1 — Is it illegal? Yes. Does anyone care? No.

That’s the first thing I was wondering before I went to Cuba: is it even legal for me to travel there as a tourist? The answer is no, it is not legal. Despite all you’ll hear on TV about Obama going to Havana and loosening up the embargo, you’re still technically unable to visit Cuba by flying directly from the US for tourism. Note that it does not matter whether you have a US passport or if you’re a dual citizen, or non-American — as soon as you’re flying out of a US airport or carrier, you’re under US jurisdiction and it’s illegal to go to Cuba for tourism.

However: no one cares. The US doesn’t care, Cuba even less (the embargo comes from the US, not from Cuba), and all you have to do is to check a box on a paper that your airline will provide you.

This is how it works in practice: First, as soon as you book your flight you’ll want to contact your airline and ask for a Cuban tourist visa and insurance. On Delta it’s about $50 which you can pay with credit card and they’ll send you a receipt via email. After you get to the airport and go through TSA, when you’re at your gate go talk to the airline representative and ask for the visa, or they will start calling your name on the intercom to see them.

They’ll give you a little piece of paper that you’ll fill in manually: this is the tourist visa + insurance that Cuba requires. You’ll get it stamped at your arrival in Havana. The representative will also give you a paper that asks for the reason of your visit to Cuba. You have a dozen options from Business Travel to Support to the Cuban People. What you want to check is People to People Exchange. But honestly, you could check any of the boxes and it wouldn’t matter. The airline will give you a number to put on the form, then they collect that paper and stack it on a bunch of other papers and probably light a fire with it or something. From this point, you’re all set, you have your tourist visa that will be required at the Cuban border, and nobody will care about why you’re here. Very important: do not lose your Cuban visa which is only good for 30 days, you won’t be able to leave the country and you’ll have to go through bureaucratic hell.

Flying back is as easy. First you’ll be asked for your tourist visa by the Cuban authorities, then you’ll go through security, take your flight home, and go through the US border. From my own experience and what I’ve read online, US officers will not give a damn fly about what you were in Cuba for, they’ll just chitty-chat about how your cigars taste like and how expensive your airfare was.

2 — Bring a shit ton of cash

Cuba is a poor country but you’ll be surprised at how expensive things can be, especially during high season and the new flood of American tourists coming in. There was a food shortage during our trip, and many restaurants were out of several items on their menu, and grocery stores were empty.

Cuban purposely price things differently for tourists and for locals, hence why you’ll be mostly using CUC instead of the CUP. Meal prices can be easily compared to San Francisco, about ~$15 a dish, maybe less depending on where you go. It’s really hard to wrap your head around it before your trip, and most tourists will run out of cash quickly.

You can only pay in cash in Cuba. There are a couple ATMs spread out around the country, but they either won’t handle your type of card, not work with your US bank, or not work at all.

What you need to do is get a shit ton of cash from your country of origin and convert it to CUC when you arrive at the airport. I recommend avoiding USD since you’ll have to pay a 10% penalty + a flat fee. Instead, withdraw Canadian dollars or euros. At the very minimum, you’ll need 700 CUC per person per week (food + drinks + accommodations + touristy stuff). A comfortable amount would be 800–900 CUC.

To give you an idea of how much stuff cost:

A meal: 10–20 CUC / person

One night for two at a casa particular: 30 CUC

A cocktail: 3–5 CUC

A small bottle of water: 1–1.5 CUC

A taxi collectivo from Havana to Trinidad: ~35 CUC / person

A day trip to El Nicho (~1 hour from Trinidad): ~50 CUC per taxi (4 ppl)

If you run out of cash, you’re in deep trouble. As I’ve said before, don’t count on ATMs since they don’t work with US banks. The only way you can find cash is by finding other people who brought extra cash and are willing to give you some sweet USD/CAD/EUR with the hope you’ll pay them back in the US. Don’t count on Venmo or Square Cash to instantly reimburse them on the spot, both services don’t work in Cuba since they detect your IP and will block the transfer even before you tap Submit. Oh, and you won’t have internet either, so there’s that.

3 — Boil your water

One thing that is underestimated is the money you’ll spend on water especially when the weather gets too hot. Cuban water — but more especially in Havana — is not drinkable for tourists. From what I understood from a tour guide in Cienfuegos, it’s about bacteria that we’re not used to but that locals are. Even Cuban people hesitate to drink tap water. One easy solution — besides buying those little water bottles for 1 CUC — is to boil the water and put it in the fridge. Most casas particulares will either have a fridge full of those bottles (which you need to pay for at the end of your stay) or something to boil the tap water with.

4 — Know how to get a taxi / taxi colectivo / bus

You’ll probably stay in Havana for your first days in Cuba, and landing in a new country brings a lot of uncertainty about how to get around. We were pretty confused as to why there was no taxi line at the airport, and kind on our defensive side when people would come to us yelling “taxi”. That’s how it works there, nothing’s organized, everything’s about improvising.

In more practical terms: when you arrive at the airport, after getting your baggages and exchanging your money outside of the airport, you’ll want to go to anything that looks like a car — old American car, yellow cab, or a shitty Peugeot — and ask for a ride to Havana. They’ll ask for your exact address (cross street + door number). When they agree to take you, ask how much it’ll cost (“Cuanto?” will suffice), and make sure you agree on the total price to avoid the confusion of a price per person / total. A fair price is $10 / person. If the price doesn’t work for you, just say no and go to another car.

It’s pretty easy to negotiate prices in Cuba. When they say 20, say something lower like 10, they’ll frown a bit and say no, say 15 and they’ll say ok. If you can find other people that are willing to share the ride, you’ll get a better price.

When you’re within the city, you’ll want to aim for old American cars driving around. Hail them, wait for them to stop, and repeat the same process: tell your destination, wait for them to agree, ask for the price, say something significantly lower, wait for them to say no, say something reasonable, wait for them to agree, and boom you’re in.

A taxi ride within the city should never exceed 5 CUC, most of the time you negotiate 4 CUC. The pink convertibles or the yellow round scooters will usually cost more: about 7–10 CUC.

Now when you want to go to another city, you have two options: taxi colectivo or bus. Buses are booked out really quickly, especially in high peak season like during christmas or the summer. You can book them online at Viazul.com ahead of your trip, or go to a Viazul station.

If you can’t book a bus seat, taxis colectivos are an excellent alternative. You’ll basically be sharing a cab from one city to the other, your luggages will probably go on the roof and you’ll have to squeeze your legs a bit, but that’s the true Cuban experience.

In practical terms: go to your city’s Viazul station and you’ll see a bunch of locals hanging out around there. Go to some them and ask “taxi collectivo?” and they’ll either say yes or point you to the right guy. You indicate your destination and day of departure and ask for a price. If it suits you — and again you can always negotiate — you’ll indicate your hour of departure and provide your exact address, they’ll come get you there. Remember to ask for the person’s name + phone number in case you need to cancel or make sure the trip is still happening (which is always good to do). The car will show up at your casa particular and drive you for a couple hours along with other tourists, and drop you off at the destination of your choice.

5 — Avoid Cienfuegos, go straight to Trinidad

We read somewhere that Cienfuegos was cool and that it was worth going to on the way to Trinidad so we booked two nights there. Let me tell you: it sucks. Restaurants are terrible, the beaches are just the ugliest patches of sand we’ve seen, and it’s just plain dead by day and night. It’s like this empty village that your grandma lives in and that you’re always reluctant to go to because you know you’ll get so bored that euthanasia is an option.

The only thing that saved it was our trip to El Nicho — a wonderful park filled with waterfalls and two great natural swimming pools. You’ll pay about $50 for a taxi to bring you there, wait a couple hours, and drive you back. The cool thing is that it’s about the same distance from Trinidad than it is from Cienfuegos, so you can just take off from Trinidad instead.

Trinidad, on the other hand, is just so freaking cool. Imagine a big village with stuff from the 1800s, paved roads, music bands, where everyone knows each other. My recommendation is to rent a scooter there — if they don’t run out — and explore the city that way. There’s also a peninsula about 10km away with a lot of small cute beaches and a bigger one called Ancon that you’ll want to ride to. Remember to reserve a day for a horseback ride within the valley, that’s the cherry on the cake.

6 — Forget about the internet

Here’s the deal: Cuba is 20 years behind in terms of internet. There is no internet at home, they’re barely starting to test it in Havana. The only internet access you could possibly have is by using one of the 50 wifi access points spread around the country. There’s probably 10 of them in Havana, 2–3 of them in Trinidad. But here’s the catch: it’s not free, at all, and it’s so freaking slow that it’ll drive you mad.

First, you need to buy an internet card either in an ETECSA selling point, a nice hotel, or from the street. The card is basically a unique login/password that you’ll need to enter when connecting to the WIFI_ETECSA hotspot. It’ll cost you $2–4 per hour depending who you buy the card from. If buying from a street seller, make sure the password is not scratched already at the back of the card. To “log out”, just disconnect your wifi and it’ll stop the countdown so you can use your card again later.

The internet is painfully slow and should probably only be used for emergencies, as it takes a few times to connect and sometimes just stops working suddenly as you’re using it. You’ll need an offline map app since you can’t count on Google Maps (even in offline mode, you can’t download the Cuba map for some reason). I recommend Maps.me since it has most of the restaurant names + points of interest. It’s buggy as hell and you might have to restart your phone a couple times, but it’s free and it has directions. Remember to download the Cuba map ahead of your trip!

7 — Cuban time is *highly* flexible

Cuban people are really chill, so chill that they forget the concept of time. Never, ever, rely on office opening/closing hours, especially in state-owned offices or shops, such as all rental services. As the popular quote goes there: “They (the government) pretend to pay us, while we pretend to work.”. If they say 9am-5pm, assume 10am-4pm. You should assume that even if the office is open, the one guy that takes care of renting scooters is on a hour long break and that the other guy who takes care of car rentals won’t help you either. When they say “he’ll be back in 5 minutes”, assume “he’ll be back in 30 minutes”. In privately-owned businesses, paladars (restaurants) or hostels though, service is not as much of a problem.

As frustrating as it can be, it can also work to your advantage. For instance, there’s no need to confirm your arrival hours with your hosts, just show up whenever you feel like it and it won’t bother them one bit. Another example would be that if you need to cancel a taxi collectivo and can’t get in touch with your contact, just don’t show up or tell them you’re not going when they come to pick you up. They’ll be fine with it.

I guess the key here is to be very flexible with your own time and take things easy, it’ll go a long way there.

8 — My recommendations for Havana / Trinidad

Havana

Do:

Enjoy a piña colada at the Hotel Nacional

Walk down the Obispo street and stop for a drink and listen to live music at Bosque Bologna

Yvan’s Chef Restaurant — great food in this affordable restaurant that has no sign. Take the slow-roasted pork with crispy skin.

O Reilly’s 304 — awesome tapas and cocktails

Don’t:

Museum of the Revolution: there’s too much random stuff, all the text is in Spanish, and we did not learn anything.

Cienfuegos: don’t. Please don’t.

Trinidad

Do: