How to travel to Cuba as an American

How to travel to Cuba as an American

Want to know how to travel to Cuba before it’s over-run with Americans, and corporations? Want to explore on your own terms without a tour group? Find out how I made this happen, and how you can too.

The USA/Cuba relations have been a very popular topic over the past year and a half. As regulations loosen, and the gates open wider for travel, the island nation of Cuba is bound to get overwhelmed by millions of Americans as 30 daily commercial flights pour into Cuba later this year.

Buying the Flight to Cuba

As someone that has done a fair amount of traveling, Cuba was a place on my short list of countries to visit. In October I came across a fare sale that I couldn’t turn down, Air China was offering RT flights to Havana via Montreal for $280 ($357CAD), all I had to do was find my way to Montreal from NYC. I was able to book a RT flight via British Airways out of LGA for 9,000 points and $50. So $330, and 9000 points for a little over a week in Cuba in January? That’s a no brainer, and with that, I was off to Cuba!

Right now you can legally travel to Cuba if you fall under the US government’s 12 approved travel reasons, including family visits, government work, journalism, professional research, humanitarian work and education. There aren’t many flights, and they are quite expensive from what I’ve seen from the NYC area. You also have to keep your receipts from the past 5 years, and it’s pretty restrictive in terms of what you can actually do. You’re constantly under someone’s watch, and have to be accounted for all hours of the day. Not the way I want to travel, what is this, North Korea?

Crossing the Border into Cuba

I was a little nervous about the whole operation. People have been doing to it for years via Mexico and Canada, and there are plenty of places on the internet to read about what to say, and what to do. Once you’re at border control all of that preparation goes out the window and it’s up to you and that other human on the other side of the glass to control your fate. In my research I had read that you could ask the border guards in Cuba to not stamp your passport, and they’d simply stamp your tourist card, and on your way out give them the other stub of the tourist card as your exit ticket. There were some reports that border guards were no longer looking the other way and were now stamping US passports, case in point, my friend Dave went to Cuba a couple weeks before me and had his passport stamped. Luckily for him, and me, we both have Global Entry, so a border guard in the US won’t be looking for any stamps upon re-entry, all you have to do is hand them your Global Entry ticket and you’re all set. In my most practiced/nervous Spanish I asked the border guard if she could not stamp my passport. I think it came out something like “no puedes marcar mi passaporte por favor?” She smiled and nodded, stamped my Tourist Card, and I was in Cuba.

For those that are looking to travel via Mexico or Canada I highly suggest getting global entry. There are a number of credit cards that offer this as one of the benefits of the card. Citi Prestige, Amex Platinum, Ritz Carlton CC are just a few, otherwise you’ll have to pay $100 for this benefit for the next 5 years (it also comes w/ TSA precheck). They are expensive credit cards, but if you’re into the travel hacking game like me, you get the most value out of them that you possibly can.

The funny thing about the whole process is that Canada was harsher on my entry into the country than I would have thought. My girlfriend got grilled on her way in from the USA, and I was grilled coming back from Cuba. I’m sure my story of visiting family in Montreal for the day might have set off some alarms, but whatever I made it through scott free.

Where do I stay in Cuba?

Before arriving in Cuba I booked a stay via Airbnb, and had some issues finding availabilities in the weeks leading up to my trip. The B&B (Casa Particulares) market is a heavily regulated industry, as are many things in Cuba. Whenever I attempted to book a room I had to provide a reason that corresponded with one of the 12 approved travel reasons. My first two attempts weren’t approved, and I’m not sure if that’s because of the reason I chose “Support the cuban people”, or because of other variables out of my control, but on my 3rd try I chose religious reasons and I was accepted. If you’re going to visit Cuba, don’t spend your money in the hotels, you should really be supporting the Cuban people and staying in someone’s home.

Searching through the Airbnb avails was tedious as all of the rooms look less than glamorous. You just have to temper your expectations when traveling through Cuba. If you can have consistent hot water and air conditioning, and in Havana Vieja you’re in a very good place. The vast majority of Cubans don’t have some of the things we take for granted.

If you haven’t signed up for Airbnb yet, you can use this link and you’ll get $20 off your next booking, and I’ll get a $20 kick back to use on my next booking.

Via Deals We Like, you can stay in an Airbnb for free in Cuba if it’s your first time. This won’t last soon, but as of 4/6 it looks to be still good.



Can I use my Credit or ATM Card in Cuba?

By booking this ahead of time I was also able to put that expense on my credit card, rather than having to pay in cash, which would have been the case if I wanted to stay at a Casa Particular upon my arrival in Cuba. Cash is king in Cuba as an American, as USA credit/debit cards do not work. When exchanging USD to $CUC (Convertible Cuban Peso) you pay a 13% fee (10% penalty and 3% fee), but all other currencies are ~3%. So I took out as much Canadian Dollars as I thought I was going to use while in Montreal using my Charles Schwab card (No ATM or foreign transaction fees), and then brought some USD as a safety net.

I highly recommend visiting Cuba before the Mcdonalds of the world come in. We’re already seeing the beginning of the end with the first Starwood hotel coming to Havana. I don’t think change will happen immediately, but it’ll be interesting to use 2016 as a guide, and see how Cuba looks in 2 years, 5 years, and then 10 years from today. As with most things in Cuba, change is slow, but when there are financial interests involved that could facilitate a faster change, along with that comes plenty of corruption. I’m hopeful that the easing of the US/Cuba relations bring more opportunity for the Cuban people, but it’s a very delicate situation that we should all be keeping a close eye on.

Stay tuned for some trip reports about my time in Cuba.