My vote for the sweetest boat I've ever sailed on is a 1968 53 foot Gallant ketch, designed by Van de Stadt and constructed by Southern Shipyards, "Alaunt", chartered for a day-sail out of Red Hook, St. Thomas, USVI. This boat originally belonged to the Royal Governor of Bermuda and was used by him in trans-oceanic races. We sailed to St. John with one reef in a fresh breeze and the boat cut through the waves like a hot knife through butter - "sea kindly" doesn't begin to describe how it shouldered its way through a considerable chop. The fit and finish both above deck and below were impeccable.
But for the Chesapeake, where I sail, I'll take my own boat with a 5ft. draft, as "Alaunt", and her 52 sisters, have a draft of 7ft which would limit access in skinny water.