Key West - Where History Wears a Smile

In the almost two hundred years following its founding, the city of Key West has established itself as a quirky little slice of paradise at the end of the road. Sure, St. Augustine may be the oldest city in Florida, but if you are looking to visit a town chock-full of colorful tales, intriguing characters, and fascinating places, then the Conch Republic is your ultimate destination. 

From as early as the 1700s, pirates such as the infamous Blackbeard patrolled the shallow reefs and waters around Cayo Hueso - the original Spanish name of this four-square-mile rock at the southern end of the Florida Keys chain. As English became the main language in the early 19th century, the term Cayo Hueso eventually evolved into the city’s current name, and Key West officially became one of the state’s oldest cities when it was incorporated in 1828. 

In the years that followed, the Cuban cigar and shipwreck salvaging industries made the city one of the wealthiest in the country. Later, the completion of the Flagler Overseas Railroad in 1912 linked the area to mainland Florida, further encouraging economic growth and bringing with it the eclectic mix of tourists, businessmen, and artists that populate the city to this today.  

HISTORY TO EXPERIENCE

When you visit the area and explore its past, you can stay in one of the city’s most historic buildings – La Concha Key West. Situated in the heart of the city’s Old Town right on legendary Duval Street, this spectacular hotel embraces the feel of the area’s elegant and stylish past while being located mere steps from the iconic taverns that the city is known for.

Originally built in 1926 and checking in as the tallest building in the Florida Keys at the time, the La Concha was the brainchild of developer Carl Aubuchon. Its reputation of luxury and convenience attracted celebrated guests like novelist Ernest Hemingway, playwright Tennessee Williams, and even President Harry Truman. Its opulent décor and sweeping vistas from the top-floor balcony soon became legendary, as did its marble private baths. Adventurers came year-round to experience the La Concha’s world-class luxury in the heart of a tropical island paradise. 

Almost one hundred years later, this classic property gracefully transitioned into the La Concha Key West, a part of the Marriott Autograph Collection of hotels. With this evolution came even more upgrades, all with a nod to the area’s tropical Cuban roots. Today, the property consists of 160 guest rooms, along with an additional 14 suites, many of which occupy top-floor premium locations, each with its own spectacular island views. The most notable of these is the Hemingway Suite – a reference to Ernest Hemingway’s time spent at the La Concha while finishing his famous novel, To Have and Have Not. 

The entire property makes use of a bright and soothing color palette that harkens back to the old days, spilling over from the guest rooms into the restaurants and communal areas. As a tribute to the literary characters who frequented the hotel, the La Concha lobby includes a library of novels for guests to peruse, and each room has an array of books on private shelves.

For those with a taste for the macabre, be sure to ask La Concha staff about the many ghosts that are said to frequent the property. Hemingway’s mischievous spirit is often reported to be seen, and many swear that they still hear his typewriter keys clacking away at his novels. Eerie whispers, disembodied voices, and cries late at night are said to be heard by guests, and local ghost tours refer to the hotel as one of the most haunted entities in the city. 

The onsite experiences are many, all with the flavor of historic Key West.   Epicurean Market, located just off the lobby, is more than simply a small store of conveniences – it offers up specialty hats, sandals, custom jewelry, and cigars created by some of the city’s most talented artisans. The rooftop pool deck includes games, umbrellas, cabanas, and shady palms. Guests on the deck are called to happy hour at 4:00 p.m. each day by the blowing of a conch shell, or la concha – a tradition that they can participate in themselves before ordering their cocktail. 

The bars and restaurants at La Concha lean into the tropical feel as well. Breakfast choices abound at Perla, the laid-back but elegant café that serves up freshly prepared dishes with Cuban-inspired flavors, combining them with a rich coffee experience to start your day. The Tropicado, a classic tapas bar that opens up onto Duval Street, features mojitos crafted by Certified Mojito Masters and made with the island’s own Papa’s Pilar rum. Specialty drinks line the menu, and Spanish-inspired tapas, tacos, and empanadas harken back to traditional flavors. There is also El Dom Café and coffee shop, which offers guests quick bites and drinks that they can take with them or enjoy in the café’s colorful surroundings.  (Continue reading below photos). 

HISTORY TO EXPLORE

Key West Lighthouse – Built in 1848 to replace the original that was lost in a storm, the Key West Lighthouse was unusual in that it was often staffed by women rather than men. It is also one of the few not built directly on a coastline, as the low profile of the island’s seashore made the potential of ruin by water more likely. However, due to the growth of trees in the immediate area, its height was raised in 1894, improving its visibility from the ocean and its reefs. Although the tower originally had thirteen lamps and reflectors, they were eventually replaced by a new, multi-faceted Fresnel lens, increasing its ability to be seen at sea.

Today, visitors can climb up the 88 steps that it takes to get to the top and enjoy a panoramic view of the city. The property also houses the Keeper’s Quarters museum, home to artifacts, antiques, and stories from the lighthouse’s long history. 

Key West Museum of Art & History at the Custom House – Situated at the city’s waterfront and originally built in 1891, the magnificent brick building that now holds this museum was once the Custom House, Post Office, and Federal Courthouse. Today, this national landmark houses two floors of exhibits that highlight the history, art, stories, and events of the past two centuries. It is a fascinating combination of permanent historical displays and rotating art exhibits, featuring such noted artists as Clyde Butcher and Ray Rolston. 

Other displays have included the history of the Key West Railway, Tennessee Williams’ paintings, and a collection of colorful cigar boxes. The Key West Art & Historical Society also offers a Museum Culture Pass that gets you entry into all four of their island museums. 

The Hemingway Home and Museum – In addition to the time that novelist Ernest Hemingway spent at the La Concha hotel, he and his wife Pauline spent nine years at a spacious home just a few blocks away on Whitehead Street. Built in 1851 and encompassing an acre of greenery in the center of the city, the home is known to be the location where Hemingway wrote some or all of many of his historic books, including A Farewell to Arms and For Whom the Bell Tolls. His writing office was situated above the garage area and still houses his typewriter, as well as souvenirs from his many hunting and fishing trips. In 1937, the Hemingways installed an in-ground pool – the only one within a hundred miles at the time. 

The house is also famous for being home to over 60 cats, many of which are polydactyl, or six-toed. The cats laze around the property and are often found in the various bedrooms, offices, or bathrooms that are showcased. All the cats are named after famous people and are descendant from Hemingway’s original polydactyl cat, Snow White. 

HISTORY TO ENJOY

Sloppy Joe’s Bar – Visit the city’s best known bar, where tourists and locals alike have been gathering since 1937. Initially located around the corner and named after Hemingway’s friend and rumrunner Sloppy Joe Russell, this iconic location celebrates Hemingway’s life and times every day with pictures and stories, but it’s best known for its decades-long annual Hemingway Lookalike contest. You can enjoy live music all day and night and grab an oversized drink at the long curving bar that proudly wears the scars of generations of visitors and admirers. 

Capt. Tony’s Saloon – Opened as the original Sloppy Joe’s on the day that Prohibition ended in 1933, Capt. Tony’s Saloon on Greene Street is the quintessential quirky Keys bar. Known for being visited by famous folks as diverse as Jimmy Buffett, Truman Capote, and President John F. Kennedy, you will find dollar bills and business cards stapled to the ceiling – along with dozens of ladies’ bras. Tales of late-night revelry and the escapades of the bar’s long-time owner Tony Tarancino fill the air, so grab a barstool and soak up some history.

The Green Parrot – Originally founded in 1890 as a grocery store at U.S. Route 1’s Mile Marker 0, the Green Parrot is another one of the Key West bars that is simply true to its roots. Heavy on live music and draft beer, it attracts a mostly local clientele to its raucous, open-air location just a short walk from La Concha. Gone are the “4-shots-of-tequila-for-a-dollar” days of yore, but in a city full of tourists, the Green Parrot is a breath of fresh local air. 

…And Chickens! – For over 200 years, Key West’s feral chicken population has roamed the island. In a city environment that has no known natural predators, these birds strut, cluck, and thrive. Though a city law prohibits feeding them, they have become a beloved tourist attraction and a symbol of island culture. 

ROUND UP

La Concha Key West

www.Marriott.com 

305-296-2991

Key West Art & Historical Society

www.KWAHS.org