When you click on links to various merchants on this site and make a purchase, this can result in this site earning a commission. Affiliate programs and affiliations include, but are not limited to, the eBay Partner Network.
Look for sailing classes. Most larger seaports or lakes have some sort of schools. They may have rentals available if you have completed training. Sailing is not as simple as it looks. If you find rental companies they may have lists of schools available.
Eric gives good advice on the lessons. I'm a parttime sailing instructor (10 years), dinghys and yachts to 50'. Sailing can be a relaxing, and/or a blast, but it can get dangerous quickly. Lessons are imperative for safety, and besides, you'll enjoy your rental dollars much more if you know what you're doing.
Try googling for the American Sailing Association (ASA) or US Sailing. They are the two competing organizations that certify instructors and many schools are affiliated with them. if you go as far as getting a student certifiication through one, it makes it easy to rent boats in many places.
If you're unwilling to spend the $$ for lessons, look up a yacht club...sailors are usually NOT the stuffy SOB's they're made out to be (at least out west) and it's easy to find someone who'll take you out for a ride.
The good news is that if you initially learn on a boat under 20' you'll be a far better sailor than ssomeone who learns on a larger keelboat. A small boat in 15-20 knots acts like a 40 footer in 30+ knots.
My favorite dinghys and small keelboats (again, informed because I'm a West Coast sailor and there are countless regional and local designs I've never sailed):
I learned sailing on a 13' AMF Sunfish off Cape Cod. Even though it's a low tech single rig, all the principals necessary for the bigger boats still apply. IMO, O-day's (13' through 19') are about the easiest to learn on. They're slow, steady and very forgiving.
I had a ride on a small sailer in the Columbia river. I remember looking up at a bridge as we drew closer and closer and wondering if the Mast would clear the bottom of the Bridge? My Depth perception would not work at those angles.
The Keel hit bottom a couple times too.
Lot's of things to worry about. But so quiet and smooth when we were way out in the River.
Worth the cost of going to a sailing school I think.
Advice? Leave the hoagie home, and bring some water to drink. I love the water...swimming fishing and boating. Sailing? Get away from me with that stuff. I was never sea sick before, then about 3 summers ago, my GF, her 6 year old cousin and her uncle took me out on a tiny, heavy (what uncle says) sail boat. OMG...I've never been so ill . I'd have done better hopping out and swimming back to shore. It was some sort of race in one of the inlets at the Jersey Shore, and we weren't even seriously competing. It was basically an obstacle for the faster boats while we bobbed in 3' inlet swells. There's a picture of us coming across the finish line, like there is for every boat. I'm actually green in it, and on another, hangin off the back of the boat .
Had a Hobie Holder years ago. Need to check for these things. That the mast is made out of a composite, no fun hitting power lines. All the gear (Rudder, keel, paddles,etc) is fastened to the boat, so when you flip it you won't loose something. That the sail is reefable, while in the water, mine wasn't and it was costly to modify. You'll need a life jacket to wear, 100% of the time, I'd highly recommend a neo-vest, front zip wet suits and boots are nice also. A helmet when you are learning is nice too, LOL.
The Red Cross holds sailing classes. I know a great sailing instructor in Maryland. You'll need your own boat. His smallest boat for instruction is 38'.
Start with the Red Cross.
When I was a kid, we sailed in 8' dingys. If you stay close to shore, and in warm water, you can learn most of what you need to without serious risk. Lessons are a good idea to get the basics. From there, it depends on your goals. There are boats for cruising, like the O'Days; racing, such as various class boats (I raced Snipes); going really fast, such as Hobie Cats; and going really, really, really fast, such as windsurfing, which is what I do now. I would like to get a nice little day sailer again, tho'.