I was looking at powerboats back in the ‘80s and checked with a buddy of mine with a couple of boats and lots of experience.
He suggested I take the power boating course, and said it was required for a captain’s license for over 50’, not that I was looking that big.
It was a simple community college night school course, the minimum, not a pilot’s class required for larger boats. I also found out that here in the Chesapeake the freighters are piloted by Bay pilots not their captain. If the boat goes thru the Delaware canal to Philadelphia they swap over the a Delaware Bay pilot.
I haven’t looked into the buying a boat since and forget ever going near 50’. Biggest I was looking at was 25’.
Yes, you're describing the Operator of Uninspected Passenger Vessels (OUPV) classes. It's a 62-hour program that is designed for people wanting to work as a charter-captain for vessels under 25 gross tonnes, and carry fewer than 7 passengers. You can obtain additional endorsements for such a license that allows you incrementally move up in weight and passengers.
Many people are under the misconception that it's a ship's length that set the parameters for how it's operated, or who may operated. It's not. In almost every state (perhaps all states), it's the vessel's weight (measured in gross tonnes), as well as its purpose - recreational of commercial, and whether or not its "inspected", which is a legal term that deals with it's registration.
In most states, if you are over the age of 18 (and in many states have the requisite but perfunctory "safety class"), you may operate virtually any uninspected vessel in territorial waters so long as you are only operating that vessel recreationally.
HOWEVER (there's always a "however"), while the state may allow you to operate that vessel, your insurance company may not. Many times - based on length, tonnage or value - the insurance company will mandate that the owner either secure for himself certain requisite certifications, or hire a professional captain, if the owner wants to obtain insurance.
Lastly, you're right about parts of the Chesapeake, and that's a similar circumstance in many different bodies of water. When a commercial ship enters a harbor, she boards a harbor pilot who takes the helm from the ship's captain. This is repeated in many canals, bays, rivers or straits where specific local knowledge is paramount to safe navigation.