We've been up and back from Annapolis
to Maine 7 or 8 times; and up and back from the Newport/Vineyard/Nantucket area 3 times; but, we've done in July and August. ;^)))
Having said that:
I trust that your not in a hurry, thank goodness. You said a motor-sailor? It would help if we had a sense for your speed and whether you're looking at some overnight cruising as an option, etc? So my observations are based on generics. I assume you have radar
? Chart plotter? Heater? etc.?
That time of year you should time your transiting of the Gulf of Maine so that you're fighting the wind plus the cold.
If you're coming from the Penobscot Bay area, I think that Booths Bay is a good stop. Then you have a choice to go to Portland
(Casco Bay) etc. We have a pretty fast boat, so we tend to go directly to New Castle, NH. We like Wentworth Marina, they aren't cheap
-- but you have a free loaner car and it's a nice place. You can load-up with groceries, wait for your weather window, etc.
Our next stop is usually Marblehead. You could try Gloucester or some other places. But Marblehead is just a great place. Walkable, etc.
From Gloucester you can either cut down to Boston, Situate, Plymouth, or cut across to Ptown. Weather and fog
can be an issue. You may see some whales if you cut across to PTown. I've always found PTown fun. That time of year it will pretty cold out there, though.
Then it's through the Cape Code Canal -- ONLY WITH THE TIDE! It's really gorgeous on a nice day. Depending on the time of day, you can make New Bedford (pretty commercial fishing
port) or South Dartmouth, a/k/a Padanaram.
If you want to go to Nantucket
or Martha's Vineyard
instead, its probably a turn to the South right out of the Cape Cod
Canal, the you have the Woods Hole run through a very tricky bit of tide, current
, and timing. Along the way there are places to stop. There will almost no one there that time of year :^))). But that may part of your special experience.
If you get to Nantucket
or Martha's Vineyard
, as you head
back East toward Newport
be careful to watch wind and tide. You will want to have the tide in your favor -- but if the wind is counter, it will be a LONG, MISERABLE, experience. Remember, Nantucket is where the billionaires are displacing the millionaires. But it is lovely. Edgartown is a neat town -- as is Vineyard Haven. The Vineyard has a convenient bus system that will allow you see that pretty big island.
Newport is special. if you haven't been there, its worth bunch of days. A mooring
in the harbor is fun. Marinas might welcome you and your credit car for less pain than later in the season :^)))
Then there is the Great Salt
Pond on Block. Worth a stop. I've not found going ashore so great, but then that's me.
I like Sag Harbor as a stop. Mystic is neat. Then you have LI Sound. That's a crisscross and tidal experience. Several places along the CT shore.
Once you get toward NY City we like Huntington. There are plenty of places to eat and a ton of boats.
There are some other places between there and NY also. You can try Stamford, CT. too.
Everyone has described Hells Gate and the run down the East River. I don't places to stop in NYC
. There's the Battery
and several places on the NJ side off the Hudson
Sandy Hook is place to bail-out. The Bridge as you go down the East River are spectacular -- capped off the be Verrazano Narrows. BUT the traffic (REAL TRAFFIC) below NYC
is AMAZING and confusing. Tide going out of the Narrows and wind are a big deal.
The only place south of Sandy Hook you should think about is Atlantic City if you want to bail-out until Cape May. I've never been there, but I've been by it.
Cape May, which I have visited once is interesting. It's entrance from the east is workable.
Delaware Bay, for me, is something to be passed through. Watch the wind, go with the current
, stay near but on the edge of the ship channel. There is a lot of freight traffic going with the current. It's orderly though.
The C&D Canal has some places to pull off -- but by then you'll be home.
Watch the buoys, ranges, and ship traffic on the western side of the C&D. It a little confusing if you are trying it at night! There is a system, but by the time you figure it our, you'll be through it. The ranges appear "right on you" when they are far away.
If you want to discuss your trip further. Send me a message, we can chat off-line.
By the way, we often go non stop from Annapolis to SW Harbor, Maine. We're about 50 nm off of Nantucket before we turn North. I think you're much better off (especially that time of year) NOT doing that. There is a lot of fog
, cold, fishing
trawlers, current going all kinds of directions, and very cold water
. If you hit a weather window wrong, there is a reason the area has a reputation for being tough.
The only other advice: Really watch the weather. Exiting NY Harbor is ALWAYS pretty lumpy (understatement) even with the current. But against the wind, it can be brutal. So are many of the other places along the way. By picking hops that you can do in 6-7 hours. If you pick your weather windows it should be a lot of fun. Keep it that way. One of the most dangerous things on a sailboat is a calendar. :^)))