If you thought you missed the chance to visit this iconic island after the recent clamp-down by the Trump administration, you might rethink. In fact, this might be an excellent time to visit Cuba simply because most Americans figure the door to individual travel has, once again, slammed shut.
Superficially, that’s true (sort of). But for those willing to do their homework and clear the bureaucratic hurdles, Cuba is still a very welcoming and attractive destination.
And, honestly, the bureaucracy isn’t that overwhelming.
Can Americans fly to Cuba for a vacation? No, and yes. You just can’t call it a vacation. You can, however, still fly to Cuba from the US. Delta, JetBlue, United, American, and Southwest all have direct flights from various American cities.
And while you can’t call your trip a vacation, the US State Department has created 12 categories of legal US travel to Cuba. These include humanitarian or religious reasons, journalistic activity (the category I chose), professional meetings or research, “support for the Cuban people,” and activities of private foundations, or research or educational institutes. Solo travel for educational reasons is no longer allowed, nor is the popular Obama-era category of people-to-people travel.
In order to travel solo to Cuba, you need to decide which category you might qualify for and try to conform your travel plans to it—at least nominally. For example, to qualify under journalistic activities, I tried to score a few writing assignments (this is one of them); I carried a copy of my resumé to prove I was a professional journalist; I kept a record of my daily activities as well as receipts from transportation and accommodation.
Requirements for each of the categories are detailed here. (Scroll waaaay down to subpart E—the 515.560 section for the exact rules for each category.) I found this dense tome of legalese helpful in making sure I at least understood what my category required—probably better than any border guard I might encounter.
All these categories qualify under the general license for Cuban travel. (There are specific licenses that are much more complex and difficult to obtain. You don’t want to go there.) No application or form is required for a general license. (There is no actual license, in other words.) Your travel activities just have to nominally qualify for your chosen category. I found examples of generic forms distributed by educational groups to their participants. Then I composed and printed off a document that sounded official, just in case someone asked.
No one did.
You will be asked for your category of travel many times—when you purchase a flight, every time you check in to a hotel or casa particular, and for some other, incidental reasons. So it helps to be confident that you’ve covered the bases for that category.
Because the Cuban military and government controls most of Cuba’s very lucrative tourist industry, the State Department has created a list of “restricted” entities that US nationals aren’t supposed to patronize. These include many hotels, marinas, and holding companies, such as Gaviota, a name you will see often.
To my way of thinking, this is no big deal. I’d rather stay with a local family in a casa particular than a resort hotel any day. AirBnB has hundreds of listings in cities throughout Cuba. Whatever you might think of AirBnB, Cuban families have been extremely enterprising in listing and interacting on that and other hosting websites—an endeavor even more remarkable since most of these people don’t even have internet access in their homes. For me, staying with local families was one of the highlights of my trip.
Americans visiting Cubamust have a tourist card or visa, which is good for 30 days. Half is stamped when you enter Cuba and the other half when you leave. (So don’t lose it.) I had read that you must also show proof of health insurance coverage, or you’ll be required to buy it there, but I was never asked.
Generally you buy the visa from your airline before you leave the US. It costs $50. In my case, an agent picked me out of line as I was waiting to check my luggage. She sold me the visa at check-in and instructed that I fill it out immediately. The visa and my passport and boarding pass were all required and inspected before I could board the plane.
Alternatively, you can use a third party to get your visa ahead of time for a fee. Make sure you fill it out legibly and without errors just like your second-grade teacher showed you. The Cuban government doesn’t like messy forms.
When you land in Cuba, you will first go through immigration. This is straightforward. The agent looks at your passport; stamps your Cuban visa. Your picture is taken. Then you go through another airport-like security screening. Then you might encounter a slapdash two-table affair where they check the generic customs form you fill out on the plane. I flashed my paperwork and they waved me through. Then you might have a very long wait for your checked luggage. I assume this is because it is being scanned, maybe searched. A lot of the plastic-wrap Cubans seem to love to protect their luggage in was in tatters.
There is one final checkpoint to collect the customs form. Nothing to declare? Welcome to Cuba.
For the next three weeks, I wandered from one end of Cuba to the other, having a delightful time. It was all a part of my “journalistic” business. Occasionally, I thought about my return to the US with a twinge of anxiety, but Cuba is endlessly distracting.
On my last day, I walked to the international terminal from my casa particular and joined the very long queue through security. Disconcertingly, I was plucked from the line, my passport was taken, and I was led through the security scan. Then, my carry-on was hand-searched with particular attention paid to the notebooks and folders. I was treated to a special scan—front, back, and both sides—while visions of sonic attacks on diplomats in their hotel rooms danced in my head. I have no idea whether I was chosen at random (peculiar choice—an older single woman) or if it had to do with my journalistic activity category. I do know that the Cuban government tends to keep tabs on people.
Passport restored and apparently of sound mind and body, I then had only to get through the gatekeepers back in my own country. Thus, in fear and trembling I approached the burly agent in US immigration. I had my resumé. I had my made-up general license. I had my writing assignments and my journal and a handful of receipts.
The agent looked at my passport. He looked at me.
“Where are you coming from?” he asked.
“Cuba,” I said.
“How long were you there?”
“Three weeks,” I muttered.
“Welcome home,” he said handing back my passport. He never cracked a smile. He never looked at a thing.
And that was it—the most uneventful border crossing ever. My friends, who traveled under the humanitarian general license, had a similar experience entering through Charlotte, North Carolina.
As with all things political, the situation with Cuba is amorphous and evolving. Yet, as my experience demonstrates, it’s both possible and worthwhile, but you have to jump through a few bureaucratic hoops and maybe take on a little extra risk to tilt the scales in your favor.
Alternatively, you could sign on to a group tour like those offered by Road Scholar or Insight Cuba. These outfits attend to all the legal fine print so you don’t have to. Or, if you’re determined to travel solo, you could enlist the help of a group like Viahero, which pairs you with a Cuban local to help plan your trip and attend to the legalities. I found this page on the Viahero website especially helpful.
Cuba is every bit as entrancing as you’ve heard. It’s well worth the effort to experience the country now while American tourists are mostly staying home.
What every American Woman on the Road needs to know about travel to Cuba
- Bring all the incidentals, like batteries, medications, toothpaste, shampoo, that you’ll need for the trip. These items are expensive and hard to find.
- Bring sample packets of soap, shampoo, lotions, pens, and small items for kids. I was approached many times by people asking for them. Apparently, they’re hard to find for the locals, too.
- Street food vendors are rare, and snacks are hard to find. You can get the ubiquitous Cuban pizza, but snacks for a long bus ride—not so easy.
- I reserved and paid for all my bus travel and lodging in advance (through AirBnB) in order to minimize the cash I’d need to bring. American credit and ATM cards don’t work in Cuba.
- The Cuban government charges a 10 percent fee to exchange American dollars (even though the Cuban dollar—the CUC—is pegged to the American dollar.) So I brought mostly Euro to exchange. Canadian dollars or Mexican pesos would also avoid this fee.
- Internet access is as inconvenient as you’ve heard, but I also found that I couldn’t access any of my financial information or pay bills using Cuban internet connections.
- And don’t forget to read Women on the Road’s Guide to Cuba for Independent Women!