Support the people! Stay at Casas Particulares, not at government owned & controlled hotels. The hotels are expensive anyway and to get a real people-to-people experience, you need to stay with Cubans! Practice and use your Spanish and get to know the neighborhood and locals.
Jakera Cuba organized my Casas for me; I paid a weekly fee prior to leaving the U.S. via PayPal, so it was great. If you want a private room (recommended) make sure you are very clear about that before leaving. Once you’re in Cuba, it may be difficult to organize changes and you may end up with roommates!
Casas will generally provide a nice breakfast (fruit, bread, eggs, coffee) and will often let you eat with the family for other meals for an extra charge. (Eating out is expensive in Cuba!)
Casa Particular in Cuba – some have great rooftop patios!
I especially loved the two toned models of cars in Cuba – so colorful and fun. Keeping these classics running is an incredible feat, given the restrictions Cubans face. The mechanics have utilized about everything imaginable to keep them on the road. Candy colored paint jobs, gleaming chrome, plush upholstery – these beauties are truly a work of art.
of people’s ground level homes. While walking through a little marketplace outdoors, every shopkeeper loudly beckoned me to stop and see their wonderful goods, 
The neighborhood kids played with nearly anything in Cuba. Looking down on the stoop, I saw a children’s toy box (literally a battered cardboard box with its sad selection of broken dolls, bits of plastic and orphaned Lego blocks and I cringed thinking of the incredible abundance of toys and games that my own children had had. As I watched a trio of musicians strike up the familiar Cuban beat, a pair of young boys played contentedly in the street with two small plastic army men, tossing them up and down the street, chasing them and delighting in their wild acrobatics. Simple pleasures. When I go back, I’m bringing a case of plastic parachute jumpers to give away.
