Coastal Ct. to points south

[S/V Selene]

Input please- We are planning to head south from Old Lyme/ Old Saybrook, Ct. to the Chesapeake. We are considering whether we should go out and around the end of Long Island to the Atlantic, or down the sound to NYC....... I have started some very basic planning via Navionics and Waterway Guide and I don't see any marina's or anchorages on the Atlantic side for rather long stretches. Weather planning is obviously a big factor in the longer stretches and while we have a decently powered and reliable motor we are "novice" though not newbies by any means and prefer to be fair weather sailors whenever possible at this point. Consequently we are concerned that there might not be any places to bail into if needed to do so on the Atlantic route..... THAT SAID; The LI Sound route will (obviously) offer tons of places to pull in where we need/ want to, we have heard stories (none first hand) that going thru the "City" because of the current is not for the faint of heart and could be "challenging," or even something to avoid. Our boat is a 41' Ketch with a minimum 63' air-draft, full keel and has a 62hp motor so we're powered well enough. I'm inclined to think that with proper timing/ planning for weather, tide & current we should be more than capable. It is also a shorter distance than the Atlantic. I guess what I'm seeking is some observations and information from sailors who are in these waters, to add to our overall considerations as we develop the cruise plan. Apologies for the lengthy post and thank you for any encouragement and helpful information in advance.

[Shrew]

Get a current year Eldridge Tide and Pilot book, and time Hell's Gate for slack tide. I'd run it at slack - turning in the direction your going. It's only challenging if you try to buck it at full tide, where you make painfully little progress, or if you run it at full tide with reduced rudder response.

The city is busy, so keep your head on a swivel.

[pjShap]

It's only a day and a half from Montauk to Cape May, so you can get a reasonable weather window for the passage. You are correct that there aren't any reasonable anchorages making the trip that way, but I find it more pleasant than the trip down the NJ coast. I would only go via NYC if you want that experience. It's certainly an unusual passage, and as noted above, the trip is fine as long as you aren't fighting the current and you're ok paying constant attention to both the course and any traffic. Besides the commercial and recreational traffic there are some high speed ferries operating in the East River, and the Staten Island Ferry between the Battery and Staten Island. PM me if you want to talk on the phone.

[Kettlewell]

Take LI Sound through NYC! Especially if you haven't done it before. It's a fun trip and not really difficult at all if you pay attention to the currents in Hells Gate and the East River. The run down the river alongside Manhattan, under the Brooklyn Bridge, by the Statue of Liberty, etc. is spectacular. Plus, you can await a good weather window at Atlantic Highlands or anchored at Sandy Hook before tackling the Jersey coast. Keep in mind that all the inlets in New Jersey are iffy for a deep-draft sailboat. I try to make the run in one shot, weather permitting, all the way to Cape May. Atlantic City is a possible spot to duck in, but you are in a huge marina in the middle of the action. Similarly, Delaware Bay can be nasty, so try to make a long run with the current and fair winds all the way to the C&D Canal, though there is an anchorage in the Cohansey RIver. Never do the Delaware in a norther if you can avoid it--big square waves when the wind is against the current. Once in the C&D Canal you are home free, with multiple anchorages every day all the way down the Chesapeake.

[hugosalt]

For easy fair weather sailing sound is the way to go.
Treat Hell Gate/East river with same respect you would Plum Gut and the Race out
your way. (strong wind against current and such) Yes more traffic, just be aware fore and aft and keep distance. I go up and down river in my med. disp. 30 fter with full current,
just keep rpms up to maintain steering.
Manhasset bay, just 2 miles east of East river, excellent for staging, good anchorage, reasonable moorings, West marine, services, restaurants, super market.
I agree, if possible, try to run Jersey coast without going in inlets.
I like to keep about 6 miles off coast/60 ft water at night.
Avoids tugs/barges which would usually be inboard and avoids shipping lanes which are outboard by several miles. But still have to watch for sport fisherman running full out
east/west.

[hugosalt]

Timed right, you can ride outgoing current entire way from Throgs Neck bridge (start of East River) down to Sandy Hook. Takes about 5 hours. Nine bridges and a lot of history.
(some hi lights on history if you like)

[LAGERTHA]

Over the years and again most recently we have traversed the LI sound thru NYC. You should give it a go, since you never transited it before. Other than timing the current and Hell's gate...even if your timing is off a bit, you will be alright, especially with your 60HP engine. I can recall coming down the East River going (LI) past the UN at nine knots. The sights and landmarks are like no other. Anchor overnight at Sandy Hook, always good holding and will be a great place to chill out after your new adventure.
My thoughts on the New Jersey Inlets. Regardless of where you are, Inlets art treated with respect and deliberation. After a lifetime at the Jersey Shore, this is my opinion and experience. Manasquan Inlet will not be an issue draft wise...watch your tide. Barnegat Inlet is a challenge if you intend to travel all the way into the Bay. However, for an overnight stay, just enter and travel past the lighthouse on the inside and there is an suitable overnight anchorage. Atlantic City or aka Absecon Inlet has never been and issue for us. Cape May should be the less problematic of the whole lot.

[Kettlewell]

After a lifetime at the Jersey Shore, this is my opinion and experience. Manasquan Inlet will not be an issue draft wise...watch your tide. Barnegat Inlet is a challenge if you intend to travel all the way into the Bay. However, for an overnight stay, just enter and travel past the lighthouse on the inside and there is an suitable overnight anchorage. Atlantic City or aka Absecon Inlet has never been and issue for us. Cape May should be the less problematic of the whole lot.

Good advice, but keep in mind that all of them are nasty when you have an outgoing current hitting a strong incoming wind.

[Sailorichiban]

Hello 👋
After doing your planned cruise times beyond my count I have some recommendations. The trip down the East River is a great experience.
First off, make sure you have confidence in your propulsion, the East River is generally not cooperative to transverse via sail, not a good place for mechanical problems. The same mainly can be said for the Jersey Shore, in my opinion no really good inlets exist between sandy hook and Atlantic City, certainly they are the closest that would be suitable to sail into in the event of engine failure.
Make sure and test your engine for trouble free operation for a duration of 16-20 hours. The ocean can be rough at times and stir the contents of the fuel tanks. How is the basic condition of your tanks and the filtration system?
If good fortune and fair winds smile upon you then an enjoyable sailing experience may await, but plan on motoring and you will not be disappointed.
This trip is not a daunting prospect, I have some experience with your type of boat and respect it’s capabilities.
Mainly it can be done only navigating during daylight hours, which I would recommend. I have enjoyed entering the East River to utilize the current to speed my passage, perhaps at the best speed you can transverse the river in about 2 hours, I have. Occasionally I have seen 14 knots indicated , the blocks of Manhattan flying by, a unique experience!
Good planning and preparation is the key. A current copy of Eldridge, very useful in understanding currents and timing, and appropriate charts are strongly recommended. The route is well buoyed and charted. Head between the brothers and to the west of Roosevelt island. If the winds are strong then make sure they are in the same direction as the current. I have run the River with the wind and current opposing, a standing breaking wave formed to the the west of Roosevelt Island possibly 1.5 meters in height, it wasn’t a problem. Took it at 90 degrees, the same as a bad inlet, but better to have wind and current in the same direction.
Planning; one day and anchor in the vicinity of city island, day two anchor possibly at west end of Atlantic highlands jetty, day three anchor or dock at cape may or if becoming dark then Atlantic City. Day four, Delaware bay to the C&D, being careful to avoid opposing currents with strong winds. Or if starting from AC then moving to Cape May and reprovisioning, a nice town and the closest place to depart for the C&D.
Of course run Delaware Bay and the C&D with the current, and enjoy the trip!
Best to all!

[Sailorichiban]

Correction to my previous post;
Make that EAST end of Atlantic Highlands jetty, usually possible to anchor in a relatively calm area with the jetty blocking most of the wakes and or waves.
Very relaxing after NY harbor!
Best to all !