Cuba Travel Options

2013-01-10-cuba-trinidad-santeria-temple-017As many visitors to this page will know, I’ve been immersed in a decades-long engagement with Cuba. in 1999 I led the first group of American high school students there since the Cuban Revolution, and have returned frequently ever since, often for extended periods and multiple times per year. I’ve worked as a trip leader for student and adult groups organized by formal organizations such as National Geographic and Putney Student Travel, and independently as well, for museum groups, writing workshops, art programs, and other creative individuals of varied stripes.

Cuba—the country, people, art, landscape, music, history, and more—has become an enduring fascination for me.  The pandemic has given me, and all of us, a long pause to reflect – and, not having been back to the country since January 2020, I’m itching to get back to Cuba again on a few select small group trips.  Click here for dates of upcoming group programs. To suggest your own custom small-group travel dates, or for a free general consultation, send me a note

60067474_10157118842879344_6724933300994965504_nRecent policy changes have often seemed intended to deter Americans from visiting a country that both wants and needs our continued engagement. The good news is that travel is still permitted, in most cases, for small private groups and those traveling under the auspices of educational or professional institutions. It’s more important than ever to plan ahead carefully, however, and to tap into local networks in ways that will allow you to travel in a way that is both rewarding and fully compliant with the latest OFAC regulations.


Katrina Scott photo

Working with a network of contacts I’ve developed over nearly two decades of creating and leading educational programs in Cuba, I’m able to organize a limited number of highly customized, relatively affordable trips for small and medium-size groups wishing to travel to Cuba. Trips include all accommodations in either hotels or carefully chosen, well-located casas particulares (private B & B’s in real Cuban neighborhoods), skilled drivers, highly qualified and personable English speaking guides, prearranged meals, music, dance, art, and cultural activities as desired, and detailed daily itineraries designed to be compliant with OFAC regulations.

So if you’re interested in exploring the idea of a trip to Cuba, give me a shout. I’d be happy to provide a free assessment of the possibilities given your specific time-frame and interests.

Reservations are hard to come by these days so ideally you should reserve your trip a minimum of two to four months in advance, more if possible. Please feel free to get in touch to explore OFAC-compliant group travel options.

Testimonials . . . 


“Instead of going with a tour company, we asked Tim to put together a trip for us. With his guidance, we studied Cuba, decided where we wanted to go and what we would like to see. He then made arrangements for us to stay in people’s homes, where we got to chat with the owners and their employees. Not only was this more satisfying than a packaged tour, it also cost considerably less.”

“I find that words are insufficient in conveying the depth of my gratitude for our extraordinary adventure in Cuba. Your deep relationships with Cubans allowed us to glimpse a Cuba hidden to most tourists.”

“Tim and Orelvis cheerfully and flawlessly planned and executed a two-week combined family vacation and research trip for us, with authentic accommodations, tasty restaurants, fun excursions, and lively music for the family, and the knowledge, experience, and logistical smarts necessary to search for and explore sites along the southern coast where the historical record indicates Columbus met Taíno chieftains in 1494.” (Andrew Rowen, Encounters Unforeseen: 1492 Retold)


“Our trip was fabulous – really well organized. We didn’t need to worry about anything. Our guide—Ela—and our driver—Jorgito—have become our dear friends. They were a great team, flexible, listening to our input, desires and adjusted our trip per our requests really well.”

“We enjoyed the fact that the itinerary was so varied— museums, tours, music!  Also, I can’t say enough about Elvis’s unerring ability to take us to places not included on our itinerary that were memorable.”

“This was the first “tour” that Ken and I have taken, we travel quite a bit but always plan our own itinerary, do our own driving etc. We also generally don’t travel with other people, so this was a whole new experience for us. What we appreciated so much was the initial planning by you that took into consideration what was important to each of us, along with your personal guidance. The fact that our plans were then flexible allowed Orelvis to change certain aspects as he got to know us better.”

“I would highly recommend Orelvis to be the guide for any visitors to Cuba. He is very knowledgable, patient, organized, enthusiastic, and friendly. His English is excellent. He greatly enriched my trip experience. And thanks again for all your work to make this such a fantastic trip.”

“Thoughtfully planned, interesting and varied itinerary, small group so that we could be flexible, great people. A really wonderful experience.”

“Thanks for setting up a wonderful trip! We had a number of diverse experiences that scratched below the surface of a typical tourist outing.  Very meaningful and we’ll have a lot of great memories. Our guide was fantastic—super energetic, well-educated,  sarcastic, funny, and proud.  She  was able to make changes on the fly when we got flakey or when there was the inevitable glitch. We particularly liked meeting with the couple who live in a crumbling neighborhood on outskirts of Havana.  We cooked dinner with them, checked out their communities’ artwork and music and met with the kids in their neighborhood. We may end up contacting them to buy some artwork.”

IMG_7269“It would be safe to say that our guide, Ela, was the simply the best guide ever. Fun and informative, she was a good fit. There are so many highlights, but the ballet/tribute to Alicia Alonso brought tears.There is probably a rum shortage in the country right now. Thanks for making this happen.”

“With Elvis’ help we got to experience the sights and sounds of the country and people he loves and is so proud of – music, dance, history, natural resources. We will always treasure this trip. We’d love to form our own group (our children and their families), and have Orelvis guide us through his Cuba. Thank you, thank you!”

“Elvis is delightful, a keen observer of the changes Cuba is undergoing, and we bonded with him immediately.  We all felt like we had made a real friend in Cuba rather than just having a guide – and you can’t do better than that.”

IMG_8879“Tim is great – he really knows Cuba, its history, and its people.  He’s also very approachable, helpful and a great guy!”

“Very well organized trip. Lots of attention to detail and varied activities.”

“The trip was an overwhelmingly positive experience with a great blend of history, culture, art, food and fun.”


Click here for info on upcoming group programs, or suggest your own custom small-group travel dates. For a free consultation, send me a note VIA THE CONTACT PAGE.

%d bloggers like this: