Boston is about 1.2 times smaller than Windsor.

Windsor is approximately 146 sq km, while Boston is approximately 124 sq km, making Boston 84.75% the size of Windsor.
Tip: This to-scale comparison of Windsor vs. Boston uses the Mercator projection, which distorts the size of regions near the poles.
Our free app, MapSize by MyLifeElsewhere — compare any two places, to scale on your mobile device.