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Island Hopping Beyond the Buoy

Explore what lies beyond the Florida Keys and the island influences that have drifted over to Key West. 

Once the traveler passes through the maze that is Miami, it’s island time. Known to the locals as “The Stretch,” the two-lane US 1 South wends its way toward its terminus, Mile Marker 0 in Key West, the southernmost tip of the continental U.S. The road takes over and forces the driver to temper his speed, shift out of overdrive and understand that life operates at a slower pace. And as the parade of convertibles cruise from island to island on this solitary route, it’s easy to understand the mystique of this part of Florida.

buoyThere are almost 1,700 islands in this archipelago called The Keys. Spanish for cayo or island, the Keys bring to mind a respite that few other places in the United States can boast. Not all islands are large or even accessible; some 43 are connected by bridges.

Key Largo — the first Key — offers some of the best diving, with the added attraction of a bronze statue of Christ of the Abyss 25 feet below the surface. Islamorada reels in the title of Sport Fishing Capital of the World, while Marathon is the Heart of the Keys. Passing Marathon beckons the upcoming Seven Mile Bridge, an updated concrete version of Henry Flaglar’s dream of connecting the Keys to the Mainland via rail and proves that this stretch of the east coast is indeed the new American Riviera.

It’s at Mile Marker 0 on Whitehead Street in Key West that one realizes island stopovers are addictive. Momentum cools to a simmer, time doesn’t exist and attitudes are do-what-you-dare. The tropical climate takes hold, and soon one longs to discover what lies beyond the buoy at the corner of South and Whitehead.

Hemingway’s Playground

It was quite by accident that America’s most beloved writer encountered Cuba. It was to be nothing more than a layover for he and his wife, Pauline, on their way from Key West to Spain, but it was three days that would ultimately change his geographical roots. Four years later, he and his drinking buddy Sloppy Joe Russell returned to fish the annual Marlin run. A few years and wives later, Hemingway became a resident and spent the next 20 years writing, drinking and falling in love with what most believe to be the writer’s true love.

Purchased in 1940, Finca Vigia, which means “lookout house,” was a modest home located 10 miles east of Havana. Hemingway penned For Whom the Bell Tolls and The Old Man and the Sea, as well as A Moveable Feast, during those 20 years of residency. He left Cuba in 1960 and purchased property in Ketchum, Idaho, a location in which to delve into hunting. He also harbored years of depression, rage, frustration and drunkenness, which reached its deadly peak in July of 1961. Immediately, upon Hemingway’s death, the Cuban government took control of Finca Vigia (with no permission from the estate or Hemingway’s wife) and today Museo Hemingway at Finca la Vigia is considered one of the country’s most visited attractions.

Many spots tout the Hemingway connection. There’s even a “trail” to allow travelers to explore the city that captured Hemingway’s heart. Marina Hemingway. Hotel Ambos Mundos (Room 511). Bodeguita del Medio Bar. El Floridita Bar. Papa, as Hemingway is called, is America’s most notable connection to Cuba and is reason enough for many travelers to add Cuba to their bucket list.

Getting to Cuba 

cubasignBefore 1959, people traveled daily by ferry or plane to Havana for lunch — a mere 90 miles south — and would return to Key West in time for dinner. Today, Cuba is considered a forbidden destination with the exception of a handful of tour companies who receive special license from the U.S. government to take American visitors to Cuba under the People-to-People travel provision mandated by the Obama administration in 2009. Groups and individuals must have a full-time itinerary of personal interactions with the Cuban people approved in advance by the U.S. government.

According to the federal government, currently there are 19 airports authorized to provide service to and from Cuba, although not all do. On December 30, 2013, for what seems to be an effort to rekindle the past, the first charter flight in 54 years lifted from Key West bound for Cuba. Considered an “experimental flight” by Peter Horton, Key West International Airport director, the flight carried nine passengers, including the ceremonial addition of Key West’s Mayor Craig Cates. Travelers met with Cubans at botanical gardens, organic farms and cultural centers on a People-to-People trip organized by the Florida Keys Tropical Research Ecological Exchange Institute.

“Key West is nothing close to a major hub to Cuba like in the ’50s,” says Horton, and he believes “there will be a market, a limited market, when the restrictions are lifted.” He continues by saying that the trip must be “relatively inexpensive and convenient” and at this point, it is not. “You remember the glory days when you could put your car on a ferry. No fuss. No bother. You were there in a half a day. That’s not how it works anymore.”

With most Cuban travelers departing from Miami, Carol Shaughnessy of the Key West Chamber of Commerce points out that “Key West is the closest point to Cuba across the Florida Straits,” making departures from Key West a practical option. “The two islands have shared a cultural heritage since the 1800s,” she says. Since the Cuban cigar makers crossed the straits in the mid-1800s and made Key West home, the Cuban cultural heritage is pronounced on the island.

In February, the first Cuban-American art exchange took place in over 50 years. “The pioneering cultural exchange, titled ‘One Race, The Human Race,’ features the most famous cutting-edge artists in Cuba today,” says organizer Nance Frank, art director at Key West’s Gallery on Greene. As part of the exchange, 30 intaglio prints by the late Key West folk artist Mario Sanchez debuted in January in Cuba’s Museo Nacional de Bellas Artes in Havana.

“Key West is unlike the rest of Florida,” adds Shaughnessy. “It’s eclectic and multicultural field makes it a popular destination. To add Cuba to that world would be a fascinating experience.”

However, for now, until the process becomes less complicated, Miami remains the major hub to access Cuba. You could also contact a Top Travel Agency for assistance.

Bahama Village

bahamavillageTies to nearby islands have been strong since the founding of Key West. Much like the appearance of Cuban cigar makers, shipwrecked scavengers came and remained in the mid-1800s. Together, they made Key West the wealthiest city in the United States.

On Petronia Street, you’ll find the nucleus of the Bahamian people. The Bahama Village, which covers a 16-block radius in Old Town, pays homage to a culture that remains vibrant in the city. From straw baskets on display to roosters migrating through feet of patrons at laid-back dive Blue Heaven, travelers get a true Bahamian experience.

Of course, there’s always Key West’s sister cities Harbour Island near Eleuthera and Green Turtle Cay in the Bahamas. Located approximately 100 miles apart, these cities and their relationship with Key West honor those on the mainland of Bahamian heritage. According to Shaughnessy, Mayor Cates was instrumental in formalizing this alliance; his ancestors are from Eleuthera.

With over 700 islands, cays and islets, the Bahamas carry travelers on an extreme island hopping adventure. Known as the place where “it is better,” the Bahamas are an outdoor lover’s dream and a destination for all romantics. Hemingway himself fished his way over to Bimini in search of giant tuna and marlin and ended up staying for two years. These days, getting to the Bahamas from Key West will require a private charter, boat or plane.

The Dry Tortugas

With any Caribbean island proving difficult to reach from Key West, there is one island that most forget and never visit. The Dry Tortugas National Park sits in the middle of the Gulf of Mexico, approximately 70 miles west of Key West. A cluster of seven islands, the national park’s centerpiece is Garden Key. It was once the home of the Union Army’s Fort Jefferson, which held captured deserters during the Civil War, its most famous prisoner being Dr. Samuel Mudd, the doctor who mended John Wilkes Booth after the Lincoln assassination. Today, maintained by the National Park Service, this spot in the Gulf encourages visitors to explore and marvel at one of the most undisturbed parts of the world.


It was first named Las Tortugas (The Turtles) by Ponce de Leon in the early 1500s and later took the name Dry Tortugas, signaling to mariners of no fresh water. A lighthouse was built on Garden Key to warn sailors but has since been moved to Loggerhead Key within sight of Fort Jefferson.

According to the National Park Service, they “protect its nationally significant scenic, cultural, marine and scientific values for the education and inspiration of the public.” Yet, through the eyes of every man, it is a natural marvel providing homes for endangered green sea turtles and loggerheads, a landscape of delicate coral and sand islands where pirates roamed and a flyway refuge for migratory birds, including endangered brown boobies and frigate birds.

Yankee Freedom departs from the Ferry Terminal at Grinnell Street around 7 a.m. and returns at 5:30 p.m. The 2.5-hour ferry ride provides breakfast and lunch as well as snorkel equipment and a tour of Fort Jefferson. At $170 per person (which includes the park entry), it’s pricey yet an unforgettable experience for those who consider island life the ultimate adventure. Key West Seaplane Adventures also offer half-day and full-day excursions. Prices begin at $295 for adults. Camping on Garden Key is permitted, but reservations must be made in advance. As with most primitive national park sites, what you carry in, you carry out. Strict rules apply to disturbing or collecting animals and artifacts.

For now, travel to other Caribbean destinations from Key West is difficult, but that doesn’t silence their influence on the U.S.’s southernmost city. Make time to experience Key West and its melting pot of cultures. After all, you are on island time.

A Taste of the Caribbean 

Until reaching Cuba or the Bahamas from Key West becomes easier, you can still experience Caribbean culture and cuisine on the mainland. Here’s some local favorites:


Blue Heaven: Don’t let the roaming chickens and cats distract you. Featuring indoor and outdoor dining, this restaurant is known for its Caribbean fare and mile-high Key Lime Pie. Located in Bahama Village at 729 Thomas St.

Conch Republic Seafood Company: Located on the water, it serves some of the freshest seafood available. Caribbean favorites, the Conch Chowder and Cracked Conch are classics from the sea, available at 631 Greene St.


CubansandM & M Laundromat: In the back of the laundromat (yes, a laundromat) at 1026 White St., you’ll find a tiny take-out stand called Sandy’s Cafe that serves hearty fare. However, it’s the Cuban sandwich that draws the crowd. Carol Shaughnessy contends “that every place will do it differently,” but the key to a true Cuban sandwich is the lightly spiced Cuban pork (sliced) and the Cuban bread (warmed slightly and flattened in a press).

El Siboney: There are no frills here at 900 Catherine St. It’s a family atmosphere with lots of chatter, but locals swear by the grilled chicken with Cuban spices as well as the half-grilled garlic chicken and the sangria. Always served with black beans, rice and sweet plantain, the food is an authentic experience whether you’re a Cuban food expert or not. Shaughnessy advises “you make a well in the rice and spoon the black beans on top. You know Cuban food if you handle your rice that way.”

5 Brothers Grocery: You will find the best eats in groceries and unsuspecting locations, including this little store. There’s authentic Cuban coffee and Cuban fare, including sandwiches, at the Southard Street location and at Mile Marker 31 in Big Pine Key.

Agencies That Offer Cultural Tours/Travel to Cuba

Prices may vary considerably, and it is important to do your research, confirming the agency’s license for travel to Cuba by the American government.

Marazul Charter: Specifically to Cuba, Marazul offices are in Miami and New Jersey.
Harvard Alumni Association: The Alumni Association offers over 50 programs a year to seven continents.
Insight Cuba: Six different Cuba itineraries available. Online download available of most current offerings.
Chamber Explorations: Variety of international destinations available.
Premier World Discovery: Variety of international destinations available, including rail and cruises.
Globus: Historically known for international destinations, Globus was recently granted a license to travel to Cuba.
Other Cuban Journeys: Custom travel to Cuba.
Grand Circle Foundation: International destinations with a concentration on giving back.

Photo Credits: Dry Tortugas Fort Jefferson courtesy of Andy Newman, Florida Keys News Bureau; buoy, sign, Bahama Village and Dry Tortugas view by full circle fotography; and Cuban sandwich by Deep South. 

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  • LeeH / May 14, 2014

    Love Key West. Will try and visit Tortugas on my next visit.