When strong southerlies blow (SE to SW), they tend to be bent into the wide river mouths lining the Chesapeake. Variable distances inside the river mouths these bent breezes tend to fan out and become turbulent as the higher level unbent southerlies blow over them.
So, as one starts a beat down Eastern Bay one can expect arrhythmic lifts and headers near Tilghman Point with port tack generally favored. The turbulent tumble of wind across the farms and trees lining the south shore is almost always misleading. The farther one progresses down Eastern Bay on port tack, the more of a lift one gets.
This is because the south side of the sharply receding shoreline of Kent Island tends to increase the fanning of the breeze, causing it to back about 2-5 degrees per mile down EB. If there is a foul current in EB (flood) the Kent Island side is even better as the currents are weaker here. If the sea-breeze kicks in and adds an Easterly component to the Bay winds, the north side is even more favored.
This Tuesday was like a field trip demo of these phenomenon. Rounding Tilghman we were lucky to fetch an unsteady 270°T @ 4.4kts, by the time we reached Kent Point, we were on rails, fetching 235°T @ 5.8kts. Winds throughout ranged from 12-19kts across the deck. We tacked six times (once to avoid a shoal spot that may or may not be there).
What a joy it is to sail.