I Did Cuba Wrong So You Don’t Have To, America.

So you really, really want to go to Cuba, huh? And you don’t want to book through a Cuban licensed travel group? Do you have an intern, or production team to help you coordinate the trip? No? Ok, then. Here are the things you may not have known/may want to consider before traveling to Cuba (especially if you’re a US citizen):

Is it legal to visit?

Yes and no. It’s technically illegal to go to Cuba as an American tourist without booking through a licensed tour group. I’ve heard of one or two people who have been sort of arrested (think: detained lite) but once the US implemented sanctions are lifted (tentatively Sept/Oct of ’16), you’ll be good to go full-bore.

If you want to travel independently to Cuba to see what it’s like before the new American Invasion, you can stay at a casa particulares through AirBnB, which serves as your ‘person-to-person’ experience if you’re asked coming through customs back in the US (and we were). Since Obama hung out with Brother Raul, not sure if anyone is really checking too deep into returning Americans. The customs agent we dealt with, at the end of the interview, offered to give us “a long list of off the beaten track countries you can visit that aren’t Cuba”. Thanks, dude!

Can’t tell if this is Obama’s follow through, or if he gave Raul the dead fish.

Flights

Book a domestic flight to Miami, or Tampa (or NYC as well), then charter a flight through Havana Air (or the JetBlue equivalent) directly to Havana. Fair warning: it’s not cheap (about $800 USD for 2 RT tickets). Alternatively, and probably the better option in hindsight, is the fly to Toronto, Cancun or Mexico City, and buy a separate roundtrip flight to Havana on Delta or American Air. We had to check into our Havana flight 3.5 hours ahead of time, so make sure your connection leaves you plenty of time to do so if of delays.

Visas

You need a visa to fly to Cuba. You can coordinate online before hand, buy one upon arrival, or just have it added to your charter flight. I did the latter. Don’t lose the other half of your visa whilst in Cuba!

Hola, hablo 7th Grade Spanish!

If you don’t know Spanish and you aren’t a part of one of the $3500 Insight Cuba bus tours, or have a guide who speaks English, you should probably grab a Spanish speaking friend to go with you to Cuba. Even an elementary understanding of the language will make the trip that much more enjoyable. In four days, I started dreaming and thinking in Spanish. Pretty cool immersion, but my dreams were mostly of Julio Iglesias singing with Che Guevera’s face…weird.

It’s inevitable…

Insurance

US insurances won’t cover you in Cuba and Cuba won’t accept US insurance so, you’ll have to buy travel insurance. I recommend Allianz – it’s $104 for a basic policy that goes a long way, and gives peace of mind. They may ask you for proof of insurance going through immigration once you arrive in Cuba. We weren’t asked, but those who’ve been stopped had to pay on the spot for Cuban insurance for the length of the stay.

Internet/Phone

1. There are WiFi hotspots around Havana, but they are few, and you’ll have to buy an internet card to connect. If you’re in a total pinch, there’s WiFi in Melia Cohiba Hotel lobby mid-Malecon, and it’s air-conditioned. Double bonus.
2. Buy an International Plan on your phone before going to Cuba. Do it, now. Luckily, Roam About Wife has an international plan on her phone, and it saved our asses (more on this situation below).
3. Buy a Satellite Phone. Sort of joking here…

One fedora to rule them all!

Cash, Money, Woes. What!

Bring cash. Loads of cash. Even if you’re going to Havana for 3 days, think of a number between $1500 and $2000 and add another $1000. Yorur credit/debit cards won’t work in Cuba so you can’t get out a couple more bills to tie you over for the end of the trip, meaning you are screwed if you run into an emergency situation, like we did. You can exchange cash back at the airport if you have leftover moolah.

1. By cash, I mean euros. US dollars aren’t accepted anywhere in Cuba, so you’ll need to bring a ton of euros or canadian dollars. Euros get a better exchange rate to Cuban CUCs. You can exchange USD to euros in Miami, Tampa, or wherever you’re flying out, change the euros at a bank (Terminal 2 of Jose Marti Airport had a very high processing fee, so we went to a bank instead).
2. There are two currencies in Cuba, CUC and MN. 1 CUC = 35 MN, and CUC is essentially 1-to-1 exchange for euros. Unless you’re with a Cuban friend, or a tour guide is watching transactions like a hawk, assume every merchant/vendor will try to give back MNs (happened to me 3 times). If you get short-changed, say, “Hombre! ?Que pasa? !Este es pesos normales! !Da me convertibles!
3. If you run out of euros/CUCs, you’ll need to have money wired from the US to Cuba via Western Union (there’s a Western Union in Terminal 2 of Jose Marti airport). As an American, you can’t personally pick up the cash from Western Union, so you’ll need to grab a trustworthy and willing Cuban to accept the cash on your behalf  along with their full name, ID #, address, DOB, and maiden name for women (not kidding) for your American benefactors to send.

I missed my flight out of Cuba, now what?

Once you’ve shat yourself because you realize you’re stuck in Cuba indefinitely, remain calm and find the information booth at the airport to start coordinating the process (if you don’t have a host person/tour group with you). At least you took my advice and have an international plan on your phone to communicate with people in the US and you have tons of cash, right?

1. If you chartered a flight to the US to/from Havana through the likes of Havana/Eastern Airline, you’ll need to pay a change fee of ~$150 per ticket. Remember, USDs and American Credit/Debit cards are not accepted anywhere, so you’ll have to pay cash.
2. See #3 in the section above.
3. You have CUCs, and are ready to buy your change ticket, one problem: there’s no guarantee you can get on the next flight out, or the next flight, or the next flight, and you’ll probably have to start praying to the travel gods you and yours are #1 on any of the lists, governed by the higher-ups of the airport. Look pitiful, try milking some tears.
4. If you don’t get on standby nor do you like the prospect of spending another day/week/possibly a month in Cuba waiting in the Twilight Zone of standby hell, and the Western Union has enough $ in the bank, you can pay for another flight in cash, or have family/friends in the US buy you one. You’ll just have to show proof you have a flight going back to the US, not just Mexico City or the Grand Caymans, otherwise the airline won’t give you your ticket.

What if I lose my passport?

We heard a story about a young American girl who was robbed of everything except her clothes-filled suitcase. If robbed of your goods, or you lose your passport, you can go to the US Embassy in Havana and get a temporary travel letter to show at the airport. Not sure the exact process of getting the letter, I know there’s a queue that starts lining up 4 hours before the embassy opens each day, but ultimately the girl in the story started selling her clothes to tourists at the airport to try to get cash to fly out. Sounds desperate, but this was our contingency plan if we couldn’t connect with friends/family in the US. Bye, bye, wedding ring!

I follow ‘I Heart Cuba’ on Instagram and it looks sooo awesome!!!!!

It’s pretty much all ruin porn. Or, old women/men posing with honking cigars, beckoning you to take a pic of them so they can ask for $ (it works).  The ruins of Havana are hauntingly beautiful to look at, to snap photos of, but once you start looking at the buildings (mostly apartments) as displaced lives, as the families now living in makeshift barrios just outside downtown, it starts to not feel so awesome.

Folks say Havana looks like it’s recovering from a hurricane. Try atomic blast.

Final Thoughts

I’m no travel expert, nor am I pretending to be an expert on Cuba, but I’ve been to Russia and Vietnam, and those two countries combined didn’t compare to the planning and orchestration and grey areas of setting up this trip to Cuba. I thought I was mostly ready for the challenge, and I still got my ass handed to me logistically.

If you really, really want to go to Cuba, the above is some of the stuff you’ll have to plan/deal with, along with affiliated costs, and possible ‘if’ emergency situations in a telecommunications dead zone. Cuba is an incredible learning experience for independent travelers, like the wild west for adventurers — is it worth it? That’s up to you. Good luck!

-Mike

PS: Feel free to comment below with any questions; happy to help anyway I can.