Re: Where is the best cruising in the USA?
The reality for most folks is that having a boat usually means you have to work for a living. (I said MOST folks.)
That said, the best time to enjoy cruising for MOST folks is in the summer, when vacation time permits. If you look for a venue that has reasonably predictable winds, tolerable air and water temperatures, and allows multiple ports of call within a week or two, southern New England, from Long Island Sound to Nantucket, including Narragansett Bay, Buzzards Bay, and Nantucket Sound is hard to beat. If you are looking for solitude, however, look elsewhere.
North of the Cape Cod Canal, the water is colder and fog is more likely in the summer, especially along the Maine coast. If you can handle a cooler cabin at night and don't fall into the water, Maine is absolutely delightful. You could sail in Maine for many years without getting bored.