Just before New Year’s Eve, my wife and I left our two young children at home with my parents and sneaked down to Havana for a brief getaway. You might be familiar with this uncanny sensation of kidlessness, as if you are getting away with something reckless and potentially illegal. More than once, I felt as if we had discovered a cheat code that had opened a portal into a parallel universe. Suddenly, we were allowed to get a drink. We were allowed to sip this drink. We could read more than a single page in a book at one time. We could enjoy a meal without cleaning yogurt off the ceiling.

Yet this odd feeling of defeating space and time came as much from our destination as anything. Cuba, that elusive island unfurling across the Caribbean like a tangled flag, sits barely 100 miles south of Key West. 100 miles! And yet, in some respects, it might as well be 10,000 miles. The country’s complex identity is inherently bound up in the duality of this proximity, in its ability to feel both so close and yet so far away at the same time.

Our visit came at a strange time for Cuban-American relations, as the country languishes in a period of post-Fidel, post-Obama uncertainty. Many Cubans we talked to cited President Obama’s 2016 visit as a watershed moment, a critical first step in normalizing relations between the two countries. But such optimism has given way to a kind of stagnant waiting game, filled with more questions than answers: Is the sudden explosion of private businesses (like Airbnb) on the island a sign of things to come or merely window dressing on what remains a totalitarian regime? What will happen when Raul Castro finally steps down? In this age of Trump, are Americans even allowed to go to Cuba anymore? And if I did go to Cuba, would my capitalist mind be turned into mush?