FLORIDA KEYS — Fall in the Florida Keys & Key West brings comfortably warm weather, sunny skies and an array of entertaining events. From Fantasy Fest to high-speed powerboat races to a slew of art and cultural festivals, the Florida Keys & Key West have an event to interest virtually everyone.
While this piece lists selected fall 2014 highlights, a comprehensive schedule of events can be found at fla-keys.com/calendarofevents.
Oct. 10-12: Key Largo Songfest. Key Largo. Each night from 7-10 p.m. a host of elite Nashville songwriters simultaneously perform at three waterfront venues across Key Largo. The music festival features a wide range of genres including jazz, blues, rock and roll, country and contemporary pop. For details, visit www.keylargosongfest.com.
Oct. 17-18: Goombay Festival. Key West. 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. Visit for more information.
Oct. 17-26: 35th Annual Fantasy Fest. Key West. This outrageous 10-day costuming and masking celebration features flamboyant costume competitions including one for pets, promenades, street fairs and a grand parade that stars lavish floats, marching groups and island bands. Visit www.fantasyfest.com for more information.
Oct. 18: Fourth Annual Stone Crab Eating Contest. Marathon. The much-anticipated opening of Florida’s stone crab season takes place Oct. 15 each year, followed by a tasty test of crab-consuming capacity at Keys Fisheries. Entrants must crack, clean and consume 25 stone crab claws faster than their competitors. Visit www.keysfisheries.com or call 305-743-4353.
Oct. 19: Underwater Pumpkin Carving. Key Largo. Amy Slate’s Amoray Dive Resort supplies certified divers with a hollowed-out pumpkin that they carve into Halloween masterpieces beneath the sea in the Florida Keys National Marine Sanctuary. Visit www.amoray.com or call 305-451-3595.
Nov. 2-9: Key West World Championship Powerboat Races. Key West. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge. On a portion of the course, racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power. Visit www.superboat.com.
Nov. 7-10: Key West International Latin Arts Festival. Key West. Experience “Vientos del Alma,” a celebration of traditional Latin American cultural arts featuring dance and percussion workshops, artists’ exhibits, poetry readings, culinary surprises and a spectacular theatrical concert. Visit .
Nov. 8: Key Largo Bridge Run. Key Largo. The out-and-back foot race crosses the 65-foot-high, 1.25-mile-long Jewfish Creek Bridge and the southern portion of the 18-Mile Stretch, a segment of U.S. Highway 1. The event includes a 10k, a half marathon and a 5k run/walk, which are held in conjunction with a health and fitness expo. Visit .
Nov. 12-16: Key West Film Festival. Key West. Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the Tropic Cinema and San Carlos Institute. The program includes films from multiple genres and categories as well as social events with filmmakers, actors and film lovers. Visit for more information.
Nov. 26-30: International Sand Art Competition. Key West. During Thanksgiving weekend, Casa Marina Resort will host Sand Isle’s first International Sand Art Competition in Key West. Spectators can watch and marvel as six world-renowned sand sculptors compete against each other, creating massive, intricate sculptures using their own unique designs and skill sets. For more information, email firstname.lastname@example.org.
Nov. 28-30: ART! KEY WEST! Key West. A vibrant three-day festival throughout Old Town, its spotlight events showcase the island’s multiple cultural districts. Highlights include visual, performing, literary, film and musical events, performances and exhibitions. Galleries are to have extended hours and exhibitions, and art and culinary pairings are to be offered at local restaurants. Visit 305-619-9459. or call
Nov. 29: Big Pine & The Lower Keys Island Art Festival. Big Pine & the Lower Keys.Highlights of this holiday event include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside. Visit www.lowerkeyschamber.com or call305-872-2411 for more information.
Dec. 5: Florida Keys Holiday Festival. Islamorada. This extravaganza begins with a tree-lighting ceremony at Founders Park, MM 87. Subsequent attractions include food, kids activity booths and live “on stage” performances. A mountain of snow is the favorite among mitten-clad munchkins. The big event features the Holiday Fest Parade with Santa, which includes the Coral Shores Hurricanes Marching Band. Visit www.islamoradachamber.com or call 305-664-4503 for more information.
Dec. 5-7: Fort Taylor Pyrate Invasion. Key West. Experience three days of piracy as Fort Zachary Taylor Historic State Park transforms into a British stronghold defending its shores against an invasion of pirates. Step back in time to encounter piracy from 1675 through 1825 with buccaneer encampments, living history demonstrations, live battles, strolling musicians, artisan crafts and activities for kids. For more information visit www.forttaylorpyrates.com or call305-797-1659.
Dec. 6: Key West Holiday Parade. Key West. The island city shows its holiday spirit with this annual hometown parade. Featuring marching groups and floats, the festive procession traditionally draws entries from churches, civic organizations, businesses and neighborhood and school groups. Visit www.keywestcity.com or call 305-809-3881.
Dec. 13 & 14: Lighted Boat Parades. Key Largo, Middle Keys, Lower Keys and Key West. Decorated and lighted boats are to cruise through Keys waters Dec. 13 at Key Largo’s Blackwater Sound and in Key West Harbor, the Lower Keys’ Pine Channel Causeway and Marathon’s Boot Key Harbor; and Dec. 14 at Key Colony Beach. For the Key Largo Holiday Boat Parade, visitwww.keylargoboatparade.com or call 305-394-3736; for the Key West Lighted Boat Parade, visitwww.schoonerwharf.com or call 305-292-3302; for the Key Colony Beach lighted Boat Parade, visit or call 305-743-7214; for the Boot Key Harbor Lighted Boat Parade, visit or call 305-849-0285; and for the Lower Keys Lighted Holiday Boat Parade, call 305-923-5370.
Dec. 31: New Year’s Eve Fireworks on Blackwater Sound. Key Largo. The backcountry bay is the setting for the annual New Year’s Eve fireworks extravaganza hosted by Sundowners, Jimmy Johnson’s Big Chill, Señor Frijoles, Cactus Jack’s, Gus’ Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, mile markers 103-104. Visit www.keylargofireworks.com.
Dec. 31: Key West New Year’s Eve Celebrations. Key West. The Southernmost City typically celebrates 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.; the lowering of a pirate wench from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St.; and the “splashdown” of a Key lime wedge into a giant margarita glass at Ocean Key Resort and Spa, 0 Duval St. Visit www.sloppyjoes.com,www.bourbonstpub.com, www.schoonerwharf.com and www.oceankey.com.