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Old 06-05-2009, 05:07   #1
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NYC to Montauk Roundtrip - Advice?


Newby here. Want to sail my Catalina 22 from NYC to Montauk (and back) over a long weekend, (3-4 days).

I am wondering if anyone has any experience with this sail. Is it better to go there and back in the sound? Or to go all the way around (which sounds more interesting but does put me out in open water).

Anyone done this before?


Isaac :cubalibre

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Old 06-05-2009, 05:53   #2
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I have done the trip many times.

The key considerations are... the weather and the tides!

If you are starting in NYC... and are headed to LIS then you will HAVE to have the current with you passing Hell's Gate.

Once you're in the Sound, since you will be spending some time at anchor or at marina you can choose which coast to make home for the evening. Close in either shore offers good choices, as you get out east the pickin become slim on the Long Island side.

Since you'll be sailing all day or most of it, try to use the current to your advantage. If the winds are from the south quadrants the LI shore overs some lee and smaller waves and you can stay out of the commercial traffic which goes down the center of the Sound.

The ocean part (south of LI offers no places to duck in so be prepared to do the emtire 100+ miles without stopping.

Places to stop on the LIS route of interest are:

City Island
Manhasset Bay (Port Washington)
South Norwalk (SoNo islands)
Oyster Bay
Port Jefferson
The Thimbles

plus many more

CT shore is rocky and the achorages are more exposed to the SW.

You have two choice way out east - Plum Gut or the Race at Fisher's Island or one of the passes between them. You need to pass them with a fair or slack tide and a decent motor helps. From the race it probably a beat to Montauk so consider the Gut and the options there.

You can anchor in Gardiner's Bay by the Dutch Windmill at Gardiners Island and them work your way south through the buoyed channel along the north shore of the South Fork right out to Montauk Harbor.


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Old 06-05-2009, 05:59   #3
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Hi Isaac,

This is a big sail for a small boat. Either route has it's challenges.

Inside, your biggest challenge will be the east river, Timing is critical. To catch a fair current through Hells Gate, you should leave 2 hours or so..after low tide at the battery. Check the tide and current tables closely. Once in the sound you can hug the north shore and duck in at any number of harbors. You should be able to make Huntington easily on the 1st day. Port Jeff on a long day.

Going outside can be done as an overnighter. The inlets are notoriously bad in bad weather. Fire Island and Shinnecock are your likely options.

In either case I would wait for an excellent 3 day weather forecast.

There's quite alot of Ferry traffic during the week in lower manhattan, I'd enter the east river via Buttermilk channel behind Governors Island to avoid a fair number of ferries. Keep to the left in Buttermilk and then Stay to the right as you go up the river staying clear of the ferry docks. Keep a firm hand on the tiller, keep your radio on. Make sure you have plenty of fuel and your engine is running well. Have your horn signal close at hand. I might keep the mainsail up, if for some reason you lose power. If the wind is favorable you'll get an extra push.

Good Luck, be Safe.
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Old 06-05-2009, 07:00   #4
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3-4 days is a very short time for this trip unless you just want to do nothing but travel and say you did it. Disregarding timing of tides and wind direction, you will be spending 2.5 of your days simply getting to Montauk and returning to NYC. The tides and winds will modify this - either positively or negatively. I would suggest taking more time for it if possible. That way you get to see some sights, not be continually fatigued, and be able to better accommodate the sea and weather.

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Old 06-05-2009, 10:56   #5
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Isaac... if you are in Brooklyn, my guess is your boat might be in the Sheepshead Bay vicinity. If that's true, the LIS route is definitely going to take you much longer than 3-4 days, because you will need a full day just to get up into the western part of LIS even assuming you are able to get the tide just right.

And I would caution you against taking your boat off the southern shore of Long Island for that long a trip unless you are certain the weather is going to be clear of any storms. The Catalina 22 is a fine little boat, but it was not designed to go offshore, and technically south of Long Island is offshore.

My suggestion: go the LIS route, enjoy some nice overnight anchorages, explore Peconic and Gardiner's Bays (a very nice cruising area), leave your boat at a marina for a week in Montauk or Greenport, take the train back to NYC and return to Montauk/Greenport for the return trip. If you have enough time, you can go out to Block Island from Montauk as well.... that's a real treat, but again it's open water so you need clear weather.

Will you be doing this solo? If so, additional precautions may be in order depending on your experience.
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Old 07-05-2009, 05:42   #6
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Thanks allot

Thank you all for the useful information.

I will report back when I have a plan!

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Old 07-05-2009, 07:59   #7
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Isaac, Wrote 2 e-mails yesterday and lost them both before sending...
Most points covered on above posts...
DO NOT go into East River/Hell Gate with strong wind opposing
tide...these conditions can produce standing waves. Same at
Orient Pt/Plum Gut.
Be flexible... Have a plan B or C...
Good Luck!

s/v Little Jumps
Lancer 30
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