I finally got around to looking it up.
Trinidad: 1864 sq. mi.
Tobago: 116 sq. mi.
Massachusetts: 7838 sq. mi.
New Jersey: 7419 sq. mi.
Delaware: 1955 sq. mi.
Rhode Island: 1045 sq. mi.
Apparently Trinidad is MUCH smaller than NJ or MA. I'd previously thought it around the same size.