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I am going to downsize this year from our 36' sailboat down to a much smaller sailboat in the range of 18' to 24', something that I can easily take out by myself, store at a low cost and race every so often.
I am leaning towards something more classic but really fun to sail. Something that my 11 year old son could learn more about the basics of sailing.

Also I love the classic lines of a sailboat and teak. Even a slight project sailboat would be nice. God knows how much I have worked on my previous sailboats, should be an expert by now.

I was thinking of the following:
Pearson Ensign 22
Precision 23 (not much of classic lines)
Cape Dory Typhoon
Hampton One Design

Any other sailboats that I should consider?
Could go larger but being within the 18' to 24' range would give me a option to trailer the sailboat and provide off site marina storage.
 

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Corsair 24
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ensigns are lovely...
folkboat is just a tad bigger...
bristol 24
columbia 24
columbia challenger 24 is a fave of mine

newer a j24 is a fun day sailor and can also be a very competitive racer
I like the wilderness 21 too
ranger 23
cal 21 are a nice class...simple boats but are competitive
new new a j22 is a blast

so many boats in this size range!!!!!!!!!!!!!!!
 

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69' Coronado 25
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I have a Coronado 25, it is BIG on the inside for a 25 footer, a bit heavy to tow at 4500+ lbs. I was going to suggest a Yankee Dolphin 24 But they are heavy too, being 4250 displacement. If you have a good tow vehicle then you will have a lot more to choose from.
 

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Pat, when you say 'race', casually, my first thought would be to see who's racing what in that size locally, and see what's available that would be at least competitive in that racing series or group. Depending on how far you want to pursue that...at least something that won't be an odd duck.
 

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TO me as noted, what are other boats locally being raced? Then get something that fits in to that arena. If it is literally a C class scow, that is the boat to get, Lots of San Juan 21's, again, the boat to get. If it is a laser......well, not quite what you had in mind, but might be worth the look see, or an FJ, lightning or equal daysailor may be the answer also.

marty
 

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Consider a catboat. Shallow draft, easy to handle, trailerable in the smaller sizes ( some even with with tabernacled masts and minimal standing rigging), minimal heeling for guests, and they certainly have a classic look. Not as slow as many think, either!
 

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Patrick,

How serious are you about a classic boat? The most fun boat I have sailed in years was a VX One, but it is by no means a classic, and you might get lynched at a regatta if you added teak to it. On the other hand it is rediculiously easy to sail, very light, and self righting. Plus there are no loads to high to be trimmed by a 11 year old.
 

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Freedom isn't free
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How cheap, how small, how classic, what's your venue, who else in the fleet?

If I were going small, short handed, the first boat I'd look for is a Holder 20 for small boat PHRF racing. Not classic, but a very modifiable, including a sprit and roachy main and you can easily turbo it for some cheap fun.

Otherwise, I'd say J/22 (J/70 fits, but isn't classic, and isn't cheap, J/80 same and isn't small or easy to launch/raise mast, since it's keel stepped).

If you have a bunch of cruising boats, then a tall rig fin keel Capri 22 works (and is cheap).. but doesn't fit your classic requirement.

Otherwise if you want true classic, then your Typhoon fits nicely... but what about a Star, or Soling?

When you get down to board boats, there is always a Lightning, doesn't get any more classic than that! Then Thistle.
 

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I sold my beloved Morgan 33 classic and downsized to a Herreshoff 12 1/2 (16' LOA) over 6 years ago and I have never looked back. It's cockpit is larger than the 33 and the lines are amazing "eye candy". It is the sweetest sailing boat which I have owned over the last 50+ years.
 

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Along the lines of the Typhoon and the Ensign is the McVay Bluenose:



Prettier than either the Ensign or Typhoon, IMHO. But they are hard to find - searching sailboatlistings.com I see one listed in Minnesota and another in Maryland. If one-design racing is a priority, you'd have to move to Halifax Nova Scotia.

Previous threads on topic here and on the Bluenose here.
 

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If you want your 11 YO to be hooked for life get him something you both can race every week right now, because in a couple years he's gonna want to take it out easily by himself. Honestly, get something with an active fleet at your nearest sailing area, if it planes even better. He's a kid, not gonna be interested in sailing slow for too long, he's going to want to race his buddies. I like Lido's and Thistles but what are all the other kids his age sailing in your harbor ?
 

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Yep, what others have said, you look at the venue, find what everyone else is racing (the largest fleet) and buy that... I my case that means either buying a Lightning, or an S2 7.9... neither of which I am real fond of.
 

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I am going to downsize this year from our 36' sailboat down to a much smaller sailboat in the range of 18' to 24', something that I can easily take out by myself, store at a low cost and race every so often.
I am leaning towards something more classic but really fun to sail. Something that my 11 year old son could learn more about the basics of sailing.

Also I love the classic lines of a sailboat and teak. Even a slight project sailboat would be nice. God knows how much I have worked on my previous sailboats, should be an expert by now.

I was thinking of the following:
Pearson Ensign 22
Precision 23 (not much of classic lines)
Cape Dory Typhoon
Hampton One Design

Any other sailboats that I should consider?
Could go larger but being within the 18' to 24' range would give me a option to trailer the sailboat and provide off site marina storage.
In addition to the boats already suggested to you, you might want to consider the Schock Harbor 20:



There are several Harbor 20's at Yacht World. You might also care to read some Owners' Comments
 

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Bombay Explorer 44
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What about an International Dragon?

The International Dragon is a beautiful looking, technically demanding yacht, that combines classic lines with 21st century technology.

A strong Class Association ensures competitive one-design racing for all ages of boat. Spars and sails have a wide range of adjustment during racing, allowing a skillful crew to optimize the boat for any conditions. Crew weight limits, and restrictions on hiking out allow the Dragon to be raced successfully by a range of ages and genders.

In North America there is growing interest in restoring classic wooden Dragons as well as importing newer fiberglass Dragons. There are active racing fleets on the West Coast, the Great Lakes and the South, while many individuals continue to sail this classic yacht for fun.
Ticks all your boxes. They are technically interesting to sail.

But best of all just so BOOTIFUL. Imagine owning that.
 

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What about an International Dragon?

Ticks all your boxes. They are technically interesting to sail.

But best of all just so BOOTIFUL. Imagine owning that.
now that is a pretty boat, but wow, lots of wood!

I think it would be really hard to beat an Pearson Ensign. I think they are nice looking, and have enough wood to give you a varnish fix. They seem to be a lot of fun to sail, and there are one design fleets everywhere. Quite stable for the size and available cheap, abet needing some work to get a cheap one. Seems to be "The downsizing" boat around where I am. Lots of young beginners, and lots of elderly folks. I should watch out though, my attorney has one and is neither young, beginner or elderly. I know of one that is available for $500 belongs to local boat club and it seems complete, just needs some love, OK lots of love.
 
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