RE: Getting to the rendezvous from Buzzard's Bay.
I'm pretty sure the quickest way to reach the rendezvous site on the West River when coming from up north is to go through Delaware Bay, the Chesapeake and Delaware Canal and then down the Chesapeake to the West River (as opposed to sailing all the way down to the mouth of the Chesapeake).
To get to Delaware Bay, you have two choices. Depending on your preferences and crew, you can either sail direct from Buzzard's Bay offshore to Cape May, NJ and the entrance to Delaware Bay; or if wind, weather, or short-handed crew make short hops preferable, you can go through Plum Gut into Long Island Sound, then take the East River out of the Sound and then work your way coastwise along the Jersey Shore (there are three fairly easy inlets between NYC and Cape May if you don't feel like an overnight run or if weather kicks up).
In terms of time, we figure anywhere from 36 to 48 hours to make the offshore run from Block Island to Cape May. If Toodle-oo's mast is under 55 feet, you can save a lot of time (and wear and tear) by going through the Cape May Canal into Delaware Bay. (Juno's mast is 55' without antennae so we might squeak through at low tide, but I've never tried it and always take the outside route...). If you take the inside route through the Sound, you can break it up into day sails of overnights just about any way you want. My memory is that the sound can be transited in two daysails, stopping midway at Port Jefferson. Depending on timing, you may have to wait for the tide to run the East River. Either City Island or Manhassett are easy stops at which to do this.
Shoaly and loaded with large commercial traffic, Delaware Bay is best run in daylight and even better if you've got the tide with you. It's only a run of about 40 miles up the Bay, and in good conditions it's a cake walk, but when strong wind and tide oppose each other, it is one of the roughest rides we've ever had. Then, from the C&D Canal down to the West River is about 55 or 60 miles in the Chesapeake.
In terms of wind and weather, summer winds are usually southeast or southerly. By late September, they may be turning around a bit. We're usually home from New England by late August, so I don't know for sure.
We've made the trip many times In JUNO and it can be a fun ride. Naturally, if you're trying to get somewhere and the wind isn't cooperating, it can also be a lot of motoring.
If you'd like more info. on inlets, places to stop, etc., please contact me off-list at firstname.lastname@example.org
We plan to be at the rendezvous and look forward to seeing you and any other owners there.
Roger & Cynthia Lopata
JUNO -- PSC 40 #46
p.s. JUNO was anchored on the West River Thursday night right off Camp Letts, where the rendezvous will be held. It's a nice, large bay dotted with a couple of islands -- plenty of room for anchoring.