Alumni, Family, and Friends Cuba Trip

January 7-15, 2024

Today's Cuba: Confounding Realities

with Hampshire College alumni

Led by Carollee Bengelsdorf and Margaret Cerullo 

Open to alumni, parents, and friends of Hampshire.

Participants will meet Cuban writers, visual artists, architects, and filmmakers (as well as a social scientist or two) to get a sense of the complexities and contradictions of contemporary Cuban life. Topics of discussion will include issues related to gender, race, equality/inequality, the recent protests, the relations between Cuba and the U.S, and the ways these have intersected as a result of the current and multiple crises on the island. 

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"Beyond the amazing places I visited, foods I ate, and people I met (fellow Hampshire alumni travelers among them), the best part about participating in the alumni trip was sharing all these experiences with my family. Even years later, we bond over the shared excitement that was first generated when we registered for the trip. Gather your loved ones for intellectual conversations, cultural surprises, and vivid history—don't pass up Carol and Margaret's decades-old connections to the island that no other tour to Cuba can boast."RJ Sakai 08F, Chair, Alumni Advisory Group
"What a great experience for our family. Hard to imagine a more thought-provoking, horizon-expanding trip. Our kids (in their 20s) loved it: the exposure to Cuba's history, culture, politics, incredible architectural beauty; Havana's edgy combination of stateliness and wildness; the dancing; the rich discussions of political philosophy; the amazing insider knowledge/access/jokes/banter/sociological insights of our indefatigable guides, Margaret and Carol. Highly recommend this trip for families with young adults."Cathy Barber 73F
"I was delighted by the variety of people we met: filmmakers, farmers, academics, feminists, activists. I was bowled over by Margaret’s translator skills: I would think it’s exhausting but she seemed to love it and they loved her for it! And I rarely felt “left behind”! I liked the flexibility—as we were always behind schedule, I appreciated that we could move things around (e.g. postpone beach for another day) and yet we still covered so much."Ellen Sturgis 77F
"I really appreciated how helpful Carol and Margaret were in answering questions, how enthusiastic they were in pointing out things to us and giving us information, and in how much effort they put into trying to make activities happen that interested small groups of people and/or individuals. That was really appreciated and made the trip really special. All the guides were so knowledgeable and so willing to answer questions and I appreciated that so much."Anna Joseph 05F

The all-inclusive cost of this tour is $4,375 per person, single room supplement $475. The deposit deadline is October 18.

  • Land cost only. Does not include round-trip airfare to and from Havana.
  • 16 Participants

The trip draws on the close contacts made during the College’s unique Study Abroad Program in Cuba, which began in 1997, currently operated in conjunction with the Alejo Carpentier Foundation. Participants will meet with sociologists, musicians, visual artists, architects and planners, and filmmakers and dancers for discussions and performances. Many of those leading workshops and discussions have worked with Hampshire faculty and students since the founding of the program.

Hampshire is collaborating with Holbrook Travel, a Florida-based organization. Since 1974, they’ve taken thousands of travelers on expeditions across Latin America, Africa, and destinations beyond. They combine reliable travel support with deep knowledge to create enriching travel experiences that last a lifetime.