When I went, I spent 4 days in Grand Cayman, then took a 60 minute flight to Cuba. Flew back to Grand Cayman for one last night before heading home. Grand Cayman was amazing. It's that beach vacation you're talking about. If you are going to stay in Havana the whole time, there aren't a lot of beaches there. There's a ton of music, food, drinks, culture, and history. Without being fluent in spanish, it's a little harder to get around. I speak enough spanish to get where I need at the services I need, but I'm not fluent enough to convince the locals to give me insider tips.
So to address a few of your points
1) Culture: Havana is amazing. You're never going to see anything like it. Take a good camera in the daytime and you'll leave with some amazing photos. I took my DSLR and dumped it for my iphone after the first day. I took over 1100 photos in 3 days, probably 500 were just of cars. There are statues, buildings and architectures, of course the cars, and a LOT of history. But it's all in Havana.
2) Beach: One of the best beaches in the world is
Varadero Beach. Now here's the catch, it's fairly far away from Havana. You'll have to take a bus, flight, or taxi to get there. We didn't go because we weren't there for very long, but we heard great things. It's also known to be incredibly touristy with a lot of Canadians and Europeans. I wanted to go, but we didn't make it the focus of our trip that year, so we saved the days and time.
3) Safety: It's safe. It's a communist country. Criminals are executed if they get caught. The last thing Cuba wants is to have an American shown on CNN getting robbed and killed. I've been to China as well, same thing there. And since you speak English, people WANT to talk to you and test their English. They either learned from cartoons or movies. English books were banned for so long, it's not very common there.
Random points
Cuba is poor as fuck. Full stop. Anybody who thinks Socialism or Communism is a good thing should go there and see reality. People were standing in line to get bags of healthcare and toiletries. They would get a big zip lock bag with a bit of toothpaste, deodorant, tampons, etc. Then they would go sell it to have money. This really surprised us to see. With that said, the people were great. There were no issues at all. The first night was sort of sketchy because we weren't familiar with the layout of the city and between the buildings is incredibly dark. The streets are so close, there's no streetlights. So that was sort of uncomfortable. But we got over that pretty quickly.
There are two forms of currency. One for tourists and inside Havana and one for Cubans outside the city. A loaf of bread will cost you the equivalent of $1 in Havana and $.10 outside of the city if you use the Cuban people's money.
It's a bustling city. There's a lot going on. People on the move, taxis everywhere. It's easy to just stand around watching shit happen. lol
It's not going to change. Everyone thinks, "I want to go before it changes now that it's open." It's not going to change. Not for at least 15-20 years. There's a chokehold on the city.
Watch as many shows as you can about Cuba before going. Anthony Bourdain went there a couple of times. There's some stuff on Netflix. Just watch a bunch of documentaries and food shows about it to see if it's the type of stuff you're interested in.
Feel free to ask any other questions you might have. Happy to share.
I had no idea that Amber Rose was such a cultural influence in Cuba. lol
Yes, people live there. They really live there. I thought it was abandoned when I first saw it, then the dude stepped out and I took a picture as proof.
The main part of the city center is gorgeous and well taken care of. The rest...is not.