The Florida Keys experience is all about a laid-back attitude, a sense of welcome, and an approach to living that blends individuality and a deep appreciation for relaxation. But it doesn’t have to end when a vacation ends. With a little imagination, the essence of the Keys experience can be savored all year long.
Now that 2025 has arrived with all its fanfare and festivities, far too many people are facing snowy winter weather and the return to a monotonous daily routine. But it doesn’t have to be that way. Instead of enduring the post-holiday blahs, take a break — and relax and recharge in the Florida Keys.
Recently the Florida Keys’ Conch Republic lost a beloved guiding spirit: Captain Finbar Gittelman. Owner and master of the majestic Schooner Wolf, he was the longtime First Sea Lord and Supreme Commander of the Keys’ picturesque Conch Republic Military. Now those who loved him, and the Conch Republic, will carry on his legacy.
Traditionally, people spend Christmas Eve anticipating a visit from Santa Claus. Yet those who love the Florida Keys (but can’t spend the holidays in the island chain) await another jolly bearded fellow: the legendary “Santa Keys.” Of course, as expected from a colorful Keys character, he does things a little bit differently …
Maybe it’s because the Florida Keys have never experienced a traditional white Christmas. Or because Keys residents are passionate about celebrating special occasions. But whatever the reason, despite the subtropical climate, people in the island chain go a little bit overboard with holiday decorations — and even “deck the hulls” for festive boat parades.
There are many beautiful places to celebrate love with your toes in the sand, but nothing compares to a beachfront wedding in subtropical Key West. This idyllic island at the southernmost tip of the Florida Keys offers an enchanting, laid-back vibe that’s irresistible to couples looking for a memorable and magical destination wedding.
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.
One of Florida Keys’ greatest “natural resources” is the friendly, easygoing people who make the region their home — charterboat captains, artists, restaurateurs, animal rescuers, attractions operators, musicians and more. By seeking local residents’ insights and recommendations for unique new adventures, visitors can begin to sample the authentic lifestyle of the colorful, magical islands.
With every lyric he sings and every chord he strums, Howard Livingston communicates his passion for the Florida Keys and the island chain’s lifestyle — a deep-rooted passion that, many years ago, inspired the dissatisfied Chicago manufacturing company owner to become a carefree, fulfilled musician who lives on the water in the Lower Keys.