Should we go? It only took us a moment to agree. We had to. Mass Humanities was sponsoring a trip to Cuba in January, 2011, and it seemed like a once-in-a-lifetime opportunity. After all, Americans don’t usually get to go to Cuba. And although neither of us had had any special interest in Cuba, the country has been a presence in our lives ever since we were frightened as children by the Cuban Missile Crisis. Cuba is an anomaly, a country with a singular history and a unique relationship with the United States. And the promise of this Mass Humanities trip was that we would not simply be tourists wandering around as outsiders. Instead, we would be immersed in activities intended to give us insight into Cuba past, present, and future.

The brief forty-five minute flight from Miami to Havana in no way prepared me for the abrupt change in cultures. Years of seeing photos of the city with 1950s American cars everywhere didn’t prepare me for the sight of a city that must once have been grandiose but which apparently has seen little in the way of repairs—or paint—for half a century. There’s still a kind of strange beauty in Havana but just as you begin to romanticize the ruins, the sight through an open doorway into a large family crowded around a TV in a single crumbling room reminds you of reality.

In the days that followed, the 21 members of our Mass Humanities group toured art museums, sugar plantations, and botanical gardens. We tested our muscles against the heavy beams once pushed by slaves in order to press syrup from sugar cane. We walked the colorful streets of Trinidad, a UNESCO World Heritage Site, and we walked beautiful beaches as a brilliant sunset fell over the postcard-perfect scene of water, sand, and palm trees. After meeting with the Cienfuegos Union of Artists and Writers, we returned with the printmakers and photographers to their workshops to rummage through the recent work that was piled on top of printing presses and scattered in corners. The Chorus of Cienfuegos treated us to a private concert of classic Cuban songs and intermittently broke out into dance before serenading us with a beautiful rendition of “Shenandoah.” And at a rehearsal of Danza Contemporanea de Cuba, we quickly moved our folding chairs back closer to the wall as the members of the dance troupe leaped over our knees and the floor shook.

Perhaps even better were the conversations we had with Cuban scholars, a representative from the U. S. Interests Section in Havana, leaders of foundations and museums, the head of a synagogue, a man who runs a restaurant in his home, an economist turned bed-and-breakfast proprietor, artists, writers, and musicians. What emerged was a complex picture of what life has been like in Cuba since the Revolution in the 1950s. Following the dissolution of the Soviet Union in the early 1990s Cuba entered an economic crisis called euphemistically by its government the “Special Period.” Today, Cubans seem aware that they are entering an even more drastic “Special Period.” Between the time we signed up for the trip and our departure, the Cuban government announced the layoffs of 500,000 government workers who will be called not “unemployed” but “available,” and plans are underway to try to address some of the crushing economic problems by loosening some restrictions on private enterprise and property ownership. The countless murals of Che and Fidel that ornament buildings throughout Cuba aren’t enough to keep the walls from decaying. Yet despite all the uncertainty, most of the Cubans with whom we spoke are hopeful. They seem grateful that Raoul Castro is willing to experiment with changes his brother, Fidel, might not have endorsed. We were struck by the warmth of the Cuban people, and their readiness to give an enthusiastic welcome to Americans, despite the fact that they believe their lives would improve immediately if only the embargo were to be lifted.

But probably the very best thing about the trip was the conversations we had among ourselves—over espresso in the morning or over lobster at dinner, while riding the bus through fields of cane or walking through a marketplace hung with table cloths hand embroidered by the women of the village. How could so many people who had been strangers to one another enjoy so many common interests and deep discussions? (And long laughs.) We’ve already made plans for a reunion and I have no doubt that many of us will keep in touch with each other in the future.

When we made the fateful decision to make the trip, we didn’t think much about the benefits of being in the Caribbean for a week in January although not a day has gone by since we returned to the perpetual snowfalls of Massachusetts that I haven’t remembered with longing the tropical breezes of our trip. But what I really think about several times a day is the beauty of the Cuban landscape (and the Cuban cities), the richness of the Cuban culture, the hope of the Cuban people, and the warmth of the new friends who shared our adventures. Yes, we HAD to go. You do too.

[For a selection of photos from this trip taken by David Tebaldi, see the “MH Cuba Trip 2011” photo gallery to the right of this essay.]