Renting a boat for several months

[MarquezDLS]

Hey folks, would love any input on this.

We live in Chicago, and have a sailboat. We also have a child, six years old. We would love to spend a couple of months in the winter on a boat somewhere. Where exactly doesn’t matter.

Shipping ours down doesn’t seem to make sense. Because we live in Chicago, we’d have to do it in maybe September, and we are more thinking about January to April.

Has anyone done this, or have ideas on how to do it? When you look at charter rentals, it ends up an absurd amount of money. But I have to believe there’s a way to do this.

Any thoughts, wild ideas, guidance, or offers are welcome...

Thanks in advance!
-M

[john61ct]

Buy, use, then sell

[Joe P]

A few ideas come to mind:

1) AirBnb

Find owners that are renting their boat already. They're already accustomed to loaning out their vessel (however, for sleeping only). You'd need to talk them into letting you charter it out. I'm sure they'd want references, insurance, etc.

From talking with the hosts of the AirBnb boat we stayed on a few weeks ago in Hilton Head Island, SC, winter rates are drastically lower, and if they can't fill their dates, you might have a chance.


2) Local Marinas

Ideally, you'd find a boat that isn't being used for the winter by its owner. Contact individual marinas with your proposal. They might know of some owners who are looking for extra money, or at least may put your ad in the marina if you ask nicely.

Would you stay in the slip, or go cruising? I doubt the marina would want to help if you'll be removing the boat from its slip (since they'd be losing money).



Or,

3) Buy, use, then resell, as stated earlier.

[Drew13440]

I don't understand why you can't truck the boat south in December? Round trip would be a fraction of chartering costs.

[valhalla360]

I would guess around $10k round trip to ship your boat down and back. The nice thing is you know what you have and presumably it's a boat that you like.

If you could get a month off in September, you could take the boat down the river system and put it up in a marina until you come down later in the winter. As long as you get down to the Kentucky Lakes area or further, you can make your way to the gulf later as you are beyond where the lakes/rivers freeze over. Then only pay shipping one way back to cut the shipping bill in half.

It's a fun interesting trip. You son would probably love going thru the locks.