Cuba and the Dominican Republic are the only countries in the Caribbean that requires a visa for European visitors. The Dominican Republic issues a 90 day tourist card on arrival for 10 dollars while the Cuban visa is a tricky one. Americans have difficulties, and I can only speak for myself as a European. If you fly from Europe to Cuba, you have to apply for a visa in advance at your nearest Cuban embassy, but the trick is to fly from one of the many countries in the Caribbean. If you do that, you can buy a tourist visa at check in or in the airport before departure. Another trick is to exchange your American dollars to Canadian dollars before departure, as the exchange rate for American dollars is really bad in Cuba.
I like Cuba as a destination. I felt very welcome everywhere, and the city has many things to offer and I truly regret only spending four days. I could easily spend two weeks and plan to re-visit the country again later on. Right now is the time to visit Cuba, because it looks like the country will soon be much more easy for Americans to visit. Compared to the other Caribbean islands, Cuba doesn’t have any world-class resorts, but the Paradisus is as close as you get. I have a passion for great hotels, but as long as its comfortable and the destination is interesting, I will have a good time. The Paradisus properties are big and mostly with all-inclusive concepts, where you can easily get a great bargain, especially in low season.
Another thing I have a passion for, at least in this period of my project, is hitchhiking. In Cuba, it is very easy to get a ride, but the culture is that you pay for it. If you are willing to pay for the rides, it is important to negotiate as you otherwise might get ripped off. It is by all means still much cheaper than taking a taxi and certainly safe as other travellers have reported. I hitchhiked with seven different cars in Cuba and only had great experiences. Only one of the cars spoke English, and a little Spanish is recommended. It is probably not recommended to hitchhike in the capital of Havana. Instead, I took the local bus from the main road from the airport to the city centre and walked around. The areas I recommend is in the countryside with little or no public transportation.
My trip to Cuba was in 2012, but as I only recently launched this website, I can only share this story now. The information above is up to date as of December 2013.