South from Massachusetts ...

[kandlekid]

Going south from Massachusetts in a 37' ketch (my goal is Maryland or south), would you sail on the north side of Long Island (through Long Island Sound) or on the south side (ocean), and why?

[mikeod]

I've done both. South of Long Island you have to do in one shot. If weather is good go for it. Inside you have to deal with timing current through East river but plenty of spots to anchor along the way.

[kandlekid]

Yeah, anchorages are a major concern for me, as I'm not sure how much crew I'll have (if any).