How you can legally travel to Cuba + Trump’s Cuba Policy Explained


With travel rules to Cuba constantly changing, many confused American travelers are unaware of how to legally travel to Cuba. In this post, I explain what Trump’s Cuba policy actually means for travelers and how that impacts future trips to Cuba. 

For starters, YOU can still travel to Cuba as an American. Many savvy travelers were visiting Cuba all along through gateways and other means which I won’t get into now.

As I mentioned in my other post on Cuba, many travelers fail to follow the rules during vacations to Cuba even though we’ve been warned.

Cuba is not open to Americans for tourism but you can still go! Click To Tweet

What the heck does that mean, exactly?

You are not to visit Cuba to parlay without people-to-people immersion experiences. So, here’s what that might look like: you only hang on the beach, chill in your hotel room or casa, fail to interact and spend the bulk of your time on authentic people-to-people immersion experiences.

Here’s what you need to know about Cuba travel restrictions

Travel records can be audited for up to five years. Keep receipts of your itinerary and records just in case. If you’ve booked through an authorized US tour operator, they usually should keep this for you.

You can still travel to Cuba even though President Trump tweaked travel rules as of June 16, 2017.

As an American traveling to Cuba, you’re expected to engage and interact with Cubans in meaningful ways. Basically, each day of your stay should include full days of immersive experiences. That might look like humanitarian efforts, cultural tours, educational and history tours, and other (documented) activities that connects you to the people of Cuba.

When I went to Cuba last year for Christmas, my engagement included arts immersion (culture, music, dance) history and nature tours. Yes, I got my sightseeing on too but even that involved hanging with locals.

Ultimately, more restrictions are forthcoming under current administration. So, consider the following travel tips when booking travel to Cuba to maintain compliance:
  • Now, travelers must use tour operators in the United States. Purchasing tours from Cuban companies not incorporated in the United States is now illegal.
  • The Office of Foreign Assets Control (OFAC) regulates travel to Cuba and requires tour operators provide proof of licensing authorizing them to conduct Cuban tours under approved categories. It’s your right as a traveler to request this information.
  • US tour operators cannot use Cuban government/military owned services to arrange your tours. In other words, you must interact with the people of Cuba, not the government.

Be smart! Cuba travel reminders:

A few essentials you need:

  • a valid passport with at least six months before expiration
  • a Cuban visitor visa (check with your airline or vessel & how I obtained mine)
  • enough cash for the entirety of your trip, plus entry/exit tax

All these rules, who cares?


Of course there are workarounds for every rule in life. However, when traveling, especially in foreign countries, best to follow rules. While you may not have trouble entering and exiting Cuba, you can run into drama with US customs and immigration upon return with the implementation and enforcement of new rules.

What changed exactly for travel to Cuba?

Many Americans (like myself) traveled to Cuba in recent years under people-to-people individual self-directed general licenses. President Trump canceled as of June 16, 2017.

OFAC has 90 days to adopt and issue the new regulations which is why you may hear people chatting about booking travel before September 16, 2017. Note: The announced changes do not take effect until the new regulations are issued.

In light of the restrictions, people-to-people travel sponsored by US tour operators was not canceled.

You can travel to Cuba legally (in a group) if arranged by an US tour operator.

Remember, prohibited services include those provided by Cuban military. Booking through US tour operators helps to ensure your compliance.

More questions about travel to Cuba? Check out the Department of the Treasury Office of Foreign Assets Control (OFAC) Frequently Asked Questions.

Need help coordinating your trip to Cuba? Drop me a line.


Hey, drop me a line...