Getting there: Traveling to Cuba on a US passport involves a little more prep work than the average trip abroad. While restrictions have loosened, the official word is that you should register for a special license. Many also opt to go with people-to-people programs with cultural/educational components, and still others take their chances at getting fined and simply book travel to Cuba by way of a third country, like Mexico or Canada.
Where to stay: Depending on your budget, you have a couple of lodging options. Hotels offer a piece of history and Cuban architecture, some amenities like internet and TV, and tend to cost about the same as staying in a major US city. Alternatively, you can find a more affordable place to stay, bed and breakfast style, through a Cuban government rental program called Casas Particulares. AirBnB recently seized the opportunity and features these casas on its site, so booking is relatively painless. I recommend staying in a casa over a hotel, which generates income for a Cuban family and allows tourists a chance to connect with locals.
How to deal with finances: If your only bank accounts are tied to US banks, you’ll want to withdraw a boatload of cash and convert it to euros before you leave — you will get a much better exchange rate to CUC (Cuban convertible pesos) than the 10 to 13 percent penalty coming out of a conversion from US dollars.