Touring Old Havana is within legal reach of American travelers now.
As with everything related to Cuba, it’s complicated. But yes, Americans can now come to Cuba — legally, and on their own, without having to pay for an expensive organized tour. The key is to follow an itinerary that includes a full schedule of educational, cultural, and professional activities during which you interact with locals.
General sit-on-the-beach tourism is still banned and, as a result, American travelers need legitimate reasons to visit. Before boarding your flight, or when buying your visa, you will be asked what category of travel your trip falls under. The Department of Treasury allows people to travel legally to Cuba without additional permits if they fall into one of 12 categories. Among the categories are “visiting family” and “help for the Cuban people.” However, most travelers will qualify under several categories that have been dubbed "people to people" travel, including "professional research and professional meetings; educational activities; religious activities; public performances, clinics, workshops, athletic and other competitions, and exhibitions." New rules also allow family members to accompany an American who is traveling legally under the 12 categories.
To be safe, you should keep a record of your itinerary and evidence of your educational activities and meetings. (For example, an itinerary with names and contact information, diary entries, or receipts.) “People to people” activities could also include interviewing people you meet on the street (as long as you have notes) or setting up meetings with professionals in your industry. According to travel agents, educational activities could be classes involving cooking, salsa dancing, Spanish language, art, music, architectural history, or anything else that might pique your fancy. Travel guides on Cuba can provide information on such classes. Also to come in future posts, I’ll also explain how to book your flights and accommodations, and I’ll suggest some worthy “people-to-people” activities.
For Americans, travel to Cuba is also getting easier with the start of new direct flights. So far, they are still limited and don’t arrive in Havana, the destination of most interest to tourists. But beginning in November, travelers will have more options with new flights from several U.S. cities to Havana. In future blog posts, I’ll explain your flight options and how to book accommodations on your own.
Of course, some Americans have come to Cuba illegally for years, spending time on the beaches and doing usual tourist activities, without getting into legal trouble on their return to the U.S. But given that Cuba is not a resort paradise and you’re better off going to Cancun or another Caribbean island if you just want beaches, my personal opinion is “people to people” travel offers a more rewarding experience. If you come with a sincere intent to engage and interact with locals while you’re here — it’s almost impossible not to, given how friendly Cubans are — you'll satisfy the legal requirement and have a more fulfilling experience. If you want more information, please visit the U.S. Department of Treasury's page on Frequently-Asked Questions Related to Cuba.