There are only a few countries in the world that have intimidated me; places where the social and political atmosphere is so electric, and paradoxical, that the only way to understand them (or begin to) is to experience them.

One such place was Burma. For years, I avoided travel to that country during Aung San Suu Kyi’s house imprisonment, reluctant to put a single coin in the hands of the psychopathic regime that took power in August, 1988. When I visited at last in 2003, the place was nothing like what I’d imagined. Even with a cruel dictatorship in power, the people were a revelation. Their kindness and courage convinced me that no people on earth, regardless of their leadership, deserve to be ignored.

Another example is Israel. Here’s a place so huge in its global influence that, when I showed a classroom of Nepali villagers the tiny country on a world map, they couldn’t believe their eyes. Whatever the reason, it took me fifty years to work up the courage to visit. Israel may be a place where everyone has opinions, and no one has solutions—but no one can form a credible opinion about Israel, I discovered, until they have bought a cup of coffee on both sides of Jerusalem.

Finally, there’s Cuba. It’s funny how a country so close to home can seem so foreign, so unapproachable. Why did Cuba never before suggest itself to me as a travel destination? Back in 1986, Islands magazine offered me an assignment there. I turned it down, claiming it might be more appropriate to send someone who spoke Spanish. What a mistake! But my first book about Nepal had just been released, and my focus was on South Asia. There it stayedÖ until an impromptu dinner in Berkeley in February of this year.

I was sitting next to Mickey Gaynor, a retired Chicago-based attorney who, with his activist wife Judy, was a (very) early supporter of Barack Obama. Mickey, at 76, still hikes, bikes, and pilots a twin-engine airplane. He and Judy were visiting from the Midwest, and had just seen a performance of my solo show, Strange Travel Suggestions, at the Marsh Theater in Berkeley.

“So,” Mickey said. “Is there anyplace you haven’t been that you’re dying to go?”
There was no warning, or any particular forethought. It hit me like a flash. “Cuba,” I said.
His eyes lit up. “Me, too,” he said. “Exactly.”
We looked at each other. “Let’s do it.”

There was one caveat. I very much wanted to make my first trip to Cuba with Malia Everette, the brilliant and passionate director of Global Exchange Reality Tours in San Francisco. Malia has led more than 20 trips to the island; her two sons are half-Cuban. Though she had no trips scheduled for 2011, she agreed to join us during her two weeks of vacation time—if her way could be paid. This would involve a group of at least 10 people. And so I sent out some emails, made some phone calls, and cobbled together a small, simpatico group of friends, colleagues and acquaintances.

Friday morning, June 17th, we are off to Havana. Our trip has been licensed through OFAC (the Office of Foreign Assets Control), so we are able to fly directly from Miami.

The past two months have been a riot of Spanish lessons, Cuba cramming, and doing everything possible to make this infinitely complex country comprehensible. I’ll have a terrific ally in Malia, and a more distant but highly knowledgeable resource in Tom Miller, whose Trading with the Enemy remains one of the most articulate and entertaining books about the country.

“The map,” wrote semanticist Alfred Korzybski, “is not the territory.” Nor are newspaper headlines, radio broadcasts, travelogues or TV specials. Tomorrow, everything I’ve read and heard about Cuba will explode into three dimensions. It’s a breathtaking prospect.

Join me for my dispatches, come as they may. I hope you’ll find them provocative and enlightening—but my goal, as always, is to inspire your own journey.