Visiting Cuba as an American (or an American visa holder) is actually much easier than you might expect. The U.S.-Cuba relations have become increasingly politicized, but despite the recent media coverage, many of the legal avenues to visit Cuba legally remain open.

Here is a quick guide you can use to begin planning your dream trip to ‘forbidden’ Caribbean island. This is by no means legal advice, so I do recommend checking with the U.S. Department of State for the latest regulations:

Book a round-trip ticket through a U.S. Airline

  • Buy a ticket from one of the few U.S. Airlines offering round-trip service to Cuba: as of December 2017, Alaska, United, and Delta all offered flights to/from Havana, Cuba.
  • When buying your ticket online, you will be required to mark the reason for your visit. You’ll want to mark “Support for the Cuban people.”
  • When you arrive at the gate of your Cuba-bound flight, an airline employee will see you the “Support for the Cuban people” visa on-the-spot. I did not need to provide any documentation to obtain this, but bring printed copies of your itinerary just in case.

“Support for the Cuban people” Visa

  •  Under current regulations tourism is prohibited unless expressly approved by the U.S. Government. However, the Obama Administration, authorized 12 reasons for travel to Cuba, which includes “Support for the Cuban people” for:

Individuals and non-governmental organizations that promote independent activity intended to strengthen civil society in Cuba;

  • Some of the 12 authorized reasons do require more strict documentation and/or sponsorship; however, the requirements for “Support for the Cuban people” visa are intentionally vague, so as long you avoid explicitly banned activities (e.g. supporting Government- or military-run businesses), you shouldn’t have any trouble. A full list of restricted businesses is housed on the State Department’s website.

Support Local, Family-run Businesses

  • In addition to avoiding businesses on this list, here’s some general guidelines to follow:
    • DO: Eat at Paladar’s, family-run and privately-owned restaurants.
    • DO NOT: Many restaurants in the cruise ports or at large resorts are Government-run stores or dine at Government-run restaurants.
    • DO: Stay at a privately owned hostel or apartment. There are numerous options available on Airbnb
    • DO NOT: Stay at Government-run hotels.

Book Experiences on Airbnb

  • To be safe, I recommend booking 1-2 Airbnb Experiences per day (4-6 hours worth of activities); these are activities led by Cuban locals and the exact types of activities Obama endorsed through the “Support for the Cuban people” visa.
  • Some activities you can book on Airbnb include, rum tasting, cigar making, cooking classes, salsa classes, and historical walking tours. See my recommendations here.
    • DO: Book a full day of activities planned which prove you were there to “support” the Cuban people.
      • This regulation is incredible vague and I found it difficult to find a list of activities that would be included.
      • I’ve read some websites that recommend booking 8 hours of activities to play it safe; however, if you’re dining at a Paladar or eating breakfast with you Airbnb host family, then that time would also fall under this category.
    • DO: Save your receipts
      • Under current legislation, only the U.S. Treasury Department can enforce the Cuban travel restrictions.
      • As long as you can provide proof that you supported the local people and private businesses, you should be safe.
      • I booked all of my activities online, with USD, and in advance through Airbnb, which made my trip easily comply with the guidelines above.

Take Euros not USD

  • Cuban and U.S. financial institutions still do not communicate. As such, Euros are more easily (and cheaply) exchanged in Cuba.
  • Many exchange houses will add a surcharge to buy USD.