Martha's Vineyard to New York City

[DougAnnapolis]

We just made the return trip from Martha's Vineyard to Annapolis. For your sanity and to keep your young kids engaged, I would suggest you go Thru the Race and then transit the Long Island sound. Places to stop . Port Jefferson, oyster bay (take a day and tour teddy Roosevelt house ) , then port washington. Time your transit of hell gat to go thru with the tide. Call libery landing to see if they can accommodate your boat. You will go thru hell gate very quickly and can maybe get a slip at ilberty or go beyond 20 miles anchor or slip at atlantic highlands.

The south coast of LI is not sailboat friendly, that's why I suggest LI sound. Then The NJ coast, it is also not sailboat friendly. Our two stopping points are Manasquan (very high currents) and the Atlantic City (Farley marina).
We skipped cape May. you can anchor in Lewis harbor. From Lewis it is 🤓65 miles up Delaware bay and river. Catch the tide up. If not it will be rough rough at the top in an outgoing tide. Delaware bay connects to C&D canal. Take canal to to summit north marina. Just an ok Marina, but after 65 miles, it is nice stopping place.

[SailFastTri]

Originally Posted by Symphony

the Race is west of the West End of Fishers Island.
the flood or ebb current is quite strong in Fishers Island Sound (which is on the north side of Fishers). lots of boats, very scenic and great wind tunnel in there, you might want to avoid it if the usual westerlies are blowing.
The other route is to way south of Fishers Island and out of the current and the wind tunnel, reach the Race at slack water or start of the flood and roar in.
You could also go into Long Island on Gardiners Bay, always great sailing there as long as you can time the current through Plum Gut. current can reach 5 and 6 knots easily. You could spend an entire season puttering around inside the eastern end of Long Island.

very nice anchorage in East Harbor of Fishers Island, West Harbor OK too. Stonington has moorings and anchorage, very nice. Mystic is a little ways up the river, could be fun to go through the bridge.

Once you are past Plum Gut there are very few places to stop on the north shore of Long Island (other than Mattituck Inlet) until you get to Port Jeff. South shore of CT has many many marinas and anchorages.

fantastic area to visit. Light winds will be OK (since they are usually westerlies).

Not trying to be argumentative, but I think the info above is not entirely accurate.
1) The Race is the area SW of Fishers Island (not west) stretching between the SW tip of the island and Plum Island.
2) The currents in The Race are much faster than those in Fishers Island Sound, which is more protected. The fastest current in FIS is at the northeast end of FI and they are more than a full knot slower than the Race, which has faster current over longer distances.
3) Fishers Island Sound is not especially windy, (not more so than the surrounding area on any given day).
4)General prevailing winds in summer are SW (not W) in LIS and all of New England.

Edit: Other than that I agree with the rest of Symphony's post. Many other good suggestions by all posts in the thread so far

[SailFastTri]

The suggestion to visit Mystic is a good one, with kids. If you call the museum for reservations you might be able to get an overnight slip on museum grounds, which also gives you free admission and full access to the exhibits before opening time.
We did that when our kids were that age, and we woke to roosters crowing - walked around to talk to the blacksmith as he fired his coal and he gave us quite an education about iron work in colonial times.
If you can't get a slip, anchor in the river off the museum and dinghy ashore.

[SecondBase]

Originally Posted by hugosalt

Interest/entertainment for your crew...
Look for the Longhorn cattle along the beach of Nashawena Island when sailing
Vineyard Sound/Buzzards bay. last island before Cuttyhunk.
Cuttyhunk is throwback in time, a favorite of many, a bit quiet for your young crew.
Up the bay from Newport in Bristol, R.I. is the Herreshoff museum, years ago i could not pry my young family away, much to my delight.
Up the Ct. River, Essex great town, Deep River... steam locomotive train ride, call ahead for info/reservations. Just missed the largest Fife and Drum gathering.
Western Long Island sound ct side ..anchor in Norwalk Islands, can (approach carefully) go in behind Goose Island swim, dinghy to island for picnic/bbq will almost surely be only boat there if you overnight.
Little further west, surprise crew and go to Rye Playland, amusement park right on the sound. Fireworks on Friday nights in summer.
On Long Island side western sound, village of Northport, all very close to waterfront
(Seymours Marina has moorings) concerts Thursday or fridays evenings.
Also Oyster bay, a short ride to Theodore Roosevelts home at Sagamore Hill.

+1 on Hugo's whole post. I can only humbly add stop at the Thimbles. Be sure to arrrive during daylight and save time for a dinghy tour or water taxi ride.

[SailFastTri]

If you go to Essex, the Connecticut River Museum is a very worthwhile visit.

I'm not a fan of The Thimbles as an anchorage. Nice to cruise on through, but you need to navigate carefully to avoid the numerous reefs and boulders in the area. It's an unusual spot, with some pretty houses and small islands that make interesting site seeing for an hour or less, but to anchor you're exposed to the prevailing SW winds and on the bottom there are numerous chains, cables, not to mention boulders and debris that could snag an anchor.

[akprb]

Eldridge and currents.

Hells Gate in particular you want to time perfectly and I found Navionics app tide/current feature invaluable.

Made that run last year solo and it was a blessing over thumbing through Eldridge like we did "back in the day." Hells Gate was a puddle and I've been there when it was a washing machine.

With kids, keep the passages reasonable. A structure for the day we found very helpful, actually during night watches I would write up a POD (plan of the day) and post it in the galley.

Every morning the girls would read and set it into motion. Favorite activity? "Free play" (which is code for nap for dad)

We still joke about it today.

Atlantic City a fun stop, the marina at the casino and we like Cape May as well. Makes to hop up to the C&D a little shorter 😉

[SecondBase]

Originally Posted by SailFastTri

If you go to Essex, the Connecticut River Museum is a very worthwhile visit.

I'm not a fan of The Thimbles as an anchorage. Nice to cruise on through, but you need to navigate carefully to avoid the numerous reefs and boulders in the area. It's an unusual spot, with some pretty houses and small islands that make interesting site seeing for an hour or less, but to anchor you're exposed to the prevailing SW winds and on the bottom there are numerous chains, cables, not to mention boulders and debris that could snag an anchor.

+1. Daytime arrival and pickup a mooring. I would even add IMO dangerous as an anchorage for the reasons SailFast mentions.

[Suijin]

With two sons that age if you don't stop at Mystic Seaport and visit Sagamore Hill (Teddy Roosevelt's home) you should be charged with child abuse. They will be captivated by both. If you can get a reservation to tie up at the seaport itself you can run around the grounds after the museum is closed and the crowds are gone. It's wonderful.

No trip down the sound is complete without stopping in Essex to wet your whistle at the Gris( Griswald Inn), the oldest continuously operating inn and pub in the US. Even kids find it cool.

Definitely get a copy of Eldridge's. The diagrams for current and tide make it much easier to plan than dealing with data on your plotter.

Rule #1 for transiting down the NJ coast; wind against tide at the inlets can make them seriously treacherous. I personally hump straight to Cape May /Lewes and stage for the tide going up the Delaware. Avoid stopping in Chesapeake City on the canal unless you like cheek to jowel anchoring and noise all night.

Down the Chesapeake and up the Potomac is pretty straightforward. Another great stop for kids is the museum at the Naval Academy in Annapolis. If you go don't miss the floor which has one the the world's largest collections of antique ship models. If you're there on a Wed. or Thurs. night the racing boats sail through the anchorage to finish at the Annapolis Yacht Club which is a nice festive event.

[Hoodsail]

Just came thru the Race 2 wkends ago from Guilford, Ct to Block Island. Rode the ebb out and even 3 hrs after the start of ebb recorded a max of 10.5knots on the gps (motoring)...felt like I was on a power boat...of course coming home a few days later, we paid for it as the wind was SW to W (typical LIS wind) with a foul current = motoring at 3.5 knots after tacking across the sound a couple times just to say we sailed that day..
should be an excellent trip..
Not certain when you're leaving but small craft advisories remainder of this wk in LIS and last nite they were easterlies, so would blow you to NYC.