We were young and dumb and surviving on rum - so it seemed a good idea at the time.
At a bar on a hilltop, with sleeves rolled to our shoulders and a man sucking a smouldering Cubano nearby, we settled the debate and decided to pursue an adventure. What's the worst they would do; lock us up?
Santiago de Cuba is a big town on a blazing Cuban coastline that reminds tourists of Johnny Depp as a pirate.
It's the birthplace of Fidel Castro's first and failed revolution, mangoes grow wild and, like most spots in Cuba, the locals are keen for anything that might earn them some cash on the side.
But as three travel nerds from New Zealand would discover, enterprise didn't extend much further east.