Even with the latest round of changes to the U.S.-Cuba tourism policy, American vacationers can still legally visit. Our reporter sets out on a weeklong cycling trip in the Cuban countryside

MY LAST TRIP to Cuba had been in 1997 when the country was still enduring the periodo especial—the euphemistically dubbed “special period” of deprivation after the Soviet Union’s collapse. At that time, traveling under a journalist visa, I noted roads devoid of cars and bare store shelves. Despair and paranoia pervaded the air, with Cubans miming a long beard when criticizing Fidel Castro rather than speaking his name out loud.

I found things distinctly different during my trip to Cuba two months ago, nearly two years into...

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