Leaving from Chaguaramas/Scotland bay is an 80nm trip to Charlotteville and with prevailing easterly winds. From Trinidad, hug the island's north coast where the wind is usually lighter and sometimes there is a reverse current. Do NOT stop along the coast as it is NOT SAFE. Between the two islands is a north-westerly flowing current which runs at around two knots. Avoid crossing during a full moon as the current is usually stronger.
You can landfall in Store Bay (South East of Tobago, 60nm trip) but you will have to ask the Immigration and Customs in Chaguaramas to draw a letter with permission to anchor in Store Bay and go to Scarborough to check in.