I just came back from a week in Tobago. We stayed at the Rex Turtle Beach resort. I posted a review under the hotel, so won't repeat that here. But, in hopes that some people might find my experiences informative, I am posting some general comments.
First, the good. The island is beautiful. Driving along the coast is just one scenic overlook after another. The beaches are lovely. We snorkeled in 4 different spots and while the coral wasn't stellar, the variety of fish is fantastic. The vast majority of the people we met were friendly, helpful, and welcoming. We had some great meals at local restaurants. We did some tours and we also rented a jeep for 2 days and did some exploring on our own.
After all that, you will probably be surprised to learn that, while we had fun, we do not plan to return nor will we recommend the island to friends. The biggest issue we had is that we were all too often the targets of unwanted attention. People wanted to sell us all kinds of stuff. They wanted to talk us into one kind of tour or another. Young men wanted us to come party/drink/dance with them - and we are sedate older ladies who most definitely do not give off an "I want to party" vibe. It was stressful. And a polite "No thank you" was generally not enough to get them to leave us alone. We found ourselves becoming reluctant to engage in casual conversation with people who may well have just wanted to chat, out of fear that another pitch was coming.
Yes, I know that Tobago is not unique in this. I have experienced it other places. But, there are also perfectly lovely places to vacation where this is not a problem.
Other negatives are mostly minor. Tobago is kind of expensive. Many of the tours are a bit rough around the edges - little things like them forgetting basics like ice, water, and beverages on a "Refreshments Included" boat trip. Driving yourself around is not for the faint of heart. Stuff like that. Nothing of the "make-or-break" variety.
We did not experience any crime nor did we feel unsafe anywhere we went. However, our hotel was literally crawling with security guards day and night, which was a bit disconcerting. One can't help but think they wouldn't be there if crime wasn't a problem.