Cuba will break your heart.

This is a land of contrasts: Young and old, vibrant and tired, joyful and hopeless. It is an architectural gem that rises to greet its visitors from impossibly blue waters.

There are outdoor cafés, nightclubs, fancy restaurants. There are happy times.

But there is also crumbling infrastructure. And shanty towns. And the boat carcasses that litter the landscape – reminders of Cubans' failed attempts to reach the mainland.

I have come to Cuba as part of a growing cultural exchange and tourism program instituted by President Obama in 2011.

In this system, a person gifted in the sciences could wind up working in tourism. And your doctor may have made a better plumber.

- Lion Calandra

My group, comprised of 10 Americans, is among the first in five decades to get government approval to set foot on Cuban soil. U.S. citizens are barred from traveling to Cuba without permission under a trade embargo imposed half a century ago which can only be lifted by Congress.

The Cuban government keeps a short leash on the Americans who travel here. U.S. visitors must be accompanied at all times by a local Cuban national tour guide; there is little to no free time and no wandering from the pack.

The U.S. government has its rules, too: No souvenirs made at a government-run factory can be purchased. Handmade crafts, books and music CDs are allowed; T-shirts, cigars and rum are not. The trip was intended to be a cultural experience, so time at the island's world-class beaches, golf courses or diving venues is a no-no.

Americans, by order of the Treasury Department, keep a written record of each day's interactions, or "people-to-people exchanges," that must be retained for five years following the visit.

I arrive in Cuba and land in 1959.

There is no cell phone service. There is limited Internet. Twitter and Facebook are blocked. I pay for things with cash; no credit cards drawn on a U.S. bank are accepted here. The streets are filled with "Yank tanks" – those classic American cars from the 1950s and '60s that Cubans have hung onto through the decades because of government restrictions on car ownership.

My hotel, the Hotel Nacional de Cuba, is a beautiful, broken-down palace. There are marble floors and gargantuan columns. Rooms overlook the harbor. The mahogany bar is resplendent; walls are filled with pictures of the celebrities who passed through here, as our guide put it, "before the Revolution triumphed." Winston Churchill, Charlie Chaplin, Meyer Lansky, Lucky Luciano, Jorge Negrete, Spencer Tracy, Johnny Weismuller, Frank Sinatra, Ava Gardner, Nat King Cole, Ernest Hemingway. The list is endless. And so are the Mojitos.

The hall carpets smell of mold and the paint on the walls is peeling. Every afternoon, a surge interrupts electrical power to the hotel – lights flicker, elevators stall, blenders stop.

It is hard to imagine I am a 45-minute plane ride from Miami.

During the day, we visit museums, churches and a Santería temple; the group is squired through the home of artist José Rodríguez Fuster ("the Picasso of the Caribbean"); we take a salsa lesson, and visit a pottery studio and a cigar factory. We stop by a nursing home. There is a visit to a dance school, and we tour a medical clinic. In the countryside, we visit botanical gardens and an opera house. We listen to a state-sponsored choir.

The itinerary includes the Bay of Pigs Museum, a spare, two-room exhibit in the provincial city of Matanzas that offers visitors a timeline of the U.S.'s failed military invasion of the island in 1961. There are uniforms, a tank and guns; exhibits – written in English and Spanish – refer to Americans as "The imperialists" and "the anti-Revolutionary forces." There are heartbreaking portraits of the young Cuban men who died in the fighting.

In Old Havana, I meet Daniel, an architect helping to rebuild parts of the city that "look like a war zone." The group does not visit the dilapidated area; what we are shown is a scale model of the project, a UNESCO World Heritage Site. It is one of the few projects in Cuba that is not funded by the government, and proceeds from postcards and books help pay for the restoration. Daniel is asked why the Communist regime does not give money to the project. "Like most Cubans, I do not understand many things about my country," he says.

In our group, the Army veteran from Washington state introduces himself as "El Jefe" wherever we go; a woman from California claims Ernest Hemingway was an anti-Semite during a visit to the writer's home, Finca Vigía; the octogenarian in the group is asking Cubans if they've heard of "Ricky Ricardo."

At night, we eat dinner at beautiful spots like the open-air Divino Restaurante, a privately-owned organic farm with world-class cuisine. Another dinner, at El Colonial, offers us the chance to eat a traditional pork dish in a beautiful mansion as musicians sing "Cuando Salí de Cuba" ("When I Left Cuba").

This is Cuba scripted, a halftime show of "educational exchanges" put on by the Raúl Castro regime.

The propaganda is palpable: According to our guide, a twenty-something woman, "when the Revolution triumphed" Cuba rid itself of prostitution, gambling and drugs. And Cuba, we're told, has a cure for cancer – a medicine called "Blue Scorpion" that is not exported because of the embargo. There are no guns in Cuba because they are illegal. Fidel Castro closed churches because they were fronts for the CIA.

The medical system is presented as a utopian ideal in which "No one has to pay for health care, like in America." There is no mention of the tiered system that gives government officials immediate access to treatment while the poor wait months to see an overworked doctor at a rundown neighborhood clinic with limited supplies.

Education is free, too – a matter of pride for our guide, who has never left the island. "No one is out of work in Cuba like in America. No one has to look for work because everyone is assigned a job that is matched to their skills."

In this system, a person gifted in the sciences could wind up working in tourism. And your doctor may have made a better plumber.

Absent from the highlight reel is a full accounting of Cuba's double-currency system. There is the Cuban peso, used by the locals, and the Cuban convertible peso – or CUCs – which is reserved for tourists. (One CUC equals one U.S. dollar.) Most Cubans are paid in pesos, earning on average 300 pesos a month, the equivalent of $15. Some goods, like milk and shampoo, must be purchased using CUCs. Gas is four CUCs a gallon, a full-size mattress is 2,100 pesos, a flat-screen TV is 1,400 CUCs. A shortage of food and other items – like spare parts for the vintage automobiles – has fueled the black market here, and Cubans navigate long lines outside change offices to convert one currency into the other. 

"The bureaucracy is killing us," one young Cuban tells me.

A lecture on Cuban-American relations by Camilo García López-Trigo, a former diplomat with Cuba's foreign ministry, reveals that tensions between the countries started long before Fidel Castro, with the Platt Amendment. The relationship also has been hurt by America's "illegal occupation" of Guantanamo Bay Navy Base, and the "unfair treatment" of the Cuban 5, the men convicted in Miami of espionage and conspiracy to commit murder.

García López-Trigo is asked about American Alan Gross, the former U.S. subcontractor who has been imprisoned in Cuba since 2009, and journalist Calixto Martínez Arias, who was released from a Cuban jail last year after being arrested for allegedly insulting "the dignity of a public official." He is unfamiliar with either case.

He tells the group that the many books on Fidel Castro and Che Guevara hawked during our trip are "because the tourists want them."

And, regarding the embargo, García López-Trigo says, "When the U.S. goes to practical terms, it can overcome anything."

"The embargo is not the problem," Jaime Suchlicki, director of the Institute for Cuban and Cuban-American Studies at the University of Miami, tells me after I have returned to the U.S.

"Raúl [Castro] is not changing Cuba; he's muddling through," adds Suchlicki. Cuba "politically, it's no different than North Korea."

Our guide says cars have recently been made available to buyers. But there is no mention of a state monopoly on automobile sales that sees a Peugeot 508 listed at $262,000, far above its $29,000 sticker price.

Some say President Castro is championing limited free-market reforms, a Cuban soap opera has had its first gay character, and the island has a Gay Pride Day. Miami-Dade students are housed on a cruise ship for a "Semester at Sea"; the first commercial flight in 50 years recently arrived in Cuba from Key West; a new port is under construction in Mariel; musicians and dance troupes are performing overseas.

I leave the island, and replay in my mind the laughing schoolchildren, the delicious food, and my ride in a 1951 DeSoto Suburban. I am happy. The beautiful Cuban people have seen to that.

But I am left, too, with a lyric sadness. That, I know, is courtesy of the Cuban government. As they say on the island about things difficult to explain, "It is complicated."

But allowing people to be the architects of their own destiny is rather simple. And if the government cannot figure that out, history has shown that the people will.

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