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Don't Pack Your Bags for Cuba Just Yet

Sweeping new changes will make it easier for Americans to visit Cuba for the first time in decades. But obstacles and inconveniences remain.

New rules that go into effect Friday will make it much easier for Americans to visit Cuba for the first time in decades, but don't start looking for flights on Expedia just yet.

For one, as of Thursday night, travel websites were still blocking U.S. searchers based on their geographic location and their computer's IP address.

Try to search for "Havana" and the closest you'll get is Havana, Florida.

Currently, only charter flights are available, travel experts said. And first you'll have to fly to one of the popular jumping-off points, like Jamaica, Bahamas, or Cancun.

“We comply with U.S. law and do not support searches to Cuba or within Cuba,” said Kate Williams, a spokeswoman for travel search engine

The best bet for fliers who can't wait would be to go through a travel agent or a booking service, such as, said Chris Guillebeau, a travel author who has visited over 193 countries.

But, despite the relaxing of restrictions, you're not supposed to just jaunt off and start sipping rum and cokes poolside. Under Treasury Department rules, travel to Cuba is only allowed for 12 specific reasons. The pre-approved categories include family visits, educational activities, journalistic activity and others. Tourism is not among them.

Under the old rules, it was possible to visit Cuba as part of a tour group that was built around specific educational and cultural activities. Participation in the prescribed itinerary was mandatory.

Those types of trips will still exist. But the big change is that travelers will not have to apply and obtain special licenses for these activities from the Treasury Department in advance.

Neither will travel agents or airlines, opening up the opportunity for normal scheduled flights.

In other words, Friday's rules-change means getting to Cuba will be reduced to much more of a transaction, said Fodor's Editor-in Chief Arabella Bowen. And an enthralling one at that.

"The music, the beaches, its UNESCO world heritage protected districts ... it's a whole country trapped in time unlike anywhere else," she said.

Once in Cuba, travelers will be able to enjoy new freedoms, like unlimited spending (previously it couldn't exceed $188/day) and the ability to use credit and debit cards. You can also take a bit of the country back with you. U.S. visitors will now legally be able to bring back $100 in rum and cigars, and $400 in other souvenirs.

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Hurdles remain for the casual traveler for the time being and it's worth waiting for more infrastructure to get put in place, experts said. Airports have to open new gates. Credit card machines and systems need to get turned on. Pillows must be fluffed. So experts recommend holding back a bit and watching to see when the country is more ready for visits.

"It will take some time for things to shake out in terms of airlines adding more non-charter flights, people being able to book without going through the current hassle," said Bowen.

But for the adventurous who can't wait, there are definite rewards to being able to make the "first tracks," said Bowen.

Travelers who have made their way in have come back with tales of the beaches, the music at the cafes, and staying in traditional guest houses. You can't book them on or Airbnb, yet, but if you make your way down there and ask a taxi driver for recommendations, for $20 a night you can stay in a historical house featuring a mahogany bed, old chandeliers, and a huge courtyard.

"Now is a great time to visit Cuba," she said. "It's a gangbusters time of year when Canadians descend on Cuba in droves."