Home Forums Hunting & Shooting Hunter's Campfire Advice from any sailboat owners

100% of my sailboat experience came 40 years ago when I rigged up a sail on a 17' canoe. It was slow and cumbersome but it was still fun. It didn't let you do anything other than sail. You had to stay alert to what it was doing or it could go over. It got kind of boring just tacking back and forth while paying strict attention to the boat.
I'd like to try it again, though, but with a boat made for the job.

Having spent half my working life as a yacht carpenter, and sailing the Chesapeake Bay both racing (a Beneteau 39) and day tripping, I'll second the motion for starting out with a one-man day sailor. Learn the basics, have fun with it, immerse yourself in the "sailing culture" and then decide where to go from there.

Having been on blue water when heavy seas were threatening to kill me, believe me when I tell you that no boat will seem big enough under those circumstances.

I can't resist the old adage: "The two happiest days in a man's life are when he buys his first sail boat and when he sells it!"

Having been on blue water when heavy seas were threatening to kill me, believe me when I tell you that no boat will seem big enough under those circumstances.


I was aboard an aircraft carrier in the pacific ocean during a typhoon. We were just sailing around the edges of it and still taking green water 65' down the deck past the bow. I can attest that the feeling is just the same as being on a 24' sailboat in a squall with 10' waves on Chesapeake Bay.

At 72 I've lived aboard and been a boat builder for over 1/2 my life and have learned a couple things.

The cost of boat ownership grows disproportionately as the size grows. It costs many times more to own and operate a 30' boat than a 20' boat.

Learn to sail before buying a boat you don't know how to sail.

Small boats are the most fun.

I just retired 3 months ago. Now I get to learn to sail as a retirement hobby. Grew up on Lake Ontario so I'm no stranger to big water. Been on water most of my life (and underwater scuba diving) but never got around to sailing until now. All the sailing folks around here told me to take lessons at the local yacht club where they start you out on the small stuff. That's how you learn the basics. Then you can build on that experience. I'm just starting but someday my dream is something in the 23-27' range just for pleasure sailing. It's great to experience sailing, I've been on 'em enough but never really learned how until now. Now that I'm retired I finally got enough time AND money to swing it.

I really appreciate all the feedback. It seems the consensus is start small, learn, the go from there.

"More cruises have been sunk by Women than rocks".