What boat did you learn to sail on? Here’s What Our Readers Said

When I asked what you learned to sail on, I figured we’d hear the usual names — Sunfish, Hobie Cats, Optimists — and we did. But what I didn’t expect was more than 1,500 stories rolling in from every kind of shoreline imaginable. Alongside the classics were forgotten fiberglass relics, quirky one-designs, and plenty of homebuilt boats crafted in garages and backyards.

What stood out wasn’t the boat itself. It was the memory. The person who taught you. The first capsize. The first gust that made your heart race. In the end, it never really mattered what we learned on — only that we learned.

Here are the best 25 comments I found going down the list.

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8’ El Toro 69/70ish.
My Dad,brother Russ and I built two, Mom made the sails.
I still live on the BC coast, 2 minutes from the salt chuck and my brother lives smack dab in the middle of Canada…Winnipeg where it’s as far away from the sea in every direction.
Guess who took to sailing…and who didn’t?🤣 – Jim Heslop

Sea Snark 10 foot Styrofoam cooler with a sail – Gilbert Giuliani

Catalina…my Cub Scout Den leader was a lady! She and her hubby took us out on a 30-35 ft boat, it was sunny with some wind that day. When it was my turn at the wheel, I was a natural, i turned the boat to feel the sails set and grab the wind and we launched forward!! I felt the power and was instantly hooked for life!! – Dave Krouse

A broke down sixteen foot hobie we fixed just well enough to sail it started taking on water on one hull later – Mike Halligan

Tricky question…. fatty knees, 420, hobbie… there’s a difference between getting the boat from point A to point B and knowing how to sail…. after 5 years of single handing a 78ft schooner around the world in the mid 90s, I finally knew how to sail…. – Eric Bureau

Sailfish, my dad made from a kit. – Terry Ambrose

11 ft home made boat made my by Dad, had a dagger board, in 1957, was 10 yro. – David Coffill

I first sailed on Huon 36, and thereafter on a Nauticat 38 ketch, from there I started racing on a Hanse 40 and properly on a Farr 38. Since then I have cruised and raced on a variety of keel boats including a Swan 40, a Holeman and Pye 52, a Halleberg Rassey 40, through to my own boat a Swanson 30.

My point being I never raced on dinghy’s and other such really small boats – David Mitchell

Alcort Sunfish that my dad built from a kit in our basement. I always told him I helped build it but ten years old I doubt I was much help. – Michael Schultz

A sailfish or sunfish….no idea what I was doing but boy did that experience sink it’s hooks in.
I was 13 , I’m 65 now, spent the first half of my life sailing, spent the second half windsurfing and kite boarding, and now I’m back to sailing with a cat and still doing wind sports!!! Nothing better!!!! – Ronald Ternullo

I bought my first sailboat it was a 24 Columbia Challenger that I named NAVANAX. The guy I bought it from took me out on it for about 2 days. Sailed the Channel Islands on before buying the 37’ Overseas Ketch NEPENTHE that was home from 1978 to 1988. Best years of my life!!! – Peter Robblee

A James Island one design. Originally a club built boat. Some 35 were built by a member there. Whom I met that couldn’t believe I found this craft. Made of plywood with wooden mast and boom. The mast broke during a race at the Halloween regatta , a man from that club at James Island took the mast home and repaired it. I ended up donating the boat back to the club that built it. Full circle. 😎 – Dean Starr

An 11’ Sunflower! I had no idea how to sail. I just knew I wanted to learn. I had absolutely no role models therefore no one to ask for help. I read a book about sailing, took my Sunflower to the beach on the shore of Lake Huron (where I still sail today) and just did it! I was 20 years old. In four weeks I’ll be 80 and can’t wait to launch my Mirage 25 for another season! – Bill Tschirhart

AMC Force 5 in a wind storm, came out of nowhere , it was sail or die in cold water. – Jon Turnbull

I purchased my Columbia 36′ sloop 1978. Never sailed before. I’m now the 2nd oldest slip renter at Dana Point and I’m still learning how to sail – Truman Trowbridge Legg

Sunfish. I “moved up” to two others, but they fought me. I had the most fun on that Sunfish. I loved going out to Windy Point on Lake Travis. I’d stay out for hours before coming in for a beer. And I love beer. So you know I was having fun on that Fish. – Thomas Wiley

A 17′ canoe with Lee boards, a stern mounted rudder, a closet rod wood mast with upper and lower spar lateen rig. Zero instruction. Just me a buddy (his dad owned the canoe and the lake front home and dock) both of us age 10. We got wet, learned a lot, had a lot of fun. Age 12 they bought us a C-Lark 14. Probably out ot guilt. – Billy Carter

A very tippy old 12’ clicker-built converted rowing boat which had too much sail and too little centerboard. Spent a lot of time in the water which improved my swimming ability considerably. I was about 7 years old. – David Parkinson

.. a little 14 footer I think.. checked out from Special Services at Guantanamo Bay naval base! (You learned to turn around real quick, because if you didn’t, you ended on Fidel’s side of the bay! – Henry Stanley

My introduction was through the Sea Explorers on a 30′ ketch-rigged whaleboat. In addition to sails, the boat could also be propelled by up to ten what we called Armstrong Engines – five on each side. – John Redmond

Haha. Brilliant Skipper Felix Holmer took us from Darwin to Capetown 1976. I was a complete greenhorn! Then in 2012 I joined Sailability Batemans Bay (where I’d seachanged to) & never looked back! The Sailability mob taught me to race dinghies, then I joined the local Sailing Club & met more wonderful people & got to crew. All without buying a boat! – Terry McDonough

A home built skiff with a sail made from a parachute and an anchor that had been a truck generator in its earlier life. The boat had been washed up in a friend’s yard by Hurricane Donna (Key Largo childhood) and he sold me the boat for $3. – Bill Vickers

Me and campground host took his 13 sears foot aluminum flat bottom boat off the coast of California boy that was sarey didn’t catch no fish to but drank a lot of beer before we knew it we out past the oil rigs we left the oars back on the beach then the motor won’t start then we hit some thing thought it a log kinda weird in the middle of the pafic onean so he told me go push out of the way look over there was a big eye he said get out the way he looks over we shit are pants – Coins Taylor

My dad rigged a bedsheet sail on our rowboat and fastened an oarlock to the stern so I could steer. No keel so I could not tack back home. So I’d take down the sail and row back. – Dave Weddige

A barn door with one of my mother’s linen sheets . I didn’t know about keels back then and I was at the whim of the wind and tide . – Wayne Jones

Reading through all of your responses proves one thing. Every sailor starts somewhere, and every boat has a story. Tell us, in the comments, what you learned to sail on and what great story do you have from learning to sail?