Roughly two years earlier, Doug Diehl first began serious planning for a trip to Cuba aboard Consulting Time II, his Morris 486 Ocean Series sailboat. With almost 40,000 nautical miles of blue water under its keel since its 2004 launching, the Chuck Paine-designed sloop seemed to be constantly on the move, having already recorded a transatlantic voyage and extensive cruising in the Caribbean and the Med. But to Diehl, the island of Cuba always loomed large, even if it was forbidden fruit.
Despite his plans and wishes, given the U.S.-imposed travel restrictions on American recreational vessels, the possibility of actually, legally visiting Cuba remained elusive. In December 2014, as President Obama moved to re-establish full diplomatic relations and ease the embargo against visiting Cuba, that began to change. Diehl's two-year-old float plan was quickly dusted off. We would travel under a so-called "general license," granting me permission to travel as a journalist and my crewmates, both environmental professionals, to visit while conducting water-quality research. (That said, though our application was in, when we set sail we did not have in our possession a U.S. Commerce Department export certificate for the vessel.)