There are two basic types of tourist accommodation in Cuba.
The first type is a classic hotels and resorts. This type of accommodation makes sence only in beach resort areas like Varadero, Cayo Largo and Cayo Coco. In most cases this is the only type of accommodation available.
The second type is so-called casa particular. In fact, these are ordinary guesthouses and B&B's owned by locals. Room rates are usually much cheaper than in classic hotels and resorts. Sometimes these are luxury apartment in a colonial style. But in most cases rooms are rather basic.
Usually casa owners may suggest you meal options for a reasonable price. We recommend this option, because town's cafes usually are very poor and not tasty. Also it is almost impossible to buy anything in stores. While Casa may suggest you dishes like lobster (locals call it langusto) for a very low cost, possible only in Cuba.
Casa's can be booked in advance. But usually there are no problems when you try to find a room when you just arrived to town. The best way is to hire a taxi and make arrangement that you will hop as long as you need until you find a suitable casa. Best if you have minimum knowledge of the Spanish language. However, if you know only English language, it is often quite enough.
There are many flight routes to Cuba from Canada and Europe, as well as from Central and South America. There are also several flights from the U.S., but these flight are for the former Cubans now living in the United States, - not for tourists. Update (2016): As all americans now can travel to Cuba, it's not a problem to buy a ticket to any flight from US to Cuba.
Tourist transportation in the country is possible by taxi or by rental car. There is also Viazul bus network, proposed for tourists. Tickets for these buses can be purchased fot CUC's only.
Any time of year. Sea water of the northern coast is relatively cool in the winter half of the year, so this period it's better to spend your beach vacation in the southern regions of the country. For example, we recommend Cayo Largo island.
Cash payments in foreign currency are not permitted in Cuba. We recommend to bring to country euro cash and bank cards. Cash dollars are not recommended, because when exchange to local money you lose an additional 10%. Tourists usually pay by so-called CUC's (peso convertible), - local money proposed for tourists. To pay in non-tourist areas, we recommend to change some amount of CUC's to local pesos (peso nacional), - at a fixed rate of 1 CUC = 24 peso nacional. Keep in mind that you won't be able to change back local money to CUC's. Currency exchange, and exchange CUC's to pesos, can be done in banks.
Tip: Flight Havana-Cancun-Havana costs from $350. But if you buy in Mexico office of Cubana flight Cancun-Havana-Cancun, it will cost from $250. So you may optimize your route if you plan to visit both countries.
I highly recommend Cayo Machos island - not far from Trinidad. You can get there by catamaran from Ancona beach. I'm not sure if it possible to spend night there, but you can buy beer.
Vinales is a must see. Best if you rent a car, but there are also package bus tours. It is possible to rent a room in casa particulare from 15 cuc.
Vinales valley. Is it worth to visit? Where to stay?