I must be your cruise planning evil twin, Doug. We rarely leave with more than a vague idea of where we want to end up and that becomes a moving target once we're underway.

Rick, I've only been through LIS once while heading south 14 years ago, mostly following the Connecticut shore. Others here can offer you far more detailed and current info than I can. For a good overview with some interesting background history I would suggest finding a used copy of the classic Duncan and Ware, Cruising Guide to the New England Coast. I'm seeing dozens of used copies on Amazon starting at $15. None of the info will be current but it's fun to read and if you insist on planning ahead it's a good foundation reference.