charter business for a 50 ft Motor yacht

Is your boat in 3 Mile or over in Sag? The dockmasters in Sag can probably run some business to you and I'm sure you know the broker to use. However you're talking summer 2021. This season is done. This is the right time to start getting it set up for next summer though. As for chartering being a source of steady income I wouldn't count on it. Mitigate some of your expenses is more like it. Best you can hope for is a few charters July 4th weekend and maybe one day a week average through the summer if you're lucky. A lot depends on the Covid situation next summer also. You'll need a captain you can trust and who knows the area, but I can't think of one there these days I'd recommend. You'll also need to let your insurance company know. Checks can't be trusted there . So you'll need to deal in cash, CC or cash app. You might do better bare boating it if you dare. At least that way you can possibly BB charter it to one or two families for the entire summer.

Just thought of a way you can make it work. Air B&B. You know what summer rentals go for there. You could have it rented every weekend and never worry about it leaving the dock. Just make sure you have a diver hit the bottom before you come for your once a year.

You want to learn how to play tennis at the US open?

UMMMM and a marine plumber on standby for all of the toilet clogs and holding tank overflows!

Normal issues with any bare boat charter, and like any bare boat charter he'll need boat washers and housekeepers prepare the boat for guests and someone to come by to confirm the boat is ready and deal with any issues. If he's docked where I think he is he's got good mechanics close by to handle any issues and the town pump out boat can come by after each charter/rental.
Again I'm not recommending he charter in any way. Just looking for ways to make it work for him if he moves forward. My training has always been to find a way to make things work rather than excuses for why they won't. Quite frankly if I had a boat that got used once a year there'd be a big For Sale sign on it. But he could probably make $1,500 - $3,000 per night for it dockside, more for the holidays, have the boat rented every weekend from Memorial Day to Labor day, with no captain or fuel expenses and no wear on the running gear where chartering he'd be lucky to get off the dock 5 times the whole summer and barely make a dime. Of course he'll need to clear it with the marina and the town, but that's what lawyers are for.

You mean that bare boat charters are now illegal?

My mate used to charter his 50' Hatt in the USVI. He even got called by the Secret Service to cover President Carter on MY Daydream. I took Amy Carter for a beer at the Bilge Bar, nice girl.

Well I just Googled Bare boat charters and it appears that a lot of companies haven't gotten the word that they're breaking the law. All these "serious fines" should be able to balance our budget I guess.

The rules are federal, but in the last 30 years I've been boarded 3 times. And yes he's in the Hamptons where the odds are much less. Regardless though I can see the CG cracking down on illegal charters, especially in Florida. Good cause they take money out of the pockets of professionals and endangers people. But I think the cracking down would be people chartering unlicensed or carrying too many passengers. As far as I know bare boat charters are still allowed. I'd say his biggest hurdle would be if the town had some sort of prohibition, but I doubt it. You can rent an RV and have it delivered to a park. Pretty much the same thing.

Oh good. I'm glad they didn't outlaw bare boat charters. You sure can find trouble where none exists. People who rent weekend vacation homes in the Hamptons generally handle their own shopping and cooking (if they don't go out or have their own staff), and I doubt they'll burn too much fuel dockside. Btw, although I'm sure there are B&Bs on Air B&B most are just short term rentals

Good ideas, and yes your dockmaster will be a good source of business. Sag is perfect. Don't forget the real estate brokers though. Low commissions and they get the first calls for summer rentals. Should take about 5 minutes to book your entire summer as what you have will be something special and unexpected for their clients. Their clients won't expect to leave the dock although they'll also be a source of additional (commission free) income if they would like to leave the dock occasionally. Wouldn't it be nice if your charter guests treated your boat like it's their summer home that they'll be eating breakfast in the next morning. Put a list of a few captains together so you can stay bareboat. Your dockmaster will be able to help with that. Put the name of the captain you know on top. Keep it simple. 'If during the summer you'd like to take the boat out here's a list of captains. You'll work your own deal with them and I get an extra $_______ plus fuel when she goes off the dock'.
Good luck.