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Just starting out....am I thinking right?

Jun 27, 2019
NoneYet NoneYet NoneYet
Hey folks! I am pretty new to sailing and trying to figure out what I want to do. Hope that is ok to post here since I am not yet an owner??

I loved going sailing with my grandfather as a kid who had a decent size boat (dont remember what it was) several times. He loved to sail and crossed the Atlantic several times. I recently took a several day long trip aboard an 75 foot schooner, and while I didnt get to participate much in the operation - it was a blast and renewed my love of being on a sailboat.

I am trying to figure out how I should start before I get too old lol (I'm 50). At first I though of just getting something like a Hobie to learn techniques on, but the cost of a trailer sailor doesn't look like much more money. I also want something that I could spend the night on occasionally. I already own a camper and a tow vehicle so I am good at tinkering, electrical, repairs, mechanical, learning new things, etc. I want to keep it under the $8-10K mark, which I would think would give me lots of options.

I also like the idea of having a boat I could put in the back yard, fix up to my liking, and learn how to operate and work everything while on land. Is it a reasonable idea to think I could then take this thing on the local lakes and teach myself how to sail it over time, knowing I have the motor as a backup to get myself back? Right now, I am not looking to race or anything...just putter around the lake and enjoy the day. Am I being realistic that this is a good way to start in sailing or do I need to go back to thinking small like a Hobie to start?

Any advice appreciated!
Nov 26, 2012
Hunter 34 Berkeley
Trailer sailor. I nice trailer-able, swing keel boat like a Catalina 22 would do it. That's about as big a boat as you would want. There are lots of choices. You're not going to learn how to work everything while on land. You're gonna have to go sailing to do that. A good, reliable outboard is a big plus.
Jan 19, 2010
Hunter 26 Charleston
Hobies are fun. I own one but they are the Ferrari of small sailboats. I would not recommend a Hobie as a learners boat. There are things that can go very wrong on a Hobie.

Markwbird gave good advice. There are a lot of small trailer sailboats out there and the Catalina 22 is one of the most popular. Here are a few more suggestions that have good reputations in your price range. I have owned a few of these and sailed on many. I now have a Hunter 26 but some day I'd like to get another small 17' to 19' boat to keep in the driveway and take on vacations etc.

Montgomery 17

Hunter 22

West Wight Potter P 19

Com Pac 19

Macgregor 21 or MacGregor 22 or Macgregor Newport 23

And my favorite
Rhodes 22

If you go up to the next size range but want to stay in the same price range, look for a Macgregor 26S or 26D. I'd avoid the 26M or 26X. YMMV

Happy hunting....
Jun 14, 2010
Quorning Dragonfly 1200 home
Hey @armondo great first post, and welcome aboard. :)

You got some good advice above, and I also recommend you take a sailing course with an accredited sailing school that has an established methodology. Yes, you can get more informal training from others, but the combination of classroom and on the water training will help you understand all the basics, rules of the road, chart reading and navigation, and theory. It will also help you with safety basics (should be #1).
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Jun 27, 2019
NoneYet NoneYet NoneYet
Thanks for the info! I had been researching quite a bit into the Catalina 22 already and reading books on the trailerable boats. I just wanted to make sure I wasn’t getting over my head thinking i could teach myself and use something like that as a starter.
Jun 27, 2019
NoneYet NoneYet NoneYet
Hey @armondo great first post, and welcome aboard. :)

You got some good advice above, and I also recommend you take a sailing course with an accredited sailing school that has an established methodology. Yes, you can get more informal training from others, but the combination of classroom and on the water training will help you understand all the basics, rules of the road, chart reading and navigation, and theory. It will also help you with safety basics (should be #1).
Agreed. I have taken some basic instruction such as right aways, charts, navigation (even learning to use a sextant!), and sailing theory on my week on the schooner but not enough to think I know what I am doing. Always a lot to lean. Thanks!
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Oct 29, 2016
Hunter 41 DS Port Huron
Trailer sailor's are a nice way to provide flexibility as to what venue you would like to put out on, but, they are a bit of pain to step and unstep the mast, which invariably leads to looking at the boat in the driveway, my vote would be for a boat in the 22' range which can be hauled on a trailer, but kept it in the water, with a swing keel you can find very reasonable dockage in the shallower areas and you will tend to use the boat more frequently. Just my thoughts.....
Sep 30, 2013
1988 Catalina 22 central Florida
I had been researching quite a bit into the Catalina 22 already and reading books on the trailerable boats. I just wanted to make sure I wasn’t getting over my head thinking i could teach myself and use something like that as a starter.
I'm pretty sure more people got their start on a C22 than any other boat. :thumbup:

Nobody loves their C22 more than I do, but there is one caveat I would mention when we're talking about day sailing and/or solo sailing: you may get weary of the setup and takedown procedure, especially when hauling the boat to (and back from) your lake. I myself might lean toward something in the 16' - 18' range, if I were just day sailing (or even weekending) on a lake by myself. (You were using "I" rather than "we", so I assumed it was just you?)

Everyone is different, but even with my wife to help me (and she's good) I have grown too lazy to take the boat out for just a day. There has to be at least one night aboard to make the process worthwhile for me. On a smaller boat, that might not be the case.

Your mileage may vary, as they say. Just something to consider. :beer:
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Jul 25, 2013
Macgregor 26S near Vancouver, BC
For what it's worth, I went straight from sailing dinghies to a classic Macgregor 26 without any problems. My wife had no background at all, other than an online course for the permit (Canadian requirement) and a radio course. We started on small lakes and we're working our way up as we gain experience. If you did a good sailing course I can't see why something similar wouldn't work for you. The Mac might be bigger than you want but something in the 20-24 foot range would also work.

Like you, I really enjoy that the boat is at my house. I like to work on it and it's so easy having it right there. Also, it literally costs me nothing when I'm not sailing it. (Well, trailer insurance, but that's not much.) It's true that having to launch and rig the boat every time we sail is a bit of a pain, but minor in comparison to all the advantages. We tend to always stay on the boat at least one night every time we sail to maximize the sailing-time to set-up-time ratio.


Apr 3, 2019
Macgregor 26M Mobile AL
@armondo; You might want to add your location to your profile for better feedback. Often, the area you sail impacts the advice.

@rgranger 's list is spot on. Your budget seems reasonable. I bought my first sailboat (over12ft) when I was 56. Be aware that water ballasted boats should only be sailed with the ballast tank completely full. Water ballast is a wonderful thing for trailer-sailing, but must be respected.

As far as setup/takedown time, I enjoy the mental challenge to continually refine the process to reduce the time required. I have a 10 mile tow that includes a 50+mph stretch, so everything must be secure. I have setup time down to 20 minutes (from arrive at the ramp to backing into the water). This is not much slower than arriving at your slip, hanking on a head sail, putting the main in its track and getting everything in order for sailing. My boat has some permanent ballast, so I can launch, load, and fill my water ballast as we're motoring away from the ramp. Takedown time is my next challenge. I haven't gotten below 40 mins yet, but have some ideas.

Trailering allows you to pre-load the boat at home with snacks, drinks, and gear. It allows you the flexibility of "cleaning up tomorrow", if you're too tired. We had a front come through yesterday with over 60mph straight-line winds that made me glad that my boat was where I could check on it. This week, we're in a cycle of very hot days with little wind, and evening thunderstorms. If the boat was in the water, I probably still wouldn't be sailing.

I have a friend with a Potter 19 that I sail with often. Small enough to easily be handled, but big enough to weekend on. I have the 26m Macgregor, which is a hybrid powersailer. It suits my needs, but isn't everyone's cup of tea. The 26x is the earlier version powersailer. Both are good candidates in your price range, but as @rgranger indicates, only if you're looking for a hybrid.

The classic Macgregors 26 would be good candidates. A bit more interior than the Potter, but still fairly easy to rig and manage.

Get a mast raising rig to safely manage the process. Scour YouTube for quick rigging ideas. You can get your setup time down to a reasonable point. One other option, if you have a marina with a ramp, is stick up storage on the hard. You leave your boat on the trailer at the boat yard with the mast up. This greatly reduces setup/tear down times and eliminates the angst of trailering in traffic. Usually costs less than slip storage.

Good luck and welcome aboard.


Jul 25, 2013
Macgregor 26S near Vancouver, BC
I second Jim26m's comments. Optimizing the launch and rigging has been fun. With the set up I have now I just arrive and launch like a powerboat, and raise the mast on the water. I'm motoring away about five minutes after arriving at the ramp, and half of that time is parking the trailer. Where we sail it's mostly powerboats at the ramp, so it's nice not to be in anybody's way.

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Nov 26, 2012
Hunter 34 Berkeley
Gene makes a good point about the raising/lowering of the mast of the C-22. I am not someone who enjoys the challenge of doing that. It's a pain in the ass and can become the reason to just stay home and watch Russian car crash videos on You tube. A little smaller boat in the 18-20 ft range is easier to handle.
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Jun 5, 2014
ODay Mariner Guntersville
Try to borrow or rent sailboats before you buy. Don't buy a daysailor if your sailing area is more than 1-hour from home (or whatever your reasonable daily commute time is; don't forget to double for there and back). Add in at least 1/2 hour for set-up and at least as much for de-rigging. Keep in mind that sailing your own small boat is much more fatiguing than being a passenger on a 75-foot schooner.

If you are set on a Catalina 22 or similar, line up a wet or dry slip before you buy. That's my opinion. There are already opinions here that dragging a boat like that to water, setting it up, sailing, then reversing the process is doable for a day sail, but it is not doable for me. IMO, there are better boats for day trailering.

Get the right type of boat for where you will be sailing. Don't get hung up on a particular model of boat. Go to the area that you will be sailing and see what others are sailing. It will be more fun if you are sailing the same model or similar model to what others around you are sailing, especially if you want to get into racing later. An active and helpful owners' association is worth a lot.

With a Catalina 20 or even a bit larger, and certainly smaller, you can bring her home and work on her in the off-season. But buy a boat that is sailable from day 1 and sail on the good sailing days, do boat projects on the crappy days.
Nov 8, 2010
Beneteau First 36.7 & 260 Minneapolis MN & Bayfield WI
If we are going to jump right in to suggesting a boat, based on your post I’d suggest a Capri 18. It’s a little big boat, with all the sails and controls of a bigger boat in an 18 foot package. Easier to tow and rig, and cost-wise should run you about $5k, and for that money you’ll get a much newer, more modern boat than say a Catalan 22.
Jun 27, 2019
NoneYet NoneYet NoneYet
Wow! Thanks for all the great feedback. Will be busy digesting this weekend. Also reading “The Complete Guide to Trailer Sailing”. Lots of great info all around. My goal is to hopefully find something at the end of the summer Or fall as the season ends... Great winter project to get ready for spring sailing I hope.
Aug 1, 2011
Catalina 270 255 Wabamun. Welcome to the marina
It's all relative. I was chuckling when I read the commentary about stepping a 22 or a M26. I could only -wish- that the 270 was as easy to step as the 26c was. They are all a tradeoff. I'm sure there are people who will read this with a much larger boat who step their masts, and think my efforts are easy in comparison.
Mar 2, 2019
Oday 25 Milwaukee
We previously owned a Catalina 22 and now are on our 15th year with our Oday25. Stepping the mast every time would get very old very fast. We keep our on a mooring on Lake Michigan. We own the mooring so our maintenance cost is almost nothing from year to year.
If I was to do it over I'd have bought a Com Pac 16 or 20' cat boat . The mast is hinged and the mainsail stays on the boom while being trailered. Launching is very very quick. The resale is very good. You'll get out almost every penny you put in if reasonable care is taken. They are very pretty as well.
Mar 20, 2015
Catalina 22 New Style SHSC, Lake Winnipeg
I have to disagree with the idea that a Hobie is a bad learners boat.
I learned on a 18ft SolCat.

Had my wife not been taken out on a Hobie 16 for her second attempt at sailing, she would never got into sailing. "That was a lot of fun. Let's buy a boat"

Thw trick is learning from others.

People don't just get in a car without any knowledge and drive around the streets for a couple summer to learn to drive.
A sailboat is.more complex than any car so best to shorten the learning time with formal training.

We bought a 16ft dinghy then took Dinghy classes with friends [as part of a holiday] instead of me reaching my wife.

Soon we took 4 week long courses in the Pacific northwest on keel boats where you stay aboard.. Started bareboat chartering 11 years ago...

Then picked up a Catalina 22 due to it's popularity and portability.

A dinghy is the ideal learning platform for beginners. Very easy to rig by one person
Might not even need a trailer. You get a real feel for all the nuances of sailing due to it's respnsiveness. And they can be a blast to sail.

Once you have a season or so of dinghy sailing, get a bigger boat.

Get a dinghy that will be easy to sell later.


Jan 31, 2009
Macgregor & Endeavour 26S and 37 Utah's Canyon Country