Just 112 miles from the tip of Florida, Cuba has been off limits to American travelers since Kennedy clashed with Castro.

They say life happens when you’re making other plans. Earlier this year, when I was planning a trip to Amsterdam, I stumbled across a company called Cross Cultural Journeys, a travel organization that escorts groups of U.S. citizens to Cuba. Although technically, it’s not illegal to go to Cuba if you’re an American, it is illegal to spend money there without a special license. Thanks to the “people-to-people” license the U.S. government granted to Cross Cultural Journeys, I was about to fulfill one of my longtime travel fantasies, deciding that Amsterdam could wait and defied the repeated question from friends and family: “Cuba??”

I flew to Miami where I joined a group of 11 fellow travelers (mostly from California) for a quick 45-minute flight to Havana. It was there that we began our weeklong tour. Or, uh, people-to-people exchange.

I didn’t know what to expect from Havana, but found it to be strikingly charming and picturesque. Havana is a modern city, yet feels like stepping back in time. The streets are filled with American-made cars from the 50s. Old Fords, Chevys, Dodges. What we would consider classic autos are simply standard transportation in Cuba. They’re all in remarkably good condition, kept running, we were told, with Russian parts.

Alongside the vintage autos are scooters, horse-drawn carriages and pedi-cabs (I nearly got lost one day because of the language barrier between me and my pedi-cab driver). Havana is also a walking city, easily traversed on foot, and we found it a great way to experience the sights.

The architecture in Havana is uniquely beautiful, faintly European in appearance but with a definite Caribbean flavor. A surprise to me was the bold and colorful appearance of the city. Many of the buildings are painted in bold primary colors: blues, yellows, reds, giving Havana a unique and vibrant feeling. Although many of the buildings have fallen into disrepair, we saw renovation work being done throughout the city.

We were told in advance that Cuba isn’t noted for its cuisine — it’s true. Pork and fish are the main meat dishes, accompanied with rice and beans. Although the food was nothing special, what was special were the so-called paladars: privately-run restaurants, often in homes, converted into casual eateries. They were consistently pleasant and charming. The wait staffs were always friendly and attentive, and although the food itself was nothing special, our hosts did their best to present it with artistic flair.

We took a walking tour through the Vedado neighborhood of Havana one afternoon, escorted by a local guide who told us about the religious traditions of the nation. We visited several homes where we saw homemade religious shrines. Catholicism is still practiced in Cuba, but somewhat discretely and often mixed with other spiritual practices such as Santeria and Palo Monte.

We found Cubans to be friendly and welcoming; it’s the governments that don’t get along. Although Cuba is unquestionably a poor nation, a surprise was that it didn’t feel depressingly so. The impression we got was that most (not all) Cubans have the basics: food, housing, transportation, and they seemed happy with what they have.

While in Havana we also visited an art school called the Instituto Superior de Arte. The paintings, sculptures and other art projects were eclectic: sometimes humorous and often quite beautiful. The art students were enthusiastic and seemed happy to show us their work. We also visited a ballet school where we watched rehearsals in progress. We were all impressed by the importance placed on arts and culture in Cuba. During a visit to a local church in a town called Cojimar, the minister’s 11-year-old son played the violin for us. We were all impressed by a musical ability that seemed beyond his years.

On our final night in Havana we were scheduled to attend either a ballet or a movie (titled “Juan of the Dead”) but a citywide blackout — a not uncommon occurrence in Cuba — left the theaters literally dark.

Leaving Havana, we were driven by bus to the French colonial town of Cienfuegos. Located on the southern coast of Cuba, it was a charming place, with a town square that was particularly picturesque (a local band was playing in the gazebo while we were there). Along the way we stopped to visit the former home of Ernest Hemingway. The living room walls were adorned with animal heads, his typewriter was still in place in his den, and behind the house were the graves of his departed pet cats. We were told Hemingway paid the then-exorbitant price of $18,000 for his sprawling estate.

Our final destination was the Cuban town of Trinidad. There we visited a number of sights including a sugar plantation. Sugar production has traditionally been one of the key industries in Cuba. Earlier, in Havana, we visited a cigar factory, another key export for Cuba. No photos were allowed there, which is a shame, because it was an amazing sight to see. The cigars are entirely made by hand—even the boxes are made and decorated by hand—and it was fascinating to watch as hundreds of workers seated at individual desks each rolled a new cigar every couple of minutes.

Our hotel in Trinidad was located next to the beach. Being that we were on an education journey, we weren’t legally permitted to be taken there. So we all found our way there on our own free time. But you didn’t hear that from me.

From Trinidad, we drove back to Havana for our flight back to Miami. As much as we all enjoyed our stay in Cuba, it was also apparent that everyone felt ready to be home.

Our final night in Havana was marked by another blackout. It’s such a common occurrence in the city that both the hotel and restaurant were equipped with generators. In Trinidad we were without running water for a time, and throughout the trip we found that hot water was only intermittently available.

Many buildings are air conditioned, but it works only sporadically (as I discovered in my third floor room in Trinidad, stifling in the 90 heat and 65 percent humidity). During meals it was typical for flies to buzz around the tables, both indoors and out. Cuba was a remarkable experience, to be sure, yet it also gave us a renewed appreciation for our U.S. passports.

Of course, it came as no surprise that Cuba didn’t offer all the comforts of home. Even if we hadn’t been aware of what to expect, the travel materials we received prior to the trip stressed two words: “be flexible.” That phrase became a sort of motto for the trip and was repeated good-naturedly throughout our stay. Everyone in the group saw these little travails as simply an authentic part of the experience.

And a great experience it was.

Copyright © Gary Conrad/2012 Singular Communications, LLC.