top of page
  • Writer's pictureBill Kinney

What Sailboat Should I Buy?

This question in one variation or another, is probably the most commonly asked question on internet sailing forums. Since this is the internet, there is never a shortage of people with opinions.  A few of the opinions are carefully considered, some are totally hare-brained, and all are passionately argued. One thing almost of these opinions have in common is they have very little to do with the person asking the question and a great deal to do with the person answering it.

Following is the condensed wisdom of every smart person I have met who knows a lot about sailing, and a lot about boats.  Some of it is my own research or opinion, some has been learned through the hard lessons of life, and some of it is common knowledge that is, sadly, not so common. Although is is written specifically for people interested in buying a cruising sailboat, the general concepts apply to most kinds of boats.

I am going to present some "Rules" here.  Maybe they are better described as "guidelines", because things are always a bit "squishier" in the real world than I can summarize in a short paragraph. Certainly, each of the following rules could be expended into its own feature length article, and this post itself could be a book. I assure you, if you look for the take-away lesson, and do not pick nits, you might learn something. I have professionally helped people select their "perfect" boat in the past pretty much by following these rules, and I believe that those choices were all good ones.


Bill's Zero of Boat Buying Happiness: Anyone giving you advice about what boat to buy who does not spend (at least!) an hour asking you questions about YOU, is actually telling you what boat THEY want to buy.

Even before we talk about boats, we have to talk about the people who will want to give you advice. Most free advice you get is worth less than you pay for it.

It is obvious if you know even a tiny bit about boats that there are thousands of different kinds.  No one boat is perfect for everybody.  Less obvious is that no boat is completely perfect for anybody! All boats are compromises. I could not recommend a boat to you if I do not know where you are sailing, your experience level, the amount of maintenance you want to do yourself, your short and long term financials, number of people in your family, other hobbies, etc. Even how big you are can matter.

So, start out by ignoring any and all advice from someone who is not very nosey about you, and your hopes and dreams. With that said, let us proceed:


Bill's First Rule of Boat Buying Happiness: Do not buy the biggest boat you can afford. Buy the smallest boat you can tolerate.

Everybody wants a bigger boat. Well, almost everybody.  The problem is that almost everybody will be happier with a boat smaller than the biggest one they can buy with the cash on hand, or far worse, with the biggest loan they can get.

You will sail a smaller boat more often. You can sail it with fewer, and less experienced crew. You will be able to go more places. You will have more money to take proper care of the boat, and to spend in the fun places your boat takes you.

To be sure, this is a rule that bends to fit. Not everybody has the same needs or tolerances. If you are buying a boat to sail by yourself on a small lake, you obviously have a very different set of needs than family of six living aboard full time and regularly crossing oceans.  If you find that every boat you "need to have" is at the very top of your budget, you really might want to take a look at the definition of the word "need."

To give you a feel for relative costs, boat purchase and maintenance costs rise very closely with the length CUBED. This means that the maintenance and purchase costs of a 31 foot boat are HALF that of a forty footer, and the forty footer is about HALF a fifty. This is true no matter if you want to believe it or not.  The range of prices in the used boat market can obscure this relationship, but it is very accurate for new boats in the same build class, and it always is true for maintenance costs.

Bill's Second Rule of Boat Buying Happiness: It will cost more than you think.  A LOT more than you think. Think of a number. A big number. Nope, not big enough.

You'll find many "rules" promoted about what it costs to maintain a boat. Most of them are obviously wrong, because they are based on what you paid to buy the boat.  An older boat with a lot of problems is going to sell for less than a shiny new boat in great condition.  Do you really think that older boat will take LESS maintenance? If you get a boat for free, is the maintenance free?  Of course not. We need a "rule" based on a more intelligent starting point.

My guidelines make the assumption that you are starting with a boat of average complexity for its size, that is in good shape, and you want to keep it in condition as close to "like new" as possible.  In what most traditional sailors would call "Bristol condition." I am also assuming that you will do a significant fraction of the work on the boat yourself.  Not everything, but the basics.

What you paid for the boat has very little to do with the cost of keeping her in good shape. Rather the number to use as a basis is what would it cost you to buy that boat NEW TODAY. Obviously, many boats are long out of production, so you'll have to make a best guess based on similar boats.  Once you have that number, expect to pay 5% of that number, on average, every year to keep and maintain it.  Yes, that is a big number. If it sounds too big, see Rule One, above!

Let's put some hypothetical numbers out there:  A middle-of-the-line, 40 foot, ocean cruising sailboat sells, new, today, for something on the order of $400,000. By my rule, you can expect to pay roughly $20,000 in an average year to dock, insure, supply, and maintain such a boat.  It makes no difference how old that boat is, or what you paid for it.  The average cost to keep it going does not go down with age, but rather rises every year with inflation.

Obviously, this can vary by a very large margin depending on where you keep the boat, how you use it, and your desire/ability to do some, most, or all the work yourself. Also, some years will be "cheap" and others very much not so.  For example, every 10 to 15 years you'll need to replace the standing rigging on that 40 foot boat.  That will cost something like $8000. About the same frequency you'll need a full set of new sails, about $10,000.  

Suppose you start out by buying an old, neglected boat that is really cheap?  How much money will it cost to get her back to excellent condition?  See Bill's Third Rule...

Bill's Third Rule of Boat Buying Happiness: If you want to go sailing, don't buy a crappy old boat! Never! Ever! Just say "No!"

If you are buying a "project" or a neglected boat in the hope for a bargain, it is far more likely you will be disappointed and frustrated than happy.  Even people with many years of experience get burned when they take on an old boat as a project.

If the thought of bringing an old boat back to life is more appealing than actually going sailing, then have at it!  There is certainly nothing wrong with rebuilding old boats, it can be a fun and rewarding hobby.  But do not confuse it with going sailing.

Look at it this way:  If you want an inexpensive, reliable car to get you to work every day, would you jump on that 1953 Studebaker rusting away in your Grandfather's barn? Of course not, even if it was free!  If your dream is to rebuild an old car it might be the perfect opportunity, but if you want reliable transportation today, it would be an obvious mistake.  

So if you are a sailor, and especially if you are not yet a sailor but want to be one, don't go buying a boat that only a boat restorer would want to have.  You'll have way more fun SAILING a smaller, better found boat in the years (yes, years!) it will take you to fix up a junker.

Bill's Fourth Rule of Boat Buying Happiness: Pay a bit more and get a better bargain.

You likely would not believe this if you heard it from a yacht broker trying to sell you a boat. If you hear it from me, hopefully you accept it as containing more than a grain of truth.

It is a little understood, and very rarely articulated, fact that the REAL bargains in the boat world are closer to the top of the market than the bottom.  Boat buying in the internet age is a world-wide market.  Boats in poor condition drive down the price of those in excellent shape.  

Boat repairs are very expensive and very time consuming, and are never properly deducted from the price of the derelict boat, or even the one that has simply been neglected.  

In the same way,  all the money, work, care, and love that were put into the top-shelf boat are never recovered in the final sale. Spend $50,000 on a 50 foot boat, you will probably have bought yourself a money pit nightmare.  Spend the same money on a 35 foot boat, and you might just have a new sweetheart.

33 views0 comments

Recent Posts

See All


bottom of page