A Guide to Havana Cuba From the USA

Peter and I both live in Florida, so when direct flights became available from Florida to Cuba, we both decided to make our bucket list dream come true by booking a trip. This article is based on our own personal experiences of visiting Havana, from booking our flights, to the places we’ve seen in Havana, where we stayed, and maybe even feature a Q&A as well in the end. Note that we might be making this in different parts, the articles of which will be linked to this original post.

Guide to Havana Cuba from the USA
Guide to Havana Cuba from the USA

A Guide to Visiting Havana, Cuba (from the USA)

Resources/Additional Reading:

A Background: Why Visit Havana (or Cuba in the first place)?

Ever want to go back in time to see how life was before? Well, Cuba is the place to go. Filled with Ladas from the Soviet Union Era, 1950s Chryslers and Pontiacs without any catalytic converters, houses that were built in the old Spanish colonial style, plazas that make you feel like you’re in Europe – all of these are main reasons why you should want to go to this lovely city. In the good old days, Havana was a rich city, way back when the gangsters were there and Americans would fly in just to stay a weekend and fly back to their normal lives. Think Vegas, but in the Caribbean.

It was all good and well until the Cuban revolution happened, the country turned communist, and the US put in various sanctions that effectively made Cuba stuck in a time warp from its heyday in the 1950s. It’s like Groundhog day for inanimate objects, but with a different cast of animate people/animals that change and age throughout the decades.

That is the Cuba that I want to see before the country truly opens itself up to tourism and becomes Cancun or something. I want to see at least a part of the Groundhog Day Cuba, and not a cleaner city. I want to be able to show future generations that this was what Havana was like way back in 2017 and go back when it is a bit more developed and compare the two.

That was our main reason why we wanted to go in the first place. While our reasons were quite selfish, we also want to learn more about the country. For a country that was cut off from America (but is open to others), it is good to learn more about our neighbor and, after all, it is only an hour’s flight away from Orlando.

You make your own decisions about why you want to visit Cuba.

Know Before You Go
Know Before You Go – Peter & Anthony discussing where to go after our first day

Important Things to Know Before You Go to Havana, Cuba

Even though Cuba is sort of open, if you are an American Citizen or a Permanent Resident (green card holder), you’re still technically not allowed to visit the country as a tourist. So never, ever say to the immigration officers back in the USA that you went to Cuba for tourism. When booking your flight from the US to Cuba, you are asked by the airline to declare what visa type you are going to Cuba on. Most people choose ‘People to People Exchange’ or ‘Support for the Cuban People’.

Those visa types are a bit vague – people to people exchange can relate to you staying at a Casa Particular with your host and end up staying up for most of the night as you talk to each other about the culture and history and how the country has changed. You go to museums with a tour guide and that can also count as a people to people exchange – you are learning something.

Support for the Cuban People is also vague Рif you spend money on the country, does that mean you are supporting the Cuban people? By eating at a paladar (a local-run restaurant) or staying overnight at a casa particular, does that mean you are supporting the Cuban people? So, what we are trying to say is that if you do want to go to Cuba from the USA, you can opt to use either of the two but in no way are we endorsing lying to the authorities. You have to make sure that you are indeed learning about the culture and the country if you do go.

Also – Cuba, despite its past, is very, very safe. In fact, it was dubbed as the safest Caribbean country. The people love tourists because it is helping their economy improve, and as our host said, if you harass or do something to at least one tourist, world will get around and they may get a bad rep and lose valuable tourist revenue.

In fact, visiting Cuba has a sort of domino effect. You help the taxi driver that drives you from the airport to your casa, you help your host (ours was amazing, and is very hospitable – she treated us like her real children while we were staying with her) to earn CUC (Cuban Convertibles, more about that later), you help the owner of the paladar (while tasting great home-cooked food), you help the vendor of the books from the Plaza de Armas, and also the souvenir store owner. True the country is slowly becoming more capitalistic but in this world of globalization, a little capitalism surely won’t hurt anyone, right?

The Logistics

Getting to Havana

Now that we have covered the know before you go, it’s time to start booking your flights. Gone are the days when you had to fly to either Canada or Mexico and fly to Cuba. Also gone are the days when you had to fly a chartered flight from the USA to Cuba and paying around $500+ for the benefit of doing so. Major airlines now fly to Havana non-stop from various cities within the USA.

In our case, we live in Florida, so we have choices to fly to Cuba from Miami, Fort Lauderdale, Orlando, and Tampa. These are serviced by the big airline companies: low cost and low service. In this case, we decided to fly using JetBlue direct from Orlando to Havana. We chose JetBlue because the price for the flights for two people was only 5,200 TrueBlue points + $94. It was a steal we couldn’t say no to. That and there were dates available for President’s Day Weekend so off we went.

The flights to Havana are apparently not as full as what the airlines had expected, so the price for the flights has gone down significantly than when they were first sold online. Now you can get a flight for less than $120 from Orlando (if they’re on sale). When we flew to Havana, however, our flight was full. Maybe it was the holiday weekend but there were no empty seats and the plane was full of happy buzzing people ready to travel. There were even some people who brought their children. Talk about a main event! These US airlines also fly to other Cuban cities like Varadero, Holguin, Camaguey, and Santa Clara. Worthy places to go next time perhaps?

Note that every airline has their own set of rules. JetBlue offers visas at the airport, which you can buy for $50. They also include the travel insurance required for your trip, which is great. For other airlines (like Spirit), you’ll have to source the visa (the tourist card) yourself by contacting the Cuban embassy, which will mail you the tourist card, although not sure how much that costs.

Alternatively, you can cruise into Cuba. When the country first opened up, the cruises were all too eager to go. In fact, when we were there, a cruise ship was docked in downtown Havana Vieja, an MSC ship. We also saw people being guided in town as part of their shore excursion. This is a more expensive approach but if you want a bit more luxury and staying in hotel like quarters then a cruise may be for you.

Peter sleeping in our casa particular
Peter sleeping in our casa particular

Where to Stay in Havana

The most cost-efficient way to stay in Havana will be at a casa particular. Think AirBnB where you’re renting out a spare room from a local (if you’re new to AirBnB, sign up using our referral code and we each get $20 in travel credits when you book your first stay with AirBnB)! This is the one of the best AirBnB experiences we’ve ever had. We’ve never been taken care of so great by our host, Zaira. The name of her casa particular is Casa Habanera, and if you do want to stay, make sure you book early.

The AirBnB has two rooms, which we booked both as we are a couple who need 1 room and our other friend wanted to stay in his own room. Both rooms have their own bathrooms (with hot water, something that’s not all that common in Havana just yet), an internet router (faster to connect to using the scratch off internet cards, but more about that later), air-conditioning, and filtered water. Our room is the more private one, with one double bed, and a bunk bed – so it’s perfect for families or larger groups of friends who want to stay together in one room. We didn’t use the air conditioning as I get cold quite easily and the fan was more than enough. Our friend did and it was cold in his room when we popped in the next day. Note that the rooms don’t have any windows, so if you’re super scared of pitch black places (like I am),¬† you can turn on one of the small lamps in the room and off to bed you go!

You can request Zaira to make you daily breakfast. Every single morning, we would get something different. The first morning we got sausages, the next day, we got ___, and on our last day, we got a hamburger. Every single meal comes with bread, juice, vegetables, fruits, and Cuban coffee, and only for an additional 5 CUC (around $6 or 5 EUR!) We loved her cooking so much! In fact, Zaira said that she used to own a small restaurant that serves breakfast and lunch before converting her business into a Casa Particular. She did mention that Cuba was slowly turning back into a tourist area, and recommended other places like Matanzas and also Varadero (she asked if we’ve been to Cancun and we said yes), which is like Cancun where the hotel zone rules.

The AirBnB is located in Industria Street, within walking distance to the major sites like the Museum of the Revolution, the Prado, Capitolio, and Havana Vieja. Win win, we saved a lot by not taking a bus or taxi!

If you are choosing where to stay in Havana, make sure you stay at a casa in the Havana Vieja or Capitolio area because that’s where all the major tourist sites are. If you stayed in Varadero or Matanzas, you’ll have to grab a taxi daily or a bus to the major tourist sites in town. Varadero is sort of the new Havana, not so crumbling buildings, and is the more affluent part of town. Most of the major chain hotels are located in this area.

To be Continued

We covered how to get to Cuba by plane and where to stay. Our next post will be getting around Cuba, some health and safety issues, changing your money, and getting around the city.

Hopefully this post helped you in planning your trip!




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  1. Michael

    This is my first visit to your blog Ruby. Great introduction to Cuba! I have question with regards to US Immigration.

    US allows travel to Cuba, but not for tourism. According to rules as they stand today, one can visit Cuba to learn their culture or to support Cuban people, but not for tourism – is that correct?

    1. Post
      Ruby Escalona

      Hi Michael,

      Correct – you can learn their culture and do the People to People Exchange visa type or Support for Cuban people type.
      They asked us when we got back exactly what visa type we used when we went to Cuba and what it meant, so best to have a proper answer if you do go back to Cuba.
      While they didn’t really ask for proof, we brought back books that we bought about Cuban-American relations, the revolution, and a history of the country as whole, as well as kept receipts of our airbnb accommodation.

      Thanks for visiting – our next post about Cuba is about the sites we visited in Havana

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