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How to Buy a Sailboat – Part I

By Captain David C. Bello

President, Fair Wind Sailing School

There is plenty of advice available on how to buy a sailboat. Unfortunately, much of it is written by those in the sailboat building or sailboat selling business – in other words, someone with a vested interest in steering you one way or another. If you have read those articles, you will quickly realize that this article is different. The suggestions contained in this article (and subsequent ones) are written from the perspective of a sailboat buyer and are the collective wisdom of someone who has purchased 8-10 sailboats and discussed sailboat purchases with dozens of other sailboat owners. The lessons learned apply to both new and used sailboat purchases. I hope you will learn from all our mistakes!!

There is a multi-step process that involves answering a series of questions. Successfully answering those questions will lead you to choose exactly the best boat for you. In the course of this series, I will discuss all those questions and cover the whole process. This article covers only the first step in the process because in my view, the first step is by far the most important.

The first – and again, most important step – is to answer the question "How will I use this sailboat?" When I say this, I don’t mean a general answer like "to race" or "daysail" or "to cruise." If you can only answer the question to this level of detail, you have a very high probability of making a very large (and probably very expensive) mistake – buying the wrong boat. When I say "How will I use this sailboat?," I mean in extensive detail. Here are some examples of questions you should be able to answer immediately and without any thought BEFORE you consider buying a sailboat:

  • If you intend to cruise, how long will your cruises be? Weekend? Week long? Month long? Extended?
  • What waters will you sail? Lake ? River? Bay? Ocean? Salt? Fresh?
  • How many people will be with you and how often will you be aboard?
  • How far away will help be?
  • How many spare parts and tools will you need to carry?

The answer to these sub-questions will dictate the optimal storage amount you need, recommended safety equipment to carry, type of rig, overall size of boat and power management system. It will also play a large role in determining the age of the vessel and which builders you should even consider (due to very high variance in reliability, stability, and seaworthiness among sailboat manufacturers – more on this in subsequent articles). For example, a boat sailed hundreds of miles offshore obviously would need to have a much different energy management system, provisioning ability, design reliability and manufacturing reputation and be quite different in design, rig, weight and size than a weekend lake cruiser. This extreme example seems obvious enough. However, even small differences in usage can lead to big differences in boat acceptability. For example, two extra people on board or one extra day at sea may require large differences in power requirement (i.e., alternator output, battery banks, voltage regulation, alternative generating). Yes, some will say that many of these items can be modified after purchase – and in some (not all) cases that is true. Yet, I would want to know my total budget – boat, repairs, updates, upgrades, etc., before entering into a transaction, not after the fact. I’d also want to know exactly what to look for, so I could accurately compare one vessel against another on all dimensions. Again, the point here is to know exactly how the boat will be used before starting to shop.

If racing is your game the same logic applies. What kind of racing? Is it around the buoys? Windward-leeward? Distance? What level of competition will you face? And how big are their budgets? Will you trailer the boat for national or regional races or just race locally? How experienced is your crew? Watch how long those carbon-Kevlar sails last the first time an inexperienced crew blows a tack and flogs the sails for awhile. Answering these questions will go a long way toward determining the importance of rod rigging, number of spreaders, sail technology and inventory, just to name a few toys you may want on board.

Sailboats are the stuff dreams are made of, but buying the wrong boat can be a nightmare – expensive, unpleasant and dangerous. The most important way to avoid making a mistake is to know exactly how you will use the boat – in great detail – before you begin shopping for your dream boat.


Capt. Dave is President of Fair Wind Sailing School, an ASA affiliate sailing school offering sailing instruction in the Virgin Islands, Chesapeake Bay , Florida and on Lake Erie and Lake St Clair . (See Captain Bios page.)

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