Thomas:
I sailed my 30 ft sailboat from the Chesapeake Bay to Maine and
back three times. My marina was in Swann Creek on the Eastern shore,
north of Annapolis. As others indicated, the shortest route is through
the Chesapeake-Delaware Bay canal.
Delaware Bay has significant current, and the trip down Delaware
Bay is much easier in a sailboat if you have a favorable current. There
is a small anchorage at Chesapeake City on the canal where you can stop
until you have a favorable current. There is a canal at Cape May that
allows you to cut the corner there. Most people think there aren't any
anchorages on the northeastern section of the Delaware Bay, but I've
anchored several times in Back Creek.
Atlantic City and Manesquan are the only inlets I recommend along
the NJ coast after you leave Cape May. There is a lot of barge and ship
traffic along the NJ coast, so make sure your crew members know the
light markings for different types of vessels. The barges are usually
being towed, not pushed. Sometimes they have very long tow lines and
this makes identification difficult at night.
I did not have enough fuel to go from Cape May to Block Island if
the wind was not favorable. If I had good wind, we sailed around Long
Island to Block Island. But if I had to do a lot of motor sailing, we
went in the NY harbor and down Long Island Sound.
We encountered a lot of fog in Buzzard Bay in the Newport,
Elizabeth Islands area. A good radar reflector and sound signals are a
must. Radar would have been wonderful, but I did not have radar on my
boat.
You will need to wait for a favorable current to go through the
Cape Cod canal. There are lots of places to stop after you exit the
Cape Cod canal, but on our three trips, we went straight to Boothbay
Harbor.
Note that my last Chesapeake-Maine-Chesapeake trip was in 1995, so
my information is not current. I've been sailing on Galveston and
Pensacola Bays since then.
Dave

Thomas Wentworth wrote:
Hypothetical question ,,, if you were buying a sailboat somewhere up in
Chesapeake Bay. And you needed to sail the boat back to New England, to
downeast Maine ..

Would you go up the bay and take the Delaware Canal and then down Delaware
Bay toward Cape May or::; would you go down the bay and out to the Atlantic
?

If you decided to go to the Atlantic: once you turn north after leaving the
mouth of the Chesapeake are there good harbors along the stretch of coast
Virginia, and Maryland, Delaware, and then north along the New Jersey coast?

I always see postings that say the New Jersey coast has no place to put in.
Is it just that the harbors are not good for sailboats? What about along
the coast like near Ocean City Maryland?

Thanks