With a full schedule of Florida Keys events, travelers will be able to join in plenty of fun activities no matter what time of year they visit. Key West events are scheduled for every night of the year because one of the biggest celebrations occurs as the sun is setting. Every evening, Mallory Square is filled with activity for the Sunset Celebration as the arts fest at the water's edge is crowded with artists, street performers, locals, and visitors, all as the sun dips below the horizon into the Gulf of Mexico.

Every October, revelers flock to Key West for Fantasy Fest. During the ten days of festivities, travelers can enjoy the nightlife with costume balls, a street fair, a pet masquerade, and a Caribbean-flavored Goombay celebration, filled with music. The Saturday night parade and amazing floats close out this colorful Key West festival.

Pirates, once feared in the area, are now something to celebrate with two Florida Keys events: the Pirates in Paradise Festival in Key West and the Key Largo Pirate Fest. The festival in Key Largo comes first, occurring in October, followed by the Key West special event in late November. Both of the celebrations feature costumed pirates, music, rum tasting, and other fun events.

Florida Keys Map

Some Key West events have a historical flair. The Little White House throws a birthday celebration every year in honor of President Harry Truman, who traveled to the Keys for working vacations while he was in office. An accompanying symposium looks at Truman in the context of the era in which he lived and Key West's twentieth-century history. Old Island Days, a celebration of history and culture, begins in November and runs through May. Over that time period, these Key West events include concerts, craft shows, theater performers, special tours, and even a conch-blowing contest.

One of the biggest Florida Keys events is the Key West Songwriters Festival, which features five days and five nights at the beginning of May packed with concerts, special events, and live performances. The free concerts are held at many of the island's favorite watering holes. Music also is a feature of one of the events in Key Largo—the Singer & Songwriters Festival. Held over the various weekends in May, the special event brings days filled with live music, food, and drink to the tropical paradise.

Other events in Key Largo offer a variety of experiences. At the end of stone crab season in May, Keys Fisheries launches the Outdoor Crustacean Vacation. This celebration includes live music, lots of ice cream, cocktails, and raffle prizes. Many of the other special events draw anglers from around the world, who compete for prizes and the largest catch, especially of tarpon and bonefish.

Chefs, gourmands, and culinary experts look forward to their favorite of all of the events in Key Largo when August arrives. The nine-day Key Largo Food & Wine Festival pairs tastings with special events, progressive dinners, cooking shows, and a chance to enjoy the local attractions and shopping.

For travelers who are stopping elsewhere on the island chain, festivals in Florida Keys aren't limited to Key Largo and Key West. Islamorada hosts the annual Florida Keys Island Fest in April, and Big Pine Key in the Lower Keys stages an art festival during the holidays.