My First Sailboat: What Should I Buy?

first sailboatAlthough some sailors choose to just charter periodically or join a sailing club, most aspire to eventually have a sailboat of their own.

With your own sailboat, you can go sailing whenever you want, you can set it up to suit your own needs and preferences, and you can leave all your personal gear on board so it’s easy to pop down to the marina after work and head out for a sunset sail or for a weekend at your favourite anchorage.

When to Buy Your First Sailboat

So much of sailing is about the feel of the boat and the wind that you really need to just get out on the water as much as possible and sail.

As soon as you have learned enough to:

  • get to and from the dock,
  • understand who has right of way on the water,
  • get back to a crew overboard,
  • and have reasonable confidence in sailing a boat from point A to point B,

it’s time to get regular access to a sailboat so that you can practice, practice, practice (oh, and have fun, fun, fun, too).

Your First Boat vs Your Forever Boat

Many people have a goal in mind when they learn to sail. It might be sailing amongst the local islands for two weeks with the family or it might be sailing around the world. The right boat for these goals is often in the 30-45′ range.

The natural inclination is to go buy the “forever boat” that will meet these dreams. This is usually a mistake.
You first boat should either be a small sailing dinghy if you’re willing to get wet (what better way to remember what not to do than to end up in the water?) or a 22-28′ “keel boat” (a sailboat with a heavy keel that keeps it upright).

Why buy a smaller first boat that you know you’ll need to upgrade later?

Learning: The smaller the sailboat, the more immediate the feedback. It takes a long time for your inputs to have an effect on a 16,000 lb 35′ sailboat compared to a 4000 lb 26′ sailboat. To learn quickly, you need that instant feedback. This is why many of the best sailors started by sailing dinghies.

Safety: The forces on the lines of a smaller sailboat are such that you need minimal mechanical advantage and you are less likely to get injured when you make a mistake. This includes manhandling the boat around the dock as you learn the sometimes challenging art of docking.

Cost: The cost to buy, dock, and maintain a boat goes up roughly by the cube of its length. A 40′ sailboat costs about 3.5 times more to own than a 26′ boat. If all your going to be doing in the first couple seasons is sailing around the bay and to nearby anchorages, why be paying for a boat that’s designed for crossing oceans?

The Right Fit: This is by far the most important point. At the beginning of your sailing career, you just don’t know enough to really know what “Forever Boat” will be right for you. This is especially important if you plan to do any longer term voyaging. Your boat will be your transportation and also your home while you’re on it.

There are thousands of unique boats on the market and owners and brokers who are eager to sell them to you. Unless you have some experience, you really don’t know what you’re looking at and you don’t know how it will handle under sail in different conditions, what the maintenance burden will likely be, and even what it will be like to live on for a week or more.

How can you evaluate an anchoring set-up if you’ve only anchored a couple times during a course? How can you really understand the implications of the access to the engine if you’ve never done any engine maintenance on a boat?

Sailors love to endlessly debate the virtues of catamaran vs monohull, full vs fin keel, cored vs solid hull and deck, ketch or cutter vs sloop rigs, the list goes on and on. Only with experience and research will you develop an idea of what all of these terms even mean and what is important to you.

There are no right answers. Different boats are right for different people and different missions. Give yourself some time to learn to sail and learn what will work for you before you take the leap.

Ironically, larger sailboats aren’t very “liquid” assets. They take time to sell, sometimes a year or two. Buying a large sailboat on a whim and then deciding it isn’t right for you can take longer to correct than buying a small boat for a couple of years of sailing while you look around, talk to sailors, and find the right larger boat for the long haul.

I met a new sailor last year who’d made a horrible mistake. He just didn’t know it yet.

His first sailboat was a 46′, 40 year old, full keel ketch in poor condition. He’d paid way too much for a boat that was way too difficult for him to handle on his own. He couldn’t find anywhere to moor it locally and had no budget left over for maintenance. He was relying on friends to come and help him sail it, but friends get busy (especially when there’s maintenance to do).

The Right First Sailboat

The perfect first sailboat will be affordable to buy and own, large enough for an overnight or a week away, and easy to sell in a couple years if you want to upgrade.

The exact manufacturer doesn’t really matter, but I would recommend buying something that’s fairly common in your neighbourhood. This will make it easier to find parts and advice and easier to sell in the future. This point is by no means crucial, though.

The perfect first sailboat is:

22-27′ long: This is right in the sweet spot for size. My first was 26′ long.

10-30 years old: Any younger and you will see a lot of depreciation when you sell it. Too much older and you may have extra maintenance issues (though this really depends on the boat). My first was 40 years old and the deck was starting to go.

Fiberglass: Fiberglass lasts forever and needs little maintenance.

Sloop rigged: This means that there is a single foresail and a main. This is both the simplest and most efficient rig. There’s no reason for anything else on a boat this size.

Fin keeled: There are those who believe a full keel (which goes the full length of the boat) is better in very heavy weather, but you’ll be avoiding these conditions and a fin keel boat will perform much better and be much, much easier to maneuver during docking.

In Good Condition: No project boats! The point here is to get out on the water and sail your butt off. Make sure that it’s a boat that you can sail away today, even if it does need some work (all boats need work all the time. It’s called “the list”).

A Note on Trailer-Sailors

Trailer sailors can be great boats. You don’t need to pay marina fees and you can take them “at 60 mph to windward” to new cruising grounds.

However, you need to be confident that you’ll take them out sailing frequently. If the mast is difficult to put up and take down, you’ll start to find reasons not to go. Carefully evaluate the ease of rigging and your own willingness to fiddle with it daily.

Some places have dry storage yards next to a boat ramp so that you can store the boat on its trailer with the mast still up. This is a great compromise.

So start scouring the local clasified ads. It’s time to find your first sailboat!

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14 thoughts on “My First Sailboat: What Should I Buy?

  1. I will be starting the ASA school in another four weeks . I don’t own a boat as of now but I’m planning to buy 22-25 ft when I feel the time is wright…just going back and fourth on weather to trail and sail or pay for a slip….so when the time comes the numbers will do the talking.

    1. That’s great, Mark! Let us know how your classes go. Where are you located?

      The great trailer-sailor debate is very individual. Will you put in the effort to rig and de-rig? Is there somewhere next to a ramp where you can store the boat on the trailer with the rig up? If you can say yes to either of these, then the savings are great and you can just drive it to new cruising grounds.

  2. I am a novice sailor who just completed a basic ASA course and got my “beginner’s ticket”. I am also 69 years old, in good health, but not as nimble or strong as I once was. I am thinking about getting a used “first boat”, and your advice in this article is very helpful, especially concerning makes/models that are especially easy for a sole sailor to operate, as well as features to make such sole operations easier. I do have a question that wasn’t covered. I would like my first boat to have an inboard diesel engine (single screw) so I can operate it under power. I realize that a small outboard is an option, but I detest the sound of an outboard. How common is it for boats in the 25+/- foot range to have an inboard diesel? Any particular make/model that I should focus on in terms of the inboard diesel?

    1. Hi Bob,

      This is a great question. I totally hear you on the annoying noise of the outboard. Let me throw out some of the good things about them, though: They are super cheap, there are a ton of cheap boats with outboards, and you can remove them from the boat for service and parts and labour are also super cheap on them. The new 4-stroke outboards are also much, much quieter than the 2-strokes that you’re probably thinking of.

      Now the disadvantages: They are loud for extended motoring (unfortunately, sometimes you have to motor for hours at a time, depending on your sailing grounds and patience), and in any sort of chop, the prop tends to come out of the water. We even had the problem that when I took the anchor and bucket of chain to the bow of our old Haida 26, the prop would be pretty much out of the water!

      In answer to your question, there are many boats available with inboard diesels (or the old Atomic 4 gasoline engines) in the 25-29′ range. One way to get an idea of what models might be available in your area is to go to and do an advanced search. You can choose a sailboat in your length range and geographical location and then choose fuel type as diesel. Here’s an example. It’s a 1985 Bayfield 25 for $8500. There are many more.

      Good luck on your hunt, and let us know what you end up buying!

      1. Thanks – super helpful. I am willing and able to pay a bit more for maintenance, etc to avoid having to deal with the noise of even the quieter 4 stroke engines. I will check out the website and begin my search. Any other tips for this newbie would be appreciated. BTW, I am not interested in a “trailerable” boat – too much work and hassle for this old guy to get the boat in the water.

        1. I totally understand, Bob! Yachtworld is a great place to get ideas about different boats because it’s so well set up, but it’s really for people selling through brokers and tends to be on the expensive side. For boats of the size you’re looking at, I’d be checking Craigslist, walking docks, and the like (each area will have its own best online classifieds and I’m sure you’ll figure out where the best boats for sale by owner are located).

          1. Thanks – I live close to Annapolis MD so I will have lots of chances to check out boats for sale, once I educate myself more on what is out there and the general price ranges for particular sizes, makes, and specs. Scanning through YachtWorld has already begun that process…should be a lot of fun! For one thing, I am running across various terms and brand names for accessories like winches, furling this or that, and so forth that will lead to additional lines of educational research – all with a view to getting a setup (sails, winches, etc.) that is as easy as possible for one newbie guy to safely sail solo without dashing from stem to stern and enjoy myself while doing it.

          2. Good stuff. Yeah, I would say you should look for a boat with a furling headsail, self-tailing winches, and some sort of autopilot/tiller-pilot (the latter are very cheap and are an advantage of tiller boats). The actual brand names don’t matter so much, I don’t think.

          3. I am now interested in a 1982 Capital/Newport 30. From what I have read in a number of online reviews and chat rooms, it sounds like it might be a good fit, and is in my price range. Going over to look at the boat (its in the water) in a few days. Anything particular comments on this boat in general or anything (recurring problems, etc.) I should look especially hard at? I will of course have it surveyed if it passes my very uniformed “eyeball check”. Also, the boat has minimal communications/nav electronics (just a basic depth finder, compass, and a VHS radio), so any advice on what I should think about getting to upgrade both would be appreciated, as I will need to factor that upgrade into my overall cost?

          4. Hi Bob,

            That’s a good sized boat for a first boat. On electronics: It really depends on your personal preferences and how you intend to use the boat. You can do some good navigation with a tablet that has GPS, for example. I would recommend:

            • A VHF radio with DSC and onboard GPS or connected to a reliable GPS. This will let you call for help quickly and easily. It will transmit who you are and your locaation.
            • An autopilot so you aren’t stuck at the helm all day and can solo the boat (trim/raise sails while the autopilot handles the boat(
            • A reliable depth sounder for navigation in shallow areas and for determining scope when you anchor
            • Optional but nice when learning: A wind instrument so you can start to get a feel for what 10, 20, or 30 knots actually feels like and looks like. This helps you understand what you’re in for when you hear a forecast. Less important the more experience you get.
  3. Hi. My son & I have completed RYA 1 & 2 dinghy and have just returned from a two week flotilla in Greece on a 32′ . We would like to buy a dinghy to use in a couple of reseviors near us. I have seen a merlin rocket for sale which is within my budget. I like the teak deck ect and the lines of the boat but could you give me some advice on this as a first boat please.

    ps I am 11 stone, my son is and 9 years old.

    1. Hi Mark,

      Thanks for your question. In general, I think a sailing dinghy is a great first boat if you’re fit and willing to get wet. You’ll learn a ton about sail trim and balance, and you won’t break the bank.

      That particular sailing dinghy seems to be a bit of a racing dinghy with lots of sail area and designed for hiking. If you are in a low wind area or are just choosy about when you go out, you can do this safely, but you might want to talk to some owners first. I see they have an active association if you google “merlin rocket.”


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