I went there about 15 yrs ago, via Canada.
Stayed in an all inclusive resort (food and booze) on the south end inside a National park.
Every room viewed the water.
Took a tour to Santiago as it was close by using a 'borrowed' van for a cost of $25.
Everyone was friendly, outside the resort most only spoke Spanish, I don't so it was a challenge.
I went because it was CHEAP.
Some of the buffet meals were very mysterious in origin, all the staff were wonderful.
I was offered a tour to go overlook GITMO, which I declined as viewing Americans was not a novelty to me
There was a lack of army patrols/police considering it was a communist as I had expected to see them all over.
Saw lots of 1950's cars, and other modes of transportation like bikes, donkey carts.
It was easy to see the wear and tear in the city due to the lack of materials/pride of ownership.
The official things like where Castro gives a speech (I missed it by 2 wks) looked fine and were totally polished.
I literally brought $450 to blow on trinkets and tours and came back with $400.
One store I went in on my tour was a local type store (not a tourist destination) and its shelves were maybe very bare, possibly about 40% used with lots of empty areas. I was told by the guide this is because the store owner simply could not get the stuff to stock the shelves (or got paid more to sell it out the back).
I would go back for a vacation, but your standards have to be low as its not like most civilized places, yet it was safe.
I drank the water to the alarm of my companion, and I didn't get sick.
When I cut my foot swimming, I went to the resort medical room and found out they only had some bandages, so I went back to my room and poured vodka over the cut to clean it.
We walked alone for miles in the park along the road, and fellow travellers told me about biking for tens of miles the other direction and nobody had any dangerous issues.