The biggest challenge by far in Cuba for Americans is the money situation. You MUST bring enough cash to get through the WHOLE trip. This might not seem so complicated but if you’re like me, I’ve never been in a situation where I couldn’t use either a credit or debit card. Adding to that, getting money from home is also impossible (unless you happen to have family who are Cuban nationals living abroad). So if I had run out of cash, I would have been truly screwed. Someone would have to fly there to bring me more money. Thus every decision I made haltingly because it’s not enough to have enough for the whole trip, I needed some for taxis and to save for emergencies too. I could not run out. I simply could not. Normally travel and don’t sweat the small stuff, especially in poor countries where $5 to me means nothing compared to them. However, in Havana I found myself being cheap and tight to avoid disaster. I can’t convey how much it weighs to have to worry. So do yourself a favor and price out each day honestly and then double it. Take that much cash with you!
Also make sure they are perfect bills. Ripped, curled, or otherwise damaged notes will be rejected if you try to exchange in Cuba. Also they have a 10 % penalty and 3% service charge. So as of the time of this writing, $100 US is only 87CUC. It doesn’t seem like much but of the $500 US I brought, $65 was lost to exchange rate penalties. I didn’t think that through. Be smarter than me!