Re: Maine to Chesapeake Fall Passage
A lot of your progress will depend on the weather and how much the crew can take. On one passage we left Harpswell ME at about noon on Saturday, and arrived in Southport CT on Monday morning before breakfast. Most of that trip was made under a reefed mainsail and fully furled jib. We entered the Cape Cod Canal with that combination up, against the tide, doing better than 10.5 knots according to the GPS. We had some breeze. The last time we headed south, we left Rockland at about noon on a Saturday and had to essentially power upwind most of the way to Gloucester. There we grabbed a mooring and some sleep before continuing into headwinds & rain to catch the tide at the canal. Small craft warnings were flying in Buzzards Bay when we to the other end of the canal, and we wore ourselves out in the slow, wet beat power/sailing up to New Bedford.
We had a miserable experience in Padanaram (South Dartmouth) There are few/no facilities there any more, and the New Bedford YC was inhospitable. Friends had a much better reception in New Bedford proper, where the waterfront has been entirely redone and marina slips, facilities, restaurants, hotels and moorings are plentiful and eager for business. We ended up coming back the next weekend to bring the boat down the rest of the way, and the weather was more favorable. Going with a crew of 2-3 will limit how far you can push in a day. I like having at least five for overnights because it allows getting some sleep in. That way when you get to a place where the navigation is tricky, someone is more likely to be awake enough to make the right decisions. Even then, the trip you plan is long enough that you'd want to stop and get some real sleep along the way. Depending upon when and where you are, there will be logical spots to pull into while you wait for the tide to change at the Race, or Hell Gate, for example.
Your idea of giving it three weeks should provide you enough weather window to avoid the bashing we pushed through.