Havana a Good Time in Cuba

Painful history aside, Cuba is full of depth, authenticity, and class. Even though it is decades behind us, its people definitely have something Americans have lost. They are uninhabited by the consumerism, falsification, and attention cravings that ads and social media produce. They’re constantly present and tapped into their creativity instead of televisions, laptops, and cell phones. They are free in ways we are not, and for that I envy them.

I got back from Cuba a few weeks ago, and I’ve gotten more questions about this trip than probably any other trip I’ve taken. Rightfully so because Cuba is a fascinating place that despite being so close, still feels out of reach for Americans. Like every country I’ve explored, the photos I posted on my Instagram account hardly do justice to the sites, colors, smells and sounds I took in. I’ve said it a hundred times before, and I’ll say it again… you have to experience it for yourself.

“But how exactly do I travel to Cuba?” is one of the many questions I’ve gotten on repeat the last few weeks. Well, I’m here to tell you everything I learned, and subsequently, what you need to know.

1. Choose your dates

The best time of year to visit Cuba is November to May when it’s dry and not too hot. Depending on how much exploring you want to do and how much time off work you can take, I recommend staying at least 4 or 5 days. This will give you time to dive into Havana and also take a day trip to two to places like Vinales, Varadero, or Trinidad. 

2. Book your flight

As a U.S. citizen, when you book your flight to Havana you will be required to select one of 12 categories that you’ll be traveling under when you check out on the airline website. Choose “support for the Cuban people” and you’ll essentially get to roam Cuba like a normal tourist.

3. Purchase your visa and health insurance

Travel visas are required to enter Cuba along with Cuban health insurance. Luckily, most airlines make this super easy and allow you to purchase both through them. I booked through United and they automatically tacked on $25 extra to my flight for health insurance. I didn’t have to do a single thing for it. They also let me purchase my visa ($75) at the gate before boarding my connecting flight. Again, SUPER easy.

4. Book your lodging

There are quite a few resorts and fancy hotels in Cuba, some of which are all-inclusive. Personally, I hate nothing more than traveling to another country and living the American lifestyle, so this would not be my recommendation. But if that’s your type of vacation, the option is certainly available. If you’re wanting to indulge in the culture a bit more, you should look for a local boutique hotel or stay at a casa particular where a family actually hosts you – including cooking your meals! Outside of hostels (which are great if you’re traveling solo), casa particulars are actually the most affordable option. They also provide the most genuine Cuban life experience.

Regardless of your lodging preference, make sure to check the most recent Cuba restrictions list to ensure you’re not staying at a place that is banned by the United States government.

As for location, you will likely be spending most of your time in the heart of the city in Old Havana. Old Havana is very walkable everywhere you go. It is the loudest and busiest though, so if you’re looking for something a little quieter at night, Vedado and Miramar are very close neighborhoods with short and cheap cab rides into Old Havana. Miramar is a bit more uppity and refined. Vedado is a bit more hipster-like. I stayed in Vedado mostly because I booked this trip last minute and places in Old Havana were sold out. However, I do not regret this because I got to know a neighborhood I probably would not have explored otherwise. I stayed at a boutique hotel called ARTeHOTEL on Calle 2, and it was AMAZING. I cannot say enough good things about the cleanliness, uniqueness, convenience and friendliness of this hotel and its staff. It’s prettier than any photos you’ll see online, and the owner is a world-known photographer and gem of a human being (as is his wife).

5. Get cash

There are almost no credit card machines or ATMs in Cuba, especially ones that take American bank cards. Your only method of payment there is cash. That means if you run out, you’re screwed. A couple we met from Mexico City ran out of cash and asked if I had any to spare until they could Venmo or Paypal me when they got home. I was running very low myself but was able to loan them $60 to get them through their last day. I’m serious when I say no cash means you’re done.

That being said, bring plenty of cash with you ($50 per day per person is a good estimate, and tack on an extra $200 or so to buy things like cigars, rum, or art), but don’t convert it all! There’s a VERY high exchange rate to convert US dollars to CUC (Cuba’s currency) as Americans pay an extra 10% tax in addition to the 3% conversion fee on the US dollar. So if you convert too much you’re wasting a lot of money – plus the cost to convert it back. For the record, 1 CUC is equal to 1 USD which makes for very easy math. There are exchange booths all over Havana so converting money every day or two is not a hassle. We were able to get 87 cents back on our dollar at the exchange booths, but if a local is offering you something higher, take it! You don’t have to use the government official booths to exchange money.

6. Go there

In my opinion, this is where your pre-trip planning should stop. Just go there. I realize I’m on the far end of the free-spirited spectrum and am exceptionally laid back when it comes to travel, but I’m telling you, you really don’t need to do any more prep work. You’ll realize shortly after your arrival that the locals and hotel staff do great with English, are eager to help out, and are full of helpful tips and recommendations for places to go. Plus Havana is a walking city so you will come across nearly all the “must-sees” simply by just walking around Old Havana on your own. You should also take a city tour (about 2 hours) in an old vintage car. Again, no need to book ahead – they are EVERYWHERE in the city. Just grab one and go. You’ll stop at a lot of places in a short amount of time all while riding in style.

Depending on how many days you have, I highly recommend doing a day or two out of Havana and seeing more of Cuba and its countryside. Vinales, Varadero, and Trinidad are some of the most popular destinations. I only made it to Vinales so I can’t speak to the others, but I can definitely say Vinales was WORTH IT. It was a short 2.5-hour bus ride with the most breath-taking scenery. I got to tour a cigar and coffee farm, see what small-town Cuban life is like, eat in some huts surrounded by green and mountains, and explore a cave. It was $60 for the entire day (including food) and gave me a look into a stunning side of Cuba I never knew existed. My only regret is that I didn’t go horseback riding there which I’ve heard is incredible! You can book day trips while you’re in Havana. There are companies all over the place that offer them so no need to book in advance. It’s better to keep your itinerary loose because you’re sure to discover things you didn’t plan on doing.

For nightlife, two of my favorite spots were Fabrica de Arte Cubano in Vedado and El Floridita Bar in Old Havana. They are VERY different but both famous for good reason. I won’t spoil the surprise and tell you too much about them other than to check them out. 🙂

7. Draft your itinerary

All Americans who travel to Cuba need to have an itinerary that fits into their chosen category of travel. It’s only needed when you go through immigration on the way back to the United States. Officials ask to see it less than 1% of the time, so the chances that you’ll actually need it are slim. Nevertheless, have it ready JUST in case. On the last night of your trip, or even while you’re waiting at the Havana airport for your flight home, write up a list of all the things you did on your stay. Refer to back to pictures you took to help trigger your memory. Make sure your itinerary includes activities that support the locals such as dining at local restaurants; purchasing art, Cuban cigars or rum from the locals (all of which are legal to take back to the U.S. by the way); old car tour with a local; etc. Also make sure it does not include anything on the Cuba restrictions list (even if you did it). Here is a copy of mine if it helps (though it’s not an exact agenda of the things I did or did not do). Remember everything is a cash transaction once you’re there so there’s no way to track your activity.

Things worth noting

Cuba is very safe. Surprisingly safe actually. Gun crime is virtually nonexistent and overall murder rates are very low. There are almost no violent crimes, organized gang culture, teenage delinquency or danger zones. There is a strict and prominent policing known as the Committee for the Defense of the Revolution (CDR) that keep the streets safe. Scams are the main thing to watch out for… meaning locals will try to upsell you things or persuade you to buy something, but I didn’t experience any type of scamming that wasn’t easy to spot or turn down. You’ll get an idea for how much things cost after a day or two and will feel more confident in knowing whether or not you’re getting a good deal.

Cuba has one of the best healthcare systems in the world! Just an interesting fact that I never knew.

Tipping is fairly common for tourists but not at the same rates as the U.S. For example, I usually left a dollar or so after a meal at a restaurant. Food and drinks are so cheap anyways.

Don’t count on Wi-fi or cell phone data service. If you want, you can purchase wi-fi cards once you get there which allows you to get on wi-fi at places that offer it – which is a short list. Even hotels that say they have wi-fi still require these cards. You should know though that even at places where it is available (again, with your card) it’s still really spotty and slow. Print or screenshot materials (like articles, maps, restaurant names, etc.) for reference when you’re there.

Cuba was easier to travel to than a lot of other countries I’ve been. Don’t obsess over the “rules” too much as once you arrive in Cuba virtually everything is a cash transaction and is untraceable. They don’t have printers or offer receipts either so if you accidentally go somewhere that’s restricted, don’t sweat it. The U.S. government really doesn’t have a way to know about it (hope they’re not reading this 😉).

That’s it! I can’t think of anything I left off this list. And if I do, I assure you it’s updated by the time you read this. Just relax. Don’t overthink or overplan your trip. And above all, ENJOY IT!!!