All joking aside, I'd like more info on who goes between your area and mine, seasonally or for a sailing cruise. I can't envision a website that would collect enough people that make this sail, to be interesting. You could post it on various venues and local media, if something worked.
My meeting in the hardware store had me thinking about this. A lot of people like you or me on vacation, delivery captains, etc., make this trip regularly. But many people I talk to or read on the web, consider it for "when I have time" sort of thing. Most simply don't, it seems a big jump for many. The guy above(in the hardware), made the trip mostly because I mentioned it to him, and that it can be a fun 2 week cruise. So he went down to Nantucket from Penobscot Bay, and was back in 12 days.
It might also help connect people that may be contemplating the cruise. I know rallys are a sore spot here , but for new sailors, maybe with kids, and little experience, they may like to sail in company with another boat. It would be nice to help those people get together, I know we've made many longer coastal sails with other boats when we were new to it all.
It's a much easier trip to plan if you've done it before. If not, info from those currently doing it, would be handy.