Someone a lot smarter than me said that you can learn to sail in an hour, but it takes a lifetime to perfect.
I'm seconding all of this advice to start small. In a very small boat (think 14'), everything about sailing is intuitive, and you can roll it without damaging anything. My local swimming pool, growing up, offered classes on righting small sailcraft. They took kids as young as four, and I never saw anyone fail at getting these boats back up. The worst thing that might happen in your manmade lake is the mast getting stuck in the mud.
From there, step up to a pocket cruiser. Something 20-25', with a day cabin or just a shelter. San Juan 21s are excellent for this, as they're common, cheap, simple, and lightweight. If you get one with a trailer, you can store it in your front yard and not have to pay moorage fees. My family (of 4) cruised in one of these until we two children were in our early teens. I can shove it around on its trailer by myself, it's so light. They sail very easily, and you're learn everything you need to know about sloop sailing rigs in one. But it's not a boat for going around the world.
For that, you're going to want a bluewater cruiser. Something with a full keel, small portals and hatches, and a very sturdy mast step. Albin Vegas are great. I'm hoping to find me a Contessa 26 for the same purpose. Sailing these is a little more advanced. They're deep and narrow and can be anything from 22-55' (for single-handing, anything bigger than 35' is ridiculous). If you get knocked down or capsized, they'll right themselves, every time, but that's because they're heavy, so you'd better trust your drainage system. You'll want a wind-vane self-steering rig like a Monitor, and solar panels, and if you visit New Zealand without an actual life-raft aboard, they will confiscate your boat.
You can't learn sailing from a book. It's all muscle-memory and reflexes and sunburn. But there are a pile of books that have been helping me.
Anything by Lin and Larry Pardy is valuable stuff. They've been around the world six times together in a variety of boats they built themselves, with the mileage logged for another 5 go-rounds, probably. Even their website is filled with great little tips. One particularly excellent book of theirs is /The Cost-Conscious Cruiser/. Another is their book (and DVD!) on storm tactics.
/Things I Wish I'd Known Before I Started Sailing/, by John Vigor, is another one I couldn't live without.
And a few books about other people doing this too: /Maiden Voyage/, by Tania Aebi. She had a great circumnavigation; never got dismasted or caught in a storm. /Dove,/ by Robin Lee Graham. He was the youngest to do it solo until just recently. Didn't have the easiest time of it; hallucinated often when he was alone, lost two masts and a boat, and lost a cat overboard on his homeward stretch. The first guy ever to do it alone, Joshua Slocum, wrote /Sailing Alone Around the World/, which I'm reading right now. He was a bit of a strange one, but it was 1895.
And blogs, too. BIKA is a Contessa 27 from Norway currently sailing in the Gulf of Mexico. Zac Sunderland just became the new world's youngest solo-circumnavigator, at 17.
As for local resources, go down to the nearest marina and ask around, or even put up a flier. Most sailors love nothing more than to talk about their boats and cruising, and if you find the right day and the right person, that could mean an invite out for an afternoon's sail. The office would know if there's a sailing or cruising club around, too. I was in Sea Scouts when I was young, and that was an incredible learning experience. I know they take on passengers for summer sailings to help defray costs.
The really important thing is to by God never let anyone make you feel ridiculous for wanting to move to this lifestyle. People live it. Successful, ambitious people live it, and it's a whole different plane of living.
By all means, skip straight to the small pocket cruiser. Find one with a centerboard instead of a fixed keel: You can run them right up on the beach if you need to. (If you leave the pin out. Some have a locking bolt or pin for when they're down. It takes the tension off the cable used to raise and lower them, but you need to take it out of you're in shallow waters.) A boat like that'd be fine for sailing in both lake and coastal waters, and the smaller ones are really, really fun. I've raced in a 21, and they can pull very close to the wind, which is nice. And they handle very lightly, meaning you can do some maneuvers in light winds that a larger boat would never be able to match.
If you're going to be doing anything coastal in your pocket cruiser, you'll also want a small outboard motor. Nothing big, 4 or 6 horsepower at the most, burns about half a gallon an hour. A small sailboat has a hull speed of about 4-6 knots, so a big motor's an absolute waste and a lot of unnecessary weight. You won't use it often, hopefully, but getting becalmed in the shipping lane without a motor is a terrifying experience you'd rather not have.
And have someone show you how to anchor. It's not hard, but getting it wrong once can cost you your boat. Rules of thumb: 1lb of anchor per foot of boat, carry a spare, and lay out seven feet of rope or chain for ever foot of depth.
Learn to varnish, and to tie knots and splice rope. Learn celestial navigation. A GPS is great, but batteries only last so long. A sextant lasts a lifetime. Learn how to read coastal charts and pilot charts. You won't need most of these for the little pocket cruiser, but they're a necessary foundation for the lifestyle. And they're all things you can learn on your own. Look to youtube for help, believe it or not, if you get stuck and don't have anyone to ask.
Get a little camp stove, and a tupperware bin for a larder, and you'll always be ready to go. Waking up in your own boat, tucked into some gorgeous and silent little cove is absolutely fantastic.
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Depending on how far away your long term goal is, buy a small-ish boat to sail on your local lake, and go from there. Lots of people start out with small boats and continually upgrade over the years as their finances and available free time allows.
posted by entropic at 11:16 AM on July 12