Often described as the most precious jewel in the Greater Antilles, Cuba has an allure that is hard to resist. For many, the island is “forbidden fruit” because most Americans couldn’t enter the country legally after the U.S. broke diplomatic relations and closed its embassy in 1961. For others, stepping back in time to a place where vintage cars dominate the roads and Internet access is limited sounds like a dream vacation. For me, traveling to Cuba meant a chance to meet the people and hear in their own words how they feel about their neighbors to the north. 

“You are American?” an elderly man asked me as I took a photo of his shiny 1957 Chevrolet Bel Air on my second morning in Havana, the capital city of 2.2 million people. The moment I answered “yes,” he grasped me in a bear hug and sincerely said, “Welcome to Cuba. We are so glad you are here.”

While Cubans are ready for more Yanks to experience their country firsthand, their government is still debating travel rules with the U.S. Getting to Havana isn’t as easy as just hopping on an airplane—at least not yet. General tourism, as of press time, remains prohibited. Many U.S. citizens visit on people-to-people educational programs, which require contact with Cubans and an itinerary based on a particular area of interest. (See “Traveler Fast Facts”  below)

Those who do manage to enter the country will find much to see and do. Start with a ride along the picturesque Malecón Boulevard in a flashy, old American car. Known as “tanks,” these autos line the streets, and you’ll see many of them waiting as taxis for tourists outside the José Martí Airport. When I was in Havana, the cost of a city tour in a vintage car was about $35 an hour but the price has since increased to $50. It’s worth it—if only to hear the drivers’ invariably colorful stories. 

As we passed Havana landmarks in a 1950 cherry-red convertible Chevy, driver Carlos Alberto told me he had inherited the car from his grandfather, who had bought it before the 1959 Cuban Revolution. Owners like Alberto must be ingenious to keep the old cars running, because the U.S. embargo on exports to Cuba prohibits parts from being shipped there. If they can afford it, Cubans buy parts and paints from Mexico or Canada, and cars are often jerry-rigged with pieces from non-American cars. 

About a decade ago, Europeans—who can travel freely to Cuba—were buying the vintage autos. Fidel Castro put a stop to it because even he recognized how iconic the cars are to Cuban culture. Today, a reported 60,000 pre-revolutionary cars are still on Cuban roads. 

The Spaniards founded Havana in 1515 to be the “strongbox” for the gold they accumulated in the New World, and it was the principal port for Spain’s New World. The city was designed following the Spanish “Law of the Indies,” which required a central plaza surrounded by public buildings with portals to shade inhabitants from the hot Caribbean sun. 

Today, the Spanish Colonial buildings survive alongside architectural influences from Great Britain, France, and Italy, all of which played a role in Cuban history. The people of Havana take pride in the exquisite architecture, which is a reminder that the nation once had considerable wealth. Unfortunately, that wealth evaporated after Castro’s revolution and many buildings fell into disrepair. Today, this “pearl of the Antilles” may lack its luster, but with the help of UNESCO many of the city’s historic gems are being restored and transformed into tourist-friendly destinations. Numerous major sites of interest are centered on three squares: Plaza Vieja, Plaze de Armas, and Plaza de la Catedral. 

Once in complete disrepair, the Plaza Vieja (Old Square) now features restaurants, boutiques, a photography museum, and a planetarium. I particularly liked Plaza de Armas with its outdoor book market. Look closely to find a vintage copy of Hemingway’s For Whom the Bell Tolls, which the Nobel Prize-winning author began writing just down the street at the Hotel Ambos Mundos. Photo opportunities abound at the Plaza de la Catedral, where locals in costumes or with gigantic cigars will pose for a tip. And don’t miss the iconic, baroque-facade Catedral Colon (Columbus Cathedral), which was described by Cuban novelist Alejo Carpentier as “music turned to stone.” 

Havana’s significant sites and cultural attractions are numerous. Having a planned itinerary—which people-to-people trips require—helps to narrow choices. For my group, the arts were the focus and allowed us to have off-the-beaten-path experiences, such as exploring “Fusterlandia,” the studio of avant-garde artist José Fuster. 

The Callejón de Hamel street performers in Salvador’s Alley in Old Havana provided colorful and lively Afro-Cuban rhythms along with a story about the Santeria gods. The Institute Superior des Artistes, on the grounds of the former Havana Country Club, is a national school for musicians, dancers, painters, and photographers where we talked with students about their visions for Cuba’s future.

To understand the importance of art in Cuban culture, visit the Museo Nacional de Bellas Artes (National Museum of Fine Arts) where you’ll “fill your eyes with Cuban color” as our guide Omar Diaz Linia explained. Covering five floors, the museum contains the world’s largest collection of Cuban artwork, beginning with 16th and 17th century pieces.

A trip to Havana isn’t complete without a visit to a cigar factory. The government-owned facilities offer strictly controlled tours, and access is impossible without a guide. No photography was allowed during my H. Upmann tour, which ended in the gift shop. Be aware that you can bring only $100 worth of Cuban cigars back to the U.S.

Offering a cigar is a gesture of friendship. I received one from a tobacco farmer in Viñales. My husband, Tony, was shooting photos on the Malecón Boulevard when he struck up a conversation with a young man who offered him two cigars. The man, who wouldn’t accept any money in exchange, smiled broadly and, in halting English, said: “You are American. You are my friend.”

About Travel Restrictions

Visitors from many parts of the world have long been able to travel freely to Cuba, but visiting from the U.S. has been difficult until recently. In December, the U.S. and Cuba agreed to restore commercial flights between the two countries, and several U.S. airlines immediately announced plans to request approval to begin flying the route. American Airlines, which has operated charter flights to Cuba since 1991, hopes to introduce commercial flights as soon as possible. Jet Blue, which operates charter flights through ABC Charters, also plans commercial service.

The number of U.S. business aviation charter operators with approval to fly fo Cuba continues to grow. Among those to receive FAA authorization to fly to Cuba are New York-based ExcelAire and California-based JetSuite. The former, which completed its first flight to Havana last December, offers departures from 19 U.S. cities. The latter provides flights on Citation CJ3s and Embraer Phenom 100s from seven Florida locations as well as New York, Chicago, and seven other U.S. cities. 

In addition to carrying a passport and a Cuban visa (referred to as a tourist card), Americans must travel with a general license from the U.S. Department of Treasury’s Office of Foreign Assets Control (OFAC), which offers 12 categories of authorized travel to Cuba, including family visits, humanitarian projects, and educational activities. 

Many U.S. visitors arrive via people-to-people exchange programs, one of the permitted educational activities. OFAC rules require that these programs include a full itinerary of activities such as visiting schools and talking to teachers, meeting with tobacco farmers, or visiting a Cuban culinary institute. Many university alumni groups, museums, cruise lines, and OFAC-licensed travel agencies hold people-to-people licenses and offer programs. The Latin American Working Group Education Fund maintains a list of organizations that coordinate licensed travel to Cuba at lawg.org/storage/documents/people2people.pdf

For up-to-date information about travel restrictions, call the U.S. Embassy’s Cuban Interests Section in Washington at (202) 797-8518 and visit travel.state.gov/content/passports/english/country/cuba.html. To determine the appropriate visa for your visit, contact the Cuban embassy in Washington, D.C. (cubadiplomatica.cu/sicw/EN/ConsularServices.aspx). —M.A.D.

Beyond Havana

Many Americans trek to San Francisco de Paula, about eight miles southeast of Havana, to see Ernest Hemingway’s home, which is maintained just as he left it. Also worth a visit is Cojimar, a tiny fishing village on the Straits of Florida to the east of Havana where the Pulitzer Prize-winning writer berthed his boat. When he died in 1961, local fishermen donated their boats’ brass fittings, which were melted to create a bust of the author that now looks out to sea from a columned rotunda. After viewing it, stop at La Terraza for a Cocktel Fuentes, a turquoise concoction honoring Gregorio Fuentes, Hemingway’s skipper and the model for The Old Man and the Sea. 

Some of Cuba’s most beautiful scenery is in the Valle de Viñales, a two-hour drive from Havana to the west. The area’s rich, red soil makes it Cuba’s top tobacco-growing region. Just five kilometers north of Viñales is the Cuevas del Indio, a large grotto with an underground river where tour boats wind their way through a maze of limestone tunnels. —M.A.D. 


WHAT IT IS: Known as the “pearl of the Antilles,” Cuba is the Caribbean’s largest island. Only 90 miles from the U.S. mainland, it has been worlds away politically since the 1959 revolution led by Fidel Castro.

GETTING THERE:  The U.S. Transportation Security Administration has authorized charter flights to and from Cuban airports in Havana, Camaguey, Cienfuegos, Holguín, Manzanillo, Santa Clara, and Santiago de Cuba. 

CURRENCY:  Cuba’s currency is confusing, because there are two types—one for visitors and another for residents. Visitors must use Cuban Convertible Pesos, called CUCs. The Cuban government is reportedly working to unify its currencies. ATM cards and many credit cards don’t work here although MasterCard said it would accept charges in Cuba beginning March 1. Check with your credit card company before leaving. Cash is still king, and you’d be wise to budget $100 for each day of your visit. 

CLIMATE: Cuba is in the tropics, so prepare for hot, moist weather, especially during July and August when temperatures can approach 100 degrees Fahrenheit. The rainy season is mid-May to November, with September and October having the highest probability of tropical storms and hurricanes. The coolest months are December, January, and February, when average highs are between 70 and 80. Winter evenings can be breezy, with temperatures in the 60s. 


ACCOMMODATIONS (B+):  Most Havana hotels are clean and many have ornate lobbies. Though many are working to upgrade accommodations, however, rooms are usually small and can look threadbare by U.S. standards.

Built in 1930, the landmark Hotel Nacional de Cuba (A-) towers above the Vedado District’s famed Malecon thoroughfare and offers first-class restaurants. 

On the pedestrian street of Calle Obispo in Old Havana, Hotel Ambos Mundos (A-) doubles as an Ernest Hemingway museum. Room #511 remains just as the writer left it, complete with his Nobel Prize and a copy of his bar tab. Check out the rooftop café and bar for a spectacular city view. Rooms were being updated in 2015.

The magnificent lobby in the 1908 art nouveaux Hotel Raquel (B+) reveals poignant references to Jewish culture, including biblical-themed paintings by Cuban artists. 

With its retro 1950s look, Hotel Capri (B+) offers a comfortable, convenient location in Havana’s Vedado District. The cafeteria looks utilitarian but serves substantial, delicious breakfasts, and the rooftop swimming pool provides a great place to unwind after a day of sightseeing.

RESTAURANTS (A+): Cuban cuisine is a delightful surprise, especially at the family-owned paladars. Favorites include La Casa Restaurante, open since 1995 and one of Havana’s first family-run establishments, and La California in the Columbus neighborhood. Café del Oriente, one of Havana’s most elegant government-run restaurants, is in the Plaza de San Francisco near the cruise-line terminal. For the best coconut gelato in the Western Hemisphere, head to Divino, on the organic farm La Finca Yoandra. For fresh seafood, visit Mediterráneo Havana, which gets fish four times a week from its own fishing boat.

ACTIVITIES (A+): If you’re an arts or music aficionado, look into the many international festivals that take place annually, such as the Havana Biennial, which transforms the city into the world’s largest art gallery (May–June); the Havana International Book Festival (February); the International Jazz Festival (December); and the International Festival of New Latin American Cinema (December).


Click on the link to read "Exploring Cuba's Water World" by Thomas R. Pero.

Florida-based freelancer Mary Ann DeSantis, who paid her own expenses for her Cuba trip, specializes in travel, food, and wine. This is her first article for BJT.