I would think that you'd want to cut across the main shipping lanes as quickly as possible. I'd suggest a route more like this.
Cutting across Mass Bay down to Cohasset will force you to deal with a lot more shipping traffic, which is no fun. By going a bit further out, you'll miss a lot of the congestion, or at least spread it out a bit...
Given that the wind will generally be out of the Southwest, this route allows you to have a pretty easy sail for most of it, reaching almost the entire trip. It crosses the main E-W shipping channel almost perpendicular to the TSS.
The route I've listed is about 45 NM... so it'd be a pretty good eight hours or more of sailing for you. If you left early in the morning, it might be a really nice day sail, if you get the weather.
I do like Sailingfool's suggestion of breaking it down into two days... but that is only if you've got the time to do that. One major advantage of doing this is that you can pretty much assure that you'll get into P-Town during daylight hours, which will simplify your anchoring, picking up a mooring ball, or finding a slip. However, I'd reverse his suggestion and do Plymouth on the outbound trip...and Scituate on the return trip—because if the winds are out of the southwest, it will be easier to go from P-town to Scituate, than it would to go from P-town to Plymouth.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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