Havana, Cuba

I am SO glad I got the chance to visit Cuba, especially Havana. Joe and I had been waiting for the commercial, direct flights to open up for awhile, and Southwest had only been operating to Cuba for 5 days before we boarded our flight there! (Yes, things were very hectic on that flight! I think it was many people’s first time being on an airplane, and there were more children than any flight we had ever been on. We connected through Ft. Lauderdale, so I think a lot of people on the flight were going to visit family in Cuba for the first time in a long time. There used to be direct charter flights for Cubans and those with authority to visit, but they were around $400 so many could not afford them. The children were yelling of joy when we would have turbulence like we were on a roller coaster – it was an interesting ride!) Since service had just started, we had to fly into Varadero instead of directly into Havana, which resulted in an expensive Taxi ride to Havana. (Now there is nonstop service from Florida and NYC to Havana on multiple airlines.)

What I keep telling people about Cuba can be summed up here

  •     Go!
  •     A long weekend is enough time
  •     It’s so cheap, you’ll feel like royalty
  •     People are friendly. Some are nice, but yes, some want your money

Go AS SOON AS POSSIBLE – the city is changing every day, and the best part is feeling like you’re trapped in time. I’m so afraid this will dissipate over the years as more Americans visit, and more outside influences take over, and the government (hopefully) improves. If you are on the fence about going, go at least for a long weekend. We were in Cuba for 10 days, which felt like too much. I am very glad we got to go to Viñales, where we were for 2 nights (more about Viñales later) but even with 10 days we didn’t feel like we had enough time to get to Trinidad or Santa Clara. The infrastructure is so bad that it would take around 6/7 hours to drive to one of these towns. Even though we read amazing things about them, many people liking them more than Havana, we weren’t willing to sacrifice a full day. I think if we decide to go back to Cuba, we will fly into a town in the middle or eastern part of the country, and then have quicker access to these cities. Anyways, since we were only in Havana and Viñales, I felt like we had more than enough time. It helped that I know rudimentary Spanish, but you can figure things out with English if you have a helpful airbnb host or hotel concierge, and a pocket dictionary for basic terms (especially food and drink items as some menus are in only Spanish.)

One of the advantages about Cuba is that everything is very inexpensive. Even with the 10% tax to convert USD, everything is extremely affordable. At the fanciest restaurants we went to, we never spent more than $30 per person for dinner, including alcohol. At the normal restaurants, you’d walk out leaving $15 for two entrees and a handful of beers. Tired of walking? Don’t think twice about grabbing a cab or pedi-texi. Want to try a dish but aren’t sure if you like it? Order it anyways. Thirsty? Grab a huge bottled water that won’t cost $8. Generally the response I get from friends who want to travel more is that they don’t have the money or the vacation days, so this is the perfect cheap and quick trip that is also exotic and a once in a lifetime experience.

Be wary.  We talked to a lot of people that truly were just friendly and happy to speak to a “real American” (Vs. a Cuban who has moved to Miami, haha) However, there were a few minor scams we experienced. Having a couple we were speaking to recommend a restaurant that was 5X more expensive than anywhere else, for mediocre Italian food. We sat for 10 minutes feeling awkward as the couple was still standing outside. If someone walks you to a destination, odds are they’re getting a finders fee, or taking you to a friends spot. On the bright side, we never felt unsafe or thought they would rob us or hurt us in any way. When we leaved the people called us out “my friends my friends! why are you leaving!” but they didn’t follow us or anything.

The other scam was more elaborate and pretty genius looking back on it. A man walked up to us, asked us where we were staying (we told him Muralla street – it’s a long street, we didn’t feel like we gave anything away about where we were staying!) He mentioned a cigar festival and walked away. He didn’t walk us anywhere! It was clearly a legit festival! 5 or 10 minutes later, another man come up. “My neighbors from Muralla!” We had been in Havana a few days, and saw many of the same people around where we were staying, so this really didn’t seem strange to us. Maybe he was the man who worked at the restaurant next door, or one of the apartment neighbors – we would stick out to him more than he did to us, right? So, when this man mentioned the same Cigar festival, we told him oh yes! We’ve heard of that! And he told us he was walking the same way and would take us. We ended up in someone’s living room, being shown a few boxes of cigars at the “great price” of  the equivalent of $100. We could tell by then it was a bit of a scam, and walking out with 2 single cigars for $20 as we didn’t want to risk making anyone angry by buying nothing, since we were at a big of a disadvantage being out of the public. They didn’t get angry  or push us to buy more, and let us leave, but it was scary for a few moments when we realized we were completely out of view from any third parties. Our fault for trying to experience a local event! As soon as we exited and processed what happened, we realized the first man must have texted his friend our description and street name, so we’d find his story credible. I hate being taken advantage of, and when we saw the same man on the street talking to a middle aged American couple I told him off and warned them. “My friend! What are you talking about!” Again – probably not my smartest decision as I should not have wanted to anger a scammer… we were careful walking home that night, but we never saw either again. I don’t mean to turn you off from Cuba at all – these were two small incidents in a long and exciting trip – just want to avoid this happening to anyone else, and hey it could have been wayyy worse!

The memories of watching live bands, strolling aimlessly down the street, cruising around in a 1950s convertible, and getting misted sitting on the malecon outweigh the minor hassles that come along with visiting a third world country. There is no reason not to visit Cuba for your next warm-weather adventurous vacation. Are there any questions I can answer for you? Let me know in the comments below!


Hunger: Favorite meal
Wanderlust: Most picturesque location
Travel: Favorite activity


La Guarida was definitely the best food we had in Cuba. Lots of seafood (ahi tuna tacos and carpaccio here) which to be honest we were hesitant about eating at some other restaurants (may have been fine, but we were paranoid to not get sick!) I didn't mean to creep on this couple in my photo, but wanted to show some of the unique decor - felt like you were eating in someone's living room. Tip - we couldn't get a dinner reservation so walked in at lunch! Same menu 😋


I thought Paseo de Martí was the most picturesque street in Havana. Not only does it hold the Gran Teatro and the capitol building, but when you walk just south, you are greeted with the most beautiful row of rainbow buildings. Joe and I had the pleasure of finishing our half marathon on this street, which made it just a little bit more memorable!


My favorite activity aside from walking the streets was the vintage car tour. For a cheap tour of the city, you just have to approach the many old cars and barter a deal with one of the drivers. There are many parked across from the Teatro and next to the Parque Central. For about $20/hour, a driver and a guide in the passenger seat will drive you anywhere you want in the city and tell you about the history and landmarks you pass, and accompany you inside when you'd like. Make sure to get a car that has both a driver and a tour guide, and make sure the guide speaks your language! We got lucky the first time, but the second time we just got a driver and he was not able to tell us much. Our guide took us to various spots in the city, the Plaza de la Revolución, the Castillo de los tres Reyes across the bay, the Hotel Nacional, and the Havana Forest.

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