Thanks for the tips! We did two trips south now.
On the first sail in August, we went to Scituate on a Saturday. We had to tack down against southerly wind, and arrived so late that we wouldn't have made it any further. We called Cedar Point Launch for a mooring and they were extremely helpful. They run very late hours and are very friendly, also the harbor is easy to get in. So definitively one of my favourites now. On the way back there initially was no wind at all, so we motored for some time. It was extremely hot that day so we decided to put down the anchor
at Tar Pouch and jump in to cool down a bit. After the wind picked up we had a great sail back to Boston.
For the Labor Day weekend, my wife and I set out on Friday in the late afternoon. Wind was to weak, so we turned around and anchored off Peddocks Island for the night. On Saturday we then were able to sail down to Plymouth and were able to get a mooring there.
Getting into Plymouth was a bit an adventure as the tide was still going out, carrying a lot sea grass and other things. Right when passing Duxbury Pier, something got into our prop and we sat drifting there between the rocks and the sand shoals at the head of Plymouth Beach. Luckily we recovered after letting down the anchor
and then putting the gear in reverse and forward for some time.
We had thought about anchoring in the Cowyard but decided to not for convenience as we planned to go to town. The area parallel to the channel and perpendicular to Plymouth Beach, that is often recommended for anchoring, seems to be filling up with moorings by the way. At the end, going for the mooring in the protected inner harbor turned out to be a good decision: during the night, the wind picked up quite a bit and became gusty due to a high pressure system. I doubt I would have gotten any sleep anchored in the Cowyard however protected it is.
On Labor Day we sailed back to Boston in light winds. At the end we surrendered and used the motor.