Is Annapolis OK?

https://watermarkjourney.com/private-yacht-charters-weddings/

https://schoonerwoodwind.com/private-sailing-charters/

I used this. They have 3 different sized boats. All $$ but beautiful
https://www.nautiste.com/

You could try Freedom Boat Club. I think you have to join though.

Are you looking to hire a crew as well or do you operate boats?

A few years back we chartered a boat with a captain and first mate for a very small party we had. It might have been Capital River Cruises, but I'm not positive. If you Google Map Washington Harbor there are several tour companies. We found one that did private tours.

What about Annapolis?

Find the names of the marinas and look up the marina websites, they usually have rental providers listed.

I'm looking for the same thing and found getmyboat.com. Unfortunately I'm finding most underwhelming. Good luck and please post if you find better options.

How do you rent a yacht for an evening in DC? Trying to plan a small party. I put this in travel because I don’t know where else to put it. TIA