Whilst there are certainly those who would commit petty thievery and take u protected expensive items, wallets etc. in La Habana and possibly resort areas, it’s actually pretty darn safe.
My friend “Mantagirl” has made over thirty trips to Cuba since 2013, many of them as a tour guide for American “People to People” tour groups. Locally called “Anita la Loca” by some (walking long distances isn’t a “thing” in Cuba), she just completed an unsupported solo walk of Cuba, the long way. 840 miles / 1,400 km with a backpack, no plans, staying in homes with a room for rent or just comped by friendly Cubans. She was hit on a few times, she was cat-called a few times by young men, no surprises there, but that hike was a good indication of safety and Cuban friendliness.
She arrived at Maria la Gorda, at the western end of Cuba, yesterday, where she was met by her husband “Sharkman” and a couple of friends. You can read more of her Cuban adventures
here, on their “The aadventure Couple” website. Undoubtedly, more writing about Cuba to come (most of it right now is about an experimental 50 mile walk from Las Tunas to Guardalavaca).
“Mantagirl”is the first woman to walk the length of Cuba solo and unsupported. Amazing, but we’ve known the Adventure Couple since we met them in French Polynesia in 1995, so we’re not surprised.