How To Buy A Beginner Sailboat

How To Buy A Beginner Sailboat | Life of Sailing

Last Updated by

Capt Chris German

June 15, 2022

Will 2021 be the Year You Buy Your First Sailboat?

The recycling truck just hauled away the last of the champagne bottles you quaffed ringing in 2021 and a new decade is now perched on your doorstep.  For many, the brave new future that awaits them will involve crossing a few bucket list items off their proverbial list; and If you’re reading this article, odds are your first list item to cross off is to get a sailboat and sail into the sunset.

But that begs the question for the newbie sailor, which boat is the best boat for a beginner?

Perhaps it’s not the make of the boat that is half as important as the features that the boat might boast? Evaluating what your needs might be, what your budget might be and what your skill level might be are all keys to happiness with your new craft.


Table of contents

First Up, Don't Buy A New Sailboat

Boats are like pets in a lot of ways, they require attention, they require water, and most likely you don’t want to come home to find it roaming around your neighborhood. Buying a new boat is like buying a prada puppy when there is a shelter dog who needs a new home just down the street.  What’s more, there are literally millions of good deals on used boats that need new homes that will (a) keep one less fiberglass horror from the landfill and (b) save you thousands on day one when it drops in value the second you put the key into a new boat as it sits at the dock.

Used boats are worked in and the bugs are worked out. A used boat won’t make you cry when you t-bone the dock in your first season when you are still learning to let the main out and come to wind. Used boats cost a fraction of what you would pay for a new boat but don’t let that fool you, boats are expensive.

Start Small

Everyone knows the old adage: B.O.A.T. means Break Out Another Thousand. That’s pretty much true for anything over 23 feet. A 30 foot Catalina for example while very affordable and super common for newbie sailors has sails and motors that cost money, hauling and storage costs (odds are you won’t be able to keep this in your backyard) and of course, the toys. You’ll want the top of the line GPS plotter because without it, you will spend your first year until you learn to read a chart with it sitting on a sandbar because of its five and half foot draft.  But what’s nice about the Catalina 30 is she is a super forgiving boat meaning when you misread the weather and get caught out in your first storm, you’ll live to tell the tale because the old Catalina 30s are stiff, fat and heavy. But again a heavy boat requires more money to move it so it's always a cost benefit analysis when picking your first boat.

Trailer Sailors: The Answer To Where Do I Park My Sailboat?

I have an admission to make. I have a 42’ Endeavour, a 35’ Morgan, and a 23.5 Hunter and my favorite is the little Hunter. She sits in my back yard all year long and costs me NOTHING. The other two boats cost me thousands just collecting dust in yard fees but the Hunter can be dragged down to the sea anytime I want and with a somewhat quick flip of the wrist her mast is up and she is ready to sail. I can even pack her for the weekend in my own driveway.

But when you put two dogs, a wife, a bunch of gear and cooler in my little giant, she gets much much smaller. If I had little kids or older parents the boat would be a nightmare. I sold one of these last year and an older couple wanted to buy it to get out and go sailing. The four foot freeboard would have killed them and there is no way their calorically enriched derrieres were going to fit together in the v- berth. It’s a small boat, and it rides like one in anything over 15 knots of breeze. But if you are a newbie sailor and you are still learning port vs starboard, maybe you should pick your sailing days judiciously and if there are white caps out there keep your little Hunter on the trailer. 

But seriously, there are literally dozens of makes of trailer sailors out there and you can pick a very well appointed one up for under $5K if you shop around. And because it can be dry sailed down the Interstate, you can buy it in New Jersey next week and sail it in Florida  next month and pay winter prices to sail in summer weather without having to spend a month delivering it down the ICW in winter.

Tell Me What You Want, What You Really Really Want...

Spice girls aside, you really need to know what it is you want in a boat and that is exactly why many start out sailing in community fleets or chartering in the Islands. Do you want a catamaran or a monohull? A cat is all the rage right now and the epitome of comfort, but finding a place to dock a boat with a 15 to 20 foot beam is impossible in some places. A keelboat, while easier to dock, can often force even the stoutest of souls to the leeward rail in even the most minor chop. Do you want to lay out your hard earned cash to find that no one in your family has the stomach for your newest toy? A boat can be a lonely place when your wife refuses to join you.

My friend got a great deal on a Gemini Cat in Connecticut two winters ago. The boat was on the hard and part of an estate where the family had no interest in their departed father’s fantasy. He offered the family a fire sale price and stuck to his guns and he got a great deal to show for it. But soon enough he realized that the boat was not to his liking and proceeded to spend the next year gutting the craft and rebuilding it from the ground up. He’s got a great boat now and did most of the work himself, but it’s a cautionary tale. Think about what you NEED in a boat and not just what you want.

Physical limitations including proclivity to sea sickness are a factor. Do you want to spend weekends on this boat or just day sail it? Numbers of berths, layout of the boat and galley contents can all make or break a love affair with your new boat. So be honest with yourself and ask the tough questions. Do I really need a whosywhatsit or can I get by without it?

And the reverse is true too, don’t over buy. A built in wet bar is great in a 1970’s conversion van, but will you really use it on a weekender sailboat? Some things that the buyer lists as perks and value-addeds are not really worth it and there is no reason to buy something you know you will never use. Cut cost wherever you can because there will be at least a few thousand in things you didn’t think about when it’s all said and done. And please, don’t buy things from the Boating world just because they are cool, buy them because you need them to be happy and you know their purpose and function.

Now For The Name Dropping

OK here’s the spot where I tell you which brands are the best. Now I am a sailing expert, but opinions are like ...well you know. So start shopping and pick your favorite and comment on this post so that others might learn from your experience. But my first boat was a 1969 Lofland picnic - an old British Kit boat I found in the back a yard covered in weeds that I bought for $400. I lovingly restored it for a full season and realized why you shouldn’t paint a fiberglass boat. The hours of sanding and painting was undone in the first ten minutes after launching as the tide smashed me sideways into the dock putting a giant gouge in my brand new paint job. I tell you that not because I think you will ever find a Lofland picnic for $400, but I want you to look at boats with a jaded eye and diminishing expectations. This is not your forever boat, it's your starter boat so consider more than brand name and look at the price tag.

Buy used and work your way into it. The more work you do on it, the more you will learn from it. If you installed the battery system, then you will understand how it works. Stuff that is done for you teaches you nothing and I have heard all too many tales of guys who bought a boat and can only tack left because they never learned how to move the starboard jib car.

But here’s some names I think you should know- Hunter (obviously), Catalina, O’Day, Macgregor, Vanguard, Hobie, Corsair are all boats that I find to have good entry level boats in the 20’s range and can be found on the used market for a reasonable price tag. They are simple to rig, easy to find and for the most part not too expensive to own. I stuck Vanguard and Hobie in there because big boats get the glory, but dinghies make the sailor. If you want to dabble before you dive, a small boat is a great way to get started.

Boats I would avoid like to plague for newbie sailors- for various reasons but mostly because they are expensive or complicated rigs or designed to go faster than any newbie sailor should ever consider going. (In some cases they have all three factors working against them) J-boats, Stiletto, Morgan, Swan, Hinckley, Tartan all top my list of great boats. I have sailed each of them and love them.  But I do feel that they are a little too much boat for a learning sailor so save that for your next boat, because you know there will be another eventually. By the way, anything over 30 feet should be avoided until you have at least one full year of ownership under your belt. The costs associated with and  the more elaborate systems of a 30 plus foot boat is more than anyone who is still mastering the basics of ownership should take on 

The Big Finish

So will this be the year you buy your first boat? There really isn’t a better time to do it than right now while winter pricing is still effect and Spring is just around the corner. Buying your first boat can be an enjoyable experience for the whole family. Buy smart and look at prices over brands. Assume you are going to spend the same amount of money either up front or in the end. IE. You buy a boat for $10K and want a $50K boat, you’ll need to put $40 K into it. If you buy a $50K boat and are happy with a $50 K boat, then you won’t have to lay out as much cash to get it where you want it. But then again, boats are like potato chips, you can’t stop at just one. And before you know it that 26 footer is gonna look quite meager next to that 30 footer and onward you will go. It’s the natural order of things and we all suffer boat envy eventually. The key is not to burn your family out on your first boat- so buy wisely my friend and sail far.

How To Buy A Beginner Sailboat
Capt Chris German

Capt Chris German

Capt Chris German is a life long sailor and licensed captain who has taught thousands to sail over the last 20 years. In 2007, he founded a US Sailing-based community sailing school in Bridgeport, CT for inner city youth and families. When Hurricane Sandy forced him to abandon those efforts, he moved to North Carolina where he set out to share this love for broadcasting and sailing with a growing web-based television audience through The Charted Life Television Network.

Read more articles

by this author

Home /

How To Buy A Beginner Sailboat

How To Buy A Beginner Sailboat
7 Best Places To Liveaboard A Sailboat >>Can You Live On A Sailboat Year Round? >>

Most Recent

Important Legal Info

Similar Posts

Popular Posts

Get The Best Sailing Content

Welcome aboard! Check your email...
Oops! Something went wrong while submitting the form. is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon. This site also participates in other affiliate programs and is compensated for referring traffic and business to these companies.

(866) 342-SAIL

© 2024 Life of Sailing
Address: 11816 Inwood Rd #3024 Dallas, TX 75244
DisclaimerPrivacy Policy