Hi, I went to Tobago last year in early Feb. I LOVED it. Its relatively unspoilt but very safe feeling and friendly.
Weather was really hot and sunny, occassional cloudy and rain showers, but that just cleared the air.
Have also been to Antigua (nice but VV quiet), Barbados (nice but quite developed), and Jamaica (lovely beaches and excellent hotels but not so good if you want to explore).
Tobago beat them all hands down. I liked staying in the crown pont area near the airport. Hardly any flight noise, but easy to walk around and get about and some lovely beaches at Pigeon point.