Meet a Caribbean nation in transition.

Insider Expeditions is pleased to be working with many alumni and affinity groups to lead people-to-people exchanges in Cuba. We have the approval of the U.S. government to lead such customized, cultural exchanges, and work with the best local guides and institutional partners to deliver unparalleled programs. While we can tailor any trip, we have a particular focus on medical groups, legal groups, and young professionals groups.

iStock_000016334181_LargeEvery single trip is different and customized directly to our clients needs. However, some of our programming options include:

  • Discovering Cuba’s sophisticated art traditions during visits with artists in their studios.
  • Feeling the complex rhythms of Cuban music, from son to rumba and jazz, and learning about these uniquely Cuban music styles through both performances and dance lessons.
  • Exploring World Heritage sites and learning about Cuba’s passion for preservation from the very leaders whose efforts are maintaining their architectural and natural heritage.
  • Meeting with both U.S and Cuban officials in Havana to discuss the evolving relationship between these two neighbors.

Please get in touch to design your customized trip to this Caribbean gem.


“I’ve traveled to more than 30 countries in my life — this trip to Cuba easily made it into my top 3 favorite trips of all time.”

“This was one of my favorite international trips! The itinerary was thoughtful and fueled the imagination.”

“The Cuba trip was the most unique, fun, and educational experience I’ve had in years, and I would recommend it to anyone!”

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