For decades, Cuba has been mostly closed to U.S. visitors. That is slowly beginning to change as tourists take advantage of newly relaxed travel restrictions.

These new rules allow people to travel directly to Cuba on cultural exchanges. They also permit residents of the United States with relatives remaining in Cuba to visit the country using an expanded family visa.

In mid-October, I applied for one of the new family visas and traveled to Cuba with my stepmother, Isabel, to visit our extended family and to explore some of the neighborhoods where she grew up.

Isabel, whose name I have changed out of concern that she won't be allowed back into Cuba and for her family still there, fled the country in 1962 to live with her mother in New York and hadn’t been back to Cuba since. A year after she took asylum, Isabel’s father fled Cuba and eventually joined her. He had been outspoken against Fulgencio Battista, the former Cuban president who was overthrown by Fidel Castro in 1959.  But by 1961 he was a critic of Castro – and a target for the dictator’s new government. Friends of Isabel’s father advised him to leave the country for his own safety.

Matthew Rivera / msnbc.com

A man sings at El Floridita, a bar in Havana, Cuba, known as the birthplace of the daiquiri.

The conditions of his escape and the many years he spent as a voice of the Cuban exile community made Isabel very nervous about returning. She feared, though, that this might be her only chance to visit, as Cuba often changes its travel restrictions. We booked our tickets, but the final details weren’t settled until two days before departure due to the complexity of her visa.

Even given these considerations, traveling to Cuba requires  more work than you might expect. First, the Cuban government requires visitors to buy temporary health insurance even if you currently have a policy. We were also warned to tell people that we were not tourists and were not on vacation, since we were traveling on a family visa. The visa was arranged by a licensed office in the U.S., which serves as a kind of travel agency responsible for arranging the paperwork and purchasing the airfare, hotel accommodations and insurance.

Straddling the border
The first way that Havana surprised me was in its proximity. The flight from Miami took 45 minutes from takeoff to landing, barely enough time for the seatbelt light to turn off. Like other border-straddling cities, the closeness between them belies some of the striking differences.  Miami remains the epicenter of Cuban refugees, and their influence can be felt in everything from local culture to national politics. Havana, on the other hand, is a city whose influence has been nearly extinguished.  By some measures it should be the Capital of the Caribbean, but that title was lost long ago.  

These were the things I was thinking when we began our sudden descent into Jose Martí Airport. When we deplaned, a plainclothes officer immediately approached Isabel at the airport. He took her aside and asked who she was and why she had come.

“I was so nervous,” Isabel later said. She was visiting family and she hadn’t been to Cuba since 1962, Isabel told the officer. ‘Do you think that, since 1962, you still have any family in Cuba?” he replied sarcastically. “You’re not really Cuban, are you?’”

She was shaken, but she replied that yes, she was, and she had all of the legal documents to prove it. Eventually he let her pass to the traditional customs office.

We were met by Isabel’s cousin, Marta, and her son, Antonin (their names have also been changed). Isabel and Marta hadn’t seen each other since they were children. They were not the kind of cousins to call each other or write often, but the reunion was surprisingly warm, and the presence of family helped Isabel forget the scene at the airport. “It was like we were sisters,” Isabel said.

In Pictures: Return to Cuba

Ground rules
Their time together freed me to travel with Antonin, who was happy to play tour guide. I had dreams of riding around in a 1950s Chevy of some kind, but Antonin’s car was an unglamorous gray Datsun, a leftover from one of the previous waves of freedom that Cubans have periodically experienced.

Matthew Rivera / msnbc.com

A vintage car drives by in the suburbs of Havana, Cuba.

Antonin told me how to behave in Cuba. He pointed out Castro’s secluded compound and warned me not to take photos. We drove east of the city and talked about the way people cut the grass by hand, swinging machetes in long, laborious strokes.

He showed me the Plaza de la Revolución, with its super-hero statue of Jose Marti, the nineteenth century Cuban nationalist.  Behind the statue we could see what he imagined was the only lawnmower on the island, an ancient red Toro, circling the government headquarters, and pushed by a man in a white coat, as if he were a lawnmower technician.

In his free time, Antonin was building an apartment in his mother’s house, which could be rented for extra income. Until recently, Cubans couldn’t rent out rooms, but as with a new law allowing real estate transactions, the government had recently permitted this freedom.

Exploring Cuba
I stayed at the Hotel Nacional, an 81-year-old building that is a snapshot of Prohibition-era luxury. The eastern patio to the hotel looks out to the old city, a view that is complimented by a wandering four-piece band playing Cuban standards and two small bars that serve fresh mojitos.  Back inside, the lobby winds away to half a dozen secluded lounges and concert halls. Frank Sinatra once performed at the hotel during a famous mobster meeting (an event that was dramatized in a scene from 'The Godfather Part II').

Matthew Rivera / msnbc.com

Hotel Nacional, an 81-year-old building known for its famous guests.

Today, it’s one of the better hotels in the city because it’s often used by the government to host dignitaries. Travelers who stayed in the other “five star” hotels in Havana showed me pictures of flooded hallways, broken toilets and walls with giant holes in them.

One afternoon, I walked through Havana with Isabel, starting at the Capitolo, which is similar to the Capitol building in Washington, D.C. Havana is a dilapidated city laid out on ambitious, Parisian lines.  Collapsed apartments parallel the once-grand boulevards, the iconic 1950s cars burn black smoke into the city air, and neglected city blocks bracket the views along the famous seawall known as Malecón.

We walked through a crowd of people begging for money, selling souvenirs, or asking if we wanted Cohiba cigars. We moved along a wide pedestrian park called the Paseo del Prado, flanked by large lion sculptures where Isabel remembered that that her father had taught her to ride her bike.

Returning home
After lunch, we went to visit Isabel’s old house in the rundown neighborhood of Centro Habana. Since she left, new families have moved in, but they were happy to let Isabel look around inside.

Matthew Rivera / msnbc.com

A composite of the kitchen, and the spiral stairs in the back, in Isabel's childhood home, in Havana, Cuba. Her father installed the stairs to reach the rabbit coops he kept on the roof. The kitchen was rebuilt after Isabel's family moved out but has fallen into disrepair after years of limited funds available from the government.

“We used to love that house very much,” Isabel said. “My father built a spiral staircase that went to the roof where he used to raise rabbits and turtles. It was like a little farm.”

Most buildings in Havana are neglected until they collapse, and Isabel’s old home is no exception. The staircase is half-destroyed, the windows are covered with plastic instead of glass, and the ceiling has caved in. The family living there said that the apartment is too large to care for. Before Cubans could rent out apartments, the only way to move was to trade with someone, and to pay the difference if one property was worth more than the other. 

We soon left the apartment and decided to walk around Havana. We explored Barrio Chino (Chinatown), a neighborhood that was once home to a close-knit Chinese community but is now a place for brightly painted lunch stands and shuttered offices.  We passed something that looked like a graveyard for late 19th century locomotive engines, parked inexplicably in the middle of the city. 

Changing times
Cubans might view new freedoms granted by the government cautiously, but signs of the changes appear in the open. As we walked, we passed people unfolding tables and tarps, preparing to sell clothes at one of the newly legal markets. Some merchants haven’t yet learned how to make the market themselves, and it takes some questioning to learn what they’re selling, and for how much.

We left on a Sunday, and at the airport we witnessed one of the most surprising views. The departure screen included flights bound for Tampa, Orlando, New York and Miami. As we waited for our American Airlines chartered flight to take off, a JetBlue charter flight landed on the runway, full of visitors who would likely discover Cuba for the first time.

After Isabel’s first experience at the airport, she was relieved that nobody bothered her as we were leaving. While we waited for the flight, she reflected on her reunion with Marta.

“I had a sense of relief that somebody was talking the same language as me, from the same family, with the same blood,” Isabel said. “It was my family, but I was away from them for so many years, from a place that’s supposed to be my country.”

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