Day Sailers for New York Harbor and Long Island Sound?

[Nyc]

I had some sailing-dinghy experience in my younger days. Want to get back into water. Not on a dinghy this time. I want to start with a keel sailboat.

What are the best day sailers or weekenders to enjoy the New York Harbor and Long Island Sound? Not easy locations to sail, I heard.

As soon as I move there, I'll take some courses and join sailing clubs. I thought that might be a good start. I should be able to get an answer during that time, I am sure. In the meantime, what does the CF community have to say about the ideal minimum day sailers for those waters?

[Nyc]

For example, will a Call22 be too small, let's say for NY Harbor?

[Chotu]

Originally Posted by Nyc

For example, will a Call22 be too small, let's say for NY Harbor?

You can sail anything you want in New York Harbor. Just find a corner where there isn’t a lot of traffic to contend with. That’s all. The size of the boat doesn’t make much difference at all.

Be ready for the slip fees, however.

[Jamme]

I would say that, in my experience, NYC harbor and LIS are two different beasts — the latter being less stressful in terms of commercial traffic. Catalina 22, J24 etc if you want a minimum of cabin space; or you could go even smaller (e.g., Sonar 19, which is used in some sailing schools in the sound). Mooring is a viable alternative to dock space.
However, I’d still start with some local classes first, just to get the feel of the area, then venture in a purchase. YMMV.
Fair winds.

[NormanMartin]

Find a sailing school and use their boats, sail with members. Pretty soon you'll have the answer. It is a "never fails" solution.

[Nyc]

Originally Posted by Jamme

I would say that, in my experience, NYC harbor and LIS are two different beasts — the latter being less stressful in terms of commercial traffic. Catalina 22, J24 etc if you want a minimum of cabin space; or you could go even smaller (e.g., Sonar 19, which is used in some sailing schools in the sound). Mooring is a viable alternative to dock space.
However, I’d still start with some local classes first, just to get the feel of the area, then venture in a purchase. YMMV.
Fair winds.

I even think about sailing between NY Harbor and LIS. Bad plan? Possibly not a good idea in a Cal22, but maybe a Catalina 27?

[pjShap]

I kept my boat for a few weeks in the Hudson River on the west side of Manhattan. NYC harbor is cool to sail through once or twice a year, but too busy, dirty and lots of current make it unappealing to me as a regular location. Port Washington, on the Long Island side of Long Island Sound, is WAY nicer. Good train service on LIRR, short walk to the town dock, and a very reasonably-priced mooring includes tender service to and from your boat. Sailing between NY Harbor and LIS requires carefully timing the East River currents, particularly Hell Gate which can run 6 knot current. Probably not something to plan on doing often. It's fun once or twice a year, but not relaxing.

[Brioche]

Think first about where to dock. LIS has a lot of marinas, and Staten Island has some. Alternatively, there are a few several miles up the Hudson. Getting between LIS and NY Harbor means going down the East River, which is interesting but not fun. If you plan on doing that a lot you would probably want something a bit bigger and with an engine. I have sailed the area in boats from dinghies to 44 feet, and my preferences would be something pretty small and handy on the Hudson side. Sailing west of Manhattan the wind gets very messy most of the time and you have to motor out to the south and get past a lot of busy harbor traffic. Once out in the bay you have nice sailing, perfect for a smaller boat. LIS gives you a lot more water, and you if you wanted you could enjoy a bigger boat, cook some lunch on a grill, or venture out to Block Island. But getting between the two areas is always a bit of a pain, often very rough water and heavy traffic, and dependent on getting the right tides.

[Brioche]

[Nyc]

By the way, I want to sail single-handedly. Deep fin keel, spade rudder, fractional sloop. Preferably tiller. Perhaps an inboard diesel would be a better idea. These are what I learned in the light of what I want to do; doesn't mean anything to be honest. I am open for ideas.

[Nyc]

Originally Posted by pjShap

I kept my boat for a few weeks in the Hudson River on the west side of Manhattan. NYC harbor is cool to sail through once or twice a year, but too busy, dirty and lots of current make it unappealing to me as a regular location. Port Washington, on the Long Island side of Long Island Sound, is WAY nicer. Good train service on LIRR, short walk to the town dock, and a very reasonably-priced mooring includes tender service to and from your boat. Sailing between NY Harbor and LIS requires carefully timing the East River currents, particularly Hell Gate which can run 6 knot current. Probably not something to plan on doing often. It's fun once or twice a year, but not relaxing.

LIS is where I'm interested but I want to be able to sail to NY harbor too when I feel like. Maybe I should forget about that with the first keel sailboat. I start to think something like Cal22 in LIS would be the best for the start.

[Nyc]

Originally Posted by Brioche

Think first about where to dock. LIS has a lot of marinas, and Staten Island has some. Alternatively, there are a few several miles up the Hudson. Getting between LIS and NY Harbor means going down the East River, which is interesting but not fun. If you plan on doing that a lot you would probably want something a bit bigger and with an engine. I have sailed the area in boats from dinghies to 44 feet, and my preferences would be something pretty small and handy on the Hudson side. Sailing west of Manhattan the wind gets very messy most of the time and you have to motor out to the south and get past a lot of busy harbor traffic. Once out in the bay you have nice sailing, perfect for a smaller boat. LIS gives you a lot more water, and you if you wanted you could enjoy a bigger boat, cook some lunch on a grill, or venture out to Block Island. But getting between the two areas is always a bit of a pain, often very rough water and heavy traffic, and dependent on getting the right tides.

Yes, around NYC is expensive. I also would hate to jump into the water when necessary around NY Harbor. I think I should sail only on LIS with gas outboard, tiller. Maybe a 28 ft? You've made good points.

[Wumbug]

I've never sailed the LIS but I don't see any problem with a boat like a Cal 22. Some smaller keelboats (eg rhodes 19) do not have self bailing cockpits and would be at a disadvantage.

In general, larger boats are more seaworthy, and there are certainly tougher boats than the Cal 22, but the Cal is enough boat most of the time. While not advisable, with some luck and preparation you could probably sail a boat like the Cal across Atlantic, or even around the world and survive. Certainly people have crossed oceans in lesser craft many times

With older boats condition is everything, so it's best to search for a boat that is in good condition and meets your criteria, rather than search for a specific model.

[Danm1]

A 9.9 high thrust outboard has gotten me up and down the East River on a 25 footer a couple of times, so doing it on a 22 is certainly possible. But, timing the tides makes it an all day commitment. You could go down, stop at a marina in NJ or Staten Island or Atlantic Highlands for a day or two, then come back to the LIS. Frankly, it's probably something you'd only do once for the experience. On the other hand, a 22 is fine for day sailing the western Sound and Liittle Neck Bay, Port Washington, and City Island are convenient to Manhattan.

[Nyc]

Originally Posted by Wumbug

I've never sailed the LIS but I don't see any problem with a boat like a Cal 22. Some smaller keelboats (eg rhodes 19) do not have self bailing cockpits and would be at a disadvantage.

In general, larger boats are more seaworthy, and there are certainly tougher boats than the Cal 22, but the Cal is enough boat most of the time. While not advisable, with some luck and preparation you could probably sail a boat like the Cal across Atlantic, or even around the world and survive. Certainly people have crossed oceans in lesser craft many times

With older boats condition is everything, so it's best to search for a boat that is in good condition and meets your criteria, rather than search for a specific model.

I don't know if Cal22 has self-bailing cockpit.
If I buy something 22 ft then I will only sail in LIS; I won't sail it to Ny Harbor.
Cal 22 is just an example to express my thoughts. Here are my desired features in a keel sailboat:
Fin keel​
Spade rudder​
Tiller preferred
Fractional sloop​ rig
Self-bailing cockpit
Seaworthy, easy to handle, comfy, simple head & galley, a bimini hopefully, a good sailboat to learn on, easy to maintain.
Of course, a masthead sloop or a transom hung rudder or a wheel steering or lack of bimini wouldn't be a deal breaker.

These are the knowledge I learned and figured out reading here and there, nothing organized. I haven't sailed anything but a dinghy. I've been seeing a lot of Cape Dory Typhoons for sale lately. I wouldn't be surprising myself if I found myself in one of those one day despite their specs being pretty much the opposite of what I look for.