Private trips to Cuba

I’ve been getting a lot of inquiries lately about private trips. That is, someone calls and says, “My friends and I want to go to Cuba, just the four of us. What can we do, and what will it cost?”

Here’s the thing. The trips I run are People-to-People programs, legal because we spend time with Cuban nationals in meaningful ways. Within that framework, there’s a lot of flexibility to tailor a trip to your interests. It just means you can’t spend the day snorkeling, sleeping on the beach, etc. But if you’re into cars, we can spend time with people who restore classic cars. If it’s architecture, we could spend time exploring Havana with local experts. If it’s home cooking, we could hit up a friend of mine to show us how she does it. And so on.

For example, on my last trip, my travelers were especially interested in art and dance. So we spent time with some of Havana’s leading artists, learning about their work and their lives. I also have some friends who are professional dancers. They taught us casino, the Cuban style of salsa dancing, and offered to show us around some of their favorite places to go out dancing.

Now, there is a big limitation on Cuba travel, beyond just what’s a legal way to spend our time. This is simply a crazy time to travel to Cuba! If you want a week at the Saratoga, Havana’s best hotel, that’s not available until next May. All the best hotels are booked for months. So if you want a good hotel, I’ll see what I can do – but the more lead time you give me, the better! If you prefer to stay in a casa particular (a private home with rooms for rent), that’s much easier. With some work I can normally find a good casa, even on short notice.

A 20-something artist stands in front of three small prints.

On a recent trip, we visited this artist and viewed some of his pop art. Much of it’s political. A lot of political statements in Cuba are expressed through art.

The other question – What will it cost? – is both easier and harder to answer. It’s easier because the numbers are pretty straightforward. The hard part is, the price feels high compared to other destinations. You could go to Mexico on your own and have a blast, or just hire a local guide to show you around. But if you hire me for a legal Cuba trip, I don’t just send you on your own to have a blast. I accompany you personally (in compliance with Treasury regulations), and I hire a Cuban guide because it makes for a better trip. I have a legal team and special insurance, because Cuba is such a special case. All that adds up.

Anyways, here’s an example of a recent trip, just to give you a ballpark idea. We spent 3 nights in Havana and 5 nights traveling around “the provinces” (everything that isn’t Havana). We chose less expensive lodging and transportation options. It cost $6,000 per person for a group of two, $5,000 for three, and $4500 for four. If you want to stay in historic or elegant hotels, or engage in high-dollar activities, it’ll cost more. If you want the tightest budget possible, it can cost less.

It’s typically less expensive to take more people due to economies of scale. So 8 people is less expensive per person than 4. But above 8 people, you have to go through official government channels, running the trip through a state tour agency. That raises the price a bit. So 10 people is actually more expensive than 8. But above 10, the more people you have, the less expensive your trip.

For more information, drop me a line. It’s not that hard for me to get a sense of what you want and draw up a quote. And if it turns out I’m not the guy for you, I can try to point you in the right direction.

A building is painted with a Cuban flag and patriotic slogans.

The Cuban government also loves political messages. Here’s a pretty standard example of a patriotic display on the side of a building. You see stuff like this all over the place.

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  1. Hello, I need a tour guide for my trip to Cuba. I booked accommodation in the website and travel to Havana on January 5. Can you recommend someone?

    • From the little you’ve written – and assuming you’re a U.S. citizen – this trip doesn’t sound legal, which means I won’t get involved. If I’m wrong, and it’s legal, then by all means get in touch! I don’t share my expertise for free – but you could hire me as a travel consultant to help you plan the trip. This is a bad time to show up to Cuba without a solid plan.

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