How crazy is Cuba travel right now?

Very crazy.

This keeps coming up lately. People often come to me thinking that going to Cuba is way easier than it is. So I’m posting about it again. (I wrote a few months ago on similar themes: Traveling to Cuba These Days.)

Here’s the deal: This is a tricky time to visit Cuba. Too many people are trying to go, Cuba is over capacity, and that plays out in predictable and not-much-fun ways.

Because it’s so difficult right now, you should:

  • Book your trip at least 2 or 3 months ahead if your dates aren’t flexible
  • Book 5 or 6 months ahead if you want to stay in one of the good hotels
  • If you can afford it, go with me – or someone else who knows what they’re doing – instead of trying to navigate the mess yourself

You should not:

  • Expect to throw a trip together on short notice unless you’re willing to be very flexible – on dates, cities, lodging, and transportation
  • Expect things to be bargain priced, or even reasonably priced
  • Expect everything to go as planned or as budgeted
This billboard in Cienfuegos, Cuba is one of my favorites! It shows the fist of Cuba punching out Uncle Sam's embargo.

This billboard in Cienfuegos, Cuba is one of my favorites! It shows the fist of Cuba punching out Uncle Sam’s embargo. It’s always interesting to see how the Cuban government tells its story. Now, I don’t personally encounter this kind of animosity from the Cubans I meet every day. They’re friendly towards Americans as individuals and consider the embargo a conflict between our governments.

The backstory

Cuba’s in the middle of a ridiculous tourism boom. For one thing, it’s getting tons of hype in the news, sparking interest around the world and especially in the U.S. The number of people visiting from the U.S. has skyrocketed. And tons of tour companies are trying to ride the wave, organizing more tour groups than Cuba’s ever seen. This is on top of all the Europeans and Canadians who have been enjoying Cuba for decades while the U.S. market largely ignored it.

For another, everyone wants to experience Cuba as it is now. Some people are worried about the McDonald’s and Starbucks effect – that large multi-nationals will move in and displace Cuba’s culture and personality. Others worry about what happens when U.S.-based cruise ships start unloading hundreds of passengers into Old Havana. So lots of people consider that now’s the moment to visit… and they’re all trying to show up at the same time.

The upshot: Too many people are going to Cuba. And by too many, I mean far more people than Cuba’s tourism infrastructure can handle.

What it means for planning a trip

For planning purposes, this means some flights get booked far, far in advance. So you can’t plan a trip two months out and expect to have your pick of dates. Many hotels are also booked far in advance. Every hotel I like in Havana is booked a good 4 or 5 months out, especially for the high season. Renting a car can also be tricky.

Often people come to me and say, “I want to go to Cuba on March 15th and come back on the 23rd.” If you want specific dates, come to me early – at least 2 or 3 months in advance. If you have a specific hotel in mind, come to me 5 or 6 months in advance. If you have a group of 10 or more people, that’s 5 or 6 months in advance too. If you have some combination of the above, make your plans even earlier.

Here’s a weird curveball, though: At the moment, Cuba is behind schedule in one key area – granting permission to airlines for their flights to and from Cuba. One airline I use has been getting permission for their flights just one month out! And I don’t know any airlines with April flights approved yet. So anyone trying to buy flights from these airlines is stuck waiting until they get official permission and can start selling seats on their flights. I’m in good with the airlines I use, so I know they’ll take care of me. But for a random traveler trying to plan a trip, it’s kind of a free-for-all, with no guarantees of when flights will go on sale, how quickly they’ll sell out, etc.

So we’re in a situation where you have to book the decent hotels several months in advance, but can’t book a flight two months out to make sure your travel dates correspond to when you’ve got the lodging. Incredible.

A shot over the rooftops of Trinidad, Cuba to the bell tower of the San Francisco de Asis church

A shot over the rooftops of Trinidad, Cuba to the bell tower of the San Francisco de Asis church

How it looks on the ground

Once you’re there, you can expect a few things. First, many typical tourist stops are overrun. Last fall I visited a spot I used to enjoy and found a half dozen tour buses parked there. It felt like a cattle call. I read a similar story in a recent Reuters article. I’ve crossed that spot off my list of favorites, along with many others. So having the kind of experience I like – away from the tourist masses – takes even more work than it used to.

Next, reservations can be hard to get and/or hard to rely on. Everything is overbooked, so someone’s always getting screwed. Recently an acquaintance of mine went to Cuba on her own and on a limited budget. At some point she got in touch, freaked out because she couldn’t get the rental vehicle she’d arranged, and the alternative was going to be much more expensive. Her question was, “Is this normal?” Well, of course it is. My exact words were, “Nothing would surprise me.”

I felt badly for her. It sucks to stress over your budget overruns… and to spend some of your limited time in Cuba dealing with something like this. But I was also thinking, Are you so poorly informed that this was a surprise? Cuba’s a mess right now, and if you did your homework – or just read my blog – you’d have seen this coming a mile away. Anyone who’s going to Cuba for the first time should expect at least a few surprises when things don’t go as planned. That’s very Cuba, especially at a time like this.


Plan your trip early! If you possibly can, get help planning and managing the logistics. And expect things to be complicated once you get there!

Fun language note
I just emphasized the word complicated. Complicado, “complicated,” is the all-purpose word used in Cuba to describe anything that’s going wrong. That could mean things are slightly wrong… or it could be a euphemism for something much worse, a la Brazil:

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