit the Pigeon Key Foundation.
The Islamorada Half Marathon and 10k (Feb. 3-4; islamoradahalfmarathon.com) includes a Saturday “beer mile” event and a Sunday main race with cash prizes.
In Marathon the Second Annual American Legion Riders Coral Head Music Festival (Feb. 17-18; coralheadmusicfest.com) is a weekend filled with fun and music by national and regional bands. Event proceeds benefit local and regional charities.
Key West’s popular Conch Shell Blowing Contest (March 3; oirf.org) has been an island tradition for over 50 years. Held at the Oldest House Museum, this unique challenge celebrates the historic importance of conch in the Keys and features contestants attempting to make “music” using fluted conch shells.
The family-friendly Original Marathon Seafood Festival (March 10-11; marathonseafoodfestival.com) lures thousands of seafood lovers to the Middle Keys to sample lobster, stone crab, shrimp, fish and more harvested from area waters. Other attractions include nationally recognized musical acts, a boat show and artisan wares.
Headquartered in the Lower Keys, the FAVOR Outdoor Fest (March 10-17; favorfloridakeys.org/outdoor-fest) offers outdoor adventures in the Florida Keys National Wildlife Refuges with guided birding and nature walks, kids’ programs, kayak excursions and more.
In Islamorada, the 27th annual Florida Keys Island Fest (March 24-25; islamoradachamber.com) showcases more than 100 artists and crafters, live music and a popular “Taste of the Islands” foodie competition.
BayJam24 (April 8; facebook.com/keyiceFL/) is a music and art fest at Islamorada’s ICE Amphitheater at Founder’s Park. Attendees can savor the sounds from the hammocklike performance center set against the aqua waters of Florida Bay.
Seven Mile Bridge Run (April 14; 7mbrun.com/) attracts a field of 1,500 runners to Marathon to compete in a course across the centerpiece of the Florida Keys Overseas Highway and one of the world’s longest segmental bridges.
Mote’s Ocean Fest: A Community Celebration (April 14; https://mote.org/oceanfest), held at the Florida Keys Eco-Discovery Center on Key West’s Truman Waterfront, showcases the Keys’ marine environment. Presented by the Florida-based Mote Marine Laboratory, the family-friendly event features marine-themed games, music, food, vendors and more.
Conch Republic Independence Celebration (April 20-29; conchrepublic.com) commemorates the Florida Keys’ symbolic 1982 secession from the United States and rebirth as the independent Conch Republic. Events typically include a parade, parties, a mock sea battle and a bed race billed as “the most fun you can have in bed with your clothes on.”
The Papio Kinetic Sculpture Parade and weekend (May 4-6; papioskineticparade.com) celebrates the legacy of late Key Largo folk artist Stanley Papio, a renegade metal sculptor, with wacky events in Key West. The highlight is a people-powered parade of mobile sculpture and art bikes.
The Key West Songwriters Festival (May 9-13; kwswf.com) features America’s foremost performing songwriters at dozens of concerts staged in intimate, audience-friendly island settings. The event typically includes more than 50 shows and over 200 country and pop music hit-makers.
The Key Largo Original Music Festival (May 17-20; keylargooriginalmusicfest.com) treats music lovers to live performances with pop, rock, blues, jazz and country artists at multiple stages and venues.
The waters off Marathon’s Sombrero Beach are transformed for a day of dragon boat racing at the Battle in the Bay Dragon Boat Festival (June 2; battleinthebaydragonboat.com). Attractions include the pristine setting and unique, direct-from-the-beach launches of the 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 drag shows and parties, a cocktail competition, on-the-water adventures, a street fair, pageants and a lively highlight parade.
The Florida Keys Guitar Festival’s Guitar Summit (June 15-17; floridakeysguitarfestival.com) is to feature three virtuoso Florida Keys guitarists entertaining audiences in genres from classical to contemporary to Latin. Performances are to take place in Islamorada, Marathon and Key West.
The Key West Island Swim: FKCC Swim Around Key West (June 29-30; fkccswimaroundkeywest.com) is a clockwise 12.5-mile swim, open to all ages, around the island of Key West through Atlantic Ocean and Gulf of Mexico waters.
Key West’s Key Lime Festival (June 30-July 4; keylimefestival.com) draws fans of Key lime pie to salute the tiny fruit that inspired the Florida Keys’ signature dessert. Tasty events include a Key lime pie–eating contest, culinary adventures and the Key Lime Pie Hop.
In the Lower Keys, the 34th annual Underwater Music Festival (July 7; lowerkeyschamber.com), a nationally acclaimed submerged songfest, is held at Looe Key Reef in the Florida Keys National Marine Sanctuary. The only-in-the-Keys event promotes reef preservation.
In Key West, the life and work of legendary author Ernest Hemingway, who lived and wrote in Key West during the 1930s, are showcased during the annual Hemingway Days Festival (July 17-22; hemingwaydays.net). Highlights include the three-day Hemingway Look-Alike Contest for stocky, white-bearded aspiring “Ernests.”
The Powerboat P1 Islamorada Grand Prix (Aug. 17-18; p1superstock.us), an exciting spectacle for powerboat fans, features a tight and fast course with boats racing at speeds over 70 mph. The adrenaline action is presented by Mercury Racing.
Labor Day weekend features the annual Key West BrewFest (Aug. 30-Sept. 3; keywestbrewfest.com), highlighted by a tasting festival, with close to 200 beers and micro brews on tap. It benefits the Key West Sunrise Rotary Club of the Conch Republic.
Heroes Salute Weekend (Aug. 31-Sept. 2; floridakeysheroes.com), a Middle Keys tradition, features three days of patriotic fun with moving tributes, All-American fireworks, a 5k run and walk 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) draws 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 performances.
Islamorada’s 8-mile open-water Swim for Alligator Lighthouse (Sept. 15; swimalligatorlight.com) gives distance swimmers a chance to test their endurance. Solo and relay participants chart a course to the landmark lighthouse and back.
Key Largo’s REEF Fest (Sept. 20-22; reef.org) celebrates marine conservation with educational seminars, social gatherings and eco-adventures with prestigious leaders in diving and marine conservation.
In Islamorada, Mote’s Islamorada Ocean Fest (Oct. 13; mote.org) is a family-friendly educational event to celebrate the Keys’ vibrant marine environment.
During the Key Largo–based Humphrey Bogart Film Festival (Oct. 17-21; bogartfilmfestival.com), cinema buffs can celebrate the life and films of the legendary actor at an event typically hosted by his son. Held at Playa Largo Resort & Spa, the 2018 festival also marks the 70th anniversary of the films “Key Largo” and “The Treasure of the Sierra Madre.”
Masquerade madness takes center stage during Key West’s annual Fantasy Fest (Oct. 19-28; fantasyfest.com), an outrageous masking and costuming festival recognized around the world. Colorful events include a costume competition for pets, a headdress ball, street fairs and a dazzling parade with lavish large-scale floats, marching groups and island-style bands.
The adrenaline-fueled Key West Super Boat World Championship (Nov. 4-11; superboat.com) features high-speed offshore powerboats in an annual challenge 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 and provide fans breathtaking displays of skill and power.
The Key West Film Festival (Nov. 14-18; kwfilmfest.com) showcases films that illustrate creativity, diversity, sustainability and beauty — elements that capture the essence of the island city.
In the Lower Keys, the Big Pine & The Lower Keys Island Art Festival (Nov. 24; lowerkeyschamber.com) features locally produced arts and crafts, live music and food. Attendees can show their holiday spirit and choose unique artisanal gifts for friends and family at the annual open-air fair.
The Key West Holiday Fest (throughout December; keywestholidayfest.com) spotlights a wide range of 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. Events begin around Thanksgiving and continue through Dec. 31.
In Islamorada, the Florida Keys Holiday Festival (Dec. 7; islamoradachamber.com) is a magical seasonal gathering — complete with a 30-ton snow mountain, holiday parade, community tree lighting and visit from Santa.
On Stock Island, the I Love Stock Island Festival (Dec. 7-9; ilovestockisland.org) offers music, food, history and art studio tours, watersports and straight-off-the-boat seafood celebrations. The family-friendly festival salutes the seafaring tradition, culinary riches and creative enterprises of the area renowned for its eclectic working waterfront.
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 103-104.
New Year's Eve “Drops” in Key West (Dec. 31; sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest/.) 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, at 0 Duval St., watch as 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