come on, he's never gone farther than the power cord can reach from the dock

You have some interesting tide and current conditions along your way.
Timing them to your advantage from City Island to Vineyard Haven is
difficult without layovers. You might want to consider a leg to Block
Island, another to Cuttyhunk and a passage thru Quicks Hole to
Vineyard Sound and on to Vineyard Haven. Coming back, realize that the
prevailing is SW and unlesss you plan your stops carefully, you'll be
hard on what ever wind there is, all the way.

BTW, have you taken your boat to Martha's Vineyard? I seem to remember
that you
did. We are plannng that for next season. We plan to make a straight
passage
with no landfall, then thread our way back.
Any suggestions?

RB