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7 Crucial Things To Consider When Buying A Sailboat

Buying a sailboat is no small thing. You’re not going down to the grocery store to pick out a loaf of bread. Any old sailboat won’t do. And unfortunately, Consumer Reports doesn’t do a yearly review of the best sailboats on the market. So unless you happen to be a sailboat expert, it’s hard to know what to look for when choosing a boat.


That’s where we come in. In this post, we’re going to give you a checklist of 7 things to consider before purchasing a sailboat. Of course, due to the significance of the purchase, we recommend doing thorough research before making a final decision. The last thing you want is to be stuck with a sailboat that you don’t like.

#1 - How Big of a Boat Do You Want Or Need?

You want your boat to be large enough to meet all your needs. Will you only be out cruising by yourself, or will you and your family be boating together? Are you hoping to entertain guests aboard your sailboat? Will a crew be joining you on your sailing expeditions? Will you be sailing overnight and need sleeping accommodations? All these factors will determine the size you need.

#2 - Where Will You Be Sailing?

Additionally, consider where you will be boating. Boating on the Atlantic Ocean is much different than boating on Lake Michigan. Boating in small rivers requires a different vessel than can be used on the Chesapeake bay. The boat you choose must be appropriate for the environment where you’ll be boating.


As Sara Clemence says:

In the Northwest or Maine, for example, the water is deep enough that you don’t have to worry about how far your keel goes into the water. But try squeezing a 16.5-foot draft into Long Island Sound or Chesapeake Bay, and you may be in for an unpleasant grounding.

#3 - How Much Experience Do You Have?

Consider your own boating experience. If you are new to boating, purchasing a large boat is probably not a wise decision. There are numerous horror stories of people purchasing large boats and then losing control of the boat in the open water. Instead of starting large, start small and then trade up as you gain additional experience.


#4 - What Is The Purpose Of The Boat?

This point was addressed above, but it needs to be considered in conjunction with your budget. If you need a boat large enough can carry ten people, it will cost more and you may need to cut some of the luxury items you had hoped to include. After all, it’s pointless to purchase a boat with a kitchen if the boat isn’t large enough to hold people who could enjoy it. Size will probably need to take priority over luxury when purchasing a sailboat.

Additionally, consider these words:

Nothing improves comfort more than size. Within limits, everything on the boat can be changed except size. But size is a double-edged sword, as costs and maintenance even in slightly larger boats are disproportionately higher.

#5 - Are Your Purchasing New Or Used?

If you are purchasing a new boat, it will be ready to sail the moment it becomes yours. However, if you purchase a used sailboat, you may need to make repairs or want to make upgrades. Will you be doing the work or hiring someone else to do the work? Also, do you have the time necessary to shop around for the gear and learn to do the work? These repairs and upgrades will obviously cost money and should be considered when calculating your total budget.

Consider this:

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).


If you are purchasing a used sailboat, be sure to, at a minimum, closely check the following areas:

  • Engine. Have a mechanic thoroughly examine the engine to ensure it is in proper working order. 
  • Electrical work. Rewiring a boat is a complex process. Have a certified electrician examine all the electrical systems in the boat. 
  • Deck and hull integrity. The deck and hull should be, at a minimum, dry and intact. If they’re not, repairs will be necessary. 
  • Safety equipment. Insurance companies require a certain amount of safety equipment aboard a sailboat. Missing equipment will need to be replaced.

#6 - What Will The Additional Costs Be?

Unfortunately, there are numerous recurring costs involved in owning a boat. Insurance, which is more expensive the larger the boat, is necessary. Storage is necessary unless you happen to own property on the waterfront. Docking and mooring at various locations costs as well. When calculating your overall budget, take time to research these additional costs.

Cruising World makes this helpful point:

Focus on the total acquisition costs: the purchase price plus the inevitable refit. A good rule of thumb is to use only half the boat budget to buy the boat, then employ the other half for the requisite upgrades. A common boat-buying mistake is not reserving enough money for the overhaul. Also, prepare a realistic annual maintenance budget before the purchase. A boat stuck on the dock provides no joy.

#7 - Is This A Boat You’ll Be Using For Many Years?

Many first-time boat buyers make the mistake of thinking that their first boat will be their “forever” boat. In other words, they go into the buying process assuming that they’ll be sailing their first boat for decades and thus need to purchase a boat that will meet their every need.

This mentality can lead to the mistake of buying a boat that’s too large. This is a mistake for several reasons:

  • Safety. Large, expensive boats require a significant amount of skill to operate. If you are not a skilled boater, you are putting yourself and your passengers in danger by buying a boat that is too large.
  • Learning. It is much easier to learn the finer details aboard a smaller, easily controllable craft. A smaller sailboat gives you almost immediate feedback when you make changes while sailing. This feedback is critical for learning.
  • Cost. The bigger the boat, the higher the cost. Initially, your sailing will probably be limited to smaller locations. Why purchase a boat designed for oceans when you’ll be sailing on small bays?
  • Fit. When you begin sailing, you simply won’t know what type of boat you truly want. If you purchase a big boat too soon, you may end up being stuck with a boat you don’t like. And the unfortunate reality is that big boats are difficult to sell.

Ideally, your first sailboat should be:

  • Between 22-27 feet long.
  • 10-30 years old (if buying used). Younger boats will depreciate too much and older boats will require too much maintenance.
  • Fiberglass, due to the long-lasting, low-maintenance qualities.
  • Sloop rigged. These are easy to control.
  • In relatively good condition. You don’t want to purchase a project boat for your first one. It’s too easy to burn out and give up on sailing altogether.


Buying a sailboat is an exciting purchase that shouldn’t be taken lightly. If you do your research, you can set yourself up for years of delightful outings with minimal hassle. However, if you simply go out and purchase a boat without doing the appropriate due diligence, you can create additional costs and work for yourself.

Vito Dumas said, "It's out there at sea that you are really yourself."

A sailboat can be a delightful thing that truly allows you to be yourself. Happy sailing.