Are you going through Okeechobee, or around through the keys? Are sailing outside the carolinas, or through the
ICW? That will help.
Broad strokes....take the time to sail up through the Chesapeake. If you like
history, go to Yorktown. But, if you need to keep moving, Overnight at Solomon's, then St. Michael's. St. Michael's to
Annapolis.
Annapolis to Rock Hall. Rock Hall to
Baltimore, if you wish the big city.
Baltimore to Fairlee creek. From Fairlee
anchor in the bohemia and wait for a favorable tide to go through C&D
canal.
Down the Delaware to Cape May, NJ. If your
mast is less than 53 feet, you can go through the Cape May
canal into Cape may. Otherwise, you'll have to go around the tip of
new jersey. Either way, Cape May is a worthwhile one or two day stop. There are a bunch of marinas there, but also you can
anchor out if that is your preference. There is good protection at Anchorage inside the Cape May inlet. From cape may, if want the casino's, go to Absecon (Atlantic City) and stay at the marina. Otherwise, from Cape May
head to Montauk point or block Island if you want to go direct, or if you want to go through Manhattan, hug the Jersey coast. Atlantic city is the last usable all
weather inlet, for the most part on the Jersey coast. There are some bail outs, Manasquan, but not at night or in bad
weather, and it is a haven for
commercial boats. Very unsettled water.
Once you leave Atlantic city, you are committed to either going straight to Montauk point, or you can follow up the coast and go into Manhattan under the Verrazano narrows bridge.
I must say it is awe inspiring to pass the Statue of Liberty by sailboat. There are some marinas behind the Statue of Liberty on the
New Jersey side and there are some marinas on the Manhattan side. From here, you would go through the East River through Hell's gate and enter into
Long Island sound. There aren't that many
ports on the
Long Island part of the sound. There are many more ports on the Connecticut side. All of this said, it's a really nice trip to go from either Cape May or Atlantic City all the way to either Montauk point or block island. Then, you're home!
Definitely get an Eldridge coastal and tidal pilot. I would not make the trip without that.
Have fun!
Ben