History and Culture: Key West’s many distinct customs and cultures are a reflection of the island’s rich mix of ethnicities, intertwining social classes, and accompanying diverse ‘life-styles.’ Since the early 1800s, through an ongoing process of nurturing and preserving and blending on a speck of an island situated 150 miles out to sea and just 90 miles from Cuba, Key West culture and customs have peculiarly evolved.
In the 19th Century, most of the residents settling on the island were former British loyalist immigrants moving from the nearby Bahamas, Cubans who were arriving in increasing numbers after 1830, and African Americans who were fleeing southern states looking for freedom from Slavery. Some of these newcomers joined the sponging and turtle industries and most early immigrants joined the island society by following Cuban cigar manufacturing and businesses.
A plethora of Cigar manufacturing plants was founded and operated by determined businessmen from the mainland of Florida who lobbied for the economic development of the tropical island. The strategic geographic position of Key West in the Florida Straits created a natural and important Caribbean seaport that became both a world shipping location and a Navy stronghold. Lucrative trades in Cuban cigar making, fishing, and sponging salvaging, and rum-running were developed. Today fishing is still an important local industry, treasure hunters continue to scour the sea bottom for ancient galleons lost at sea, and you can still find tiny open-air ‘mom and pop’ cigar stores owned and operated by Cuban cigar rollers. Through these trades that originated in the 1800s, the island manifested into one of the richest cities in the U.S. – both financially and culturally, and during this time a large collection of some of the most charming wooden Victorian architecture in the world was built and it still stands today as part of a preserved indigenous landmark in the authentic historic district of Key West.
By the mid 20th Century, Key West was attracting some of the more famous intelligent and creative minds of the time, such as Henry Flagler, Harry S. Truman, Ernest Hemmingway, and Tennessee Williams, setting a precedent for an ongoing influx of remarkable individuals and intriguing characters seeking a more independent and artistic lifestyle. With more bars and more churches per capita than anywhere else in North America, the 1970s and 80’s attracted a whole new wave of creative free-thinkers with the arrival of literary groups, actors, musicians, treasure hunters, artists, designers, photographers, and film makers, entrepreneurs, tradespeople, sailors, philanthropists, self-proclaimed ‘pirates’ and members of the hippie ‘counterculture, openly gay and lesbian people from every walk of life, and expatriates – most of whom flawlessly blended into the tiny existing community of local Conch’s, Cubans, and African Americans. From thenceforward the tropical island of Key West has morphed into an intriguing microcosm and one of the most interesting places to live and unique tourist destinations in the U.S.A.
One Human Family: A continual welcoming and accepting attitude toward all kinds of people to this tiny island has created a unique cultural convergence of different ethnic groups, languages, traditions, religions, foods, and free-thinkers and has resulted in a remarkably distinct cultural character that the community refers to as the “ONE HUMAN FAMILY” philosophy. In the year 2000, Key West artist resident J.T. Thompson coined this phrase to formally capture the essence of this all-accepting and all-inclusive ‘state-of-mind and it was formally adopted by the City of Key West Commission as the ‘official philosophy’ of Key West.
While the unique neighborhoods of Key West reflect and retain their distinctive and delightful flavors by celebrating original Bahamian Conch, Cuban and African-American cultural heritage through unique customs, celebrations, and architecture, the citizens of the island honor and practice a remarkably accepting lifestyle by readily integrating “newcomers” and then striving to live harmoniously and work side-by-side with one another, setting aside social differences, regardless of ethnicity, social class, or sexual orientation. Regardless of the inevitable flare-ups of small-town political foibles, there is a constant undertone in the community that reflects an undying feeling of, “we’re all in this together”.
One ongoing way this special sense of group connectedness is ritualized on this speck of an island is through the generosity of its citizens to reach out to one another and strive to continually support each other and positively improve the community through a constant myriad of institutionalized annual ‘parties-turned-fund raisers’, (e.g. Fantasy Fest, Parrothead Meeting of the Minds), grants, charity work, and endowments that meet multiple needs of the tiny yet diverse island community. And one unique example of the manifestation of community cohesiveness you find on the island is the efficient and heart-felt manner in which its diverse citizens immediately unify the in the aftermath crisis of a hurricane to care for one another at every level – from providing emergency food, shelter, transportation, medical service, and immediate financial assistance. It has been said by some locals that ‘by the time FEMA arrives, most of the human emergency work has already been done by the local people.
While the practices of small island local politics, claims to property boundaries, debates about land development and arguments over the presence of feral chickens in the streets can sometimes seem worthy of a comic or tragic theatre performance, there is nonetheless an underlying and uncommon sense of compassion and commitment that people seem to have for one another, their critters, and ‘their island’ that is pervasive in the island culture. Perhaps this naturally stems from the geographic isolation the island has from the mainland of Florida. Even though Key West is connected with the continental U.S. by a ribbon of narrow bridges that stream down over 100 miles of narrow islands – “there is only one road in and one road out” and once you get to Key West you’ve landed and become part of a tiny diverse and yet harmonious social microcosm that is closer to Havana, Cuba than Miami, Florida!
Come As You Are – Be Who You Are: Key West is full of great history and the intrigue of this small island community has always attracted a diversity of visitors, some famous and legendary. The impressive list of famous contemporary tourists includes the likes of Bill and Hillary Clinton, Oprah Winfrey, Maya Angelou, Shel Silverstein, Jimmy Buffet, Calvin Klein, Laurence Fishburne, Kelly Mcgillis, Nick Carter, Peter Fonda, Mike Peters, Jeff MacNelly, Tom McGuane, Margot Kidder, Warren Oats, Elizabeth Ashley, Goldie Hahn, and Jamie Lee Curtis to name a few. Celebrities have easy access to the island with an airport equipped to land private jets and dockage for private yachts at several marinas.
Of course, most tourists are people who are drawn to the authentic laid-back lifestyle and the carefree attitude of ‘come as you are and be who you are.’ Key West is as exotic as it gets within the United States and today is a wonderful tourist destination, and the best way to really live the island lifestyle is by staying in a vacation rental in a Key West neighborhood. Check this list of amazing privately owned properties from historic cottages to elegant seaport estates.