Cuba. Must know.
Before leaving to Cuba
Coming to Cuba can get a little bit on a nerve for people who like spontaneity. One not only needs a tourist card but also - travel insurance. I should admit, I travel often, but never bother to get an insurance, unless I plan diving, snowboarding or some more dangerous activities. About obligatory to have a travel insurance I found out only a day before plane from a just bought guide. Oops, what can I say.. But well, it appeared not to be a big problem as a tourist card and insurance can be obtained at the arrival airport from the travel agency just before passport control (such a relieve for residence of the countries which don't have Cuba's consulate/embassy). Otherwise it can be ordered through internet (for example for UK residents) or offered by some airlines.
Tourist card extension might be a hustle. It might be prolonged only max 5 days before the date of expire, so one should be prepared beforehand. If you plan overstay, just in case make copies of required documents before leaving to Cuba (passport, flight tickets, tourist card, insurance (which need to cover all your travelling days)), pay in a Cuban bank for “visa” extension and keep the “tickets” and receipts for it, have a booking copy for the last days/weeks of stay or at least business card of your home stay or a hotel. Check in advance the working hours (and days) of the immigration office (and actual department for the visa extension as it not necessary located within immigration office). Warning! In a office man can not wear sleeveless t-shirt, so be modest to avoid a kick-out. Don't ever consider the idea of the paying penalty for the overstay instead of the extending travel documents unless you are stupid and long hours in a officer's office, possibility to miss your flight and deportation sounds like a great adventure.
Another thing to keep in mind before arriving to Cuba – money. Nobody likes to keep a big amount of cash on themselves, however, money melts very quickly in this country and many ATM don't give more than 200-300 dollars at once (or sometime doesn't give you any). Every withdrawn might cost fortune, so it's better to take cash at home country, exchange it on arrival and spread it all over your secret pockets and money belts (so if stolen – not all at once). Prepare to pay around 100$ a day (15-25$ the cheapest home stay, 4-5$ per person - breakfast, 15-30$ dinner for two, the rest of money are being spent on a water as I say: dollar for coffee, dollar for city transport, dollar for every single who asks you and suddenly Cuba is a very expensive country to travel).
One more idea to consider before check-in to your flight – registered luggage. I usually try to travel as light as possible, but here buying a sunscreen can cost same price as your extra 15kg, so better pay those and stuck in there everything you might need: shampoo, conditioner, sunscreen, cream, snorkeling equipment, hiking shoes and clothes, which can be exchanged for the souvenirs. I should admit, I didn't expect to see a such shortage of the products in the shops. Even post-soviet deficit I remember in a brighter light than I see shelves of the stores in Cuba. (How funny it sounds but tampons (if founded) are being sold by one sometimes (“9 tampons, por favor!”). Another advantage of the registered luggage is that you can fill it with rum, cigars, coconut or/and coco oils, chocolate and coffee on the way back.
In Cuba
Money. There are two currencies in the country: CUC and CUP. CUC (convertibles) = US dollar, mostly used everywhere where tourists can be found, probably designed for touristy prices too (to avoid inflation, I speculate).
CUP (national currency – pesos) = CUC/25, money used by locals in a places where tourist is a rare find. For example if tourist want to go to the caves and it's ticket office has prices in CUCs and CUPs, expect to pay in CUCs as a foreigner. If it's a horse-carriage taxi or bici-taxi, locals would pay 1 peso for a ride, but as a tourist expect to pay 1CUC per person (or 25x more than local pay). If you decide to travel like a local by truck-buses (rather than “Viazul”), you will be charged by your knowledge. If you have CUP, you will be paying in between 5-20pesos per ride, but if you don't see difference between money it can be accepted in CUCs without change (still cheaper than air-con buses or even collective taxis from 50-ies). Sometime you can find ice-cream cafes with prices like 2,5$ per portion but still full of Cubans customers. No, that won't be a place for big spenders, that's a place for a cheap treat! Yes, that's a place where for a huge portion of ice-cream one is expected to pay 5CUP (or 20 dollar cents).
Sounds complicated? It is. Expect to find this country expensive and only sometime to treat yourself for cost of peanuts. Last, however, requires effort, knowledge, sharp eye and sometime inconvenience. Have two currencies and see a difference. Have an eye for the local places and transport so you can spent CUPs. You can save on every CUC if spending 20CUPs instead. Learn to count as a local: 1CUC=25CUP, 4CUC=100CUP, 125CUP=5CUC and so on. Check all the change you get or you can find yourself cheated by 10 dollars (instead, let's say, 16CUC change you can receive 1CUC+5CUC+10CUP). Refuse changing money on a street. They can agree exchange CUC into CUP for 1=24 rate (not too bad deal), but when dealer will slowly recounts money (when you notice that 20CUP note is missing), he will return your missing 20CUP, but invisibly will keep few (from so carefully counted pile) notes for himself (Bugger!). You can change your money in all official changing points for the same fixed price, but if you have US dollars, exchange them to Euro or GBP back in your country, otherwise you will be charged 10%. CUC can be exchanged to CUP in the same changing places.
Internet. Well, I decided, we have to have a rest in our relationship. I brought a guide and a book to read instead. Would be perfect if I load more films on my laptop thought. But well, if one is more into the Wi-Fi, “Etecsa” card can be bought with a prepay for internet and can be used in city parks/squares with public Wi-Fi. So, yes - internet exists in this country, but no - don't expect to sit in your room logged into Facebook all day - you need to go out for it! And yeah, don't forget to turn of Wi-Fi when done with internet, otherwise your credit will finish sooner than expected.
Transport. Uh, my favorite. So, one can find horse-carts, bici-taxi and motorbike-taxi (in a bigger cities) for city interiors and price for a foreigner usually 1CUC/p.p. To travel in between towns I would suggest to use “camiones” (buses made out of tracks) or jeep-like “collectivos”. It doesn't have AC but it contains crowded bunch of friendly locals, some feeling of the adventure and a great save for your wallet. For longer distances and AC comfort (sometimes seen as a freeze) take “Viazul”. “Collectivos” or shared taxis are slightly more expensive but can save a great amount of time. I don't mention trains as I heard about their existence and even saw some, but non was ever moving.
Safety. It is safe, but don't expect to make friends with locals (especially met on streets) if you don't sponsor them (sometime cup of coffee will do, but they see foreigners as a rich uncles. Deal with it). Despite of kindness, good nature and sincereness, people will try to make money off you. To deal with tourists for one day can be worth a month teacher's salary. It's a small loss for a tourist, but real misfortune for the country, as all brains shifts into the tourist business or flee the country for the better future abroad, leaving academic and professional platforms abandoned.
Culture. Cuba it's a cocktail of Caribbean mixed with Africa, colonialism - with slavery, communism - with tourism. All in a 19th, mid. 20th., start of 21st. centuries shake. All being cooked together in a broken oven. History moves slowly in here and only speed in highways (when old cars move with a speed of 80km/h, it feels like 180km/h!) reminds that time exists. It settled in the old generation and inpatient in young people's hearts. Time breaths in historical buildings so they fall and kill people, and it dies and resurrects again and again depending on the Wi-Fi signal strength, shared between fifty other curious young people in a park. Communism is present. It is scary for only western spoiled tourists. Otherwise it has some good lessons of equality, our actual needs, importance of collaboration (all works on “I help you, you help me” principle). It of course has a huge downside too. It unfit for the generation which didn't touch the Revolution. Their gazes oriented towards Wild West with non or almost non of criticism towards it, while criticism towards stagnated policy of Cuba cannot be exposed as it accepted as a betrayal. As one very intelligent girl said: “Education is for everyone, unless one opposes the system”. Situation makes young people feel hopeless.
Architecture. You can see it better from the middle of the road. Besides it safer. Don't expect to see renovated buildings everywhere. Think of Colonial architecture as of a Roman Empire's – only left overs of it.
Beaches. Varadero is The One. But better come just at the end of a busy season (May), so sun (not a hurricane) can be caught and tourist can be forgotten. Other beaches are sometimes too unspoiled (read: sea weed, not enough powdery sand, afterhuricanial mess or mosquitoes). Great country for the diving thought.
Places to see. All. No seriously, take your time and money and visit it all. Ok, very must see: Havana, Trinidad, Santiago de Cuba, Baracoa, Varadero, Vinales, natural parks and cities like Cardenas, so you know how life with no tourist going on.
Good luck!