I had been wanting to go to Cuba for years. There are few Communist countries left, much less one with the historical ties and proximity to the U.S. Even with the easing of restrictions under the Obama administration I didn’t know how I would be able to get there. Instructions online are kind of vague about it. In reality, it is incredibly easy. Trump may have changed it some, but in general, if you can buy a ticket from the U.S., you can go.
In general, Cuba is actually not that great. It is kind of a hassle to get around, it is not as cheap as many similar destinations and the food is shockingly terrible.
As of this writing, Cuba has two worlds, one with tourists and one without. Everything for tourists costs a lot more (obviously), has English, and is much nicer. Not nice enough to be worth the extra cost, however. Additionally, Cuba can either be a resort-type experience with Coca-Cabana and Veradaro, or more of a backpacker adventure with Vinales. Either of these experiences is accompanied by Havana.
Havana (2 days is enough)-
There is not a lot to do in Havana. I do recommend seeing the usual sites like the museum, national hotel, capital, Ernest Hemingway’s favorite bar, and the fort. Also, stay in Old Havana. It is a little more expensive than other parts of the city, but well worth it. Cabs are surprisingly expensive here, and while the classic cars are fun a few times, they add up quickly as your primary means of transportation. Also, it is crazy hot and so it is nice to be able to walk home for a break here and there.
Vinales (2-3 days is nice)
This town was actually pretty great. We didn’t expect much, especially after a disappointing Havana, and so I am sure that help, but this was a nice place. There isn’t a ton to do, but it is beautiful, and the few things you can do are actually great. Also, while the food in the rest of the country is terrible, there are some farms you can get meals at that are spectacular. So, be sure to take advantage of that, the tobacco farm, the caves, and the views. If you can, rent a motorcycle or something and ride around.
Varadero (Not relevant)
This is a beach resort town. I didn’t go but my understanding is that while pretty, it is just like any other beach town. So, generally, you’re likely better off going to Mexico as the cost should be similar, but Mexico is easier to get to. The exception would be if you just really wanted to see Havana. I’d prefer Vinales over this, but if you don’t care about the outdoors so much, you may consider it.
Cuba was a big disappointment. I had wanted to go for years and didn’t because of all the conflicting information about what was necessary to go. Ironically, it was quite easy to get to, just book a flight and let the airlines take care of the rest., but in the end, it was a bit boring.
Country difficulty rating (4/10)