OK, so you wanna go to Cuba. I don't blame you; it's a mysterious country that's glamorized by travellers everywhere. And I'll tell you right off the bat, it lives up to the hype.
Here's a couple questions I think you probably have if you're seriously thinking about going:
Is food expensive?
Is accommodation expensive?
Is there wifi?
First off, food. It's really, really cheap. You shouldn't be paying more than $4 CUC (which is almost exactly on par with USD) for an entire meal. This will probably consist of chicken/pork/fish, with brown rice and plantain chips (portions are usually huge too). Beer is about $1 CUC, and mixed drinks are usually about $2. From what I gathered from the locals, the majority of Cubans don't buy groceries because it's so cheap to eat at restaurants.
Second, accommodation. Also, really, really cheap. Always bargain for a cheaper price. In Havana, we paid $9 CUC per night per person; in Trinidad, we paid $7 CUC per night per person; and in Cienfuegos, we paid about $3.75 CUC per night per person (please note these are hostel prices).
Third, wifi. It sucks, and it's expensive. It's only available in parks (yes, actual parks, like with benches and grass and jungle gyms). It's all run by the government, and in order to log on you need to buy a little card with a scratch off number on the back. Save yourself a half hour by walking around the park with your phone out until a local offers to sell you a card. You should be paying about $2 - $2.50 CUC per hour. We found that going to hotels that have their own connection and buying cards from them was the best option because a) there's A/C, and b) almost no one is using the wifi there so it's much, much faster.
Next is taxi's. I'll start off with taxi from the airport - we stayed about 30 minutes away and it cost us $20 CUC. In Havana, we were staying roughly 15 min from the center (where the capitol building is) and only ever paid $5 CUC to get there. You're gonna see a trend in things costing you $5 CUC. Most of those old cars from the 50's you see will be taxis, just hold your hand out and one will stop for you.
The locals. They're extremely nice people. They have a ton of pride in their nation, and they are very helpful to foreigners. But, be weary. We had way too many people to count come up to us and get super friendly, offer to take us to cool restaurants and bars, only to have them demand a tip, or to pay for their dinner, or buy them drinks. You can find a lot of cool places and good restaurants on your own. I understand Cuba, by North American standards, is a poor nation. I do feel bad for these people that are just trying to make ends meet, their intentions are good, but sometimes it got out of hand.
We stayed in Havana for four days and made our way down to Trinidad. We found a private taxi at the bus station that took us there for $80 CUC. It's about a four hour drive, so it's worth finding someone with a decent car to take you. Trinidad is a charming town with cobblestone roads, dilapidated buildings, and horse drawn carriages. Protip: there's a gorgeous beach just on the outside of town by the Marina.
We found a guy that took us on a 5 hour horseback tour in the mountains for $15 CUC. Along the tour we stopped at a restaurant and made raw sugar cane cocktails, drank coffee and smoked cigars from an authentic Cuban coffee farmer, and stopped at a gorgeous waterfall with cliffs to jump off. Definitely worth the price of admission.
After Trinidad we drove about an hour West to Cienfuegos (literal translation: 100 Fires). It's a more touristy town, and a popular stop for sailers to take land and stock up on necessities. There's a yacht club, plenty of great restaurants, and a large community center where we actually caught a pretty rad rock festival. Check it out if you're in that part of the country.
The weather is mostly hot. Most days were 90F/32C, but they do occasionally get wicked rain storms. They last about an hour and are unlike anything I've ever seen. Rain and thunder start coming down hard and you'd swear a hurricane is rolling in. Then, just as quickly as they arrive, they're gone. Sun is back out, and you're back in the streets sweating your ass off.
All in all, Cuba was an amazing place. I wish I could have explored more, but Jamaica is calling.
Feel free to email me here if you have any questions about Cuba!