Enjoy a Weekend in Cuba

If you visit Cuba, you are not allowed to have fun. The United States lists 12 approved reasons to travel — excluding tourism, which rules out a sybaritic vacation at a beach resort but not much else. Most independent travelers select the people-to-people category because the reason most people travel is to connect with others. While more timorous travelers join groups promoting educational or religious activities — paying a premium for the guides and arrangements — the recent introduction of Airbnb and commercial flights have eliminated many barriers.

The largest island in the Caribbean and once forbidden fruit, Cuba is only an hour’s flight from Florida. Lured by cheap fares from Tampa to Havana, we planned a long weekend trip and convinced friends to join us. Traveling as a foursome was economical for sharing taxis and accommodations. Our early morning Thursday flight and our return Sunday evening gave us four full days and three nights to explore Havana.

Havana, Cuba, is filled with once classically beautiful but now crumbling mansions. Photo courtesy of Philip Courter
Havana, Cuba, is filled with once classically beautiful but now crumbling mansions. Photo courtesy of Philip Courter.

Due to a scarcity of comfortable lodgings, hotels are expensive, but already Airbnb has more than 10,000 Cuban listings. We were delighted that our apartment turned out to be far more deluxe than we expected. Although the third-floor walkup in still-swanky Miramar — a neighborhood of ostentatious mansions confiscated by the state and now leased to embassies — had a drab exterior, our modern suite had three bedrooms, each with mini fridges stocked with water, beer and sodas; three spotless baths — one with bidet; a full kitchen; large dining room; several comfy seating areas; and a small balcony. Most surprising — and welcome — were new air-conditioning units in every room.

Our host, Jose, arranged for a taxi to pick us up at the airport, helped with exchanging currency and provided us with a Wi-Fi card. Internet access in Havana is new and rare, but it worked (most of the time) in the apartment. Jose and his family are pioneer entrepreneurs in still-communist Cuba. If you rent a hotel room most of your money goes to the government, but the average Airbnb host makes $250 per booking. When you realize that a physician earns only $50 a month and the average worker even less, the sharing economy is a huge boon for Cuba’s early entrepreneurs.

If I squinted, Havana’s pastel modernist houses reminded me of my visits to Miami as a child. While we expected to see a few antique cars, we didn’t realize there were thousands of these grand dames in sherbet colors available as taxis — the perfect way to get the vibe. We spent the first day touring in a ’52 canary-yellow Chevy convertible.

Colorful automobiles from another era serve as taxis in Havana, Cuba. Photo courtesy of Philip Courter.
Colorful automobiles from another era serve as taxis in Havana, Cuba. Photo courtesy of Philip Courter.

As we drove along the waterfront Malecon and through the narrow streets of old Havana, Cuba’s architecture telegraphed its history from the crumbling colonial mansions begging to be put out of their misery to the bleak Soviet-era apartment blocks to Art Deco symbolized by the iconic Bacardi building. Looming over the skyline is the Russian embassy with its colossal watchtower that reminds Cubans they still might be under surveillance.

While imagining Fidel Castro haranguing a cheering crowd as we stood in the Plaza de la Revolucion, our guide, Enrique, told us about surviving the “special period” — a euphemism for the era after the Soviet Union’s demise when they stopped supplying oil, food and other vital materials. Food was so scarce that his family chewed floor mops and other inedible items to quell hunger pangs. He is frustrated by his choices: either working as an engineer for $50 a month or squiring tourists for $30 an hour. He despairs of ever leaving the island, even for a vacation.

“Nobody will give me a visa,” he said, “because I have no family, no wife, no reason to ever return.”

Curious to see how artists cope with their repressive environment, we visited the Museo National de Bellas Artes (Cuban section). While we expected sanitized landscapes and portraits, the raw, honest and often disturbing portrayals of the harshness of Cuban life made us feel as if we were complicit in an anti-communist plot. One of the most searing is Abel Barroso’s “Teora del Transito del Arte Cubano” (Theory of Sending Cuban Art). The names of Cuban artists are painted on boomerangs mounted on a wall in the shape of the island nation. The installation is festooned with parachutes, letters, stamps and wrapped boxes that depict the hopelessness of getting artistic messages to the world at large.

Nobody goes to Cuba for the cuisine — yet. Until recently “Cuban food” was an oxymoron based on rice, beans and not much else. While there is more food now due to reforms in Cuba’s inefficient agricultural system, tourism — the island’s economic lifeline — has driven up the prices and diverted the best produce to visitors. On the return flight our seatmate told us he had spent a week on his grandmother’s farm just outside the capital and had not eaten meat for a week. Guests fare better. One result of Raul Castro’s reforms has been an upsurge in paladares, private restaurants. Tourists who pay with CUCs — the Cuban convertible peso — are able to order steak, shrimp and lobster, which are out of reach of citizens who use the CUP — the regular peso, worth far less.

We selected most of our cafes because they were within walking distance of our apartment. Our first lunch was at El Aljibe, a state-run restaurant. Despite a lengthy menu, the only acceptable order was the succulent pollo asado, a slow-roasted chicken with rice, beans, fried plantain and salad served outdoors under a thatched roof. The next day in central Havana we ended up at Chachacha, which uses old LP records as placemats. At one point the electricity went out, but everyone acted as if this were normal and went on eating.

The following evening, at La Carboncita, we enjoyed superb homemade pasta in a garden setting. Tamara, the owner, explained how she went from a job in the Ministry of Foreign Relations to running a popular private restaurant. La Cocina de Lilliam is justifiably so popular that we could only get reservations for lunch, when we sat outdoors amid eclectic antiques. A basket of scrumptious homemade breads heralded an unexpected array of fresh, creative and delicious dishes with a Creole flair. An appealing arrangement of cabbage, carrots and cucumbers made up for a lack of salad greens, which are scarce on the island.

The most uplifting moment of the weekend was a visit to Fusterlandia on Sunday before heading to the airport. Mosaicist Jose Fuster has created a wonderland in homage to artist Antoni Gaudi, featuring stars, hearts, hands, lizards, chickens and Picassoesque portraits. Not content just to cover every surface of his home with brilliant shards, the exuberant artist has extended his whimsical folk art murals to the surrounding neighborhood. His life-affirming joy was contagious.

Fusterlandia in Havana, Cuba, is a wonderland created by mosaicist Jose Fuster in homage to artist Antoni Gaudi. Photo courtesy of Philip Courter.
Fusterlandia in Havana, Cuba, is a wonderland created by mosaicist Jose Fuster in homage to artist Antoni Gaudi. Photo courtesy of Philip Courter.

Go to Cuba now to experience the time warp before the inevitable development. Tip well because your money is a lifeline. But remember, having fun is not a permissible activity — so don’t tell anyone that we enjoyed ourselves immensely!


While President Trump announced on June 6 that he is “immediately” canceling independent travel to Cuba, the reversal of President Obama’s deal relies on regulations that could take months — or years — to finalize. Go soon or lose this short-lived travel freedom.

JetBlue, Southwest and Alaska offer direct flights from New York, Los Angeles, Miami, Fort Lauderdale and Tampa. All include the mandatory health insurance while you are in Cuba. The airlines facilitate a visa for $50 per person, which you can pick up when you check in for your flight.

Airbnb (www.airbnb.com) offers the largest array of lodging at affordable prices and promotes people-to-people contact better than a hotel, as does the Cuban version: Casa Particular (www.casaparticular.com) .

Taxis are ubiquitous. Some warn that the Lada drivers charge more. Best to negotiate the fare before entering the cab. An hour for touring is usually $30, but shorter rides vary widely. Vintage Tour Cuba is a reliable agency that features classic convertibles with set prices by the hour or day, including airport runs. Their English-speaking driver-guides are highly knowledgeable, and riding around in a ’52 Chevy convertible was especially evocative of earlier times: vintagetourcuba@gmail.com.

Take cash — and more than you expected. U.S. credit cards are not accepted and few places other than hotels take Canadian or European ones, either.

Havana video courtesy of Emmy-award winning filmmaker Philip Courter