So I was in Cuba at the beginning of March, spending 2 weeks there. We drove up from Seattle to Vancouver, and flew directly to Varadero which had the most amazing beaches my wife and I have seen anywhere (and my wife was all over SEA when she lived in Khabarovsk).
First 4 days: stayed at Melia Varadero (a Spanish hotel chain) all inclusive. Amazing beach. Food was pretty bad in general. Through trial and error, I found items that tasted good. These were generally things cooked in front of you. Anything brought out and kept heated was horrible. I did one shore dive at Playa Coral that was a nice, long shallow dive.
Next 3 nights: Trinidad. For me as a history buff, I enjoyed this more than my wife. I'd recommend 2 nights here, as we went to supposedly the best beach on the south side of Cuba, and it was nothing compared to Varadero. We arranged for a driver through the hotel to drive us there for ($160) and another to take us to Havana at the end of our stay ($120). On the way to Trinidad, we stopped for a couple hours at Cienfuegos, which my wife liked more than Trinidad. We were only in the core central area. Though in retrospect, I wish we spent a night there. Our first night there, we happened to be on this rooftop restaurant where some famous Cuban singer was dining. Delicious food.
We spent 3 nights in Havana, and we couldn't wait to get out of there at the end, as the contrast of dilapidated, crumbling buildings next to other ones was too much. You could see that prior to the revolution, Havana must have been one of the most beautiful cities in the world. While there is restoration of some buildings going on, the decay of others is happening at a faster rate. Next to the capitol are a number of abandoned buildings, though some people were living there without windows, and it simply wasn't safe. It was shocking to see the least, as while I've seen rather extreme poverty in Africa, I have never seen anything like that in a capital city. A couple of days is all you need and I do recommend going here. We stayed in two AirBnBs here as we were planning on spending 5 nights. The second one was quite nice inside, near the capitol. We made up an excuse that we had to leave, but we didn't cancel and try to get money back. Didn't think that was fair to the people as practically everyone struggles. and they had obviously invested a lot of money into the accomodation we rented and it was immaculate.
We then spent 4 nights at 2 different Malia all inclusives, one more modern, one more island style. Food the same in both. Nice beaches though. We did a day trip out to Playa Blanco, and man it was hot with the sun reflecting on the whitest sand I've ever seen. I did a boat dive near Varadero, first dive was okay, second dive was awesome, better than Southwater Caye or Glover's Reef in Belize (more fish, much healthier reef, but no sharks).
Food: when eating out at independent restaurants, the food was generally good, often delicious. The worst food was at the all inclusives as I said before.
People: no anti-American sentiment in general. People were glad we were there as they know we jump through hoops to be there.
I will say that the embargo is pointless and evil. It just makes people suffer needlessly.
We did hire a driver who had been a civil engineer (hydrology). He was educated in the Soviet Union, retired, and drove a taxi/acted as a guide for extra income. He certainly outearned his wife who was a doctor who earned 5000 Cuban Pesos per month. That's less than $500 in the official exchange rate. Exchange money on the street, and you are talking about $300/month. Restaurant prices are not that much less than what you see in the US. Not exactly affordable for Cubans. At least not the places we went. It took a bit to get him to open up about the real situation. He didn't speak much English, so he and my wife spoke and she translated between us.
I saw horse drawn carts on the main interstate of the country. Very few cars. People struggle to get enough food to eat. Much of the previously fertile land has been poisoned, so you don't see people growing their own crops like is so common in other countries.
If you want more information or even to chat on the phone about our experiences, DM me. I highly recommend Cuba as it is an eye opening experience, the people are in general wonderful, and many of the beaches are first rate.
Oh, and as I'm a complete wuss when it comes to water temperature, I loved just being in the water.