Some things to know

Boats- the type you choose is a big consideration.  Most of the Loopers (boats cruising the Great Loop or any part of it) we connected with had power boats a bit larger than ours.  Ours being 33 ft motor sailor with masts down, and 10ft 2 in width.  Some of the power boats, trawler style,  were from 36' to one we met from Marathon, Fl. a live aboard, at 58 ft, a bit larger than they had anticipated, to a 48 ft live aboard.  These couples no longer own land homes, their boats are their homes.  A little scary for me at present although, I would like to perhaps have a 36' ft trawler on the intercoastal down south.  And there were a few hard core sailing people making the Great Loop in their 40 some feet sailboats. One couple we met were from Finland and sailed to the US from there to travel the Great Loop.

Coming from South Coast Massachusetts down to NYC, there are many coves and tucked in harbors and marinas to spend the night, not much in anchorage or moorings. Many along the way to NYC charge from $2.50-3.50 a foot for dock space. We had to tuck into some of them as our weather beginning the trip was not ideal- much rain, wind, and high seas. We were able to get  free moorings with the town of Fort Washington in Manhasset Harbor but is was too windy and wavy for me that day so chose to go into a dock.  You can anchor behind the Statue of Liberty if the waters aren't too busy.
As you journey farther up the Hudson River you can find Anchorage and Moorings at least 50, 60 miles from the Statue. There are many areas to tie in the Canals or at a Lock with nice parks you can be on land for a while. 2017 is an Anniversary for New York so the NY State canal system is not charging for canal travel and tie up.

Marinas- Many of the larger and better equipped Marinas, especially on the Hudson River,  are very familiar with Loopers and welcome them. The boats traveling the Great Loop or any portion of it Triangle, Champlain Canal Loop, will spend $$$ for supplies, groceries, any boat repairs, restaurants, laundry, fuel, pump outs, at the Marinas with these conveniences. The dock fees range from$2.25/ft to less than $3.00/ft plus a few $$$ for electric. on Hudson River Marinas as you get up the river about 50 miles.  Sometimes the dock fee is worth it if you have been traveling 6-7 hours a day for a few days,  and need a shower and laundry, or a meal you did not prepare on a boat. Stay tuned for the Hudson River and the NYState Canals