Traveling to Cuba as an American: Havana

This will not be your ‘Cuba was magical, romantic, a moment stuck in time’ post. If you’re looking for that – there are plenty out there, believe me – I’ve read them all. It’s natural to put a positive spin on experiences when looking back and reflecting, and to be honest, I’m currently fighting the urge to do that right now. A week removed from the trip and I already find myself wanting to tell you all about the brilliant architecture, the strong drinks and the smiles. But sharing a small percentage of the experience won’t be helpful – or entirely truthful – so that’s not what I’m going to do.

How We Got There

We spent 6 nights in Cuba – 4 in Havana, 2 in Trinidad, 3 rooms total. We explored completely on our own – no tour guide, no help with meal + room reservations – no local knowledge assistance of any kind. There are two options when it comes to accomodations: hotels or casa particulars. We opted for the casa particular route to stay more authentic to the cultural experience we wanted to have. What’s a casa particular, you ask? Cuban families open their homes to tourists to supplement their income. With average monthly incomes ranging around $20 a month, many families choose to do this – there’s no shortage of places to stay. We booked via Airbnb, but there are a number of other sites that offer booking. You also can just head down without reservations and knock of one of the thousands of doors with the ‘room for rent’ symbol – an upside down anchor.

We flew through Canada for one reason only: to save money. Direct flights from the US are now possible, but difficult to book without a travel agent (many are still chartered flights) and expensive. Our round trip ticket was easily half of what we priced flying from the US. I also was able to introduce Grayson to St. Hubert  while hanging in the Montreal airport, so, worth it. Going through Canada also allowed us to switch our US dollars to Canadian, which helped us avoid the 10% exchange penalty when switching to Cuban CUCs. We traveled legally under one of the 12 general licenses and had our passports stamped in Cuba. No questions were asked as we came back into the US, but we still had paperwork and answers ready to go if they were.

The Basics

Wifi. It isn’t a thing. You can purchase internet cards in major hotels or on the street in wifi “hotspots” – generally parks & bus stops throughout the city – but the service is spotty. Just go with the intention of being off the grid for a few days and bombard your Instagram feed with Cuba shots the moment you’re back in the States.

Money. There are two currencies in Cuba – CUC and CUP. CUC or ‘kook’, is the currency most often used by tourists and what you’ll receive at most exchange stations. CUPs are used my locals at places like cafeterias, produce markets, etc. and while you can use them as a tourist, most places we visited accepted both. When we were there, 1 CUC equalled 24 CUPs.

Making calls. My iPhone worked in Cuba using international call + text rates. Check with your provider, but you should be able to make calls by simply adding the country code in front of the number you’re dialing. I made a number of calls back to the US throughout the week, as well as to other lines in Cuba.

Cabs. Meters don’t exist in Cuba. If you can, have your host arrange cab pickups for longer-distance rides (the airport is 35 minutes outside of Havana.) For rides around town, be prepared to negotiate a price and ALWAYS agree on one before stepping in. We learned that the hard way. There’s no shortage of cabs around the city, just know that most will rip you off if you don’t know any better.

centro habana_street 1

centro_colorful street 2 centro_colorful street

centro_old car centro_pink house

Here’s what months of research did not prepare us for:

The language barrier. Yes, I know English is not the first language spoken in Cuba, and I know it’s lazy (and ignorant) to assume you can get away with not speaking some amount of the language spoken when traveling abroad – but hear me out. Cuba is a heavy tourist destination – especially the areas we visited. Europeans, Australians, Canadians – they’ve all been vacationing in Cuba for quite some time. Everything I read noted that while not every local spoke English, many had some level of knowledge – especially in situations tourists frequent (cab rides, museums, bars, etc.) This isn’t true. I speak zero Spanish – gracias, hola, queso, that’s it. Grayson can get by with some key phrases and numbers, but we struggled every. single. day. Our hosts didn’t understand us well – cab rides were difficult – even the currency exchange desk at the airport was a challenge. If you don’t speak Spanish somewhat fluently and you don’t have a tour guide, you’ll have some definite moments of frustration.

The level of poverty. There are ways to shield yourself from some of the poverty that exists – just look at how the Kardashians explored Havana (conveniently while we were there, also.) If you want to experience the reality of the country, be prepared for economic hardship, dirty streets, rotting food, poor plumbing and an overall vibe of defeat. The Cuban people are wonderful and full of life – don’t get me wrong – but as you start learning more about their lives, you start to see the frustration that comes with a socialist government emerge from behind to the smiles and laughs. Many don’t have enough food, live in crumbling buildings with no air conditioning, and work hard each day for monthly paychecks that amount to less than what we see in a day. An economic upswing will take time.

The amount of political conversations we were pulled into. The amount of times I read ‘don’t bring up politics in Cuba’ is laughable, because the moment you say you are from the United States, the conversation takes a direct turn to our governments and their relationship. Many support Fidel Castro and the revolution he created – many do not. In a country where government spies still exist throughout neighborhoods, chatting about our opinions was not only uncomfortable, it was kind of terrifying. Propaganda is everywhere (we even pulled up next to a billboard of a Cuban fist knocking Uncle Sam out – you’re from the US, welcome!) and hard to ignore. One common love among all we met – Barak Obama. If you aren’t a fan of Barry, don’t mention it while you’re visiting.

The food. It wasn’t good. To keep things simple, I’ll break dining into 3 options: government-owned restaurants, paladares and street cafeterias.  A paladar is a privately-owned restaurant, often located in people’s homes, where there is more opportunity for higher-quality ingredients and creativity. We tried to stick to this option but many of the places we had on our list required reservations made further in advance than we had anticipated. We did fall in love with a few paladares, but the food was far from “traditional cuban”. Street food isn’t a thing in the way I had imagined – rather than carts selling sandwiches & snacks, there are cafeteria windows. You won’t find a Cuban sandwich (at all – the glorious panini-style sandwich we know in the states comes from Florida – surprise!), delicious bowl of black beans or fried plantains. You’ll find pizza, fruit juice, maybe a ham & cheese sandwich. Street food in Cuba truly highlights how low incomes affect local cuisine.

centro_old and new

dachsund_on street densil_rooftop

centro habana_floor cuba_ casa densil mirror shot cuba_ casa particular densil roof 2 cuba_ casa particular densil roof cuba_ casa particular densil

What we’d recommend in Havana:


We truly loved our Airbnb experience. The images online were accurate and the hosts were welcoming and lovely.



  • Habana 1791 An old perfume shop where the scents are handcrafted and bottled there. I came home with the Mariposa (Butterfly Jasmine) fragrance – Cuba’s national flower – and I’m already stressing about what I’ll do when I run out.
  • Drinks from the outdoor bar at Hotel Nacional de Cuba. It doesn’t hurt if Fast & Furious 8 is being shot in the same spot while you’re there.
  • Meander through the rows of marble graves in the Cemetario de Colon.
  • Walk. Everywhere. It’s the best way to see what the 3 areas of La Habana have to offer. Touristy Habana Vieja has beautifully-restored buildings, Centro Habana is gritty & real, Vedado feels the most like you’ve stepped back into the 1950s.
  • Buy a box of cigars. Here’s the deal with cigars in Cuba – one of the easiest ways to scam tourists is to sell them crap cigars on the street. It’s a safer bet to purchase from hotels or cigar factories, but here’s the best option of all: find yourself in Havana during a day of the month where factory workers can sell from their homes. Each month, the government allows workers in the cigar factories to take home a bundle of high-quality boxes. They have a day to sell these to tourists at half-price, but finding these homes can be challenging. If a local brings you to the home and helps with the sale, they are given a ration of food from the government as payment. Another example of how dire things can get – but if you’re going to spend $ on cigars while there, put your money directly in the hands of the people. And go home with a box of Cohibas for $150 instead of $300.
  • Grab a ride from a classic American car parked outside of Parque Central Hotel.
  • Most will tell you about the Malecón at night – but we preferred walking it and taking in the sights during the earlier morning hours. The breeze is perfection, all is quiet and you can see take in the sights across the street without constant traffic.

Stay tuned for a dive into our second leg of the trip: Trinidad! And if you’re looking to explore Cuba and have any questions, I know the feeling, and I’d be happy to help!

cuba_ centro capitol

centro_green graffiti centro_boxing ring cat in front of garage

cuba_ cohibasvedado_blue houses plants in window old car_steering wheel

nacional flag nacional fountain


vedado_pink car

vedado_barber shop vedado_matter pants

bananas on street corner blue car_woman in window

la floridita jeans pink building hidden terrace_1 habana vieja_old car habana vieja_man waving

cafe bohemia_2 cafe bohemia arte artobenial

centro_purple car church_birds chocolate shot

centro_nice blue car centro_hotel sarasota

window clothes vedado_grocery shot

malecon_white van malecon_orange building malecon waves

cuba_ old car on malecongreen building with car

cuba love building

plaza mayor_1 rooftop_man in window cuba_ blue hotel

habana vieja_prado_ cuba_ casa blanca 1 cuba_ casa blanca 2 casa blanca lemonade casa blanca_floors

cuba_ kids playing soccer_ cuba_colon cemetery cuba_vedado building

cuba flag

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