Never sailed, but thinkIcan.

Jul 12, 2011
1,165
Leopard 40 Jupiter, Florida
As a follow-up to smaller boats, I used to own a Hunter 216. Fun boat to sail, but a pain to rig for trailering. I agree with @tjar 's estimates, it took us the better part of an hour to setup, and half that to break down, and we were about 40 and it was hard work. Another point with small boats that we learned as we aged, they require more physical abilities to move around and are less comfortable (cushioning, bathroom facilities, autopilot, etc.). I've gotten to the point that I'd rather have a soft cushion under my butt, and a head less than a couple miles away. Now learning to sail is much easier on a small boat - the smaller the better. Learning on my boat is like learning to drive with a bus.
 

Gunni

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Mar 16, 2010
5,937
Beneteau 411 Oceanis Annapolis
Did I mention that I am old, retired, and unable to outrun determined women, especially when they have been drinking? LOL.
All the more reason to have the dock boys prepare your chariot, stock the galley and help the ladies aboard! Do not spend even one day over a varnish brush or sweating a gin pole. Go now.
 
Feb 18, 2018
16
trojan f34 toronto yacht club
Drank gin from a bottle,once. Didn't like it. Too per-fumy. Can't imagine licking it off some kind of pole!
 
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Jul 1, 2010
962
Catalina 350 Lake Huron
We also came from a power boat background (about 30 years worth) before we set foot on our first sailboat (and never went back). That was about 12 years ago. We have a local sailing club that gave us a lesson or 2 on their boats. After that, we joined for the second part of that season, and were able to sail their boats that year as part of the membership. We bought a Hunter 23.5 (great boat to learn on, btw) and things progressed from there. So yes, learning to sail by doing, especially since you have a boating background is very doable. Suggest you get a lesson or 2 under your belt first, though, and pick up some sailing books to get yourself acquainted first. Maybe there's a sailing club like the one we found somewhere near you?

On the boat, don't underestimate the time stepping the mast, etc. It's not like launching a powerboat. We found with our Seaward 25 that we would rather keep it in a slip here. We do trailer it places but it isn't worth it unless we can spend at least a week at our destination.

For lake Ontario, I think you'd want something in the 25' range. We've sailed our Seaward up there, and it was fine, but I don't think I'd want to sail there in a boat much smaller. I'm biased, of course, so recommend the Seaward 25 and 26. But Oday 26 and Catalina 25 come to mind. If you're trailering much, the water ballasted Hunters sail well and are easier towing.
 
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Feb 18, 2018
16
trojan f34 toronto yacht club
I was just looking at Yacht "Club" lessons near Toronto and Hamilton ,Ontario. Way too much decorum for me. Same reason I declined to join flying clubs. I'm more of a good ol guy.
 
Jan 11, 2014
11,319
Sabre 362 113 Fair Haven, NY
I was just looking at Yacht "Club" lessons near Toronto and Hamilton ,Ontario. Way too much decorum for me. Same reason I declined to join flying clubs. I'm more of a good ol guy.
Try Etobicoke YC. RCYC is kind of stuffy.
 

DArcy

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Feb 11, 2017
1,690
Islander Freeport 36 Ottawa
Other alternatives for less snooty clubs in Toronto are Ashbridges Bay Yacht Club and the Toronto Island Sailing Club. Sometimes you can sign up for lessons without becoming a member. I'd really recommend getting a few lessons before shoving off into the lake. After that you can probably figure it out on your own.
 
Sep 7, 2018
82
Chrysler C-22 Battle Creek
I took the plunge this year and tried my hand at sailing. Like you I have had a long history with motoring boats. Albeit not as large as the boats you are describing.
I can say this, sailing is a lot of fun and a great day on the lake. I am in a somewhat similar situation as I can not afford to keep a large boat at a Marina all summer and afford to hard dock it all winter.....so we went the trailerable route as well.
I am a little bit of a "rigging is actually fun" kinda guy so I dont mind the setup and tear down time. Its all part of the boating experience for me. My wife, not so much.
Others have allready shared their rigging time invested stories else where within this topic. So I wont regurgitate everything that was said. I will say my wife and I are no where near the, in the water in 30 minute goal! It takes us all of an hour and even a little more. Which is very taxing on my wife, because she just wants to be on the water and does not enjoy the "work" part of it. On the flip side of it, we are no faster at getting the boat ready for a the trip home. Which again wears on her.
For next summer, I am going to try to figure out if there is a place near the launch where I can leave the boat. It is appx an hour and twenty minute drive one way for us to the nearest launch. So if I can find a place that it is capable of storing the boat, and I can leave it rigged, and I can afford it the storage fees.........then I think it will be more enjoyable next summer.
The only alternative is to get a transient slip and put the boat in, leave it for a couple days while sailing as much as possible, and then take it out. That way we can get alot more sailing for our setup time than just a few hours. Good luck and if ya get a boat soon we are gonna need to see pictures.
 
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Feb 18, 2018
16
trojan f34 toronto yacht club
Thank you'all for the club suggestions, and no disrespect intended, but they are way too commercial for my liking.
Initiation fees, membership fees, food and drink assessments, UGH.
Ideally, I'd like to find a like minded mentor, knowledgeable and inclined to teach others (me ?) with cost sharing assumed. I do have a degree in marine survey, and mechanical engineering, which may be of some use.
I was employed as a marine electrician, early in my career, before the army( A.C.E.) decided I was a pilot.
 
Feb 18, 2018
16
trojan f34 toronto yacht club
Hello, and yes, that is very close to my envisioned sailing experience. I had a friend who built a sailboat out of a 30'
Great Lakes Freighter steel lifeboat, sailed it down the Mississippi from Chicago, and lived on it in the Florida Keys for seventeen years. Lots of adventures along the way, and no marinas ever.
I'm about 40 minutes from Lake Ontario, or two hours from Lake Erie. Ramp fees are okay, but don't like to leave a trailer unattended, as I have lost parts while away. Had to make up bits before I could load.
 
Feb 18, 2018
16
trojan f34 toronto yacht club
I like your choice of a Chrysler, well engineered, and nice to trailer. I bid on a 25' chrysler, but was a little too low on my offer.
 
Oct 3, 2011
825
Anam Cara Catalina 310 Hull #155 155 Lake Erie/Catawba Island
Catalina 22 or 25, parts are available, lots of advice through forums, MADE TONS of them, solid safe boat!
Easy to sail or learn how and if you want to move up can be easily sold!
Find a sailing club and crew first!
Its all good!
 
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Nov 8, 2007
1,523
Hunter 27_75-84 Sandusky Harbor Marina, Ohio
You don’t have to join a club to take a sailing course. Toronto Sailing School is one example. They offer lessons on your own boat as an option.

I recommend some version of this combined with reading about how to sail, then heading out to put it into practice.