Cruising Options: Connecticut vs Long Island

[alofns]

We're in the process of researching and mapping out a trip from Nova Scotia to the Bahamas in the fall on our 33 foot sailboat.

My planning so far has gotten as far as Block Island. I am now wondering if we should head along the Connecticut Coast up the Long Island Sound, or come down the Long Island Sound side.

We prefer to limit or days to 35 - 40 NM and our preference is anchoring or mooring with an occasional marina stop to provision, shower, etc.

Does anyone have a strong preference for one side of the sound or the other?

[rwy36]

Towards the western end of LIS I think I'd prefer the Long Island side generally (it seems to me there are more options for anchoring/mooring/slips). I don't have much practical experience there, though.

East of Port Jeff I've cruised quite a bit, and I think I would cross over the the CT shore side where you'll find more anchoring/mooring/slip options around Clinton, Old Saybrook/Essex, Niantic/Mystic, and Stonington/Watch Hill, RI. Stonington has a <sometimes rolly> anchorage behind the harbor seawall and it's a pretty short hop to Block from there. Watch Hill is a large anchorage with good beach access so definitely a favorite of LIS boaters!

You could also stay on the Long Island side east of Port Jeff but other than Mattituck you'd likely be looking at Gardiners Bay for a place to tuck in overnight. Lot's of nice cruising in Gardiners too (we're particularly fond of Coecles Harbor) but that is a much longer ride in a sailboat from Block to there (with Montauk being another option depending on max daily range).

Sounds like an exciting trip (and hope to hear about it when you get out there)!!

[pjShap]

I don't know if going through NYC's East River is part of the attraction, but if not, you could consider going straight from Block Island to Cape May, NJ. If you go up the Long Island Sound and through the East River, you would generally do an overnight to Cape May. There aren't any particularly good stops along the NJ coast. From Block to Cape May is about a day and a half, so not much longer than along the coast.

If you want to do NYC, then a great last night in Long Island Sound is Port Washington, on the Long Island side a few miles east of the Throg's Neck Bridge. Moorings are $25/night and include tender service into town or to a dock near grocery and liquor stores and a West Marine. It's a lovely town.

If you PM me an email address, I can send you a short document with Long Island Sound anchorage info. Or, if I did this correctly, it might be attached to this post.

[psk125]

The tides are generally stronger along the Long Island side of the Sound, so people who want to take advantage of them head to that side. As others have said, there are not as many spots to stop overnight on Long Island, so you need to plan the distances carefully in tune with the weather. Anchoring is easy in Port Jefferson and inside of Eaton's Neck, though there are also yacht clubs and marinas if you need additional services in either place. The Connecticut shore offers many more places to duck into, but they tend to be more developed with moorings or slips. Just about every coastal town will have something along those lines. There are also anchorages in Stonington, Fisher's Island, Duck Island Roads (off Clinton), inside of Charles Island (Milford), and in the Norwalk Islands. The question is more whether you want to experience the places along the route, or simply get to where you're going.

[hugosalt]

With 35 or 40 mile days there are many options in the sound both on the CT. and LI sides.
I would not limit to one or the other letting the wind help me decide.
(If not a particular port you want to visit) Most are great with some taking more time in/out.
Important points.
Timing current with you very important at east end of sound and extreme west end when entering East river, in between current not much of a factor approx half knot max.
CT. side more rivers. rocks, inlets , some easy some not, All lovely.
LI side west of Mattituck all easy access, wide protected bays, good protected anchorages. Lots of sand.
From Block Is. approx 35 miles to mouth of CT river and North Cove. very protected and free moorings 1st few days. And lovely town short dingy/walk. If time go up river, Essex is a treat. (6 miles)
On LI side on nothing for 20 miles until Mattituck. Long, about a mile in nice anchorage,
short walk to nice town.
Then approx another 20 miles to Port Jefferson, large anchorage and moorings.
From there plenty of spots to overnight on LI side (as there are on Ct. side)
Northport, Huntington, Cold Spring Harbor, Oyster Bay, Hempstead Hrbr. and Manhasset bay/Port Washington, Little Neck Bay.

[Jamme]

Originally Posted by alofns

. . . trip . . . in the fall . . . 33 foot sailboat . . . prefer to limit or days to 35 - 40 NM . . . occasional marina stop to provision, shower, etc.

IMHO, simply based on the above factors, the north side of the Long Island Sound (what you call “CT”) is the winner. Plenty of places where to moore / dock, or wait for a better weather window if needed; the only tricky part is timing the tides correctly, especially at the entrance (Plum Gut or The Race) and exit (Hell’s Gate)

[malbert73]

Originally Posted by pjShap

I don't know if going through NYC's East River is part of the attraction, but if not, you could consider going straight from Block Island to Cape May, NJ. If you go up the Long Island Sound and through the East River, you would generally do an overnight to Cape May. There aren't any particularly good stops along the NJ coast. From Block to Cape May is about a day and a half, so not much longer than along the coast.

Agree Block-Cape May is more time effective but LIS and NYC are enjoyable if one prefers day hopping.
As for NJ coast- Hoffman’s marina in Manasquan is good and there are restaurants in walking distance. Atlantic City has an inlet anchorage or Farley state marina. Cape May has numerous marinas and an anchorage. So completely doable in day hops if that’s your style
Those 3 inlets are all easy presuming no major breeze from east.

[pjShap]

Originally Posted by malbert73

As for NJ coast- Hoffman’s marina in Manasquan is good and there are restaurants in walking distance. Atlantic City has an inlet anchorage or Farley state marina. Cape May has numerous marinas and an anchorage. So completely doable in day hops if that’s your style
Those 3 inlets are all easy presuming no major breeze from east.

I agree with that, but I would be prepared to make the trip to Cape May if the weather wasn't conducive to any of the NJ coast inlets. I forgot to mention earlier, if you stage in Port Washington, then you can spend a night in Gravesend Bay, by Brooklyn, or behind Sandy Hook at the top of NJ.

[GRIT]

We've done this trip many times, and except for the first time, we always go along Long Island. The North side of the sound isn't so easy to find anchorages, which is a priority for me. We cruise on a budget, and the north side is less "cruiser friendly" if you're staying on the hook. Some places you can anchor, but you can't go ashore. Newport is our last stop on the north side, when going south.

Whichever side you go on, remember to stop in Port Washington. They have a new dock across the street from the grocery store, and the train station there is very convenient to take a ride to NYC. It's also a cute town in it's own right. We'll be spending some time there this spring, on our way back to PEI.

You can anchor outside of the mooring fields. It's a few minutes in the dinghy, and more if you're rowing, but it's certainly worth a stop.

If you'd like to chat about our previous trips from Nova Scotia to the Bahamas (on our monohulls) we'd be happy to talk about it.

My wife's working aboard now, so when we make jumps, they tend to be much longer than we did on our monohulls.

Cheers, and we hope to see you next fall!

P&C.

[Time2Go]

Really no big deal to go back and forth
as you please, Depending on the wind direction
and your tolerance for lee shores.
Pick up a copy of the “Eldridge” book to
familiarize yourself with the tides and currents.
Cruising down the East River and past the
Statue of Liberty is not to be missed
Cheers
Neil

[Emouchet]

I am wondering is anybody can add a comments on Mont Sinai harbor ?
I never went there but have consider this spot a few times.

You seems to be a Canadian boat: so you will need to request a cruising license on your first port of call arriving in the US.
If you alternate between the Connecticut coast and the Long Island side, you will have to report to a different phone number every time you anchor, as NY CBP and CN CBP office are not the same.

I did this trip a couple of time. Here are my favorites:
-Block Island
-Fishers Island West harbor
-Montauk
-Greenport (Peconic River, and go around Shelter Island, this is very scenic)
-Thimble Islands weather permitting
-Mystic River ($$)
-Port Jefferson (Strong Neck side - Note: between Montauk and Port Jefferson, there is nothing really to visit/anchor on the Long Island side).
-Northport
-Oyster Bay
-Port Washington
-East River and Hell's Gate is actually an easy passage if you time yourself for slack time
-Mooring at the 79th street Marina on Hudson River if you want a cheap (30$/night) access to NY downtown,
-Atlantic Highlands (Sandy Hook) to wait for your weather window to overnight to Cape May.

[Scubaseas]

Make sure you have a current copy of Eldridge on board.

[malbert73]

Or Navionics current tables were quite accurate for me last season when I transited up and back from Chesapeake to RI

[Jamme]

Originally Posted by Emouchet

I am wondering is anybody can add a comments on Mont Sinai harbor? I never went there but have consider this spot a few times.

Very strong tidal current if you stay close to the mouth of the harbor — see it for yourself here at 04:53:

https://m.youtube.com/watch?v=_PnAS6wrQ40&t=04m53s

The day of that video I had a few close encounters with a couple of motor-boaters that almost hit me as they figured out why their boats were moving diagonally [emoji24][emoji24] — to the point that I left the (paid) mooring and continued on to Port Jeff, which I personally prefer way more, especially the NW and NE (‘Sand Pit’) mooring / anchoring zones.
Fair winds!

[Kd9truck]

The island side west of eatons neck lots of rocks on the north side. Oyster bay fuel, water, bars restaurants and a supermarket close to the Oyster Bay Marine Center ch 71.

Stage for hell gate at city island or little neck bay if you plan to do it in the AM hit it an hour after the top of the tide, the gate currents run 6+ between Rikers island and the queens bough bridge.

Breezy point is a great place to wait out a weather window, it is the most west part of the barrier beach off of Long Island there are bars restaurants, hardware store and a market.

The only foul weather port on the Jersey shore is Atlantic City my vessel draws 7.5 ft.

And other stuff PM me we can chat it up.cheers