Getting there
We flew Interjet from Cancun to Havana, I would recommend booking a flight ahead of time rather than just showing up when you want to fly, everything takes longer than you think here (being Mexico or Cuba). Also, it was nice that they take US credit cards, Cubana Air doesn’t. They were also the cheapest, it cost about $500 for 2 round trip tickets and 2 Cuban visas.
It took 45 minutes to get money exchanged in front of the airport. It was an insidiously slow line and would be worth the effort to beat as much of the plane as possible to that line.
There is a 10% hit on USD exchanged, bring Euros
A standalone GPS is not a permitted item in Cuba, they supposedly will confiscate it if they find it.
On that note, we weren’t hassled at all by customs coming or going, don’t declare anything and just walk out. Also passport control was nice enough to ask whether or not you want your passport stamped on the way out.
Don’t sweat a place to stay or how to get around. The casas particulares are everywhere, denoted by signs on the doors, it’s just getting over the initial communication barrier that could be the challenge. People are very happy to help and everybody has a friend who can take care of you.
Being There
You can use the public bus service, but I wouldn’t rely on it (it isn’t for tourists)
There is no wifi, no data on AT&T, but Verizon had data for $2/MB. It was clear which hotels had wifi, just walk by their grounds to see if there were 100’s of people sitting on their fence with their phones in their faces.
We operated completely without the internet during our stay, it takes more planning and time to do things when you don’t have all the answers in your pocket at all times. It would be worth doing a fair bit of research from home before you arrive and have some items on your list as starting points.
We weren’t hassled anywhere coming or going, felt safe at all times day and night regardless of how many people were around, there was no overbearing police presence, and everyone local and tourist generally seemed to be having a good time.
There is no shortage of people watching here
Not may people speak English here, and my (not very good) Spanish wasn’t as useful as it was in Mexico. Since you probably can’t just translate words on your phone, a Spanish/English dictionary would be handy.
The food was disappointing, don’t go to Cuba for the food and avoid any place that has any indication of Chinese food. Our most memorable meal was in a quaint up stairs apartment turned restaurant on the first night.
Get small bills and change when you exchange dollars. Nobody seems to have any change here, and it will make your life much easier and cheaper to be able to pay people the price that you negotiate.
Speaking of negotiation, we seem to always end up with someone handling us as a middleman to the final party doing the service, this seems to cut down on our ability to bargain for much in many situations. The street prices that are quoted in many blogs don’t seem to be very obtainable for us. It’s only a few dollars here or there, but it’s not as cheap as you would think it should be and not being able to get outside information on the fly certainly contributes to this.
Along those lines, we found a number of blog posts complaining about the constant barrage of street vendors and other tourist targeting schemes. This didn’t seem to unpredictable to me but it’s something to keep in mind. We didn’t come into any situations where we felt nervous in anyway, just a little targeted, but that’s part of the game.