Re: Marthas Vineyard, Greenport, Block Island, Port Jeff, Matiuk, Stonington, New Lo
I understand. I have to agree, and that's why we come up there on August. Tht turns around in September and October. Not saying there isn't good sailing on the Sound in the fall, but that is primo time on the Chesapeake. Most who even take there boats out here don't do so till mid November. Days are warm and so is the water. Colors re out at all the many anchorages and quiet rivers and creeks. Power boaters leave .
While my Odessey seemed long , you really need a month in many ways. The worst part is always getting from here to there. The Jersey coast and Delaware River are arduous but the rewards once arriving on the Sound or the Chessie are worth it.
The biggest differences we found were that there are Far more places to just drop a hook on the Chesapeake and they are closer. No needs to always travel iChat distances between harbors or inlets.
People are nice both places. Great little towns both places. More Mainas on the Chesapeake. Substantially less moorings meaning that the prime anchoring locations on the Chesapeake are not restricted by hundreds of moorings not allowing travelers to anchor in protected areas like on the Sound. I understand why for the boat owners there it's a safe place to keep your boat, but sometimes makes it tough for a visitor who just wants to anchor.
I would find a way to cruise here. Maybe you and friends bring the boat own and have your wife take a plane/ train nd meet here in Baltimore. I would help yu bring your boat down. Have a captain bring your boat here in 3 days tops.
If you come in the hot humid airless August you will pass me heading north.