I have been boating in Boston for over 30 years. There is a lot to do including numerous places to eat and drink in the area of the city and both north and south of the city. There are also many islands with old Civil War/WWI and WWII forts to explore. The islands make parts of the harbor well protected, and if it wasn't for the sometimes heavy commercial and private boat traffic, it would be relatively calm. Just north is Salem Harbor and Glocester Harbor and the Annesquam (sp?) river, great daytrips. One of my favorite things to do is sit just off the city early in the morning/late night (especially when the tide is high) and check out the skyline, the city really is at sea level. Attached are some pics from an early fall trip to one of my favorite islands. PM me if you want any more info.