For about 20 years we were moored in Scituate, MA...about 25 miles south of Boston. However, our absoulute favorite ride was to Provincetown, at the very end of Cape Cod. Now I do have to warn you that P-Town is different. There's great restaurants, terrific beaches, very senic town, whale watching boats, and lots of folks who live by an "alternative lifestyle".
Due to the 30 mile distance we usually went when we had a 3 day weekend. We'd try to leave Scituate right after work on Friday early evening... set the autopilot,watch the sunset, the moonrise, the occasional boat, and sometimes whales off in the distance. After a few hours we were out of site of land, with a gentle evening breeze pushing us along. Then what looks like an island would appear off in the distance. It allways seemed like it took for ever before we'd see the rest of 'the cape' comming into view.
Arriving in P-Town at night is not difficult. There's a few lighthouses, the well lite Pilgrims Monument, and very deep water. Usually we'd get in arround midnight and anchor in the lee of the penninsula that protects P-Town. Then the next morning we'd anchor near the town or get a mooring. The mooring have a launch service which is great especially when you bring kids. Although mooring is great especially if your are going to raft up with friends.
Now remember the 'alternative lifestyle'. My wife and I would allways get an ice cream, sit on the stairs of the town hall and people watch. People watching takes on a whole new meaning here. It's a constant parade of folks 'letting loose', and the show is free!
One of my fondist memories was rafting with friends. We all had kids, and in the evening the adults would end up in one boat, while the children would be next door in another boat.
As the Father of two daughters I would try to possition my self so that my back was to the kids so I could listen in. What a toot...you had 8 year old telling the others what they saw, then the 12 year olds (who thought they were 18) would re-explain to the other kids what REALLY was going on. It was a panic.
Today we live in Maryland, about 460 miles from P-Town. It's a little far for a 3 day weekend. However, we will go back.