I have no experience with Long Island Sound, but plenty with a broadly similar body of water, the Santa Barbara Channel in Southern California. There are days when you can safely cross the SB Channel in a bathtub and days when you are at risk in a sixty foot power boat (true experience!). I imagine the same is true of your body of water as well. That is where experience is indispensable. Leaving Long Island to get to the mainland sounds to me like a classsic case of jumping from the frying pan into the fire. In a disaster, I would rather take my chances on the Channel Islands than on the mainland, so I think you are relatively better off on LI than trying to reach a doubtless already burdened mainland.<br><br>You ask about what boat to buy that will safey cross the Sound - it depends to a great deal upon the experience and judgment of the skipper, rather than size and number of gizmos. The money you might spend on a boat and related paraphernalia would probably be much more effectively spent on enhancing your home and surroundings. That way you will have home field advantage over the hordes from Connecticut who will be fleeing to Long Island.<br><br>I am glad you are planning through possible problems. Hope this helps.