Go get your basic keelboat cert to lock down the basics. Then do a bunch of beercan races until you’ve got the hang of it.

Volunteer to crew anywhere and everywhere.

You’ll be a salty dog in no time.

Go to your local marina or their website and see if there are sailing classes.

Join the Navy and tell them you want guaranteed placement as a bosun. You will save money by never wanting a boat of your own.

Contact your local sailing club/yacht club. They often have classes and rental boats. Even if they don’t, you can sometimes find someone with a boat who is willing to teach a beginner.

Yacht clubs often have Wednesday afternoon sailing races and those crews often need extra folks on board. I learned sailing that way when I was in university. An inexperienced reliable crew is member is better than an experienced unreliable crew.

See if you can find a 3 hour tour to get you started

I don’t have any personal experiences with any of these crew finder sites but I know lots of people who’ve used them. The catamaran designer I *apprenticed under met his wife through one. She had no prior sailing experience but was willing to learn, and he needed crew to do a Caribbean crossing, and that’s how the story began for them like 25+ years ago. They still sail together all over the world.

The other advice is good too. Just walk the docks and ask around. People love talking about their boats.

you’re definitely going to want to get on the Sailing Anarchy forums

i did the basic free course at nauticed.com and got a boating license for my state and that was enough to buy and sail a racing dinghy 8 hours up a river my first time out. Sailing is a blast you’re gonna love it! You can get a dinghy on craigslist for less than the cost of lessons so if you’re into DIY it’s a fun inexpensive way to go.

Please invest in Dallas Murphy’s ebook “Plain Sailing”.

https://www.amazon.com/Plain-Sailing-Sail-Trim-Manual-Sailors-ebook/dp/B00593YTJG/

It gives you all the fundamental-understandings, & by making you basically-competent-in-understanding sailing, it gives you significant advantage over everybody else looking at having a bit of sailing-time on someone’s boat.

Authors to know of include:

• Tom Cunliffe ( I can automatically recommend anything instructional of his, & he has a youtube channel )

• Nigel Calder, if you’re looking to invest in a cruiser for yourself, you want to read his books.

• John Kretschmer’s books are excellent.

if you want to have a cheap boat of your own, then there are 2 books I recommend, the white-cover book by Dynamite Payson & the Building an Outrigger Canoe book.

https://www.amazon.com/Instant-Boatbuilding-Dynamite-Payson-Paddle-ebook/dp/B00UYB5EGK/

https://www.amazon.com/Building-Outrigger-Sailing-Canoes-Construction-ebook/dp/B00CKMG7E4/

Do keep in mind that in some jurisdictions, human-powered hulls do not require registration ( canoes, kayaks, rowboats, etc, ), whereas powered hulls ( including motor AND SAIL ), legally do.

Between those 2, you should have some understanding of how to get yourself afloat, affordably.

Please do not compromise safety, though: alcohol massively multiplies the death-rate on the water, so segregating alcohol from operating-aquatic-vehicles is a good thing, see?

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Could just get a personal size boat to get accustomed to the feel of it. Be aware of the boom when you turn with the wind (jibe if I recall the term) lest you get whacked out the boat.