Most probably, you will be traveling to Cuba with a group. Your trip will have been organized by professionals, and transportation and lodging will have been taken care of in advance.
Depending on the size of the group, you will be picked up by a van or a bus belonging to one of the government run tourist companies. These vans and buses will be staffed with one or two drivers –depending on your immediate destination, whether the City, or a resort further away, that requires longer driving– and a guide/interpreter who will accompany your group most of the time during your visit.
These people are mostly well prepared professionals, who will show you the highlights of the usual tourist routes and places. They are also responsible before their employer, the Cuban government, to paint the rosiest picture, take you only to approved places, and make sure your interaction with the locals is limited to what is desired by the authorities.
But you will usually have some time on your own, without the official guide shepherding you around. Those are the nights –usually– or maybe days or weekends, or afternoons, that you have scheduled as “free”, depending on how your tour was organized. Some tours allow for more free time; others try to squeeze as many programmed activities as possible in your visit.
This “free” time is what you will spend trying to interact with the locals, trying to know the real Cubans, trying to understand how people lead their everyday life… If you are a normally curious person, one of the main things you travel abroad for, is to learn how different or how similar to you the natives live in the place you’re visiting.
Don’t be afraid to go out on your own. Cuba is a safe place to be. Everybody will know you are a tourist. I have a friend who is a well known author, who has published a couple of books on Cuba. In one of his books he writes, “In Cuba, they knew I was a tourist by my shoes”, even though he does look like the average Cuban, and he tried to dress like one.
But do not wear flashy jewelry that may provoke someone to grab it and run. Likewise, be always careful about holding your bag. Either carry a small backpack, a fanny pack, or wear a messenger style bag with the strap crossed over the opposite shoulder. Always keep your camera well held, and with the strap around your neck. There’s always a bad apple that may spoil the barrel, but you will absolutely not be mugged at gunpoint, or attacked with a weapon.