Closed off to American visitors for over 50 years, Cuba now is shaking off the slumber and has opened its doors officially to us. It’s a very exciting time to go to Cuba, and our specially-crafted Cuba travel programs offer you the chance not just to witness history, but to take part in it by living life with local Cubans. Come immerse yourself in the vibrant Cuban way of life !

Looking for info about traveling to Cuba in light of the new restrictions? Click here >

Cuba Gallery

Our kids had, for the first time, an appreciation of where they live and an understanding of what it would be like to live in another part of the world.
Shari L.

This is My Cuba


From $1,995


7 – 10 days


Custom dates available year-round







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“This is My Cuba” allows you to experience the real Cuba with locals as your guides who will show you the Cuba they love. This is a people-to-people trip at its best with our great guides showing you the culture, history, music and arts of the land they call home.

  • 100% locally organized and led programs
  • Stay in local family homes
  • Explore Cuba’s history and encounter its culture through the eyes of locals
  • Invitations to local events, visit hidden art studios and music shows, outdoor adventures and more!
Trip Details & Itinerary →


Crooked Trails is a non-profit organization focused on transforming tourism into a positive force in the world. We create travel programs that reflect our values and are worthy of the trust placed in us by our travelers. By traveling with us, you can be assured that your money will go to support our partner communities, the causes we support, and our on-going work to make tourism better. We do this by:

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    Selecting locally-owned hotels, restaurants and transportation in order to ensure your money benefits local people.

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    Employing experienced local guides who are paid a fair wage.

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    Offsetting the environmental impacts of travel through initiatives such as our Travelers Against Plastic (TAP) campaign, demonstrating ways to protect local resources, and encouraging the purchase of carbon offsets.

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    Educating travelers in cultural sensitivity and the social, economic, and environmental impacts of their travels.

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    Acting on our commitment to the social and cultural protection of people in our host countries.

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    Offering unique experiences and opportunities for authentic engagement.

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    Donating a portion of your trip fees to the community development projects we support.

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