THE SPRAWLING ESPLANADE known as the Malecon winds from the mouth of Havana Harbor to the city’s Vedado section: five meandering miles of sidewalk and sea wall that attract Cubans and foreign visitors alike at all hours of the day and night. Couples and families stroll along or lounge around, stopping to cast a fishing line or play catch with a baseball, to dance or make music with friends, to savor an ice cream cone or smoke a hand-rolled cigar — all with a joyous, intoxicating spirit.
For six of us making our first trip to Cuba, walking along the Malecon was not an unexpected pleasure. We had often discussed what traveling to the island nation on a people-to-people visa should mean with our unofficial tour leaders. Travel purely for tourism is still prohibited in Cuba, so the cultural exchange embodied by these people-to-people meetings is a requirement. In some cases, there would be prearranged meetings with Cubans. At other times, there would be unscripted encounters and random conversations, though none in our group spoke much Spanish. But even with total strangers, the talk could swing around to baseball, Cuba’s national sport (the Red Sox have a budding Cuban-born superstar in Yoan Moncada); or to thawing US-Cuban relations in the post-Fidel Obama era; or to Carlos Varela, Cuba’s answer to Bob Dylan.
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We were lucky to have two knowledgeable guides, Victoria Dosch and her husband, Steve. The daughter of a former British ambassador to Cuba, Victoria lived in Havana in the early 2000s and fell in love with the country and its people. Six years ago, she’d taken our daughter’s eighth-grade class on a tour of Havana, and my wife and I had been lobbying to go ourselves ever since.
Now that our dream was finally becoming a reality with a weeklong trip with two other couples, we wisely left the planning to Victoria and Steve. Music and art were high on our collective wish list, and I was able to get baseball added on. By design, our days would be a blend of people-to-people meetings, visits to important cultural sites, and absolute indulgence. Some plans might change once we were there, Victoria warned us, mobile communications and human nature being what they are in Cuba, where Internet and cellphone service remain sketchy (although that, too, is changing) and scheduled meeting times tend to be, well, fluid.
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In early March, our group of eight flew from Boston to Cancun and then on to Havana, a half-day-or-so trip in all. Later that month, Barack and Michelle Obama, Major League Baseball, and the Rolling Stones would all visit, making Havana, temporarily at least, the hippest destination on the planet.
FOR MOST AMERICANS, entering Cuba is far easier today than just a few years ago — and it’s becoming even easier. Earlier this year, eight US airlines won permission to schedule direct flights to the island. In late August, JetBlue became the first carrier to start its new route, leaving from Fort Lauderdale, Florida, with tickets as low as $99 each way; New York, too, will be on the schedule. US travelers are now eligible to apply for people-to-people visas, something previously restricted to charter groups. For American tourists, the floodgates are just beginning to open.
We breezed through customs and motored into town in a 1957 Cadillac sedan taxi (cost: $25 US) — in Havana, that’s how they roll — before disembarking at our first overnight stop, the Hotel Raquel, a charming Art Nouveau-style hotel in the city’s Old Jewish Quarter.
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Rather than spend the night resting, we booked dinner at San Cristobal Paladar, a chef-owned restaurant tucked inside a palatial World War I-era home. Not exactly undiscovered — the Obamas would dine there on their first night — San Cristobal is one of a growing number of restaurants in private homes, called paladeres, that are rapidly transforming Havana into something of a foodie mecca. Any travel cares melted away as we sipped 12-year-old Ron Santiago rum while feasting on ceviche, lamb stew, garlic shrimp, and pineapple ice cream (the bill came to around $70 US per couple).
Havana is a city of vibrant colors and jarring contrasts. Ambling down its side streets and boulevards, we passed handsomely preserved buildings that went up before the 1950s Revolution that carried Fidel Castro to power. Many more city buildings appear half-crumbled and overcrowded, a reflection of the economic struggles that Cubans continue to face, even as a more entrepreneurial model has begun to emerge under Raul Castro’s presidency. Even the Cuban currency is two-tiered, divided between the national peso (CUP), used by locals, and convertible peso (CUC), used by tourists and other visitors and pegged (and roughly equivalent) to the US dollar.
Our first morning began with a stroll through Old Havana and its Plaza de Armas, filled with bookstalls and street artisans, before we headed to the Hotel Saratoga, where we would spend the next two nights. Renovated in 2005, this 1930s-era hotel is among the city’s most luxurious, with a rooftop swimming pool, sumptuously appointed rooms, and seductive air of Old World elegance.
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But in Havana, great luxury never seems far from great need. After checking in, we paid a visit to La Merced missionary church, led by the Rev. Gilbert Walker, a New Orleans native who has spent the past 13 years in Cuba. His church, which sits in one of the poorest neighborhoods in Havana, ministers to the needy and the elderly, the latter Cuba’s fastest-growing population. Walker invited us to return the next morning to help serve breakfast for local schoolchildren.
We ate lunch beside the Saratoga’s rooftop pool overlooking the Capitol building. And we indulged in some late-afternoon salsa dancing at Casa de la Musica, a trendy dance club in Central Havana, swaying to the beat of Pachito Alonso and his band, Kini Kini. A late supper of tapas and mojitos followed at Sloppy Joe’s Bar, a famous watering hole near the Parque Central, one of Havana’s main public parks. These activities, like all the others to come, would fit comfortably within our travel budget of approximately $100 US per person per day.
The next morning, we returned to La Merced, where uniformed schoolchildren had already begun lining up for a breakfast of buttered bread and chocolate milk. This is often the only substantial meal they’ll have all day. Several of us sat with them as they ate. As they left for school, we exchanged hugs, nourished in ways we had not anticipated.
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Rejoining the rest of our group, we taxied to the Plaza de la Revolucion, where Cuban heroes Castro, Che Guevara, and the poet Jose Marti are memorialized (Marti by a 358-foot-tall marble tower). Then it was on to Finca Vigia, the home of Ernest Hemingway from the late 1930s until 1960, when he was at the height of his fame and productivity. I had proposed this stop in part because the property and its archives are supported by the Finca Vigia Foundation, a Massachusetts-based nonprofit.
Open most days from 10 a.m. to 4 p.m., the Hemingway estate is 9 miles outside Havana, in the rustic suburb of San Francisco de Paula. Admission is a bargain at 3 CUCs. Ada Rosa Alfonso, the estate’s executive director, led us on a tour of the main house and grounds, which contain many of Hemingway’s original furnishings along with acres of gardens, a now-empty swimming pool (Ava Gardner reportedly swam here in the buff), tennis court, and Hemingway’s 9,000-volume library.
With a wink and a nod to “my new assistants,” she lifted the rope blocking off Hemingway’s office and escorted us inside. There on Hemingway’s desk was the typewriter he used to compose such classics as The Old Man and the Sea and For Whom the Bell Tolls. Down a pathway on another part of the estate was the Pilar, the customized motorboat on which Hemingway fished, drank, made love, and burnished his larger-than-life persona.
That evening, we could hardly pass up a cocktail or two at El Floridita, a Hemingway haunt famous for its tangy house daiquiris of white rum, maraschino liqueur, and lime, where a life-size statue of the writer occupies one end of the bar. The evening ended at Paladar Dona Eutimia, where we dined on grilled octopus and a mutton stew called ropa vieja and quaffed frozen mojitos, a house specialty.
Built into our travel itinerary was an overnight stay at a Varadero beach resort, a three-hour drive east of Havana. En route, Victoria had arranged meetings with two families who hold special places in her heart.
Our first stop was the Havana home of Carmen Vallejo and her husband, Rey Febles, who run an organization serving pediatric cancer patients and their families (think of it as a small-scale Jimmy Fund). Carmen’s father served as Fidel Castro’s personal physician during the early days of the Revolution and her mother, briefly, as Castro’s private secretary. The couple were inspired to launch their organization, Carmen and Rey’s Kids, after meeting Mother Teresa in the 1980s. Over coffee and cookies, they spoke about the strengths and weaknesses of the Cuban health care system. They also introduced us to a teenage cancer survivor, whose story was at once heartbreaking and uplifting, and they accepted our modest gifts — over-the-counter medications, medical supplies — with grateful smiles.
Our second stop came in the city of Matanzas, where Lili Sanchez and her family greeted us with open arms. Lili lost a teenage son to cancer — she and Victoria initially connected through Carmen and Rey’s Kids — and works at a nearby university. A passionate baseball fan, she lit up when we brought out a few presents: Red Sox T-shirts and baseball cards featuring Cuban-born Major League stars such as Luis Tiant and Yoenis Cespedes. When Lili heard I was interested in bringing a Boston youth baseball team to play in Cuba someday, she insisted we all come to Matanzas. “So I can watch them play,” she said firmly, making me promise to be her guest when I got there.
From Matanzas, it was on to the Paradisus Princesa del Mar, an all-inclusive luxury resort in Varadero on the Playa Azul, where we would eat, drink, read, and swim for the next 36 hours. The 630-room resort offers nearly two dozen restaurants and bars, three outdoor pools, a dance club, and a large, sandy beach area with access to a wide variety of water sports and activities.
RETURNING TO HAVANA ON DAY SIX, we stopped at the Museum of the Revolution and the adjacent Granma Memorial. The latter houses the 60-foot boat that carried the Castro brothers and their comrades back to Cuba in 1956, setting the stage for the Communist takeover. We then checked into our third Havana hotel, the iconic Hotel Nacional, overlooking the Malecon. Victoria had arranged for me to a meet with another old family friend, Jesus Barroso, a high-ranking Cuban baseball official.
Ah, baseball, Cuba’s national sport. The top-level season runs from August to March, when playoffs commence. Among our biggest disappointments was missing a Cuban League playoff game. Blame that one on Major League Baseball, which had hastily scheduled an exhibition game between the Tampa Bay Rays and Cuban national team to coincide with the Obamas’ visit. When we were there, Havana’s main stadium was temporarily closed for renovations. It’s since reopened, and game schedules and other details can be found on the Spanish-language site baseballdecuba.com.
Even though I missed out on a game, I wanted to meet with Jesus to fulfill a more personal mission. A few days a month I work for The BASE, a Roxbury baseball and academic prep program. We send travel teams to tournaments and college showcases all over the United States. I wondered, might we someday take a team to play in Cuba? As we sat on the Nacional’s sprawling veranda, Jesus, who oversees 1,500 coaches on the island, had many questions about The BASE and its mission to promote urban baseball.
After a stroll along the Malecon and another superb meal of stuffed plantains, grilled pork, and paella at El Litoral Paladar, we returned for the Nacional’s famed cabaret show, where dinner and the performance cost around 65 CUCs. We watched two dozen costumed dancers, singers, musicians, and acrobats perform in a two-hour Las Vegas-style revue straight out of 1950s Havana.
Our last full day was spent exploring Vinales, 125 miles west of Havana, in the heart of tobacco growing country. Our hired car took us to a tobacco farm and to a cigar-rolling factory — US visitors are allowed to bring back $100 worth of Cuban cigars and/or alcohol each — two stops sandwiched around an amazing lunch at Finca Agroecologica El Paraiso, an organic farm-to-table restaurant overlooking the Vinales Valley. The meal began with a round of El Paraiso’s famous “anti-stress” cocktail — a combination of coconut water, rum, mint, and other ingredients — followed by a multi-course feast of soup and platters of fresh vegetables, fried yucca, corn tamales, pork, lamb, and fish, and finishing with a flan cake large enough to feed a dozen. The bill came to just 10 CUCs per person; such a feast would have been four times that in Boston.
Back in Havana for one final night, we headed for Fabrica de Arte Cubano for a multimedia arts immersion unlike any other. Opened in 2014, it was conceived and designed by X Alfonso, a popular Cuban rock musician-artist, in a re-purposed industrial building that now houses a multilevel art gallery, exhibit and performance spaces, several bars, and a jazz club. Films, fashion shows, concerts, dance performances — all take place in an ultra-cool setting packed with Havana’s youngest and hippest denizens. On the night we visited, its galleries hosted a show of painting, photography, and video structured around a theme of fighting domestic violence.
The vibrant sights and sounds, its pulsing music and kinetic art, were a fitting way to end a trip that still resonates for us. Our meaningful and magical trip was so satisfying on every level that we could not have imagined a better introduction to a Cuba that many more Americans will soon be getting to know. And, one hopes, to love.
IF YOU GO . . .
HOW TO GET THERE
Round-trip flights to Havana from Boston or New York (via places like Cancun) can cost around $700, but new routes are coming online from a number of carriers. JetBlue now offers direct flights (some prices as low as $99) to three airports in Cuba from Fort Lauderdale, with more to come. Our guides Victoria and Steve don’t book trips, but you many services do, including Friendly Planet Travel (friendlyplanet.com), Road Scholar (roadscholaradventures.org), Cuba Trips (cubatrips.org), Geo Ex (geoex.com), and Cuba Cultural Trips (cubaculturaltrips.com ).
WHERE TO EAT
> San Cristobal Paladar
Criolla-influenced cuisine; reservations recommended. San Rafael No. 469, Central Havana, sancristobalpaladar@gmail.com
> Paladar Dona Eutimia
Authentic Cuban recipes handed down by the restaurant’s matriarch. Callejon del Chorro 60C, Plaza de la Catedral, 7-861-1332, d.eutemia@yahoo.es
> El Litoral
Outstanding seafood and cocktails. Malecon, between K and L streets, 7-830-2201, ellitoralhabana.com
> Finca Agroecologica El Paraiso
Extraordinary 10 CUC all-you-can-eat buffet. Carretera al Cementerio, Vinales, 5-818-8581
WHERE TO STAY
> Hotel Saratoga
Restaurants, bars, gym, room service, pool, free Wi-Fi. Rooms start at 246 CUCs double occupancy. Paseo del Prado 603, Havana, 7-868-1000, hotel-saratoga.com
> Hotel Raquel
Art Nouveau stunner with restaurant, bar, and gym. Rooms start at 150 CUCs double occupancy. Calle Amarguara, No 103, Havana, 7-860-8280, hotelraquel-cuba.com
> Hotel Nacional de Cuba
This Cuban national monument has restaurants, pools, tennis, and Wi-Fi. Rooms start at 175 CUCs double occupancy. Calle 21 y O, Vedado, Plaza, Havana, 7-836-3564, hotelnacionaldecuba.com
> Paradisus Princesa del Mar
Sprawling, adults-only eco resort on Varadero beach, with restaurants, a dance club, spa and much more. All-inclusive rates start at 520 CUCs. Autopista del Sur, Carretera Las Morlas KM, 45-66-7200, paradisus-princesadelmar.com
Joseph P. Kahn is a former Boston Globe staff writer. Send comments to magazine@globe.com.