Sunny subtropical holidays in the Florida Keys & Key West are filled with warmth and good cheer throughout the 125-mile-long island chain. From Key Largo to Key West, the 2022 holiday season features spirited events such as lighted boat parades, historic inn tours, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.
From Key Largo to Key West, the calendar is packed with events designed to spread seasonal cheer — including a traditional Islamorada favorite that features actual snow. Yes, despite the Keys’ typically balmy winter temperatures, grownups and kids of all ages can delight in snow Friday, Dec. 2, during Islamorada’s Florida Keys Holiday Fest.
Nearly 60 years ago, Captain Gainey Maxwell conceived a way to encourage people to visit and fish Florida Keys waters — and then come back to do it again. He called it the Key West Fishing Tournament. Today, an impressive 46 backcountry and offshore species are targeted during the free-entry tournament’s eight-month span.
The continental United States’ only contiguous living coral barrier reef, which parallels the Florida Keys, hosts huge populations of tropical fish and other sea creatures. The warm, clear water makes a long dive in the Keys comfortable and enjoyable. And around Halloween each year, divers can immerse themselves while actually carving pumpkins underwater!
Revelers can express their creativity by donning dazzling costumes during Key West’s Fantasy Fest, set for Oct. 21-30 and themed “Cult Classics & Cartoon Chaos.” The fabulous festival features masquerade parties, costume contests, music and theater shows, themed events — and a lavish grand parade of massive motorized floats and elaborately garbed marching groups.
On May 18, 1991, Queen Elizabeth II paid a visit to the Florida Keys on the Royal Yacht Britannia. Thirty-one years later, as the world mourns the gracious British monarch’s death, it seems only fitting to recall that day — and Her Majesty’s encounter with the unofficial queen of the island chain, Wilhelmina Harvey.
Shipwreck fans, treasure seekers, history buffs and those who enjoy real-life adventure tales should be in Key West Sept. 2-6. Why? To commemorate the 400th anniversary of the sinking of the Spanish treasure galleon Nuestra Señora de Atocha — with members of Mel Fisher’s family and “golden crew” who discovered the wreck in 1985.
For several thousand women, Key West is the place to be in early September. It’s the place to enjoy adventures in Atlantic Ocean and Gulf of Mexico waters, entertainment and parties with like-minded people, and relaxation on an accepting subtropical island — all during the island city’s annual Womenfest celebration set for Sept. 7-11.
There’s a new “Papa” Hemingway on the island where legendary author Ernest Hemingway lived for most of the 1930s. White-bearded Floridian Jon Auvil won the 2022 Hemingway Look-Alike Contest, the highlight of Key West's annual Hemingway Days. And Nick Henke of St. Louis earned top honors in the Lorian Hemingway Short Story Competition.
Fans of adventurous living and fine writing can celebrate the legacy of Ernest Hemingway July 19-24 in Key West, his home during the 1930s. Hemingway Days highlights include a world-renowned look-alike contest, the culmination of the Lorian Hemingway Short Story Competition and a marlin tournament that salutes Ernest’s passion for Florida Keys fishing.