Enlighten me regarding sailboatedness

[ILikeRust]

OK, so I'm pretty much familiar with boating in general and as a concept. My dad bought a 20' cuddy cabin cruiser with an inboard/outdrive when I was about 5 years old and we used the hell out of it, including one two-week stint on the Chesapeake Bay when I was about 10. When I was in my 20's, he bought a 37-foot Cheoy Lee trawler with twin Volvo Penta diesels and we made a couple nice trips on that on the ICW down from Charleston, SC to Savannah, GA, and then from Jacksonville, FL down to St. Augustine and back.

I'm now approaching 44 years old, so it's been a while since I've spent any real time on a boat or piloted a boat other than a canoe (there was that rental pontoon platform boat down in Virginia Beach about two years ago). But I'm seriously jonesing to get back out on the water again, so I've been spending way too much time looking for some kind of inexpensive but decent boat I could take my family out on for a day or two. I am reasonably familiar with power boats (although I probably should take a refresher course before trying to dock anything bigger than maybe 24 feet).

After drooling over wooden boats for the past, oh two years or so, and seeing lots of lovelies here - and after spending way too many hours browsing used boats of all varieties on Craig's list and elsewhere, I'm reaching a few conclusions. (1) Most of the used power boats out there give me nausea just looking at them. I mean, how many Sea Rays can you look at in one lifetime? Ick. (2) It seems that sailboats of equivalent size tend to be cheaper - which I attribute to (3) sailboats are simpler, with less mechanical gadgetry that needs maintaining and repair. Plus (4) (and I know I'm preaching to the choir here) the idea of shooshing along in a craft made of nothing but specially-shaped dead tree parts and powered by nothing more than moving air and some flapping fabric is pretty damn cool. Not to mention quiet and not stinky with exhaust fumes.

So I'm starting to think about maybe getting a small, trailerable sail boat and learning how to sail. I'm thinking 18 to 22 feet - something I could put in one of the several large lakes here in central Virginia, or the calmer parts of the James River - or even some of estuaries or maybe even the big, bad ol' Chesapeake itself. Something I could go noodling about in and gunkholing with the kids, or camping out on overnight by myself, or with my younger daughter (as she seems to be the only one as enamored with camping as I am), etc.

But -

I have been aboard sailboats maybe four times in my life. I mean, I get the basic theory of sailing, and I'm familiar with some (I won't say most) of the terminology for the various bits of the vessel, but there's a massive hole in my knowledge there in terms of how to actually make the thing go where I want it to without injuring myself, damaging any property or scaring the wildlife.

SO -

First, I need to learn how to sail the sucker.

And I need to figure out what kind of boat I should be focusing on.

So please enlighten me.

What should I look for? I'm a really good book learner - are there any good books I should start with? What kind of boat should I be looking at, in terms of rigging? I've been reading that catboats are easy to sail single-handedly and are relatively tame, which sounds great to me - I don't want a sailboat that's going to scare the crap out of my and my family (I could tell the story of the time I was out in Galveston Bay in a near gale on a 16' Hobie Cat and we pitchpoled it at top speed). I don't need a lot of drama, just a way to go tootling around on the water - I'm thinking of something with a little outboard on the back for puttering around when there's not much wind, or for maneuvering, etc.

I saw this one and to my untrained eye, it looks like it could be a pretty good deal:
http://richmond.craigslist.org/boa/1651213593.html

Not really big enough to overnight on, but I'm sure we could have a fun day messing about in it on Lake Anna or something.

What about something like this?
http://richmond.craigslist.org/boa/1678613889.html

Looks like it needs a bit of work, but for the price, maybe a bargain.

And then there's something like:
http://washingtondc.craigslist.org/mld/boa/1679543441.html

...which I'm wondering might be more than I should start out with. But at least that has a small cabin, so there's the possibility of an overnight.

Oh yowsa!! In writing this up and searching CL at the same time, I just found this sweetheart! http://www.flickr.com/photos/35704531@N04/sets/72157614361469080/

And then there is the constant dream/fevered vision of building my own - which I fully intend to do in a few years, once we move to a larger property with barn.

In the meantime, I'm looking around for sailing classes in the greater Richmond, VA area.

I thank everyone in advance for suffering my ignorance and for your gathered knowledge and helpful suggestions. As you can see by this rambling post, I'm obsessing - I do that.

[James McMullen]

You know, any of those you posted will do for giving you a taste of sailing. I don't think you can go wrong by just picking one of those and using it for the summer. Once you have a little experience under your belt, you'll probably have a better idea of what you really liked or didn't like about that boat, but you'll need to establish a baseline first for reference. That 23' O'Day seems like the best bargain to me. . .

Once you know better what you want, then you can build yourself your dream boat--but it will be nice to have that cheap one around to have something to take the edge off while you're busy building.

[James McMullen]

Oh and welcome to the club! Sailing is delightful.

[Ian McColgin]

The Islander and the O'Day are right normal choises and the gaff rigged boat could well be something to really love. In your position, staying small and light makes most sense.

There are lots of sailing school opportunities to explore. Look around for what's at hand. Also it's worth checking local yacht clubs to see if you can get involved, maybe crew a bit. Lessons versus crewing teach different things since sometimes racing, for the crew, can be a matter of learning limited skills and quite possibly learning them wrong. But your thought of classes is good and if you can get involved in a lesson-racing program where you both skipper and crew you'll learn very quickly.

When you're on your own, harken back to childhood for a moment. Every American kid has spent hours just throwing a ball or some equivalent. The same with sailing. Don't go out to get somewhere. Go out to tack a lot. Try heaving-to. Or sailing backwards. Bring along a pick-up buoy to toss over and then practice coming up to and stopping just where you can reach over and grab it. Or sail by and grab it on the fly. Goof off.

G'luck

[ILikeRust]

Well I exchanged a couple e-mails with the seller of this one:
http://www.flickr.com/photos/35704531@N04/sets/72157614361469080/

...because I think it's the purtiest one.

It's been in his family about 14 years, but they don't know who made it. He says "best guess is a small New England boatyard, circa 1975."

It's been on the trailer for 2 years. Hull is fiberglass-covered, strip-planked mahogany, overall in very good condition. He says there's one small crack in the fiberglass just below the bowsprit and a gap at the transom by the keel rib - both of which sound repairable, I'm thinking.

Hull paint is good, with just a little touchup needed; but topsides probably need a little more attention from sitting out there for a couple years. The exposed brightwork needs revarnishing.

If it were just me, I would be scooting up there pronto to check it out, but as it is I have not yet gotten wifey fully on board with the notion. She would much rather spend the money towards the pending kitchen renovation. I have not yet convinced her we can do both! Particularly if I worked on the guy's price - he says he's motivated to sell it before summertime and can be somewhat flexible on the price.

[Ian McColgin]

Judging by the framing visible under the deck, she's conventionally planked. This ma make her not so suitable for trailor life unless the seams are splined rather than caulked. Something to check if you're in an area where moorings are hard to get. Also find out how long she's been out of the water.

If you can maintain her, she'll keep her value more than the glass alternatives as there are more small glass boats than the market needs.

I see she has an OB. Put it in the deep freeze and concentrate on sailing. A wee boat like this does not need more than a sweep.

G'luck

[davidagage]

If it was me, I would go for the first lil 17 footer. Easy to trailer and set up and get to sailing, especially when no one else wants to go with ya. The other 2 are a bit large for solo set up and launch (IMHO). The last one is gorgeous, but...do ya really want to "maintain" a boat before you even get to get it wet? I agree though too, with everything Ian says about the value and holding it...

[Ian McColgin]

David's point is well taken about ease of just plain getting sailing though the O'Day, while at the top end of manageable trailoring, can be rigged and launched and retrieved and struck easily ONCE YOU LEARN HOW.

The Islander is most likely to get you sailing lots and maybe you can camp on the beach or make a boom tent.

For both of these like the gaff sloop, store the engine until such time as you're good enough that you don't need it. If you're making a weekend cruise, plan correctly so the weather gets you back, be more modest in the distance ambition department, and get used to calling in excuses to work.

G'luck

[ILikeRust]

I see she has an OB.

Motor not included...

Thanks!

[ILikeRust]

Well I've signed up for an ASA-certified sailing class - Basic Sailing (ASA 101) and Coastal Cruising (ASA 103). Received a big pack of information yesterday, and now I've got some studying to do. The class is on May 8, 9 and 15, 16. I'm very much looking forward to it.

I've also been scouting CL for decent, but cheap, sailboats. I don't want to drop too much $ on my first sailboat, and I figure I'll start with an inexpensive plastic (yeah, I know - yeccch) boat and develop some chops before plunging into a nicer, wooden boat. Any thoughts on a Catalina 22? I've found one that looks to be in reasonably decent condition - although in need of a good hull painting - including a trailer, sails and outboard motor, for an asking price of $2500. What appeals to me is the extra space (compared to, say, the Islander 17) to have my family (wife and two teenage daughters) along with me - and it's got a small cabin with cookstove. Looks like it would be good for an all-day sail on the Bay, and provides for the possibility of a 2-person overnight.

[James McMullen]

There's a reason why they built and sold a bazillion Catalina 22's. They don't suck at all for what they are. That's a good first step.

[Brian Palmer]

I grew up with cruising sailboats and dinghies. I have a 20 footer now, and I am about as landlocked as anyone living in Richmond, VA. No motor, no electronics, no head, no plumbing.

I would go with the 17 footer, or one like it. You will use it more, and learn more, and you should have no trouble reselling it when you are done with little or no loss.

Sailboats with engines are about twice as complicated to maintain as powerboats, because they have the engine, and all the sails and rigging to look after.

I would keep it simple for now. It will help maintain familial harmony as you learn to sail.

Definitely take the sailing lessons. Good luck!

Brian

[Kaa]

Sailboats with engines are about twice as complicated to maintain as powerboats, because they have the engine, and all the sails and rigging to look after.

I don't know about that. Simple outboards take very little maintenance and for a newbie an engine is highly useful. With a limited knowledge of sailing there are LOTS of situations when you'd be better off taking down the sails and converting you boat to something you can basically drive instead of sail.

Kaa

[Brian Palmer]

Kaa,

I was responding to the OP's assumption that "It seems that sailboats of equivalent size tend to be cheaper - which I attribute to (3) sailboats are simpler, with less mechanical gadgetry that needs maintaining and repair."

In fact, their added complexity may be the reason that used sailboats may be cheaper than a comparable power boat.

I agree that sometimes it is simpler to lower the sails and motor along, especially if it is hot, windless, and the kids are cranky. Been there, done that.

Brian

[bamamick]

I have owned about thirty different boats over 34 years of sailing and even with those credentials I would hesitate to give advice, but since you asked for it: don't buy a boat. Go take a class. Go find your local sailing club and ask someone to let you crew. Hang around sailors and talk with them for awhile. Then, if you decide you still want to do this, come back and share your experiences and your wishes and you'll get better advice.

Over the last ten years, for example, I have bought and restored so many boats I can't even remember them all, because the idea of owning this or that kind of boat fascinated me. I have few other vices. Happily married all my adult life. Don't drink, smoke, or gamble. I love boats. I mean LOVE boats, like REALLY love them, so I go out and buy them. And after a few months or years I make myself admit that buying this or that boat was a dumb idea and I move them on to someone else.

Great example: I bought an old Beetle Cat. Sounded like the perfect daysailor for me. Sail it by yourself. Simple. Roomy. Traditional. Handsome. Picked it up in West Dennis, Mass and took it directly to the Beetle shop and Charlie York. He and the young guy working with him were very nice (though very busy). Charlie took a look at the boat, assured me that I hadn't been robbed, and asked me exactly what I was going to do with it. When I told him I would dry sail it from my home on Mobile Bay he looked at me and said 'don't do it. You'd be making a big mistake'. As always, I knew a whole lot more about these boats than the guy who actually builds them for a living, and took off the 1500 miles for home.

I get the boat home, run a water hose into it until it stopped leaking, and took it to the Bay to go sailing. It leaked some, but not enough to bother me. Not enough to keep me from using it. And use it I did. Spent some of the nicest days of my life sailing that boat, right through the winter and beyond. For years, but eventually the leaking started eating away at me, and I flipped the boat and glassed it. That made it worse, since I didn't want to lay glass over the keel itself. I never could get the garboards to seal, and the last time I used the boat she sank at the dock like a stone. I wound up selling her to one of our very nice forum members, who fixed the leaking garboards properly and (I think) enjoys the boat.

That's just one of many examples. There are whole fleets of boats that I have bought on a whim. I tell myself those days are over, but my latest obsession, a Marshall Sandpiper, eats away at me daily, and until I have one hooked up to the truck towing down the road I will not be satisfied.

Be careful before you decide to get involved in this. Be very careful indeed.

Mickey Lake

[Keith Wilson]

Well, I don't dare say much about boats. That's a very personal decision; you may not know enough to really know what you want or need, and it's a lot harder to get rid of a boat than to acquire one. The latter only requires cash.

However, I can recommend a superb basic learn-to-sail book: This one is the BEST. The pictures alone are worth the modest price.

http://smallcraftadvisor.com/store/images/T/WAC001.jpg

[ILikeRust]

Absolutely GREAT feedback! I truly appreciate the various perspectives - food for thought all.

Although I never have personally owned a boat, as I mentioned above, we had a family boat when I was a kid, and we spent a lot of time on it, and then when I was in my 20's my dad bought another one, which he had for about 10 years. So, albeit indirectly, I am reasonably familiar with the burdens of boat ownership (and have had the old saw about "the two happiest days of a boat owner's life" repeated back to me many times in the past year).

Which is just to say I'm not going into this as some wide-eyed idealistic kid with no clue what I'm setting myself up for.

And this is probably the main reason I'm looking at boats in the sub-$5,000 range (more like $2,000 or less, if I can find something) - so that if in a year or two I decide it was a mistake, and I take a hit on unloading it, it won't be a truly painful hit. Also looking for something pretty simple right now.

Can't get the guy with the Islander 17 to reply at all. Either he doesn't check his e-mails, he already sold it and hasn't taken the listing down, he died, or in a week, I'll suddenly get a response out of nowhere saying something like, "sorry I didn't respond sooner - I was [sick; out of the country; in jail; busy ...]".

Thanks very much again, and keep it coming. I'm all earses (and eyeses).

[MiddleAgesMan]

My first "real" boat was a Catalina 22 and I would not recommend it to anyone. It's got a centerboard that isn't really a centerboard (no trunk) and its exposure even when fully raised was something that always worried me.

Another problem is the long boom. It barely cleared the backstay so if it was allowed to rise up even a little during a gybe it would hit and hang up on the backstay.

Sailing was never the relaxing pursuit it should be until I moved up to a keel boat--the Alberg 30.

The small flyer in your first link will get you sailing quicker but it's not really suitable for the family until you have gained a lot of experience. The Cape Dory will take better care of the novice sailor and his family so I'd suggest a small ballasted keel boat is the best way to start.

[bamamick]

I'll bet that Alberg is bullet-proof.

Mickey Lake

[ILikeRust]

However, I can recommend a superb basic learn-to-sail book: This one is the BEST. The pictures alone are worth the modest price.

http://smallcraftadvisor.com/store/images/T/WAC001.jpg

Thanks - I immediately ordered a copy.

[ILikeRust]

This looks like a pretty sweet little boat, but I'm surprised at the asking price. Although it does look to be in very good condition and pretty much ready to go.

http://norfolk.craigslist.org/boa/1690936033.html

[bljones]

ILike,
Catboats are easier to sail single-handed, but also easier to get yourself in over your head when the wind picks up.

What you need is a "stupid" boat- a boat that is at the bottom of its depreciation curve, not too pretty but not so unattractive that the rest of the family won't want to climb aboard, a boat big enough to fit everyone comfortably, but small enough for a novice to handle, a boat that allows you to do stupid sailing things and forgives you and keeps you safe, a boat that allows you to do stupid things maintenance-wise without depreciating, a boat with so little money invested that if you get really terminally stupid, you haven't lost much.

That O'day is exactly that. Go look at her- if she doesn't smell bad, if a wet cloth removes some of the crap and corruption that covers the hull and gives you a small glimpse of the pretty boat she could be, if you don't fall through the deck and the furling jib furls and unfurls, everything else is just details.

[Canoeyawl]

http://norfolk.craigslist.org/boa/1690936033.html
This would be an excellent choice.
Weatherly, comfortable, simple, built in floatation (safe), beachable and stiff as a church.
maybe just a bit high priced...
search on the Catboat forum.
That mast is a problem for trailering, there is a tabernacle rig for the Marshall version catboat of the same size that is a great thing.

[bamamick]

Looks like an awesome boat (the catboat). Lots of recent work and reconditioning. She does not list a trailer, does she?

This is exactly the kind of boat I will be interested in a year or two from now.

Mickey Lake

[donald branscom]

You know, any of those you posted will do for giving you a taste of sailing. I don't think you can go wrong by just picking one of those and using it for the summer. Once you have a little experience under your belt, you'll probably have a better idea of what you really liked or didn't like about that boat, but you'll need to establish a baseline first for reference. That 23' O'Day seems like the best bargain to me. . .

Once you know better what you want, then you can build yourself your dream boat--but it will be nice to have that cheap one around to have something to take the edge off while you're busy building.

I sailed a O'Day 34 across San Francisco Bay and it had wheel steering. I loved it! But the boat hull flexed a LOT.

Why don't you just sign up for a couple sailing lessons. And that would be a good way to get a feel for the whole deal. I would not just go buy a boat untill you know more about what you want.

[Bob (oh, THAT Bob)]

Learn to sail on a small sailing dinghy first, with no motor power, then move up to keelboats.

In some ways, keelboats let you get away with murder. Do a crash gybe in moderate winds and they will just lean. Do that in a dinghy, and it may capsize, after which you right the boat and try again. Teaches you not to do that.

On the other hand, docking is easier in a dinghy than a large boat. You should be able to easily sail away from and back to a dock under no motor power in a dinghy before moving up to powered craft. The dinghy has much less momentum, thus less likely to damage anything if you lightly bonk the dock. With a keelboat, poor docking will cause damage to both boat and dock. Sure, the keelboat has a motor. Motors fail. Read Lin and Larry Pardey's latest book, The Capable Cruiser, the chapter about "Sail Insurance", and how you should always be ready to use sails if the motor fails. And that means, sails at the ready, even if lowered, sail cover off, hanked on, and the skills to use them.

Start out in dinghies and you will be a better keelboat sailer. Look around for a local place where you can rent and get instruction on dinghies. I think US Sailing has a better dinghy program than ASA, but that's just me.

[johnw]

http://smallcraftadvisor.com/store/images/T/WAC001.jpg
This is the book we recommend in the sailing instruction program I helped start.

Sailing isn't hard. I do it all the time. You can learn to do it fairly easily and get better at it for the rest of your life, so there's immediate reward and continuing challenge. And there's nothing so nice as being able to turn off the engine and get rid of the noise, vibration and smell. It's been a while since I've owned a boat engine -- I called him Stinky Johnson -- and I don't miss them, but they are a nice thing to have when the family wants to get home on a schedule.

If the wife's not totally on board, get a boat with a cabin and have an engine on hand in case you need it. She'll want something stable. You don't want to capsize early on. So yeah, something like a Catalina 22 will get you started.

And when you turn off that stinky engine, and the boat is cruising along quietly under sail and she's enjoying a little picnic in the cockpit, maybe she'll understand what it's about.

[ILikeRust]

Thank again for all the input and recommendations. Just to be clear, I have signed up for an ASA-certified sailing class - Basic Sailing (ASA 101) and Coastal Cruising (ASA 103). I've already started plowing through the big book they sent me, which looks like a great reference. The class is on May 8, 9 and 15, 16. I'm very much looking forward to it.

I also ordered The Craft of Sail from www.half.com (http://www.half.com) last last week.

Spent a bunch of time last night reading about catboats on line and looking at various catboat sites. Man, they are really pretty little boats. I could definitely see something like a trailerable 18' catboat. Very sweet.

Hey, what about something like a Sunfish or Minifish? I've seen several of them on the local CL for only a couple hundred bucks. The problem I'm thinking with one of those is that they're essentially one step above a windsurfer - not much space, and you're really sitting on it, not in it. Seems it would be pretty hard to take someone along with me. But for $350 - $500, maybe it would be good to have just to go to a lake somewhere by myself and fool around with it.

I have a buddy who's an avid sailer - I'm going to pick his brains a lot and hopefully get out on his boat, once he's done all the work on it and gets it back in the water. I'm seriously hankering to get out on the water... can you tell?

[James McMullen]

Learning to sail? An afternoon aboard a tiny boat like a Sunfish will probably learn you quicker than a week aboard a cruising boat.

[johnw]

You might think about having something small, like an El Toro, to sail by yourself. You'll learn more quickly in such a boat. If you can get a good deal on something slightly bigger, go for it. The problem comes when you want your wife to go out with you. That's when you need something stable.

[LongIslandBoy]

Thank again for all the input and recommendations. Just to be clear, I have signed up for an ASA-certified sailing class - Basic Sailing (ASA 101) and Coastal Cruising (ASA 103). I've already started plowing through the big book they sent me, which looks like a great reference. The class is on May 8, 9 and 15, 16. I'm very much looking forward to it.

I also ordered The Craft of Sail from www.half.com (http://www.half.com) last last week.

Spent a bunch of time last night reading about catboats on line and looking at various catboat sites. Man, they are really pretty little boats. I could definitely see something like a trailerable 18' catboat. Very sweet.

Hey, what about something like a Sunfish or Minifish? I've seen several of them on the local CL for only a couple hundred bucks. The problem I'm thinking with one of those is that they're essentially one step above a windsurfer - not much space, and you're really sitting on it, not in it. Seems it would be pretty hard to take someone along with me. But for $350 - $500, maybe it would be good to have just to go to a lake somewhere by myself and fool around with it.

I have a buddy who's an avid sailer - I'm going to pick his brains a lot and hopefully get out on his boat, once he's done all the work on it and gets it back in the water. I'm seriously hankering to get out on the water... can you tell?
Give him a hand gettin' the boat ready. He'll be more inclined to share his knowledge and underway time with you, and it'll be a good opportunity for you to learn some of what's required in proper boat ownership. Best of luck!:)