21 - 23 feet is more than enough to hit all of Mass bay, and this size should hold off the boating disease 3 footitis for a while. Not sure what your budget is, but I'm a big fan of new to newer power and an older boat to get the most bang for the buck. I also like a cuddy cabin w/hard top vs center console for the protection it gives.
When you cross the bay in the morning it's usually calm, on the way back the SW wind picks up the seas a bit and can be a wet ride on the way home.
If the Ave Maria 1 is still available, that would be my pick of the litter, but I'm a huge Privateer fan.
Hybrid Mode
