In the early morning hours of May 3, Dr. Charles Grossman boarded a plane that took him about 2,900 miles away from his Portland home for a week.
The 94-year-old doctor's goal was not a vacation, but to challenge President Obama by flying to Havana.
His challenge goes back a few weeks to when Grossman read in The Wall Street Journal that Obama had lifted the U.S. ban on Americans visiting family in Cuba, or sending money to the island.
While many saw this as progress in America's 50-year history of contentious relations with Fidel Castro's Cuba, Grossman says it's an inadequate step by the new president.
Grossman, who retired in 2008 from his medical practice as a general practitioner and donating his time at a downtown medical clinic, wants the travel and trade bans on Cuba completely abolished.
"I want Obama to lift the ban now," the bowtied Grossman said last week before leaving. "Not when I'm dead."
Some federal lawmakers agree.
They have introduced legislation aimed at ending all travel restrictions to Cuba. The Freedom to Travel to Cuba Act was introduced by Sen. Byron Dorgan (D-N.D.) and is co-sponsored by Ron Wyden (D-Ore.). (Oregon's other senator, freshman Democrat Jeff Merkley, says he's still reviewing the legislation).
In the House, Reps. Earl Blumenauer and Peter DeFazio (both D-Ore.) are co-sponsors of similar legislation.
To draw attention to the legislation and encourage Americans to pressure their congressmen and senators to pass it, Grossman has intentionally committed a crime by leaving for Cuba on Sunday, May 3, from Vancouver, B.C., without a visa. He got to Vancouver from Portland by plane.
"I could go as a doctor and say I'm going to study what's going on there and possibly get permission," Grossman said. "But I think any tourist ought to be able to go.
"If I don't get arrested, I hope many more people will follow the example," Grossman said. "Give the government trouble. If they have a thousand tourists going to Cuba then they've got problems."
A member of the nonprofit Physicians for Social Responsibility, Grossman says lifting the ban would promote international diplomacy and help the United States regain its role as a leader in diplomatic efforts. Increased trade and tourism could improve the economies of both countries. And he says opening Cuba to the masses presents an opportunity to examine the pluses and minuses of a single-payer health system.
He plans to return May 10 to Vancouver and then fly back to Portland.
Under the Bush administration, the Office of Foreign Assets Control under the Department of the Treasury would typically assess a $7,500 fine on people suspected of traveling to Cuba.
Obama's administration has not made it clear whether it intends to enforce the travel ban similarly.
While in Cuba, Grossman plans to visit a few friends, one of whom is the former head of the country's health department and previously served with Grossman on the board of International Physicians for the Prevention of Nuclear War.
"People were meant to live with other people," Grossman says, "not fight."