Is it still legal to visit Cuba?
On June 16, 2017, President Donald Trump announced a directive to roll back of Obama's progressive tourism and trade initiatives with Cuba. Technically, the long-standing "tourism" ban to Cuba was never lifted under Obama, it just was never enforced. Trump's administration, however, plans to enforce the ban on "tourism" and bar U.S. companies from doing business with the military-linked entities, which control much of the island's tourism industry from hotels to buses.
According to the Treasury Department, which licenses Cuba travel, the new rules stipulate that a "traveler's schedule of activities must not include free time or recreation in excess." Trump is eliminating travelers' ability to select the "people-to-people" classification on their travel form, which was the category chosen by most Americans who planned their own trips to Cuba under Obama.
12 types of legal travel to Cuba were created under Obama to allow American travel that weren't officially "tourism." Those categories will remain, but many do not apply to the average traveler, such as visiting family in Cuba, attending a professional research meeting, or performing at a a sports event or artistic exhibition. You can still travel to Cuba as part of a group trip with an officially licensed tour operator. Again, independent travelers are barred from traveling under a privately or self-organized educational or cultural trip but can still travel to Cuba as part of a group trip with an officially licensed tour operator.
It's unsure how long it will take for the new policies to take effect but if you haven't already booked your flight, your safest bet is to book through a tour company, meaning you will be traveling under a specific, government-approved itinerary. No more booking your own flight and AirBnB and spending the days at the beach and nights as you please. Technically, Americans will be prohibited from staying in Cuban hotels, renting cars or taking buses since the Cuban government owns most of them. Approved group people-to-people travel through tour operators that stay in pre-approved accommodations and engage in only pre-approved activities will remain legal. Tour operators will be audited by the U.S. government to ensure that their itineraries are in adherence with the new policy – but it's not yet clear how aggressively travel will be monitored or the audits enforced. Trump's rules will make travel to Cuba much more expensive and prescriptive but it won't change your ability to engage with locals, enjoy a beautiful country and lively culture, and have a wonderful trip.
Considering bypassing these rules and traveling to Cuba via Mexico or Canada? Think again. If you try to hide your trip to Cuba upon returning to the U.S., you will be violating federal laws and can face serious punishment.