This response may be too late for this season, but: you should be able to get a better deal than the posted prices on charter websites. I have negotiated with them even for weekends and weeks. But ideally, you need to get in touch with an owner who already charters (so he is used to other people using the boat and already has insurance) and work something out with them. You may find them by doing internet searches on the boat name along with the make and model. I have found owners this way - as many have posted pictures, or cruise blogs or even youtube videos - you may be able to email them from there. Lastly, if you are not successful getting in touch directly, you can ask the charter company to ask owners if they'd be interested in a long term rental. Even if the charter company takes a cut it may still work out to be cheaper. If you are interested in the Chesapeake, try Let's Go Cruising (
www.letsgocruising.com). Good luck.