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Best Boat To Learn To Sail On?


Dec 20, 2009
Hunter 466 Bremerton
Lido 14 and my 11.5 kayak with a 45 sq ft sail. Sometime in 22' sloops at the Naval Academy and 44' Luders Yawls. Move up to our first boat a Columbia 8.7 then a Columbia 10.7, a Freeport 41 Ketch (too many lines, sails, shrouds, threatened to install a bow thruster so it would be easier to tack) and now our Hunter 466. Along the way time in Hobie 16, Catalina 22 and 25 and my daughter is now restoring a Catalina 30 so that will be fun too.


Alden Forum Moderator
Jun 22, 2004
Alden 38' Challenger yawl Rockport Harbor
Started on a home built Sailfish, I can't remember how old I was. One of the first recollections I still remember vividly, is trying to sail having forget to put the daggerboard in the slot. The boat is a dead log, in irons, drifting down wind.

Thrust the daggerboard in and it's like magic. The effect, mistaken for 'tracking' or similar, is actually lift, the basis of sailing a boat to windward.

You can demonstrate the effect to a newb in a dinghy.

About the time our son was a year old, I built a sailing dinghy for the family. The kids and my wife had 'sailed' for years before they learned to sail, in this dinghy with a daggerboard.
Nutshell MJ Abby2.jpg
Jun 14, 2010
TBD Looking for my next boat CT
That is some serious sailing reading.. I have read some but not cover to cover.
I have to admit I took it in small bites, and skipped some sections, but I kept it by my favorite reading spot and also used it as bedtime reading for a long time.
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Sep 20, 2014
Rob Legg RL24 Chain O'Lakes
The truth be told, I've learned to sail on every boat I've owned. Having said that, I did learn some basics from school on a Thistle. I owned a Hobie 14, sailed it a bunch, but didn't really "learn" a lot. It is a super easy boat to sail, goes fast and is well behaved. I'd say the boat I really learned a lot on was the worst boat I've ever owned. The boat handled poorly, the rudder did not steer the boat. It was slow and tender. I learned about situational awareness, as the boat was not forgiving. You had to finesse it into sailing, which meant I was forced to learn much more subtle details about sail shape and what the boat liked. It made me a much safer captain. My current boat is fast and responsive, so again a whole new set of things to learn.
So there is a couple of considerations. A really bad boat will teach you a lot. The only bad thing about a bad boat is that you may loose interest in sailing. A good boat is responsive, so you get better feedback from the finer subtleties of sail trim. I'd say what you don't want is a multihull, because those things just sail fast regardless of what you do to them. You'll think you know how to sail, but you don't.
Nov 8, 2007
Hunter 27_75-84 Sandusky Harbor Marina, Ohio
When they built a dam to create Lake Pierce northeast of Rockford, IL, my Dad got plans, and we built an Moth scow. I took it out on the Lake, and turned it over until I learned how to sail it. (We did read every book we could find on sailing small boats.) I took Joanne sailing on several dates, including moonlight sails.

Our next boat was a Rhodes 19, while at Navy OCS at Newport on the Narragansett Bay. We have a picture of Joanne, pregnant with our first daughter, setting a spinnaker while we were out on the Bay. I learned about tides, and different sail combinations there.

I really learned the details of sailing racing a Sunfish monthly among 30 other sailors of the Key West Naval Sailing Association during our 2 1/2 year posting there. Joanne joined me, (pregnant with our second daughter) on fun sails and snorkeling over the coral north of Sigsbee Island there.
Jul 12, 2011
Catalina 36 1771 Ft Pierce, Florida
The truth be told, I've learned to sail on every boat I've owned.
There's an incredible amount of truth in every part of @Davinet 's post, but this first line is the best. Every boat is like a new partner, and teaches you lessons. BTW: my first partner was a Sunfish on a small inland lake. If you mess up or fall asleep, you get a cold, wet reminder about balance and trim.
May 17, 2004
Other Catalina 30 Tucson, AZ
UPDATE: Many times we have a conversation with someone and that's the last you hear from them. No so with me -- with many of the sailing folks I interact with we become friends and they keep in touch with me even though we'll sadly probably never meet in person -- sort of like the listers on this forum -- Stu J, Joe from San Diego, Scott T, Jackdaw and other frequent contributors and the folks at sailboatowners.com, who I've never met but have been doing business with for many years.

Anyway, our FL friend found a school he liked -- Island Dreamer Sailing School in Miami. They conduct a class called "couples teaching couples" and they've taken their first lesson -- his wife loved it!!
Jan 22, 2008
Hunter 34 Alameda CA
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.
I "learned" pretty much on my own initially in a Snipe, Aquacat and Laser. We found out I was pretty terrible and my wife would never go along with my skill set back in the day. The first boat my wife and I learned to sail on from a professional was a Soling through an ASA program in Punta Gorda, Fl. We had separate instructors on different boats. I think that was the best. We had to row out to them in dinghies and leave the dinghies tied to the mooring buoys while sailing/learning all day. Those skills of operating our larger boat without benefit of a motor (ran out of fuel, broke, air in the line, clogged fuel lines, prop fouled, propeller fell off on a charter boat, etc.) were priceless. Thirty four years and only had to be towed once. I recommend adults go with the same style boat with instruction for the introductory knowledge building. Then move up to the boats with luxury items.

Of course young sprouts can learn in the dinghies in an organized environment because they don't seem to mind falling in the water occasionally.
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Sep 24, 2018
O'Day 25 Chicago
I learned to sail on Barnett 1400's when my parents sent me to a sailing camp over the summer. We learned a lot about what not to do. For close to two weeks we spent a few hours everyday doing capsizing drills. By the end of the drills i could be on the daggerboard before the mast ever touched the water. They had a few other boats. I found the Sunfish too easy to sail and the Zuma's were much more stable with its mast in the water. The two larger boats they had were a Puffer and a 420.
I was riding my bike around the lake one day after I was too old for the camp and saw some odd things sticking out of their trash area. I poked my head in there and found over a dozen boats and tons of parts. I quickly ran to the boat house and asked if I could have one. Two days later we brought home a 420 named Derelict on top of the station wagon. I was fortunate to find a miscut mainsail from a loft for $75. My parents were kind enough to pay for it. I loved that beat up old boat. I found it to be fast, challenging and fun. If anyone has a cheap one for sale please let me know
Jul 7, 2004
Hunter 30T Cheney, KS
When I heard my professor friend and his wife were going to take sailing classes this summer and wanted to get a small boat, I connected him with another friend who wanted to sell his Phantom. This friend is on Hospice and it would relieve him to know that loose end was taken care of for his wife. Besides, it was a nice boat and trailer. Anyway, they agreed on a price and the professor bought it. The sailing instructor is also a friend so I asked if the newbie would get instructed on his new boat. He said they would train on the sunfish still, but he would encourage the new sailor to use the Phantom on the last day of on the water sailing class. Sounds like a great way to ease into sailing your own boat.
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Sep 25, 2018
Catalina Capri 22 Capri EXPO 14.2 1282 Stony Point
Took sailing lessons from Steve Colgate on a Soling. Once I understood what I should be doing, I rented a Rhodes 19 at Oyster Bay Sailing school and practiced what I learned. I rented boats from sailing schools wherever I traveled. Cal 22 in SF Bay, Flying Scot on the Potomac, O'day 22's in Bermuda. Finally bought a Hunter 23.5 where the few sail controls were mastered. Now in a Capri 22 with all the sail controls I could wish for. Still shaking down the Capri tuning in the rigging and testing all of the controls to determine the best combination for the finicky winds of the Hudson canyon.
Sep 24, 2018
O'Day 25 Chicago
why would someone put that in the trash...:confused:

At the very least you could put it on the side of the road with a "Free" sign.:eek:
Liability? Cheaper and easier to just toss it? They also never billed me for storage despite giving them my info multiple times. In the end they took the boat because they said I owed them storage fees for the past three years. All in all it cost about $300 for a boat and storage less than 3 miles from home
Nov 8, 2010
Beneteau First 36.7 & 260 Minneapolis MN & Bayfield WI
Oh kinda forgot this thread changed...

My absolute first sailing happened at BSA summer camp, Camp Hiawatha in the UP of Michigan. I wanted to pick off a bunch of merit badges, and that one seemed cool. I went over to the sailing dock after my swimmer qualification test, and asked about the merit badge. The counselor handed me the sailing merit badge book, and said come back tomorrow. The next day I was out on a sunfish. For training we played follow the leader, mimicking the leaders sail trim for starting out, and then playing with it to see what happens. Hooked. Passed the written and OTW test the next day. I sailed every day that camp, and sailing was the only merit badge I got at camp!

That might have been the end of it, but within the year two great things happened.

A new kid moved into town and he had a Laser! He used to race were they used to live. There was no dinghy racing in Houghton, so most every day we would dolly the boat down to the water and take turns. Great fun, and learned a lot about trim, wind, and reading the water.

This was in the 70's sailboat craze, and my parents bought into a friends Ericson 29. While small by contemporary standards, the thing seemed like an ocean liner to me. We had several great years on that boat. While my parents were casual sailors, Mr Timm was a keen mariner and I learned the majority of my boatcraft from him on Portage Lake and the connected Lake Superior. I can still remember setting off for Isle Royale, 60MN miles away and over the horizon. When it first came into sight out of the fog is a memory I'll never forget.
Oct 19, 2017
O'Day 19 Littleton, NH
My first memories of sailing were aboard my father's Victory 21

Still in diapers, my brother's and I crawled throughout that boat. I remember laying under the cockpit benches and listening to the rush of water against the hull on a heel. I could see the hull speed wake through the glass on a bright Clearwater Bay. I'm sure I absorbed some of the speak, I remember learning to call, "ready about! Hard-a-lee!"
Later, at the Optimist Club, I was well ahead of the other 7-8 year olds in knowing all the boat parts by name, but I made as much effort to commit that work sheet to memory as any lesson I ever did in school. As an actual sailor during the bouy sailing, I was just ahead of the middle of the pack. I didn't understand wind strategy at all. Pretty sure I still don't. Then spent a YMCA Summer on a lake with sunfish and these little trimarans. I don't know what they were called. I sailed so much they made up an end of season award for me. "The Super-Duper Sailor" award. That was cool, but I was jealous that they also awarded it to one other camper. That says more about me than I'd like it to. Life is as it is.
I got an Opti the next Summer. Very excited. This was just before we moved into a boat. That was good, because I had little opportunity to sail on my own until then. I never had sailing buddies. No one to show-off for or explore extreme sailing with. It was just me crossing the bay with an occasional friend that would join me on a trip out to one of the spoil islands. Neither I nor my parents were good about committing to scheduled club activities so my involvement with the Opti Club ended with my class.
I remember, very vaguely, one sail aboard my pram with my father. He told me how to know when my trim was good and warned me against jibing and I was good to go after that.
I read Sailing and Cruising World magazines and dreamed of crossing the ocean, even in my pram.

-Will (Dragonfly)
Jun 14, 2010
TBD Looking for my next boat CT
@Jackdaw the last line in your story made me think about the first time I sailed at night, or the first time I sailed out of sight of any land, or the first time I sailed in zero-visibility fog at night (before I had radar or GPS), or the first time I sailed offshore overnight. All of those events were meaningful and memorable experiences.
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May 17, 2004
Other Catalina 30 Tucson, AZ
I LOVED the summer growing up in RI and so did the guys & gals I grew up with. We were children of, in my opinion, the greatest generation in the world but we didn't have a lot of stuff in the 1940's & 1950"s that kids have today. We had to amuse ourselves and our center of activity was Edgewood YC on Narragansett Bay. Half of us didn't own boats but the other half did -- my neighbor and friend was the son of the owner of Cross Pen's and he sailed a Beetle Cat Boat. There were a ton of them on the Bay. Races were conducted for kid and the fathers (peppy pappies) and mom's (wet hen's). It was non stop activity during the day and great dances at night. I hated September because that's when it came to an end.

What made me think of all that was Will Gilmore remembering "laying in the cockpit and listening to the rush of water against the hull". I remember that same experience sailing across the bay on a lazy afternoon as if it were yesterday!! Thank's Will for bringing that memory back.