Read an interview with photographer Michael Dweck about his book, shot in Cuba.

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Havana is a place that has been high on my travel list for years. My grandmother used to talk about going in the early 1950s, when the city was at the height of its glamour. From her stories, it sounded like the best of Vegas and Miami with European and Caribbean influences and, of course, Cuban music, cigars and rum. So when the Obama administration reinstated travel licenses for People-to-People Cultural Exchanges, we immediately enlisted help from one of the best insiders doing cultural trips to Cuba to put together a special Indagare itinerary. (In fact, one of our team was on the first flight of People-to-People travelers that landed in Havana in August to scout for us.) And clearly Cuba ranks high on many of our members’ travel wish lists because when we offered the four-day Insider Trip to Havana to alums of our past trips, it sold out in just thirty-six hours.

Our group of sixteen flew direct from JFK to Havana on one of the regularly scheduled charter flights that caters to Cuban-Americans. We had all heard that visiting Cuba was like stepping back in time, and that experience actually began when we boarded the ancient unmarked clunker from the 1970s. Over the course of the next four days, we explored the cobblestoned streets of Old Havana, with its glorious colonial buildings, in the company of a renowned local architect; were given a crash course in Cuban art by a curator of the Museum of Fine Arts visited Ernest Hemingway’s perfectly preserved estate in the countryside; tried to learn to salsa to the music of members of the Buena Vista Social Club; and met with Cuban artists and foreign ambassadors who gave us a sense of everyday life—its challenges and privileges. For example, since food is scarce and there really is no concept of private property, even farmers cannot slaughter the cows they keep. In fact, the penalty for killing a cow is twenty years and for killing a person only eight. So maybe it shouldn’t be surprising that cows have a “habit” of wandering onto train tracks: once they are killed, a whole village can dine on beef.

One of our daily privileges was dining in the different paladares (restaurants in private homes). Our second night we climbed the grand but dilapidated stairway of a beautiful Baroque building in Old Havana, passing paint-peeling columns and murals of Che Guevara, to arrive through an elaborately carved wooden door into a dining room with crystal chandeliers, modern art and fabulous food. Another day, we pulled up to a house in a residential area to find art-filled rooms and an open kitchen. The next day we had one of our most memorable lunches on the top floor of an apartment building, where the rooms had been converted into the chic Café Laurent. In a country with food rations, how were they able to whip up such glorious meals? Cuban ingenuity. No wonder the Cubans are known for their national pride. You can see their resourcefulness in the hundreds of American cars, their 1940s and ’50s designs powered by parts salvaged from Russian and Chinese models. “We don’t have mechanics,” our guide told us. “We have car magicians.” And it’s true: the entire city feels like a vintage car rally.

Just a few days before we arrived it had been announced that Cubans would be allowed to own cars, which really means that they have the right to sell them and keep the profit. As if someone had waved a magic wand, those who previously were merely in possession of a glistening Buick convertible now have an asset they can liquidate. A similar change regarding real estate had been passed just weeks earlier, and citizens are thrilled at what these loosening of restrictions will mean. After all, in a country, where almost everyone works for the state’s meager wages, some now have valuable assets. Still average Cubans will not be allowed to buy new cars; only the elite, such as doctors and artists who earn foreign currency, may purchase the 2012 Mercedes models. Confused? That is Cuba—a place, we learned, where little is simple and where layers of meaning and mystery continually unfold.

The photographer Michael Dweck recently spent months in Havana shooting his wonderful new book Habana Libre, which documents a side of the city rarely seen. (Read an interview with him.) It is the world of artists, musicians and the privileged class. Yes, in this socialist country everyone is not equal. The sons of both Fidel Castro and Che Guevara, who most Cubans have never seen, appear in the stunning black-and-white photographs along with models in nightclubs and at the country club. Many of his subjects are free to travel to Europe and the States but they return to Cuba. Their ties of kinship to their families, friends, neighbors and countrymen, perhaps because of shared hardship seem stronger. Cubans’ sense of loyalty is fierce, as evidenced by both the touching reunions at the airport each day and by the refusal of those who left after the Revolution to ever return while Fidel is alive. It may seem contradictory but it’s Cuban. According to Dweck, who has visited dozens of times, the best way to enjoy Cuba is, “Just go with it and enjoy where you are and what that means.” Or consider the words of the author Graham Greene, whose classic Our Man in Havana still resonates. “When we are not sure, we are alive.” We certainly felt alive in Havana.

Read observations and see glorious photographs and watercolors by two of the wonderful women who joined me on our Indagare Trip at Hollye Jacob’s blog www.thesilverpen.com and on Frances Schultz’s blog www.francesschultz.com

Read Why Go Now

Read Havana: Cheat Sheet

Learn about our Insider Trips to Havana in 2012 and how to book a spot

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There is a reason that it’s taken me three months to write about my trip to Cuba . The article that I would have written immediately after my return in August is far from the piece that I am writing now. Perhaps I needed 90 days to fully process my experience, in a country that is just 90 miles from our own.

I arrived for a long weekend in Havana during the peak of the summertime heat; an eager, excited and relatively naïve traveler as part of the first group of Americans to go on freshly-legal people-to-people tourist visas since they were restricted under the Bush administration in 2004. Cuba is a place that I have longed to visit for as long as I can remember, a sentiment shared by many Americans who have an appetite for curiosity for this neighboring island nation, especially since its history is so intertwined with our own. I expected fabulous music and art, beautiful architecture, and cuisine like one of my New York favorites, Café Habana. What I didn’t expect was to turn into a weekend anthropologist, parked on dark side streets talking to locals about what life was really like in Cuba.

Despite the politics, and the palpable desperation and strife that the majority of the population lives with everyday, there has been one distinct benefit of Castro’s Revolution. It’s as if the country was placed in a bubble in the 1950s, and Americans are now allowed to participate in time-travel. The old cars, the crumbling buildings, the men smoking cigars in their guayabera shirts and Panama hats, the absence of chain stores and American staples like Coca-Cola was all really refreshing. The effects of globalization have rippled to remote crevices of the world, but Cuba has remained immune.

And the capital of the “American Riviera,” known for ritzy casinos and black-tie parties in the hey-day of the 1950s still retains its elegance. Old Havana is beautiful, and its residents are proud. Strolling through the streets at dusk, with pastel light creating pastel shadows that obscure piles of plaster crumbs in the corners, the city is very reminiscent of Venice but entirely Cuban.

Before embarking on a trip to Cuba , there are a few things everyone should know. While there are now several companies offering legal trips to Cuba (like the company I went with, InsightCuba), be aware that your guide, along with everyone else, is an employee of the government. Currently, Cubans don’t have access to information or enjoy the same freedom of speech that we do. The people are warm, and excited that Americans are flocking to their shores. Engage people in conversation, and don’t be afraid to ask questions. Changes are underway, and the Cuba of the future could be very different from what it is today.

With Obama’s presidential order easing the embargo and allowing Americans to obtain special visas from licensed companies, there has been a surge in tourism. There are several flights every day from Miami, and the four largest U.S. airlines are expected to offer 25 weekly flights from cities around the nation by the end of 2011. The José Martí International Airport is an emotionally-fueled place, where family members separated by less than one hundred miles of sea—and decades of politics—reunite. Sisters embrace and squeal with joy, tears streaming down their faces. Perhaps it’s only been a year since their last airport greeting like this, or perhaps it’s been fifty. The flip-side of the enthusiastic arrivals are the heartbreaking goodbyes. A glass wall is warm with breath, tears and fingerprints from the Cuban half of the family, who is once again staying put.

My entire weekend was marked with centrifugal moments of heavy observations, surreal shock and wanton glee. Somber political conversations whispered with my driver were coupled with the teenage amusement of cruising down the Malecón in a 1952 Chevy with windows down. What I want to remember about my weekend in Havana is the music, the dancing, and the daily sunset mojito on the veranda of the Hotel Nacional. What I won’t forget about my experience are the honest conversations about the hardships endured as an expense of the Revolution, and the simple freedoms that we take for granted just 90 miles away.

Indagare is now offering Insider Trips to Cuba, a highly-curated long weekend of art, music and culture exclusively for our members. For information on our Insider Trips to Cuba, contact Brooke Pearson at brookep@indagare.com or 212-988-2611.