Yes, You Can Still Travel to Cuba! Crooked Trails Offers Two Amazing (& Legal) Travel Options

Cuba flag legal travel

April 2018

Cuba flag legal travelLast June, President Trump proposed tougher travel restrictions for American visitors to Cuba, and on November 9, 2017, those regulations went into effect. While these tighter rules make it slightly more complicated, it is still possible to travel legally to Cuba.

Crooked Trails has been creating custom group and individual travel programs to Cuba since 2016 that are compliant with federal regulations. Find out how we can create a custom itinerary to Cuba for you and your friends and family. You can also join us on one of our amazing “People to People” small group trips!


Traditional American tourism to Cuba has been banned under the U.S. embargo since 1962. But in 2014, during the Obama administration, these regulations were loosened for Americans visitors as long as the trip fell under 12 legal travel categories. Although the current regulations enacted under the Trump administration restrict the categories of travel for individuals and small groups, they do allow the opportunity to travel under the categories of “Educational Activities: People to People” and “Support for the Cuban People”.

In short, travel to Cuba is still legal for Americans!


Cuba road travel car by Paula Rosecky

“People to People” category = guided group travel

As an American, you can travel under the “People to People” category if you are participating in a guided group travel program. That means you cannot travel independently under this category, but you can join an organized group with a pre-planned, compliant itinerary and an accompanying US-based guide.

Crooked Trails is excited to offer guided People to People programs to Cuba.  We’re currently accepting applications for our September 2018 group departure – learn more about it here!

Trinidad woman view by Lauri Jordana

 “Support for the Cuban People” category = custom, private travel

The other category you may currently travel to Cuba under is “Support for the Cuban People”.  To travel legally under this category, you will need to abide by the regulations and participate in activities that are in the spirit of the category.  These regulations state:

  • A traveler is required to provide support for the Cuban people and promote independent activity intended to strengthen civil society in Cuba.
  • A traveler is required to engage in “Support for the Cuban People” activities consistent with a full-time schedule. Examples of these types of activities include:
    • Meeting with local people, artists, musicians, accommodation owners, tobacco manufacturers and people who own their own business
    • Staying in private local homes
    • Exploring independent museums (there are some very interesting ones in Havana!)
    • Shopping in independent markets and shops
    • Participating in dance classes (popular and folkloric dances)
    • Meeting and engaging with musicians at performances
    • Attending art shows
    • Discussing Cuban society and culture with local Cubans
  • Travelers must retain all documentation, such as receipts and itineraries, and keep them accessible for five years from the travel date.
  • A traveler must avoid all transactions with a GAESA-owned (Cuban government owned) business, such as certain hotels and restaurants.

Cuba signWe can help plan your private trip to Cuba and ensure that you are not only meeting the new Cuba travel requirements, but also connected with some amazing locals and unforgettable experiences. Crooked Trails organizes custom itineraries for you and your friends and family that use casa particulars (family homes) and local hotels not owned by the government.  Our daily activities focus on meeting with local people to learn more about Cuba and supporting local businesses and independent entrepreneurs such as filmmakers, artists, musicians, guides, chefs and more.

Work with our Cuban program planners and our local Cuban friends to design a completely personalized itinerary based on your specific needs and interests, that’s also compliant with the new regulations. Check out a few of our sample itineraries here. Or, if you’re ready to start planning, give us a shout!



The Cuba travel visa is issued through the airline you fly to Cuba with. Travelers can either order a visa ahead of time through an online visa service such as Cuba Travel Services or purchase it at the boarding gate. In order to be able to qualify for a Cuba travel visa, you must confirm that you are traveling under one of the 12 legal categories.


The Trump administration has directed the Department of the Treasury to “stringently” audit American travelers. This can result in more scrutiny at US airports from immigration and customs agents, as well as the possibility of needing to produce post-travel records. Travelers must maintain a full schedule of licensable activities in Cuba and keep trip records for five years. Crooked Trails is responsible for creating a compliant itinerary and providing it to the traveler, but the traveler is responsible for keeping a copy.

Still have questions about traveling to Cuba with us? Or just ready to start planning? Contact us – we always love to talk travel!

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