The worst wake I ever encountered was heading out the Chesapeake approaching the Bay Bridge Tunnel early in the morning in the Spring of 1971. I was at the helm
of a 110' converted WWII sub-chaser/mine-sweeper. The owner and other crew member
were sleeping after the night out from the Potomac
and we were crusing at 12 knotts. With the dawn's light I saw a Sea-Land container ship over taking us from the port quarter with the entire bay, for as far as I could see, scalloped with the extending waves of his wake. I woke up the captain/owner to ask him if he wanted me to turn into this wake. Before looking, he reminded me that I was on a 110' boat without a need to turn into a wake; but after looking, he ran out to remove some loose items from the deck
as he told me to go ahead with the turn. After the spray washed the deck and our wheel
house we turned back to course in time to see the wake wash clear across the causeway before it entered the tunnel. I've never seen anything like this since, but I sometimes imagine such a surprise comming to me on a calm night in one of those shallow bays like the Chesapeake where these events
can be agumented.