WimberlyAg:
Assuming you haven't been, go to Cuba, no question. It's a different world and you'll be amazed the whole time, and it probably won't be the same in 20 years, but machu picchu will be. Cuba's essentially free of violent crime, but purses, cameras, etc. will get snatched at night, just have to be alert and not keep anything hanging around your neck, shoulder, etc. There are several very nice hotels in Old Havana that you can pre-book with an american credit card, since they're based in europe. Traveling outside of Havana & across the country by bus is definitely not first class, but very fun. let me know if you want to know more and I can tell you all about it.
PBJ Time:
In Cusco, most outfitters are selling the same trips, whether they tell you or not. As long as you get details and book w/ someone non-shady, I think it matters more which trail you take than who you sign up with. I would recommend the Salkantay Trail. It takes you higher through the mountains, and does not sell out or get crowded like the Inca Trail. I booked my trip the night before at my hostel. Just FYI, the people in my one group had booked it through all sorts of different outfitters, including several people who booked it online with a credit card in advance from the states, and paid 3-4 times what most of us paid for the exact same trip just booking it the week of in Cusco.