If you're in for this kind of thing, think of taking a trip to Sydney:
Cigars= We don't have an embago on Cuban cigars.
Cognac= We have SLIGHTLY better relations with the French at the moment.
Fine, fine Hookers= It's all legal here and the industry is pretty competitive, so there's less of a "status" thing. Australia just had a brothel listed on the stock exchange!
The girls are probably healthier than a drunken one night stand. Starting prices are a little lower, $150 US will see you well treated. In general, US dollars will make you a GOD.
If you're cheap though, you'll probably have an OK chance picking up at a bar. There's lots of gambling too for those who are interested.
Your choice.