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.
"Just 80km," we said. "A lookout is all we want!"
But no one - no one - not even for several months' worth of the average wage, would drive us to Guantanamo Bay.
The locals like to think the base doesn't exist, a cabbie in a late-50s Ford told us.
The 166 men still locked up inside must feel conveniently forgotten as well.
Until the past few weeks - as more than half starve themselves to near death - their plight and existence has been out of American consciousness for a conveniently long time.
Many have languished without ever being charged with a crime. Out of sight and all that.
Remember, Barack Obama failed in his efforts to close Guantanamo down.
Surely, if a country considers itself an authority to arrest and detain foreign men, holding them in jails on its own shores is a fairly reasonable expectation? Even the dirtiest of laundry; the most dangerous of accused terrorists, could be distributed throughout the US military prison system with little noticeable effect.
Though that would make Geneva Convention standards all the more applicable, of course. And while the US Congress is happy to continue holding alleged terrorists, most senators still subscribe to the Nimby school of thought: not in my back yard.
The Gitmo prisoners might take a little solace; their hunger strike has at least gained some headlines. But in predicting their fortunes they need only look at the recent Senate gun debate. It might turn them back to their meals.
In the US, even a nation's attention, a President's campaigning, and support is no guarantee.