Field FAQs with Holly Morris Cuba Libre: Will Obama Bring Americans Back Into Cuba?

Has Raúl Castro’s taking the helm changed anything in terms of Americans traveling to Cuba?

A. Just thinking about the glistening largemouth bass I landed in Cuba’s Lake Zaza is still thrilling. And one day I hope to return to trek the iconic Sierra Maestra and see the area’s famed biodiversity: pygmy owls, frogs the size of dimes, butterflies with invisible wings. But alas, all things Cuban still begin with politics, not adventure.

Raúl is beside the point. The better question is, Will Barack Obama’s presidency change anything? Legally speaking, the Trading with the Enemy Act forbids Americans to spend money in—thus, effectively, to go to—Cuba. Breaking this law, on a civil level, can result in up to $65,000 in fines. It’s silly Cold War detritus, but it remains operative. During the Clinton years, getting cultural or journalistic permission to visit was difficult but doable. Sliding in via another country was easy; and if caught, you just got a hand slap. More recently, our government’s hostile stance toward Cuba—and Cubans—has included new restrictions on family visits and remittances (sending funds home). Getting authorization to travel there has been nearly impossible. Sneaking in has often meant fines and exasperating legal hassles.

Which brings us to now. Obama is on record as saying he’d loosen some restrictions regarding the country, which could be just the beginning. “Cuba would see a flood of American travelers if the ban was lifted,” says Bruce Poon Tip, founder of Ontario-based GAP Adventures, which offers 18 Cuba itineraries. “There are few places with the strong island culture, the pristine beaches, and enough activities for even the most avid adventure seekers.” I’d bet a tinkling mojito and a ’57 Bel-Air hardtop that the economic embargo comes tumbling down during the Obama era. Stand by for the new political reality.

Holly Morris is a TV host (

Treks in a Wild World