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You'd probably be fine, but my suggestion would be to cut across Massachusetts Bay to Minots Ledge (Cohassett), then hug (a few miles out) the coast down to about Brant Rock (Marshfield), then cut across to P-Town. This route will give you options in case you need to duck in out of the weather and will keep you closer to shore if you require assistance.
As it stands, the route you charted out to YAB-2 takes you even further off-shore than a straight rhumline course, which seems unnecessary and unwise. (That is, unless you are hoping to do some whale watching along Stellwagen Bank!!) If you are determined to go the "off-shore" route, why not keep that initial course a bit further west since it won't add any distance? This would also put your course closer to perpendicular on the inbound and outbound shipping lanes, which will get you through them more quickly.
Of course, we can plan routes all we like, but the wind will be a factor when the departure day comes.
July is about the most benign time of year to make the trip, but as always, watch the weather. Sounds like fun and a great adventure!
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT