No amount of reading up, asking for advice or online research could have amounted to adequate preparation for Cuba. Backpacking in Cuba was much more challenging than any country I had been to at that point. Right from the get-go, I was forced to ramp up my Spanish skills to levels that I didn’t even know I was capable of. For the majority of my journey through Latin America, I could casually speak Spanish while mostly getting away with just English. Nope, not in Cuba. A taxi driver told me that only about 1% of Cubans spoke English. During our unbelievably chaotic first day in Havana, that was definitely confirmed.

My British friend didn’t speak Spanish, so I took the burden of surviving Cuba upon my shoulders. After months of backpacking, we agreed that we totally deserved one night at a resort in Varadero to reward ourselves. Little did we know that the night we booked it for, May 1st, was one of Cuba’s most widely celebrated holidays. Everyone goes on a massive parade through the streets, effectively shutting down all transportation options. Any remnants of the chances of us having an easy day were nothing short of a desperate grasp at normalcy. After an unbelievably reckless night out in Cancun the night before, we were sleep-deprived and struggling to deal with the culture shock of Cuba.

I’ve been to many relaxed countries where schedules are just formalities. Cuba took it to an entirely new level. We have heard that going to Cuba was like stepping into a time machine, but that was wrong because it felt like in Cuba, time had not even been invented yet. We got to Havana and let our host know that we wanted to go to Varadero the next day, and with it being a holiday, she just looked at us like “… well.”

Thankfully, Cubans are among the most friendly, helpful, and hospitable people the world has to offer. During our time in Havana, we were like a relay baton being passed from person to person trying to make sure we got to where we needed to be at a reasonable time.

While our definition of “reasonable time” began to grow more and more liberal as our time in Cuba went on, we did always (eventually) manage to get to where we needed to go, mostly thanks to helpful locals that gave us way more than we deserved.

A week in Cuba was not even close to enough time, but it gave us a seductive taste of the diversity that this amazing country had kept a secret for decades. It truly was like stepping back in a time machine, and I don’t think I ever got tired of seeing a sleek classic car making its way down the cobblestone roads of Trinidad or the narrow streets in the old neighborhoods of Havana.

I will admit that I romanticized Cuba significantly more than I should have before I actually arrived, but it still met or exceeded every reasonable expectation that I held. By reasonable, I mean basically everything except the fantasy of renting a pink convertible and cruising down Cuba’s Caribbean coast with cigars in hand and at least three Cuban babes in the backseat (and also meeting Pitbull).

I was told that the Cuban people are friendly and will often just stop you on the street to have a chat, which you’ll come to find is almost painfully too true. I was also told that Cuba was becoming very touristy, but I found that aside from a few main squares and Wi-Fi zones, Cuba was about as authentic of a destination you can get for a destination with so much to offer. The Caribbean beaches of Varadero were stunning and the water was perfect. The pastel-colored buildings of Trinidad stood out to me as some of the most beautiful and vibrant, despite there being some similar towns throughout Latin America, like Granada, Antigua or Cartagena. Havana truly is like entering another world and to have someone like me try to describe it would not even come close to doing it any justice.

I could go on all day talking about my short time in Cuba, but I’m sure you’re more interested in finding out useful information for your own Cuba trip. Here are some of the main things that you’ll need to know before you go.

What to Bring To Cuba

An open mind.

That’s about it.

Think that’s unhelpful? Well don’t come bitching to me when your stupid Lonely Planet guidebook doesn’t tell you that to get from Havana to Varadero, you have to get off at a specific roadside patch of trees and just hope that some form of transportation will appear to whisk you away to your 5-star all-inclusive beachside resort.

Bring A Lot More Money Than You Think You’ll Need

Everyone told me to do this, and being as unprepared and careless as I typically am, I brought about $220 US dollars. Just a heads up, that’s not even close to enough for a week if you want to do anything besides stay at Casa Particulars and eat food off of the ground. Cuba does not accept American cards anywhere. You will not be able to take money out of the ATM. You are basically screwed unless you make a friend and convince them to be your own personal ATM for the duration of your time in Cuba. Backpacking in Cuba is hard. Backpacking in Cuba as an American… yeah, I’m running low on snarky analogies.

Thankfully, I went with my British friend who had agreed in advance to withdraw whatever money we would need for Cuba. Even though she hated me by the end of our trip, I hope she knows how much I appreciated her money. Her presence, on the other hand… (looooove you Madeleine).

Learn as much Spanish as you can

One of the biggest questions I had after my first day in Havana was how the h*ck did some of my stupider friends manage to survive in Cuba? The friend that I went with is a pretty savvy traveler, but if you can hardly speak Spanish, you are basically screwed. There’s no widespread Internet to just use Google Translate at will, and although this tactic often works in other countries, you can’t just stand around and look stupid until an English speaker comes along. I was in Mexico right before Cuba and speaking Spanish in Mexico compared to speaking Spanish in Cuba is like driving a car in rural Idaho compared to driving an eighteen-wheeler in rush hour traffic in New Delhi.

If you are looking for an immersive place to practice your Spanish, look no further. (But, like, don’t just go to practice your Spanish. That’s like trying to work on your tennis game by competing in Wimbledon). Very few Cubans speak English, and if you are looking to go sooner rather than later, you should at least know how to get around in Spanish. If you are fluent, prepare for some entertaining conversations with the absurdly fun, life-loving Cuban people.

(Also, can someone comment below if the period is supposed to go before or after the parentheses? Please.).

Get Used To Not Knowing Anything

Is there a bus going to Trinidad?

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When is the next bus coming?

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Is there even a bus coming at all?

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If you have the luxury of a less structured trip to Cuba, take advantage of it. It only took us a few hours before we realized that our chances of getting to where we needed to be the following day were pretty unlikely. In Trinidad, we planned ahead to avoid this by being proactive and booking bus tickets a few days in advance, only to find out they were all sold out for the next week. If you have flexibility in your plans, there can be a factor of excitement and spontaneity in this. We, on the other hand, were trying to crash course our way through Cuba in a week. There was no room for error. We got stranded in Varadero just a couple of days after thinking we were stranded in Havana. A couple of days later, we were bus-less in Trinidad. Taxis are almost always an option, but spending more money only to be in a more cramped space is not particularly appealing to anyone.

It’s not just about transportation either. If you don’t know where to find something or somewhere, then you might as well just be prepared to go on a wild goose chase. If you can speak Spanish, then feel free to ask the locals. They’ll typically ask at least five other people to make sure, and then it basically turns into a party where at least a couple of them will probably try and walk you there themselves. Not knowing anything is not necessarily a bad thing. In fact, it’s almost cathartic when you realize how free you feel just by simply not knowing anything. Ignorance is bliss, they say.

Safety in Cuba

I did not have any safety problems while backpacking in Cuba. We were actually told that Cuba is among the safest countries you can visit, despite its mysterious reputation and historic standing as one of America’s arch-enemies (f*ck communism, am I right?). Weapons are basically impossible to find in Cuba, so don’t worry about getting shot or stabbed or blown up. Gun crime is pretty much nonexistent and compared to the rest of Latin America, murder rates are among the lowest (yeah, I just cited Wikipedia. What are you going to do about it, middle school teachers?). Petty theft does happen sometimes, but it isn’t any more of a problem than any other country in the world. 

I overheard a woman warning some tourists that the only crime that occurs in Cuba is when you become too enamored with your Cuban lover at a salsa club, they might snag your phone or your wallet while you’re not paying attention. I don’t entirely know how much of that was a joke.

Cuba is safe. Even while wandering around at night in the less-touristy areas of Old Havana, we did not encounter any problems. Cubans are awake and sitting on their porches at any hour of the day. No one is going to try anything when there are that many people around.

Travel With A Friend, If You Can

Normally, I advocate for traveling solo whenever I can, but Cuba might be one of those places where even the most hardened and experienced traveler could use a little backup, even if it’s just emotional support. I was immediately thrust into the flames of the burning oven that was Old Havana. It was beyond overwhelming. I was in shock at how far out of my comfort zone I was being constantly pushed. We reserved a room with someone in advance. When we got to her house, she simply said that she was full. We eventually came to the conclusion that Cuba hardly ever works the way that you expect it to. However, for those first few hours, hungry and running on no sleep, it was a pain in the ass. If my friend wasn’t around to pester me, I probably would have just sat outside on the streets, given up, and accepted my fate. 

I graduated college with a degree in Spanish, but even I was sorely unprepared for communicating in Cuba. Figuring out accommodation, transportation, and everything else when you don’t have a confident grasp on the language is mentally tasking. Although my friend didn’t speak Spanish, just having her around made me a lot more comfortable. I could bitch to her in English whenever I needed to, and if we utterly failed and ended up dying homeless and starving in Cuba, at least we’d have each other. You also won’t have Internet. Isolating yourself from the world for weeks at a time could drive you loco if you don’t have an amigo.

It can also be pretty expensive to go solo backpacking in Cuba. Rooms can be up to 20-30 CUC per night. The exchange rate is supposed to be $1 = 1 CUC, but if you can’t take money out of the ATM and are just exchanging USD, then it’s closer to $1 = .87 CUC, which is even more expensive. Splitting that up eased the financial burden, as does splitting up taxis. You can do Cuba on your own, but I found myself really thankful that I had someone with me to share the experience of every roadblock and disaster we encountered.

Cuban People Are The Best

Walking through the narrow streets and alleyways of Old Havana, it is inevitable that you will get stopped for conversation by a local Cuban at least once per block. The conversation could literally be anything. You might even get serenaded by a group of singers on a bike. Cuban people are very, very friendly. Don’t let the decades of animosity between the Cuban and American governments define what the people of each country thinks. Not once did I get any trouble or even the slightest hint of resentment for being American.

In fact, many Cubans went so far out of their ways just to help us find our way around. The host of the first casa particular we stayed at literally walked and waited with us at the bus stop we needed to be at before handing us off to another random Cuban to make sure we got to where we needed to be (which FYI was that specific roadside patch of trees that your stupid Lonely Planet guidebook definitely would not have known about). If you ask a Cuban for help, they will not stop until they accomplish what you ask of them. There’s no “I don’t know” in Cuba. There’s “I don’t know, but let me ask literally everybody around me until I do know.”

Also, loving life is just the way of life in Cuba. Never have I been to a place that was both so relaxed but overwhelming. There’s always something going on, and that something is usually music and dancing or just loving life in general. Every restaurant you eat at will probably have a live band and live dancers. There’s probably going to be a parade crossing your path at some point. Cuba is just great.

I’d like to end it on that note. What made Cuba a wonderful experience for me was how welcoming the people were. They treated us like their own children. Actually no, like their own grandchildren. There was nothing but love and hospitality from everyone we met. Even walking down the streets with my friend, a cute blonde girl, Cubans of all ages would stop me just to congratulate me or give me a thumbs up or high-five because they thought she was my girlfriend. She wasn’t my girlfriend, but wouldn’t you love to have that constant support and confidence boosts from your friends? Let alone random strangers? Cubans are the best. One of them even gave me a free tomato just because.

No matter how stressful it was, I would not have traded a single one of the many clusterf*cky moments in Cuba for a smooth sailing experience. Backpacking in Cuba may be difficult but it is worth it. Go to Cuba as soon as you can, and bask in the history, culture, warmth, and life that this incredible island has to offer.

Check out more of my Cuba gallery on Instagram by clicking here!

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5/19 11:34 PM Update: I forgot to mention my biggest concern going into Cuba which was the whole Visa situation. I flew from Cancún where I paid $20 and got the Visa there. It took about two minutes, and they gave me a declaration of travel to fill out. When I booked my flight, I was already sent that paper so I had it ready. Even if you don’t have it ready, it takes about two minutes to complete the form. This is the form where you state your reason for traveling to Cuba, one of which is “for the support of the Cuban people”. If you don’t have any legitimate reason to actually go to Cuba, select that one. As an American, I had absolutely no problems.