Waypoint: Key West

Photos by Dori Arrington

Southern Exposure

Sunset celebrations, vast waterways, a rich history and colorful charm are but a few reasons why we love Key West.

Eclectic, tropical, relaxed, quirky, spicy, balmy … I could exhaust a list of adjectives before capturing the essence of Key West. In a single word, the city is unique. From six-toed cats to certified castaways, Key West has always been a haven for those who don’t—or don’t want to—fit in elsewhere. This collection of independent souls has painted Key West with a very colorful palette.

Located on a relatively small island at the end of a chain of even smaller islands, Key West was an unlikely settlement. Originally inhabited with no means to get there by land, it took a hardy group to cling to existence on this remote outpost. Henry Flagler changed that with the completion of his Overseas Railroad in 1921. Word of the mild ocean breezes and epic sunsets spread quickly, drawing anyone who wanted to escape life as they knew it.

While islands are defined as land, they frequently take their identity from the water around them. This is certainly the case with Key West. The surrounding waters, with the Gulf of Mexico on one side and the Atlantic on the other, have always played an important role. From the salvage trade which supported the early inhabitants to the water sports that attract today’s visitors, Key West is an oasis smack dab in a watery world. Fishing, diving, snorkeling, paddling—you can find it in droves along the Florida Keys Reef, North America’s only tropical reef, bustling with a diverse marine ecosystem.

The Conch Republic

See more of Dori Arrington’s beautiful photography of Key West in the gallery below.

As much as Key West is a water-lover’s playground, the sub-tropical terra firma is just as appealing. From music to art to exceptional cuisine, Key West offers an abundance of land-based adventures. Visitors can stroll the grounds of President Truman’s southern White House, enjoy an amazing indoor butterfly habitat or learn about
Ernest Hemingway by touring his home and museum.

One cannot visit Key West without coming across a few flocks of “gypsy chickens.” The feral fowl are in many ways the perfect metaphor for Key West—colorful, raucous and a little hard to control. Key West residents take pride in many things, but their independent way of life and freedom of expression seem to take top billing. Known as the Conch Republic for its attempt to secede from the United States over aggressive drug interdiction in the early 1980s, Key West natives proudly refer to themselves as “Conchs.”

Key West marches to its own beat, with much of it in the form of live music spilling from cafés and clubs throughout the city each night. One of the more interesting forms of music, if one could call it that, emanates from the local and beloved conch shell. The resonate sound of the conch shell trumpet has been used around the world for thousands of years to celebrate events, call to arms and entertain. The Old Island Restoration Foundation of Key West encourages visitors to purse their lips and join the band in their annual fundraiser—a cacophonous party that takes place every year on the first Saturday of March.

Even if you don’t arrive in Key West by boat, don’t miss the opportunity to do some boating once you’re there. Small boats are available for guided charter or independent rental. Dozens of uninhabited mangrove-strewn islands surround Key West, with postcard beaches just waiting for you to plant an umbrella and beach chairs. The clear waters will happily invite you in.

While a visitor may enjoy the island’s sunshine, downtown Key West really comes to life in the evening, and the transition is breathtaking. At the end of each day, locals and tourists join a diverse band of revelers at Mallory Square to celebrate the sun setting over Key West’s cyan waters. The sunset celebration began as a collection of free-spirited individuals in the 1960s and remains a long-standing tradition. Artists, street performers and photographers are always on hand, entertaining the people and capturing the resulting spectacle.

With nearly 400 restaurants in just 4 square miles, a visit to Key West can easily become one long meal, often ending with a creative variation of key lime pie. Key West’s early sponge divers invented the island’s favorite dessert that’s now served throughout the South. Legend has it that without refrigeration, the divers could keep very little fresh food on board their boats. But with access to such basics as local key limes, canned milk and eggs, they concocted the original recipe for key lime pie, which did not require cooking. Whatever the origin, chefs in Key West have perfected the simple recipe into one that, like the island itself, will leave you wanting more.