Sometimes I like to go for an all inclusive if I'm tired/stressed out and don't want to organize stuff. When more adventurous we just book a flight somewhere (usually Mexico these days) and find lodging, food etc. when we get there. That's really neat and we always meet nice locals and find interesting places.
Hello Kalmiya If you don't want to organize anything, and you like beaches, then Varadero might be a good option for you. Bear in mind that it's the haven for package tours and so there are numerous (newish) hotels lined up along the peninsula which is on gorgeous beach. Holidaymakers often just stay around their hotels, as unlike other parts of Cuba, there aren't that many restaurants outside of the hotels. Many people like that - I don't. Many package tourists go to Varadero and don't explore the rest of this island. That's such a shame because Varadero is NOTHING like the rest of Cuba. Other great parts are the Old City in Havana, the old cobbled streets complete with horses and traps clip clopping on the old stones in Trinidad and Pinar del Rio. I didn't explore the area around Holguin which is another beach area.