how to get to Cuba as an American.

a lot of people will stress the technicalities of Americans visiting Cuba.

‘we’re allowed to go’, they’ll quote, ‘we just can’t spend money.’

this statement is usually followed with a forced twinkle in the eye/wink/smug look of aren’t you glad you asked me?

but they’re wrong.

we’re not allowed in.

the trade embargo is what kicked this off.

if the U.S. finds a stamp from Cuba in your passport, you’re in trouble.

the most common trouble will be a big fine.

it’s not a matter of ‘did they find receipts of you spending money?’, you went to Cuba. and we’re not supposed to.

I’ll stay away from the whole ‘Home of The Free’ parallels, and just explain how to sneak in.

in 10 easy steps.

1. you have to enter from either The Bahamas, Mexico or – strangely enough – Canada. what you don’t want to do is buy your tickets online. find an agent there, pay cash – no paper trail. there are plenty of travel agents in any of these places who can help you out. again… cash. you’d be surprised how many people buy online.

2. take out enough money beforehand to last you your entire time in Cuba. you won’t be using the ATM’s because of the aforementioned paper trail. if you’re wanting to sample a large number of mojitos in every place that claims Hemingway drank there, eat out at decent restaurants, stay in a nice hotel, take day trips, etc, I’d budget for $200 a day. if you’re on a budget [and I am – shockingly], then you’ll be staying in someone’s home [casa particular – more on that in a bit], eating from street carts and buying bottles of rum from the shop and drinking it someplace other than a bar, then go for $100 a day.

3. when you get to the airport, you’ll have to buy a visa there. the airline agent will direct you where to do this – it’s a pretty easy/straightforward process. for US citizens, it’s $25.

4. once you land, you’ll stand in line like everyone else. when it’s your turn, a few nice words in Spanish and a quick ‘no stamp, please, I’m American’ will do. they’ve been trained to stamp a piece of paper which will stay in your passport until you leave, but it doesn’t hurt to confirm. also – you might be asked to show proof of health insurance. if you don’t have this, then you’ll have to go to the back of the large room and pay for some. for my 10 days there, it cost me $35.

5. once you’re out, stamped, and have your bags, change a few hundred bucks or so at the banks inside the airport. the rate is horrible – as it always is, but just get enough to last you for the first few days.

6. you can find a hotel/home stay with the travel agents situated right there next to the currency exchange. there are no cheap hotels in Havana. there are big nice fancy hotels and there are casa particulars – a room in someone’s home. this might seem weird, but it’s how it’s done. plan on $20 a night, $5 more if you want breakfast. I hated mine – it was ages away from old Havana, kids were running around and there were no windows. I did get amazingly lucky that night though by eating at a restaurant with some amazing folks, who told me to rent the apartment right across the street. I took one look at the bay windows, balcony, kitchen and location and immediately agreed to the $30 a night. it was my own place, no families and right in the middle of old Havana. if you’re headed there, email me and I’ll put you in touch with the family.

7. you can change the rest of your money at any of the hotels near the main square, but if you’re changing USD., you’ll have to pay a hefty 10% tax. I checked in a few other places and they all said the same thing, so I assume this is normal. come to think of it, they didn’t charge this at the airport, so the horrendous exchange rate might have been better than the 10% tax. might be worth researching. in Cuba, it should be said, there are two kinds of currency. you’ll be given the Convertible Peso [called ‘Cul’], which is basically 1:1 with the dollar. locals use a different money, but can easily switch between the two.

8. before you leave, if you’re the very, very careful type – throw away all ticket stubs and postcards/gifts/etc you might have bought. upload all photos/videos to a hosting site/ftp and erase everything from your cameras. this might seem like overkill, but quite a few have been caught after customs took a look at their gear.

9. when flying out, you’ll need to pay a $25 airport departure tax – this can be done in USD or Convertible Cuban Pesos.

10. now, here’s where it can be tricky. if you fly back to the place you flew out of, let’s say it’s Cancun – you’ll have two entry stamps in your passport from Mexico, but nothing in between the two dates. I think this is a silly way of sneaking in/out. it’s hard to argue what you were doing [sailing, maybe?] with that right there in front of them. what I would do is fly to Jamaica, The Bahamas, etc afterwards, which would alleviate any questions that might be brought up.

a pain in the ass? sure. but it’s worth it a hundred times over.

Cubans know that Americans have to go through a few hoops to get in and they love it when you do – everyone has an Uncle in Miami, so throw that into the conversation and you’re gold.

aren’t you glad you asked me?