Join Date: May 2002
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As I was making this same decision, the most important thing in my mind was the type of sailing I intended to do. Since I knew that most of my trips would be weekend day trips and after work jaunts, I worked hard to find a location that was easily accessable from my home and office, and didn't worry so much about being close to "destinations". If you plan on making at least a weekend out of most of your saiing trips, then eastern Conn and RI are a much better choice: better wind (usually), and many, many more destinations within a short distance. But if you think that a good portion of your sailing will be day trips, then a three hour drive seems like a substantial barrier.
My boat is docked in Branford, Conn (lots of space available in my marina), about 15 minutes from my office and 45 minutes from my house. I would probably sell my boat if I had to drive more than an hour to use it; my family is rarely interested in going on board for more than a few hours at a time, and I wouldn't be able to sneak out after work for a quick hour or two on the water before heading home.