Part the Second: Getting to Cuba

Because it’s so difficult for an American company to do business with Cuba, it can be quite an ordeal to find a flight from the U.S. If you’ve got all your Treasury ducks in a row, though, it is possible.

Believe it or not, there are plenty of run-of-the-mill, passenger flights out of Miami. From what I’ve been able to gather, most of them are filled with Cuban-Americans visiting their families. They can only get a visa for 21 days total in a year, though, and flights around Christmas are usually full. If you’re thinking about going to Cuba when it’s all chilly and cold up north – what better time? – then you better plan ahead and buy your tickets in September.

Gulfstream Air, Tico Travel, and Marazul Charters are some likely candidates to get you started. We used Tico Travel on our first trip and while they got us there and back, we had some hitches that made the trip more worrisome that it needed to be (although they made right with everything in the end.) Gulfstream is a company owned by Continental Airlines and we used them on our second trip. If things go well, expect to pay roughly $350 round trip from Miami to Havana. If plans blow up in you face, you can still get there for $9014!

Let me explain.

Due to internal problems, our Spanish class at UAS was cancelled and then reinstated. Because we were in limbo, we couldn’t buy our tickets until mid-November. With only a month left before our scheduled departure, there weren’t any passenger flights left. Instead of being able to simply pay $350 each for our tickets, we had to look into more creative options.

We called all the normal places, or at least the ones we could find on the Internet. Gulfstream was still willing to take us if we wanted to charter our own 19-seat turboprop, but at $8200 we decided to keep looking. In researching our dilemma, I felt reassured that there were so many ways one could get to the forbidden Caribbean island! For example:

1) You can charter a boat out of Key West… if you can find a captain who is licensed by the U.S. government to take you.
2) You can buy passage on a speedy ferry from Miami to Freeport, and then Freeport to Nassau. From Nassau you can fly to Cuba.
3) You can fly from Miami to Jamaica and then take a relatively inexpensive day-trip cruise to Santiago, Cuba.
4) Or you can charter your own plane from a number of companies out of Miami.

Unfortunately, while all these options are possibilities, not all of them are practical. For the dates we needed it, I couldn’t find any boats out of Key West, and all the flight/boat options were almost as expensive as chartering our own plane… or at least would have been after paying extra for the necessary visas.

Eventually I found an online flight broker in Miami at 1.866.FLY.ISLANDS (also called Air Charters Bahamas.) The guy on the other end of the phone line quoted me a price of $7200 for all 12 of us and, after exhausting ourselves trying to find anything better, we snatched it up. We shouldn’t have.

With three weeks to go, we FedEx’d the company 12 individual credit card transaction agreements. He confirmed their arrival and assured us that everything was okay. I began to concern myself with getting tourist visas (because, unlike Gulfstream, he couldn’t arrange that for us) and assumed that we would work out tickets and flight instructions a few days later. 1.866.FLY.ISLANDS continued to reassure me through e-mail that our flight would be ready when we got to Miami… right up until three days before we left Alaska.

That’s right, the guy at 1.866.FLY.ISLANDS neglected to ask the owner of the aircraft if he had permission to fly into Cuba. He didn’t. In a desperate bid to hang onto his commission, he told us that he might be able to find us another charter out of Nassau, but it would likely be double the cost. With three days left, I told him to take a flying leap and then, because I was responsible for arranging flights for 12 people, I panicked.

Well, no, not actually. I called in some help. Rick, the university’s Spanish instructor, had been the one dealing with Gulfstream earlier in the process when we discarded them based on their higher prices. Without time on our side, we decided to bite the bullet and pay the $9014 charter fee. The good news was that they were able to arrange a plane for us in under 72 hours and that the sky-high price would at least include our tourist visas. The bad news was that they would only accept payment from one source. Luckily, at the last minute, our university came to the rescue.

In the end, we learned that there are some nice benefits to chartering your own aircraft. For instance, there are no seat assignments! On the smaller planes, every seat is a window seat… and an aisle seat! Also, if you show up to the airport early and clear security in a reasonable amount of time, you don’t have to wait in the lobby afterwards – the plane is ready to leave when you are!

We also learned to avoid 1.866.FLY.ISLANDS.

Okay, assuming that you get your flight (or cruise ship, or submarine, or whatever) arranged, there are still a few other things you should know about getting into Cuba.

1) Even if you’re traveling under an educational permit like we did, you’ll still need a tourist visa issued by Cuba. (There is such a thing as a student visa, but you’ll only get one if you’re studying with a Cuba institution.) My Lonely Planet guide tells me that it’s possible to wait until you get to the Jose Martí International Airport to pay for your visa, but they also caution against it. What if you’re turned down after going all the way to Cuba? Then again, I know that hundreds, if not thousands, of Americans are going to Cuba illegally via Mexico and Canada. There must be a system in place for them to get their Cuban visas upon arrival – it’s not like they can purchase them ahead of time in the States!

2) Unless you’re really inconspicuous, you’ll probably have to go through Cuban immigration and customs upon arrival. Really, it’s not a big deal. I speak a little Spanish, so it was possible for me to answer the immigration official’s questions as he looked over my passport. I met many non-Spanish speaking tourists while in Cuba, though, so they must be familiar with those types as well.

After getting your visa stamped (and your passport, if you ask for it), you’ll proceed through customs. Customs consists of a walk-through metal detector for you and a conveyer-belt metal detector for your carry-on luggage. Honestly, the attendants don’t seem overly concerned if you beep or not. Both times I did and was brusquely waved through. Don’t ask me to explain the rules… we’re not in America any more!

Once in the airport, you can look for any bags you may have checked. I know there’s a luggage carousel there, I’ve seen it, but the airlines don’t appear to use it. Twice now, we’ve found our bags in a pile in the middle of the lobby. It might pay to check over the contents of your bag before leaving. I’m not sure you could do anything if something was stolen, but I suppose it’s worth a try. Better idea: Don’t check any valuable items on the flight in the first place.

Also, I should note that out of two groups of a dozen people each, I was the only one selected (both times!) for questioning before I was allowed to leave the airport. The first time was because I spoke up for the group (in Spanish) and a government official latched onto me. The second time was because my bag was flagged.

Each time I was detained for about 20 minutes and answered many, many questions about our planned stay in Cuba. My understanding is that they were most concerned that we were there preach the virtues of the American culture to their citizens or something. At any rate, if you speak to them honestly and answer their questions patiently, everything should be fine (unless you are planning to instigate something – in that case I guess you should probably lie and then casually whistle so they don’t think you’re up to anything.) Also, they’ll probably want to know where you’re staying and what cities you plan to visit. Heck, we hadn’t decided on anything, but they bought it when I told them we had reservations at the Hotel Colina.

A couple tips: When an official leads you away for questioning, ask your friends to wait for you outside. And play dumb when they find fingernail clippers in your bag.

That’s it. Once you make it past the front doors, you’ll find yourself in a swarming crowd of gesturing people, 90% of whom seem to be asking you if you want a taxi. Find one who’s willing to take you into the heart of Havana for under $15 and you’re on your way!

Next: Money in Cuba