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The problem with Greenport is that getting clear of Gardiner's Bay out past Plum, Great and Little Gull Islands is quite a hike through some uncomfortable waters. Gardiner's Bay seems to have a nasty short chop constantly and getting out the north side requires going through Plum Gut and then The Race or all the way out past Fisher's Island. Sailing in LIS is less than spectacular most summer days. Also, I cannot imagine commuting out there on the one lane road/parking lot or paying LI prices for dockage/storage. If I was going to keep a boat to be near the best sailing, I'd want to be closer to Block/Newport and the Islands, somewhere on the northern shoreline of Conn, RI, or Mass.