In the Florida Keys, the holidays are celebrated with festivities that range from traditional to eccentric — with a unique island twist. Despite the lack of typical “winter” weather, people throw themselves gleefully into extended merrymaking. Discover some of the Upper and Middle Keys’ creative, colorful and heartwarming events sure to spark seasonal cheer.
Each year, thousands of people head to Key West for the Fantasy Fest celebration, eager to don exotic masks and costumes and escape their real-world cares in a whirl of revelry. Set for Oct. 18-27, the festivities include lavish costume competitions, street fairs, masquerade parties, unparalleled creativity and the dazzling Fantasy Fest Parade.
Thousands of Jimmy Buffett fans gathered on Key West’s Duval Street Sept. 1 for a march honoring the world-renowned singer/songwriter on the one-year anniversary of his passing. Jimmy lived in Key West during some of his most productive years, developing the “trop-rock” style and laid-back persona that helped make him a musical icon.
His long-established nickname is “Bat,” and even many friends don’t know his real name is David. But now Bat Masterson has a new nickname: “Papa.” That’s because Bat recently won the Hemingway Look-Alike Contest, a highlight of Key West's Hemingway Days festival that ended July 21 — the 125th anniversary of “Papa” Hemingway’s birth.
Key West’s Hemingway Days — set this year for July 16-21 — is an internationally recognized celebration saluting Ernest Hemingway, the legendary American author who lived and wrote on the island for almost a decade. But when Michael Whalton conceived the festival more than 40 years ago, he couldn’t possibly foresee what it would become.
The Lower Florida Keys’ sub-sea world will become a concert venue Saturday, July 13, when divers and snorkelers immerse themselves in a musical adventure that promotes reef protection. It’s called the Lower Keys Underwater Music Festival, and it’s unlike any other dive or snorkel experience — OR any other music festival — on the planet.
Fans of sweet, tart Key lime pie can salute the Florida Keys’ signature dessert, and the tiny fruit that inspired it, July 3-7 during the annual Key Lime Festival. Events include a (very messy!) Key lime pie–eating contest, “limey” dining delights, a wacky Key lime pie drop, and culinary and libation tastings.
In most places, beds are reserved for sleeping or amorous activities. But not in the Florida Keys’ colorful Conch Republic — where, on a Saturday afternoon in late April each year, beds on wheels are propelled by teams of strange bedfellows along Key West’s Duval Street in the Conch Republic Blue Ribbon Bed Race.
Want to get 2024 off to a memorable start? Then plan to savor sunshine and stellar talents at three Key West music festivals set for January and early February — featuring current and classic icons of the hard rock, Red Dirt/Americana and country/pop genres performing outdoors in the island’s typically balmy “winter” weather.
Incredible as it may seem, ’tis the season to be jolly — despite Christmas still being weeks away. But in the celebration-loving Florida Keys, mid-November brings the first stirrings of holiday spirit. So there are plenty of festivities coming up, ranging from traditional to offbeat (and all, of course, with a unique island twist).