I first went to Cuba back in 1999. I stayed at an all inclusive hotel in Playa Santa Lucia and I wrote this trip report. Obviously it was a long time ago, but Lonely Planet currently describes Santa Lucia as "an isolated resort strip that's seen better days", so I wouldn't be surprised if it had changed very little.
My second visit to Cuba was in 2016 when I backpacked around the country for almost 3 weeks, diving at Maria La Gorda and Playa Larga in the Bay of Pigs. I've travelled and backpacked extensively, but have to say that Cuba is one of the more infuriating places to try to do it.
Cuba has two currencies, the convertible peso (CUC) and the normal peso (CUP), also known as moneda nacional. The CUC is tied to the US dollar and there are 25 CUP to one CUC. Just about everything you ever want to pay for as a tourist is in CUC, though you'll probably get some CUP in your change from time to time. Although it's tied to the US dollar, that's the worst currency to exchange because there is a 10% tax on exchanging US dollars. Euros, Pounds Sterling or Canadian Dollars are a much better idea. The first thing I had to do on arrival at Havana airport was to get some money to pay for the taxi into town. This cost $25 which is coincidentally the Cuban salary for a month. As a tourist, almost everything especially taxis will be more expensive than if you were a local.
I changed money at the airport. This involved standing in a large queue. This is good practice for the rest of the stay and on reflection, I should have just changed all my money. The rate is the same everywhere. Exchange places are called Cadeca and can be found in most towns. Just don't be surprised if it's shut for lunch, or for fumigation, or because there's a power cut or for absolutely no reason whatsoever. You may also find that they've only got small bills, so you end up with $200 worth all in $3 notes.
The other place to change money is in the banks. These are quite easy to spot as they're generally the buildings with the big queue outside in town. They do have ATMs, and I had a good success rate with them, with them only failing a couple of times. The ATMs do charge 3% though and they also only work with Visa. If you have Mastercard, you have to queue up, which may take a couple of hours only to get to the front of the queue and find out the machine isn't working. Inconveniently, most currency cards these days seem to be Mastercard though I did have success with a Seasons Travel Card in the ATMs there. Very few places take credit cards. You really need to be carrying a couple of days' money at all times, just in case.
Finding the first night's accommodation proved somewhat difficult on the web as many US owned sites didn't list Cuban properties. Eventually I booked via trivago for the first couple of nights. $25 will get you a double room with an ensuite in most places in a casa particular, which are privately owned Cuban guesthouses. Once you've booked the first couple of nights, it's not a problem. The owners will all booked ahead for you. You may find on arrival that you're not staying in the place they named, but in some other casa owned by a relative, but the system works very well. If you arrive by bus, there are plenty of people touting accommodation, often quite aggressively. I would try to deal with the women who are actually running the accommodation as obviously the touts take about a $5 cut and you'll end up paying for that. The quality of accommodation I stayed in was good, often in large old colonial houses which would be worth a fortune in any other country in the world.
The main bus company for tourists is Viazul. They take payment in CUC only and most of the people on the buses are foreign. They're reasonably comfortable, they have aircon and they ran more or less on time when I used them. The meal stops seemed a bit erratic though. On one journey, we had no meal stop in 6 hours, though there were 10 minute stops when you could go to the toilet. You can book online but only a week or more in advance which is obviously not much use if you're backpacking. It would be a good idea to book the first one if you're starting in Havana as the queue was quite long there and the terminal is a taxi ride from the centre of town. Otherwise, I would go along usually the day before and book it. The queues were generally not too bad outside Havana, but there would be only one person, so don't go at lunchtime when they've taken their break. On booking, you'd get a computer printout confirming your booking. This wasn't the ticket. The next day, I'd have to go along 40 minutes before departure, queue up for the same person as the day before and be given another printout that was the ticket. This would have what looked like a seat number on it, but wasn't, and then everyone would sit where they liked.
The other choice for getting around is collective taxis, or collectivos. These are easy to find. Just walk up to the bus terminal and you'll be pestered by touts for them. The only way to get rid of them was to tell them you already had bus tickets. Generally, they seemed to charge more or less the same as the bus company. Bargaining didn't get you very far and always seemed to result in some spiel about how they provided a door to door service unlike the bus or some sob story about how they needed to eat. It's worth bearing in mind that locals pay about a tenth of what they charge tourists and whilst it is door to door, there's no air con and the novelty of travelling in a big 1950s American car wears off quite quickly if there are 5 customers packed in for a few hours.
There's also a mobile phone shop at the airport. Obviously there's a queue and they only had SIM cards so big that they wouldn't fit any phone made in the last 15 years and a broken SIM card cutter. However, it's only a 2G network anyway, so useless for data. My British mobile did roam there, but I failed miserably to get to work when I tried calling a Cuban mobile and of my two incoming calls, one went straight to voicemail and the other was dropped when I answered it. I had more luck buying a $5 card and using the public phones.
WiFi is available however, though it was never free, even in the hotels. You had to buy a card. The login process wasn't particularly encouraging. There were security warnings because the certificate had expired and some of the links on the portal page didn't work, but if you ignore all that, the actual speed was pretty good. I used all the usual sites and didn't find anything blocked. The easiest way to get a card is in a hotel. If you have to go to the mobile phone shop, there will be a queue and they asked to see my passport and took about 10 minutes filling in some pointless registration form on their computer. The WiFi is in some hotels, but usually in the squares in town. It's easy to spot a hotspot, there will be loads of locals sitting around all on smartphones from about 6pm on. There might be someone about selling cards at a markup, which at least avoids the queueing.
Eating out is relatively cheap and the food is good at the family run restaurants, or you can get them to make you a meal in the casa particular. About $10-12 is enough for a meal and you'll even get lobster at that price. The food in the bigger hotels, I've found less good. All the casas I stayed in did breakfast for an additional $5 with bread, eggs, usually cheese and fresh fruit, so it was a good deal and also your options for finding breakfast elsewhere is very limited. There aren't bakeries where you can just get a couple of things to eat like there are in most countries and whilst there are shops, the range is extremely limited for pre-made food. Some of the convenience stores seemed to have little other than rum or beer. You could get a packet of biscuits (imported) but not crisps, so finding snacks for the bus was difficult. I remember one market stall that sold ham and cheese rolls. The only problem was that they didn't have anything to put them in, no bags, no paper, so they just handed them to you with a set of tongs. There was also a cafeteria that had no cups.
Other challenges include power cuts especially when I was staying in Baracoa and the level of pestering is very high, especially by taxi drivers and cycle taxis. That said, it is one of the safer places to travel, people were helpful and friendly. They often didn't speak a lot of English though. Without Spanish, I think you'd struggle on your own.