Cuba Tips for American Travelers — Part 1: Intro

Street art (graffiti?) outside a crumbling mansion in Havana’s once-wealthy Vedado neighborhood.

I’ve always been curious about visiting Cuba. Once Obama started making moves towards normalizing relations between Cuba and the United States, though, my idle curiosity turned to urgency. I wanted to see Cuba as I’d seen it in pictures, before it was overrun with weekenders from the Eastern seaboard. So about a year ago my husband and I decided that 2015 was the year we had to go to Cuba. We had a few other friends who felt similarly, and right after Christmas 2015 we met up with six of them at the airport in Miami and boarded a charter flight to Havana.

I should say off the bat that the eight of us went legally. There’s an increasing amount of illegal travel to Cuba by Americans each year, and from everything I can tell, those who go without a visa are rarely caught and/or penalized. According to the internet research we did ahead of time and those I know who have gone through Mexico/Canada, no one really seems to care that technically most of us Americans wandering the streets of Havana aren’t supposed to be there.

That said, several folks in my group were attorneys with aspirations of government service and no one wanted to create career risks, so we decided to go legally by booking a “people-to-people exchange” through an educational travel company called AltruVistas. They run both large group tours and private tours — we opted for a private tour for the eight of us so we’d have maximum flexibility (and because as a rule of thumb we hate group tours). So, no advice here about how to go to Cuba illegally. And, because we used a tour company, I also don’t have a ton of insight on how to plan a trip from afar. What you WILL find in these posts is everything we learned about how prep for a trip to Cuba, and tips for what to do when you’re on the ground.

I decided to write these posts because one of the things I was struck by in the planning process was the amount that we felt totally reliant on our tour company. We came across so little good information online about traveling to Cuba as an American, and given the limited access Cubans have to the internet (more on that later, too), the normal solution of just Googling whatever our questions were usually came up short.

Without Google maps on our phones, we spent a decent amount of time like this

Before going, we read another Medium piece by a guy who had gone legally but on his own, and found that first person narrative of his experience helpful in orienting ourselves as we prepared to go. And now that we’ve returned, we’ve had several friends reach out, frustrated with what’s on the interwebs about travel to Cuba, for advice on planning a trip. So, in the spirit of paying it forward, I figured I’d put what we learned out there.

Because I have a tendency to get a little longwinded (if I’d had more time I’d’ve written a shorter letter type thing), I’m breaking this piece up into parts so it’s easier to find or re-find the info that you need. As I write the parts, I’ll hyperlink them below.

If you have any questions, or if you had a different experience and maybe want to provide an alternate view for folks, please add comments! This is intended to be a helpful narrative, not a substitute for a guide book or, like, doing actual research and planning.

Finally, big ups to my travel companions: my husband, Mar + Pete, SAS + Rob, Katie + Dave.


Part 1: Intro (you are here)

Part 2: Money

Part 3: What to Bring

Part 4: Food (Overview + Havana)

Part 5: What to Do (Havana)

Part 6: Viñales

Part 7: Trinidad

And for more pics from Cuba, check me out on Insta as @lewp.

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