How To Travel To Cuba

Updated March 24, 2017

Thanks to the April 2016 changes implemented by the Obama administration, as well as the launching of flights to Cuba from the U.S., travel to Havana and beyond is now easier than ever. That said, even a weekend getaway requires more planning than you may realize. Here's what it takes to make this Caribbean island your next getaway.

With the 2016 changes in Cuba policy, Americans can now travel legally on their own to Cuba — but to remain legally compliant, their stated reason for travel must fit within 12 provisions, including education, humanitarian projects, religious activities or people-to-people — the last of which is the most popular. (Not sure if your plans qualify? Check here.)

This process is more formal than typical customs forms. For starters, air carriers retain this paperwork for five years. Plus, you'll need to sign an affidavit, typically electronically when checking in with your airline, confirming that your travel plans fall within the allowances of that category.

However, you no longer need a visa. You will need to hold onto your tourism card until departing Cuba. Most airlines, including JetBlue, wrap that cost into the overall fare price, which also includes the departure tax.

Before 2016, six months was the necessary lead-time to plan a Cuba trip. "Otherwise everything from hotels to tours would be sold out," says Tom Popper, president of tour company Insight Cuba, leading getaways to the island since 2000. "Now, however, we have people booking just 30 days out," Popper says.

Of course, if you are hoping to jet off for a last-minute weekend, you can — just be forewarned that your first choice hotel may be booked, so be ready with alternative picks. However, if you're planning on arranging cultural tours, the last minute won't suffice.

"When travelling to such a bucket-list destination like Cuba, it's so important to get it just right," says Tom Marchant, whose company Black Tomato organizes custom tours primarily falling within the educational allowance. "Whether it's arts, food, music or history that's of greatest interest, we arrange immersive experiences such as art tours with local collectors and curators, behind-the-scenes tours with the Cuban National Ballet, or literary tours with local writers and historians."

In other words, the greater your goals, the more time you need to allow.

"Cuba prohibits what they call self-fulfilled travel," says Popper. That is, you can't wander Cuba as you might Las Vegas, following every whim and booking hotel, dinner plans and activities upon arrival.

Nor can you rely on your smart phone in Cuba as you would elsewhere, in large part because this country isn't as connected as other destinations.

Says Popper, "Even businesses in Cuba don't have widespread access to the Internet yet. In places like Paris or Aruba, the people working in tourism make everything accessible. There are maps and all kinds of info online. But in Cuba, a lot of that doesn't exist on a widespread basis."

If you have to, you can wait until you're on the ground to make bookings. Hotel concierge can make dinner and tour reservations for you, provided you are staying in a high-end hotel offering the service. This service is also an excellent way for non-Spanish speakers to bypass the language barrier, should it be an issue.

Travel companies such as Black Tomato arrange itineraries for solo travelers, families and honeymooners. And you can go it entirely alone if you meet the previously mentioned requirements.

But there is benefit to group travel, especially if you're looking for more intimate connections with locals. "On your own, you may struggle to find those special things, like meeting with artists, musicians, chefs and economists. Often, they won't meet with one or two people because it's not worth their time. For them to take time away from work, it has to make sense," says Popper.

Thanks to U.S. airlines getting in the game, buying a ticket to Cuba is almost no different from buying one to any other Caribbean destination. One obvious caveat: Your flight cost will include health insurance to cover you during your trip.

Since the regulations changed, not only are more Americans traveling to Cuba, so are more Canadians. The island's 61,000 hotel rooms are filling faster — and you won't find up-to-date room availability information online. "A lot of times the third-party sites don't sync up with hotel capacity," says Popper. "People will book a reservation that turns out not to be real."

Also, you will need to consider how you will pay your hotel bill. Keep in mind that American credit cards — or any plastic issued in the U.S. will not work in Cuba. Book online, and although you will be able to reserve a room with a credit card, you won't be able to use that card to pay your balance. Instead, you'll need to tote along enough cash to foot your stay. However, if a travel agent or company books your hotel for you, your room will be prepaid, and you won't have to worry about that detail.

The only way Americans can purchase anything in Cuba is with cash. That's it. Credit cards and ATMs are presently not an option for us; however, that could change soon. For now, plan wisely.

Says Popper, "Bring more money than you think you will need. We suggest that people carry at least an extra $200 in USD, which they can easily spend when they return home. I have heard stories of people running out of money. Cuba may not be a consumerist society — that is, there's not a lot to spend your money on, but we somehow always find a way."