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For the OP the chessie, NYC, LIS and New England have lots of delightful towns, anchorages and marinas a short hop away from each other. Even in a small boat should be great fun. But the Delaware and NJ are “fly over” country in my mind. Even in a stabilized NT astudiously try to avoid the NJ coast if there’s any east to things. If no east his boat should do just fine. Find this leg either breathtakingly boring or uncomfortable. The rest of his trip should be much fun and worth doing. Best of luck.
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