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Buying Your First Sailboat

Updated on November 8, 2012

I Want To Sail!

So you've been bitten by the sailing bug. You dream about endless summer days with the wind in your hair silently gliding across vast oceans in search of adventure, discovery, and the perfect rum drink. You've spent a few days on one of your friend's sailboats and have decided that the sailing life is for you.

Now all you need is a boat to call your own ...

But hold on there, cowboy! Don't just go out and throw down your hard earned $$$ on the first girl to catch your eye. Just like any long term relationship, you need to put some thought into the purchase of your first sailboat. There are many factors that new sailors commonly forget to think about (or know about or care about), so keep reading and hopefully the knowledge you gain from this article will help you in your decision.

Small sailboats are easier to learn on and will be more enjoyable for a novice sailor!
Small sailboats are easier to learn on and will be more enjoyable for a novice sailor! | Source

Size Does Matter

That's right. Size matters. However, forget about what the tabloids tell you. Smaller is better! Especially for your first boat. A common mistake that many first time boat owners make is buying a vessel too big for their novice skills. If you make that mistake, be prepared to spend the majority of the good sailing days stuck at the dock and going nowhere fast.

Buy a small sailboat to start with. There are many reasons why you should consider a small sailboat vs. a larger one. First and foremost ... they are cheap! You can pick up a 20-23' sailboat in good condition with sails, an outboard motor, and all the fixin's you want for as little as $1000 - $3000 bucks. Talk about a small investment! And trust me ... the less money you spend on your first boat the happier you'll be. This is the boat that you are going to bang up learning how to dock, run aground while you're learning how to read a chart (stay in the white), and it is MUCH cheaper to moor and maintain a small sailboat.

After a season sailing in your local waters you can sell your small sailboat and move up to a larger boat ... like a 27-30'! I know it doesn't seem like a huge change, but the difference between a 22' sailboat and a 27' sailboat is HUGE! Not only in maintenance, amenities, and sail-ability, but also in price. Once you hit the 27' range, you'll be looking at $10,000 - $20,000 easy for a used boat. And once you hit 30' ... well, lets just say that you can easily be past six figures.

So start small. You'll thank yourself later. And the knowledge you'll gain on your little $1,500 sailboat will be well worth it!

How To Meet Other Sailors

Sailors are a rowdy bunch ... but generally very friendly! The best time of the year to meet other sailors (and hopefully steal a ride on their sailboat) is during the "racing season". This is generally whenever there is sunshine, a breeze, and a full cooler of beer!

Most local marina's and yacht clubs hold seasonal regattas (sailboat races) and if you go down to the marina on these nights, then chances are some boat will have a spot open for some "rail meat" (someone who just sits on the windward side of the boat to provide stability).

This is a great way to meet other sailors, try sailing on a variety of boats, and just get out there!

Get Out Sailing

Sailboats also vary greatly based on what they are designed to do. Are you looking for a weekender to escape to a nearby island? Do you want to race in the local harbor fleet? Are you thrilled when the boat is heeled over and you have a rail in the water - or would you rather the boat stay us upright as possible?

The best way to not lament buying a boat that doesn't fit your style of sailing is to take a basic sailing course. Most marina's host a sailing school or can point you in the right direction. For a couple hundred bucks, you'll spend a weekend out on the water learning the basics of sailing as well as getting a feel for what different boats are capable of.

My first boat was a Columbia 22'. This was a spectacular boat ... for what I wanted. I wanted a sturdy, safe, tank of a boat that I could sail and camp out on for a weekend. The Columbia 22' had a huge V-berth, little place for a small camping stove, a port-a-potty, and was build like a tank. However, later that year I met a friend who raced his little Ranger 21' ... which had almost NO cabin ... but was fast as hell. I realized after skirting along at speeds twice as fast as my sailboat that I wanted less of a floating bathtub and a little more speed racer myself.

So, before you decide on what boat is "perfect" for you ... first decide what type of sailing you'll most likely be doing. Then find a boat that suits your needs.

Finding The Boat

Since we want to find a small, cheap, and in decent shape boat for your first summer of sailing, the best place to look would be the classifieds. I wouldn't bother going to a broker because normally there isn't enough profit in the smaller sailboats to make it worth their while. Instead, hit up sites like Craigslist or take a walk down at your local marina. Normally there will be a bulletin board full of "for sale" boats.

Now get ready to look at a lot of boats! Once I had decided on my first sailboat (The Columbia 22') I looked at about, oh I don't know, probably 30 boats before I found my future love. Most of the boats you'll encounter will be disgusting, rotting, cracking pieces of ... crap. But don't be discouraged! These older small sailboats were built like tanks. Most of the issues will be cosmetic. Here's what you need to look for.

A morning at a public dock on the Columbia River.  Guitar, Boat, Stove ... what else could you ask for!  This was with my first boat, a Columbia 22'.
A morning at a public dock on the Columbia River. Guitar, Boat, Stove ... what else could you ask for! This was with my first boat, a Columbia 22'. | Source

The Motor

Make sure it runs and doesn't look too beat up. A good outboard will cost you $500-$900 used (yep - almost the entire budget of your boat), so this is a large part of your purchase should you end up buying the boat. Buy a bum motor and you just increased the price of your boat 25% after you find a replacement. When I bought my first sailboat it had a great little 5.5Hp Outboard that was in like-new condition. It was probably worth $1,000 on its own. I bought the boat for $1,200. So make sure you're buying a good motor.

The Sails and Rigging

When you first start sailing, you'll probably only going to need to worry about 2 sails. The mainsail and the headsail. Don't buy a first sailboat with a complicated rig. KISSS (Keep It Simple, Stupid Sailor). The modern-day sloop is a perfect rig to begin on (learn more about different rigs here). Check the standing rigging as well. These are all the wires and hardware that keep the mast upright. Typically you'll have one attached to the bow, one to the stern, and then one to either side. The ones attached to the side will be secured to the hull via chainplates. Make sure these appear sound and secure.

Here a core cutout of a typical sailboat deck.  Notice the plywood sandwiched between the fiberglass.  If water gets in there, it softens the wood and create deck rot.  This will make the deck feel "spongy".
Here a core cutout of a typical sailboat deck. Notice the plywood sandwiched between the fiberglass. If water gets in there, it softens the wood and create deck rot. This will make the deck feel "spongy". | Source

The Hull and Deck

Now, typically while buying a boat you'll want to get a survey done before you purchase. However, if you're buying a tiny little boat that is under $2,500, then I wouldn't bother with the haul out and survey. First off, if the boat is in the water and floating - then the hull is probably fine. Check the bilge for water. If there is water, clean it out and tell the owner that you'd like to "think about it" and come back later. When you do, check the bilge again. If it remained dry, then you probably have a sound hull.

Next, walk around on the deck and check for squishy spots. This is an indication of deck rot (water getting into the balsa core). While normally not a life threatening condition, advanced deck rot is very hard and expensive to repair. However, if you just want a boat to learn how to sail on, then this won't be a hold up unless it is really bad. Again, if you were buying a larger boat, a survey would be able to help you asses the extent of the rot (and the needed repairs). But since you are being smart and buying a cheap little boat to learn on, then as long as it's not too bad, it's not a deal breaker.

Everything Else Is Just Icing On The Cake

If you have a motor, sails, and a solid hull ... then congratulations! You have a good little boat. Other things like cushions, galley, head ... these are all things you can add at your discretion if the boat doesn't already come with them. A little propane camping stove makes some wonderful meals while enjoying an evening anchored next to a secluded island! Again, there are some AMAZING deals out there. My boat ($1,200 remember) came with like new cushions, tons of little extras, the electric system "almost" complete, 3 sails (main and 2 headsails), perfect motor ...

So just keep hunting until you find the perfect little boat!

Be careful ... some small boats try to dress up to look a bit more classy then they are. I've seen small sailboats that are nearly identical ... but because one owner put a $200 coat of pain on the hull, he sold his for $3000 more than the other one. Don't be duped by cosmetic up-selling. If the sails, hull, and motor are there ... then you too can have an awesome looking boat for the price of a gallon of paint.

After 2 seasons sailing my Columbia 22' I moved up to a 27' boat that I am planning on moving onto very soon. That's how much I love sailing. If I ever choose to leave my local waters, then I'll probably once again be buying a slightly bigger and more seaworthy boat.

But be smart. Buy the small boat first!

Join My Adventure!

Come follow along on my blog as I attempt to live onboard my 27' Sailboat in a Simple Living Experiment. Join me as discover the difference between needs, wants, and what really matters in life!

In Search Of The Sea


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    • Fortadam profile image

      Fortadam 6 years ago from Portland Oregon

      @RealHousewife Sailing is one of those things that you either love or hate. I find that it is the most peaceful yet adventurous way for me to spend time outdoors. A typical sail will have peaceful times (when everything is going right) and absolutely exciting times (when the boat is heeled over going to weather and it feels like you're flying).

      I'd love it if you headed over to my blog and followed along! My boat will be in the water later this month, and I hope to have some web video episodes up in a couple of weeks detailing my transition into a simple living lifestyle!

    • RealHousewife profile image

      Kelly Umphenour 6 years ago from St. Louis, MO

      Very cool! I loved this and I would absolutely love hearing about your experiment!

      I knew a girl who decided to buy a sailboat as a dude magnet...cluck, cluck, cluck...St. Louis isn't exaclty a sailboat kinda town:) lol

      I have never even been on a sailboat...I know I would love it though.

    • Fortadam profile image

      Fortadam 6 years ago from Portland Oregon

      @ralph All very good points! I might edit some of those into the Hub :) I was focusing more on keelboats with a cabin - but it is an important fact that most people learn to sail on a small, open dingy like a Sunfish or Laser. And I completely agree ... if you make a mistake in one of those little sailboats they let you know ... either by stopping or tipping you over. Unlike a keelboat (which is incredibly hard to capsize to those that don't know), a day-sailor dingy is almost sure to get you wet!

    • Ralph Deeds profile image

      Ralph Deeds 6 years ago from Birmingham, Michigan

      Good advice. My first boat was a Cal 20. Later I bought a used Sunfish, which is one of the best boats to learn to sail on. It's easy to launch on any beach. If the sail isn't trimmed right the boat will stop which teaches you to pay attention to the wind. Also, it's easy to right if you capsize. As many as three kids or two adults can sail a Sunfish. But it's worth every penny. It's a sport that can be enjoyed all your life, with your family or solo.

      To your advice I'd add that the purchase price is the smallest cost of owning a boat. A mooring, winter storage, maintenance and insurance add up quickly.