I have been to Tobago twice. I think it is a lovely country. Yes, there are people selling drugs, it has some economic challenges for sure. One person we walked by offered us a coconut he had made into a cup with a beach scene. I told him he did this for me 10 years prior and we still have it today and even recalled his name. That struck up a conversation with many locals and we were never hassled after that. On the day we left, my husband gave his sandals to the coconut artist. He probably sold them, he wasn't used to wearing shoes, but was surprised we would do that for him. Yes, street smarts are needed but try to give them something, they don't have alot there. I recall going through the Trinidad airport and my kindle was getting alot of attention, I finally put it away.