I don't know what the travel situation to Cuba is from the US currently, though I was told even when you weren't allowed to go you just asked Cuban customs not to stamp your passport and it's all good. I went to Cuba a number of times when I lived in Canada-- it was basically Canada's version of the common US Mexican vacation and was preferred because it was untouched and obviously free from American Spring Break fratboys.
There's only one "tourist" city called Veradero that the government built specifically for tourists and privileged locals on vacation. Beaches are fantastic, nightlife is pretty good (great live music/dancing), girls are hella loose, food is decent, and everything is (or was) dirt cheap. You can also obviously do Havana, which basically looks like a city frozen in time circa 1960. Do bottle service in Havana for like $50 and say hello to your free harem/entourage. As for safety, it's probably one of the safest places I've ever travelled. As a tourist you are God-- if anybody so much as looks at you the wrong way they'll get stuffed into the back of squad car and never seen again. When on the beach you will get hit up by locals that will offer you a family cooked meal for $20 US where they'll invite you for dinner and use your coin to buy food they can't normally afford to eat (like lobster). Great food and great people.
The last time I went (10 years ago) a week in Varadero including a 2 day trip to Havana cost me $1200 including flight. That was all inclusive with free alcohol. I would buy two boxes of Cohiba cigars locally for $75, bring them back to Canada, then sell them to a Cigar aficionado in NY for $500 and pretty much pay for half my vacation..
