Cuba: Frequently Asked Questions
NB: This page was updated in June 2019, taking into account the June 5, 2019 revision to the federal regulations.
Is it legal?
Is it legal for a U.S. citizen to visit Cuba?
It is if you do it right! You just have to know what the regulations require, which I do. I’ve been leading Cuba trips for years, first working for major tour companies and now on my own. I stay on top of the regulations and run my trips by the book.
So U.S. citizens can legally visit Cuba? I thought Trump changed all that?
Yes, we can. Trump closed off some avenues of Cuba travel in November 2017 and others in June 2019. But various other avenues are as legal as ever, including Support For The Cuban People, the category I use.
What is a Support For The Cuban People trip?
Support For The Cuban People is a category of Cuba travel defined in the Code of Federal Regulations. Travel under this category is meant to “[e]nhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities.” I wrote a post with more details: What is Support for the Cuban People?
What are our legal obligations during this trip?
We just need to comply with the regulations in how we spend our time and money. While that may sound complicated, once we’re there, it generally doesn’t feel like a big deal. Then after the trip, you’ll need to maintain records of the program we followed – but I’ll help you with that. It’s pretty straightforward.
What's the trip like?
To get a sense of how my trips work, check out my Cuba brochure.
What's distinctive about going with Matt?
I call my trips Detours because they’re not the typical tourist experience. With help from my friends and connections in Cuba, I create a much 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 capture exactly what I’m going for.
How do you design the itinerary?
First, I talk with you to figure out your interests and how you like to travel. Once I get a feel for that, I program all my favorite people, places, foods, and experiences that are a good fit for you. I also allow some flexibility to follow our noses, pursue random leads and see what happens. Those are often the best moments of a trip!
Do you work with a Cuban guide?
Yes, I always work with a local guide. That guide is one of the most important parts of our trip for several reasons. One is, it takes two (or more) to provide the level of service I do. There are also ways I’ll never understand Cuba as well as a native – just as they won’t understand our cultural frame of reference as well as I do. Last but not least, your guide is the Cuban you’ll get to know best. I pick fun, nice, smart people, and spending time with them is a joy!
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. I can also build a trip around an official theme. Past themes have included LGBT, cars, Jewish, and music.
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., its socialist ideology and political system, and how quickly Cuba’s economy 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, unlike our rules for anywhere else in the world.
Do these trips prop up the Cuban government?
The U.S. government thinks our visits ultimately promote a freer, more democratic Cuba. That’s their goal in permitting this 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 a private trip cost?
Gimme a ballpark, what's it cost?
Ballpark is hard, because there are lots of different factors. The more people you’ve got, the more cost effective it’ll be. I just estimated a trip for someone, 8 nights in Cuba, including everything but airfare. The ballpark cost for 6 travelers was $3450; for 4 travelers, $3850; and for 2 travelers, $4800. You can spend more money for lavish accommodations or high-dollar, more exclusive activities.
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 nice B&Bs, all meals included at my favorite restaurants, and a private vehicle and driver for the entire trip. Activities can also make a big difference. For our farewell dinner, do I hire one of my favorite bands to play for us, or do I pay a premium for the hottest jazz combo in Cuba? Or I can skip the live music entirely to keep prices lower. It all adds up!
What makes it so expensive?
This is not a budget trip. I’m an overachiever, and I’m trying to do something special. If you want a typical trip, I’m the wrong guy to ask.
I also charge enough to do it right. That is, in tipping and paying Cubans, I’ll never be stingy. I’ll be treating them nicely on your behalf. And I’ll treat you nicely, too. You won’t feel nickel-and-dimed the whole trip, and I won’t be cutting corners.
But I found a different company that's much cheaper!
I have three answers for that. One, if you found another trip you’re happy with, go for it! Have a blast. And two, there’s a reason they’re charging less. You might still have an amazing trip at the lower price. Or you might prefer the level of service I offer. If you want, I’m happy to take a look at what they’re promising and explain the difference in what you’re paying for at their price versus mine. Three, if you really want to go with me, but the price is just a little too high, let’s talk about what I could tweak to stay within your budget.
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