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Old 20-06-2019, 08:11   #1
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Orient Point to City Island 28' Sailboat

A friend is buying a 28' Alerion from Orient Point NY to our home base near City Island; how long should it take to make the roughly 100 miles trip?
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Old 20-06-2019, 08:40   #2
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Re: Orient Point to City Island 28' Sailboat

Great boat. It obviously will depend on a lot of factors, including the wind. If the prevailing Westerlies apply, and you are not planning to motorsail, it is a long day. I have done Huntington Harbor to Three Mile Harbor, pretty close to the same distance, in a single day of about 10 hours, but that was almost entirely on a broad reach or run and with an extra push from favorable tides near Orient. Although the Alerion is a fast boat, I would expect your westbound trip to be considerably longer unless you have a following wind.
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Old 20-06-2019, 10:21   #3
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Re: Orient Point to City Island 28' Sailboat

Thank you for the fast reply; We may consider an overnight, either at a marina or at anchor. Any suggestions as to a mid-way rest stop?
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Old 20-06-2019, 10:43   #4
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Re: Orient Point to City Island 28' Sailboat

Lots of places along the entire coast. I tend to do the Connecticut side of the Sound, though there are places on both sides. When doing a marina we were very happy at Branford, but you probably want to go further West. Your options increase if you are in a yacht club with reciprocal privileges, but we have stayed at Milford Boat works, which was nice and closer to your half way point. There are just innumerable places on both sides for whenever you get tired. We were able to stay on a guest mooring at Larchmont Yacht Club, though that is probably further than your half way point. Use a cruising guide or Active Captain and you will surely find a nice place to stay. The Thimble Islands, just East of New Haven are beautiful. looking like the Maine coast, but like the Maine Coast they are very rocky and not tolerant of mistakes.
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Old 20-06-2019, 12:00   #5
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Re: Orient Point to City Island 28' Sailboat

Larchmont seems like the ideal stopover place; we are members of a Yacht club and do enjoy reciprocal privileges. I'll get in touch with them ASAP. Thanks for the info.
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Old 20-06-2019, 13:17   #6
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Re: Orient Point to City Island 28' Sailboat

CORRECTION Milford, not Larchmont, seems like the ideal stopover place; we are members of a Yacht club and do enjoy reciprocal privileges. I'll get in touch with them ASAP. Thanks for the info.
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Old 20-06-2019, 13:30   #7
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Re: Orient Point to City Island 28' Sailboat

Have a couple of spots picked out on the LI and CT side. If weather turns on you, you may want to stop early. And you will need to time the currents to get through Plum Gut and then ride it west. I sail on a friends Alerion 28 regularly. Wet boat if the waves build and the little diesel is noisy and the tank is small. Bring extrs fuel in csse you do a lot of motoring.
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Old 20-06-2019, 15:27   #8
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Re: Orient Point to City Island 28' Sailboat

Good advice; as soon as the boat deal is agreed to we will finalize our plans and itinerary
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Old 20-06-2019, 15:44   #9
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Re: Orient Point to City Island 28' Sailboat

Port Jefferson is a good mid point for a stop over and has good holding, if you can make Huntington Harbor before dark the anchorage by Sand City is a nice spot to spend a night, good holding and easy to get to, just bear east before you get to the Huntington Light and it will be to your port.
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Old 20-06-2019, 22:19   #10
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Re: Orient Point to City Island 28' Sailboat

I am immediately south of City Island at Steppingstone Marina and its a little less than 75 n miles from Orient pt.
In my 30 fter. I figure an average of 5 knots , so average of 15 hours under way.
Have done many times, 12 hours being best time under sail alone.
Most important is you want the current with you at Orient Pt./eastern LI. where it is strong as you go further west in the sound current is much less of a factor at about 1/2 knot.
If you anchor: on Ct. side ...Milford, north of Charles Is. but not good in SE wind.
also Branford behind Big Mermaid.
LI side agree Port Jeff. great.
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Old 21-06-2019, 08:37   #11
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Re: Orient Point to City Island 28' Sailboat

CT side is full of harbors, marinas, etc but you've got to cross the Sound to get there. OK if you are not in a hurry.

Port Jefferson is awesome. Mattituck inlet is beautiful. Huntington, Mt Sinai... there are lots of places on the north coast of Long Island you can make in a day before getting to City Island.

You might consider the tide more importantly, the current in places can help you a LOT. You might also consider the prevailing westerlies and southerlies. to go west I often wait for a low pressure to roll across the northern part of CT so it brings north and east winds to give following seas and beam reaching.

also, the very western end of the Sound can be a wind hole if conditions are light.
it's a great cruise and we love City Island and environs.
enjoy
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Old 21-06-2019, 10:03   #12
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Re: Orient Point to City Island 28' Sailboat

We have routinely made 100 to 200 nm passages in our 27' boat, 8hp engine. I always float plan for 4kts/5mph. If you have to be somewhere and your speed drops below 3.3 kts its time to motor sail. You will have 3 knts sog and 7 kts sog but you will be amazed how the 5sm/4nm average works out on a 8 to 12 hour sail consistently .
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Old 21-06-2019, 10:15   #13
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Re: Orient Point to City Island 28' Sailboat

That should be a fun trip! We have had many dyas with an east wid lately, so you may have an easy sail. As mentioned by others, pick out several places to bail out to. The Sound can change quickly. the Alerion is a great boat, but if the waves build, close the hatches!!! I was in a race on the east end of Long Island, when the wind kicked up and an Alerion took green water in through an open hatch. It slowed, filled, and sank! The conditions you find will probably vary, so keep a weather eye open! I would allow three days, just in case.
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Old 21-06-2019, 11:32   #14
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Re: Orient Point to City Island 28' Sailboat

Hi. Been making that run at least once a year for most of 40 years.
All the comments have been useful but suggest you buy yourself a copy of 2019 Eldridge and plan your trip around the tides, both in Plum Gut and the Sound proper. As for the wind, depending upon when you go you may get a few days of "easting" and if these winds are not too "enthusiastic" will give you a nice (if cloudy) weather window. Otherwise the summer wind wont be much help westbound.
If you need a good and easy anchorage about half way drop the hook outside Milford just "inside" Charles Island where the locals "walk on water". Check your chart. Easy in, easy out.
Fair winds!
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