• Mobile App For Android Now Online!

    Download it here. The app is searchable in the Google Play Store under Sailboat Owners.

    Sorry iPhone/iPad users, we are still waiting on Apple. :(

    Click the X in the upper right corner to make this go away

Best Boat To Learn To Sail On?

May 17, 2004
Other Catalina 30 Tucson, AZ
I recently spoke with a fellow from FL who was interested in getting into sailing and was inquiring as to what was the best boat to learn on.

Sounds like a simple question but it isn't. It's like a lot of questions we get on various subjects, which unfortunately start in the middle. To get to the beginning I asked him why he wanted to sail? He said his friend had recently taken him for his first sail and my book & chart was on the boat. Next, I asked him what type of sailing he was interested in - cruising, charter, racing, ownership? He said cruising and maybe charter and he wanted to own the boat. Next, I asked him if he was married or had a significant other and if so what was their level of interest - he is married and his wife might (key word) be interested. I could have explained the pit falls of this setup but didn't. I could have told him of the number of years I spent on my dock and never saw the wife of my dock neighbors - they were sailing widows. I was lucky - my wife was a eager participant. She didn't care about sailing the boat but went with me anyway. I could have told him about the cost involved with ownership but didn't - "a boat is a hole in the water into which you pour money".

On his desire to charter boats in the Caribbean, I explained you just don't call the charter co and tell them you'll be down on such & such a date - you have to prove to them you can handle the boat. More importantly, you have to know yourself that you can do it - "a man has to know his limitations".

We never did get to the best boat to learn to sail on. I suggested he find a good sailing school in his area and not some fly by night outfit that provides 20 minutes of instructions and then sends you off on a 30'. The school should be accredited and have certified instructors and also check on line reviews of the school. I also suggest that both he and his wife attend the school together otherwise he'd find it to be a lonely sport. Before registering at a sailing school I suggested he have a long talk with the instructor who could determine where his starting point should be - small boat or large boat.

After I hung up I thought about the original question - I wonder what would be the best boat to learn on - I learned on Beetle Catboats sailing out of Edgewood YC on Narragansett Bay (RI). Never had a lesson -- we just did it. I don't think any of us knew what sail trim really was. The boat just felt right.

Any comments on the best boat to learn on?
Nov 8, 2010
Beneteau First 36.7 & 260 Minneapolis MN & Bayfield WI
Well, the universal truth is that the 'best' boat to learn to sail on is a dinghy. Same reason all F1 drivers learned to drive in karts. You develop a feel for the wind, water and boat that nothing else can. Only people that disagree are people that have never sailed dinghies.

But to your real question, what would be be best for an adult (possibly a couple)? For sure a small modern keelboat; fractional with a jib. Big enough for adults while small enough for proper 'feel' development. But in truth, whatever your local community sailing center uses for adult training. Hopefully it matches that criteria. Wayzata Sailing uses Sonars, a great choice. So would the new Beneteau/ASA First 22.


Custom designed for Adult training.
  • Like
Likes: Parsons
May 17, 2004
Other Catalina 30 Tucson, AZ
In most cases I suspect the best boat is the one you have....I learned on this... and sometimes I flew the jib;)
View attachment 166078
Thank you. Maybe a better question for the forum is - what type of boat did you learn to sail on?
Additionally, if you had it to do over again would you use the same boat -- I would.
May 1, 2011
Pearson 37 Lusby MD
what type of boat did you learn to sail on?
26 foot Rainbow knockabout in Annapolis. Didn't really get good at it until I got my offshore Skipper D qualification on the Navy 44s. And I'm still learning stuff on my Pearson 37.
Jan 19, 2010
Hunter 26 Charleston
Yes I would choose the same boat.... I loved that little boat. My mom still owns it and uses it as a row boat.

I could rig and launch it myself and I was only 10 years old. At one point I filled it with camping gear and sailed 15 miles to an island in a lake in Wisconsin. I thought I was true Viking. Hooked is an understatement. I think I spent every waking hour of my 11 summer in that boat. I could hike out by tucking my feet under the leeward rail... it was a blast. And when the dagger board would start to hum.....:)
Oct 22, 2014
CAL 35 Cruiser moored EVERETT WA
I learned to sail on an ElToro dinghy.
I agree with @Jackdaw on this point, dinghies are simple and they are self teachers in all the elements of balance, sail power, control that are the foundations of sailing.
I have not sailed on the First22 but I sat in one at the Annapolis Boat Show and they are definitely set up for the novice sailor. They will engage all of the training facets of learning to sail a big boat.

I followed and therefore am a proponent of stepped progression and racing as tools to help the novice learn the skills of sailing.
  1. Dinghy
  2. 14-16foot sloop
  3. 25-30 foot bigger boat
  4. 35 plus Boat.
While the formal schooling is a good path to follow, so too is the ownership and sailing of progressively larger boats.
At some point the wisdom of Captain Ron come into play.


Jun 5, 2014
ODay Mariner Guntersville
If somebody asked me "what is the best boat to learn on," I would respond just as Don (...find a good sailing school in his area...) and Jackdaw (...whatever your local community sailing center uses for adult training...) already wrote.

If you want to know what boat I learned on I'd say a Sunfish. Yes, I would use the same boat - if I was an 11-year-old Boy Scout and that's what the summer camp had. Sunfish are also what the University of Florida had available for students back in the old days (no lessons nor any certification needed to take one out). And the sail club here teaches on Sunfish, too. My first boat purchase was a Hobie 16 which was great for a guy in his early 20s. I would not recommend that anybody buy a Sunfish except as for a toy for the kids. An adult over 30 should not buy a Hobie 16 unless he/she has plenty of experience on one and still thinks its fun.
Last edited:
Jul 7, 2004
Hunter 30T Cheney, KS
We both learned the basics on a sunfish in a Red Cross class. My wife would have quit if one of the instructors hadn't shown her what sailing was like on a small keelboat. Part of it was they paired her with another student who had no aptitude for sailing and it was chaos on the water. :cuss:
Jul 27, 2011
Bavaria 38E Alamitos Bay
But to your real question, what would be be best for an adult (possibly a couple)? For sure a small modern keelboat; fractional with a jib. Big enough for adults while small enough for proper 'feel' development.
For this, I would go with a Cal 20 or Santana 20. I sailed both of those during my early “formative” years. Wife and I owned and sailed a Cal 20 in Long Beach a few years back. The only one-design racing class that has survived many years in LB is the Cal 20. It has the attributes mentioned sans “modern”, plus it’s trailerable.:dancing:
Last edited:
  • Like
Likes: jssailem
Feb 21, 2013
Hunter 46 Point Richmond, CA
I started on a Hobie 16. Then I spent a weekend on a weekend sail on a friend's 32 foot sailboat and was hooked so I chartered a 37 foot Seidelmann sailboat in the Chesapeake Bay for a few years. 25 years later I purchased a Hunter 31 and within a year purchased a Hunter 386 and this year purchased a Hunter 46. Go big!!
Oct 19, 2017
O'Day 19 Littleton, NH
I'm a dinghy proponent. That said, considering the described situation, means and patience to plan for the big picture, I'd suggest something like a Pudgy with the feel of a dinghy and the possibility of becoming my larger cruising boat's tender. Then, I suggest sailing with a friend or a pro on a larger boat. Take ASA 101 and 102. Then go look at the boats you think you'ld like to cruise on (lots of reading and research here). Take sea trials and ask questions. Make connections and learn from experience.
If you are not in a hurry to cruise and you want an interim boat to learn on and get your spouse out too, a CB weekender offers an added dimension with adjustable CLR. Picnics and overnights will help clarify your perspective, expectations and solidify your plans.

-Will (Dragonfly)
Jan 2, 2017
O'Day & Islander 322 & 37 Scottsdale, AZ & Owls Head, ME
I taught myself on a Sailfish (like a Sunfish without the mini-cockpit.) Each summer, when I was young, my parents visited their friends on Cape Cod. I was left alone (those were the days!) to take their Sailfish out. Lots of wipeouts; lots of fun.
  • Like
Likes: BudGates
May 17, 2004
Beneteau Oceanis 37 LE Havre de Grace
My parents had an O'Day 28 when I was a kid, so that's mainly what I learned on. But there was one day when a guy at our marina brought a sailing dinghy down. He let me borrow it for about an hour, and I think I learned more about the perils of bad sail trim and rudder work in that hour than in years on the O'Day. The feeling of instant response to adjustments is just so much clearer on a small tiller boat than a 7000 pound structure. In college I crewed on a J33 for a season, and again learned more about trim and tactics than many years of day sailing and weekending. Not to say I didn't learn from the O'Day; I learned all of the fundamentals there and it was a great, stable, comfortable platform for that, but getting experience in a different variety of boats helped refine those skills.
Jun 14, 2010
TBD Looking for my next boat CT
I agree dinghies and small boats are the way to learn. I learned on a Sunfish, when I was about 12 years old. Got hooked big-time and went out any chance I could get. Took no classes until in my 20’s. Read a lot about it, including Bowditch cover to cover. Always dreamed of getting a boat - when I was in middle school and high school I would read sailing mags in the school library and dream of world cruising (beats studying). First boat was a West Wight Potter 15. Two years later graduated to a Shark 24 (first keel boat). 8 years later got married (she likes to sail) and then had to sell as the house and kids took priority. We took a hiatus until the kids were old enough to participate, and I sent them to a sailing camp (Lasers and JY15s). Then came my first Dragonfly trimaran 18 years ago (started at 30 feet, on my 3rd tri now at 39 feet).
(Seriously fun to sail and coastal cruise. ) ;)
Last edited: