Dylan;
Congrats on the Nauset 30, great boat and Bill is a great guy. I looked at this vessel last year and was very interested in her but found something a little closer to home.
This past fall I helped crew a Swan 38 sailboat from Belfast Maine to Annapolis so I think I can give some input.
If I was to bring the Nauset north, I would not head south out of Solomons. Instead I would head north, up the Chesapeake to the Chesapeake/Delaware Canal. Probably look to spend night at/around Chesapeake Inn & Marina (this is about halfway thru the canal). *It will be safer on a first leg of a run on a new-to-you vessel to stay inside. If you encounter any "issues" there are plenty of places to pull into to resolve heading north up past Annapolis, etc. This leg is approx 90nm (7.5hrs @ 12knts) - that's a BIG day on a new, unfamiliar vessel.
Next day head for Cape May, going south down the Delaware River. This leg would be approx 70nm (about 6hrs @ 12knts). I would suggest this because once you go outside, Atlantic City is the next place if you need to address any "issues".
Day three, I'd leave Cape May with Marine Basin Marina just inside Coney Island NY. This is a long trek at just over 110nm (10hrs @ 12knts). But you're now familiar with the boat, getting to know her ins & outs. It's also amazing to bring "your boat past the Statue of Liberty!!!". You might want to stay for another night, just to rest up and re-provision.
*Now you have to choose: Do you go back outside or work your way inside the Long Island Sound? Outside is faster/shorter route, BUT*** inside is calmer, safer and more places to tuck into if weather is bad, you have any "issues", etc. I would opt for inside if I was doing this on a boat I was not yet familiar with.
If you go outside, I'd try and make Block Island (another long day, approx 125nm, 10.5 hrs @ 12knts. If that's too far, then I'd make way to Shinnecock Bay (80nm, 6.5hrs @ 12knts.
If you go inside, I'd head to Branford, CT (Branford Town Docks), 75nm, 6.5hrs @ 12knts. If you want to go further then head to Saybrook Point Marina (Just about 96nm, 8hrs @ 12knts).
Next day you want to make it into Buzzards Bay, MA. *You'll need to figure tides for the canal...you want to travel thru the canal with the tide not against.
If the tides are in your favor, take them thru the canal and stop at "Harbor of Refuge" at east end of canal. Fuel, safe dockage, restaurants within walking distance, showers.
If the tides are against you, you can find dockage on west side of canal around Onset, MA and wait for tides to be in your favor the next day.
From the east side of Cape Cod Canal, it's roughly 125nms to Strouts, 10.5hrs @ 12 knts. If I was doing this, I'd make my way to Newburyport and spend the night, have dinner ashore (just under 70nm, 5.6hrs @ 12knts. Then I'd get up fresh and head to Strouts in Freeport and be there in 72nm, 6hrs @ 12knts and be home for dinner.
Hope this helps.
If you decide to travel north from Freeport and find yourself heading up the Penobscot, I've got spare mooring in Stockton Harbor at the "Head of the Bay" (safe hurricane hole).
Later,
John
