We still recall arriving in the Chesapeake from Vermont in November how the weather and sailing were glorious. No crowds, unlimited places to go and explore. The only problem was, we had to keep heading south as winter was approaching. A few returns to the Chesapeake since were similar. Perfect off season weather and sailing, but again, we were en-route North or South.

Since those experiences up and down the entire East coast, I think the true perfect summer sail, goes between the Chesapeake and Maine(and North if time permits), but at an entirely different schedule. Not set by calendar and clock, but entirely set by spring-summer-fall. This would allow a meandering pace with ample time for side trips, long stays, even backing up, if wind conditions and something interesting piques your interest.

The trick is to stay on the crest of what summer weather is, to you.

It requires leaving your boat in the Chesapeake, and planning a summer season on board. Planning that cruise would be the perfect way to spend a quiet winter.

Either drop off at your home port along the way at the end of the New England summer, or go back down, and start again when the perfect weather arrives at your boat.