Cuba: Frequently Asked Questions

Is it legal?

Is it legal for a U.S. citizen to visit Cuba?

It is if you come with me! In 2014, after several years of working in Cuba, I got a license from the U.S. Treasury Department to lead my own People-to-People trips. I do these trips by the book, complying with all the restrictions, so it’s 100% legal. (Not every operator is so careful about it…)

So U.S. citizens can legally visit Cuba now?

It depends why you’re going! Some trips are legally permitted, and others aren’t. I blogged about this: Yes, it’s legal! Travel to Cuba for U.S. citizens.

What is a People-to-People program?

These trips are designed to promote meaningful encounters between you, the traveler, and the Cuban nationals we meet along the way. For more, check out my post on People-to-People trips to Cuba.

What are my legal obligations during this trip?

You’ll need to participate in the activities of our People-to-People program. Outside of those activities, you’re free to choose your own adventure. There are also limits to how much rum, cigars, and other goods you can bring back from Cuba. After the trip, you’ll need to maintain records of the program we followed – but I’ll help you with that. It’s very straightforward.

What makes Cuba different?

How is Cuba different from other destinations?

Cuba is unique for its revolutionary history, its bizarre relationship with the U.S., and how quickly Cuba’s historically socialist system is changing to incorporate capitalistic and free-market ideas. In practical terms, U.S. credit and bank cards don’t work there, so we do everything in cash. And U.S. policy on Cuba limits the way U.S. citizens can visit, as mentioned above.

Does it feel like an authoritarian state?

From my perspective as a visitor, it feels similar to anywhere else I’d visit. Political differences aren’t always readily apparent -especially if you stick to the standard tourist routine. But digging a little deeper, you can learn about these differences. They’re complicated – just like everything else about Cuba. That’s part of what makes it such a fascinating place to visit.

Do these trips prop up the Cuban government?

The U.S. government thinks our visits promote a freer, more democratic Cuba. That’s their goal in permitting People-to-People travel.

How safe is it?

Cuba’s actually the safest country I know. I take the same basic precautions I’d take anywhere to prevent pickpocketing or other petty theft. I’ve never had any problems, and neither has anyone on a trip I’ve led. More serious crimes are almost unheard of.

What's the trip like?

What's distinctive about this trip?

I call my trips Detours because they’re not the typical tourist routine. They’re smaller and more intimate, and I depend on my friends and connections to help us have a more personal experience. As one traveler recently wrote to me, “I felt like a visitor and not an asshole tourist!” Another said, “Our programmed activities never, ever felt programmed.” I love both quotes because they exactly capture what I’m going for.

How do you design the itinerary?

I’ve been leading trips privately and for large tour companies for the last couple years. So I’ve learned my way around and figured out what’s worth doing. I also allow some flexibility to pursue random leads and see what happens. Those are often the best moments of a trip.

Do you work with a Cuban guide?

Yes, in Cuba I always work with a guide/assistant. There are two main reasons for this. One, we bring different perspectives to the trip. I’m the best person to understand my travelers’ cultural frame of reference. I can look around and recognize, “Hey, here’s something we don’t see every day…” and explain it in terms you’ll understand. And I can judge whether some restaurant’s food will be humble but interesting for us, or whether it just looks boring or crappy to us. Sometimes Cubans have different instincts about that kind of thing than we do.

But a Cuban is the best to understand whatever we’re seeing in depth. They’re the ones saying, “Oh, those people standing huddled together over there? Most likely, that shop got in a shipment of chocolate, and people started passing the word that there’s chocolate available…” And suddenly we get an impromptu lesson on Cuban economics, communications, and culture. Or we hear some song, and the guide understands every word and knows its cultural significance.

When there’s decent chemistry and egos are under control, we end up supporting each other constantly. The guide helps me understand things properly, and I help the guide convey ideas to you. So who’s the best person to help you experience Cuba? For me, the best is when I team up with a Cuban and we do it together.

The second reason: Cuba is a pain in the ass, and working solo, I could never provide the level of service I do. Sometimes we need one person to serve as gracious trip leader while the other handles logistical challenges behind the scenes – hunting for bottled water during a shortage, running across town to buy tickets to something, fetching the car, etc. I love when the car/water/tickets just magically show up like it’s no big deal. That kind of seamless experience is what I’m going for – and in Cuba, it’s not easy.

Is there any special theme to your Cuba trips?

My default trip is a varied look at Cuban culture and society, but I’m always happy to customize a private trip to fit your interests. Occasionally I offer a themed trip, open to the public. Past themes have included LGBT, cars, Jewish, and music.

What's a private trip cost?

Gimme a ballpark, what's it cost?

Ballpark is hard, because there are lots of different factors. But I just estimated a trip for someone, 1 night in Miami, 8 in Cuba. The ballpark cost for 6 travelers was $4350; for 4 travelers, $4950; and for 2 travelers, $6700. Another trip was $4450 for 4 travelers or $4050 for 6. And I’m doing a group for 10 people at $4500 per person.

What factors can change the cost?

Besides the obvious – trip length and group size – there’s a variety of prices in accommodations, transportation, and meals. The ballpark costs above were for good hotels, all meals included at high-end restaurants, and a private vehicle and driver for the entire trip. It’s also more expensive to go during high season (October through April). And at or above 10 people (including me), I go through official government channels, which also bumps the price up a bit.

What makes it so expensive?

Most of the legal Cuba travel out there is expensive, especially People-to-People trips. There are four big reasons why: One, Cuba has become the world’s hottest travel destination, and they’re charging accordingly. Two, the People-to-People category of legal Cuba travel requires that you be accompanied to Cuba by a representative of the tour operator. That’s part of my role on your trip. And taking an extra person with you isn’t cheap! Three, these trips take a lot of work. Some of that’s maintaining the legality behind the scenes, and some of that’s the difficulty of organizing a trip to Cuba at a time like this.

Last but not least, I charge enough to do it right. That’s a little hard to explain… But in tipping and paying Cubans, we’ll never be stingy. You won’t feel nickel-and-dimed the whole trip, and I won’t be counting pennies.

But I found a People-to-People trip that's much cheaper!

I have two answers for that. One, if you found another trip you’re happy with, go for it! Have a blast. And two, most of the time when people tell me that, it’s because the tour company is cutting legal corners. In other words, their trips violate the law. The biggest red flag is if the company organizing your trip isn’t sending someone to travel with you besides a Cuban guide. If you want to understand this better, you can: read my page on what’s legal and what isn’t; give me a call; or even better, call the OFAC Licensing Division at the Department of the Treasury: 1-202-622-2480. I’ve always found them friendly and very helpful.


    • Thanks Terry – I’m sending you an email about it now.

  1. Are u organizing 2016 Cuba gay pride tour?

    • Hello! And thanks for your inquiry. I am planning a trip, but I haven’t set the dates yet. I’ll give you a heads up when it’s all set, and you’ll have a chance to join the trip before I announce it publicly.

      • I would also like to join your gay tour in May for pride. Is this possible and what are the specific details. Do I need to obtain a special visa.

        • Hi John, sharing here the answers I gave you by email: I sent you all the details by email, and you don’t need a specific visa. I make all the arrangements, including for your visa.

  2. Hi would like to talk about tour packages. I plan to stay in Veradero and I want do some tours to Cienfuegos. Please let me know.

    • Hi Armand, I’ve emailed you to discuss. Thanks!

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