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It was a sunny summer afternoon in 2017 when we approached the Storm Petrel - our future sailboat - for the first time.  Her faded orange hull was dated, but friendly. We were novice sailors and needed a means and motivation to sail every weekend.  (Check out how we learned to sail here). We had no idea what great adventures our girl would take us on.  We did, however, know that it was our first time buying a sailboat, which is something we took quite seriously.

At Damn Skippy Wear, we feel that buying a sailboat is probably the single biggest step you can take to help yourself climb the learning curve.  It’s motivational, always available, personal and FUN. But it can be an intimidating and challenging experience for a beginner (or even an intermediate) sailor. Important note: when looking at buying a sailboat you should try to take an experienced sailor with you, who knows what to look for (WE DIDN’T 🙄).

Read on for a primer on the first things to look for when buying your first boat! This guide is specifically for masthead sloops in the size range of about 22-27 feet that don’t have an internal engine.

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Catalina 22 hull

Buying a sailboat: first meeting with Storm - our soon to be Catalina 22.

Buying a Sailboat - Your First-Time Guide

Starter Boat Costs

So first off, this isn’t as bad as it sounds.  Yes, boats cost money, and yes, buying a sailboat will be out of reach for a lot of people in the immediate future. However, if you are on the fence, we were absolutely floored by how economically one can get into sailing.

Taking the ubiquitous Catalina 22 for example: whether you are in Alaska, the Great Lakes, or the Gulf Coast, you can buy a used C-22 for $3500.  The beautiful thing about sailboats is that they have no moving parts (relatively speaking), so they don’t wear out like cars. Buying a sailboat built in the 1970’s which is still completely seaworthy is a reasonable proposition.

We came to this realization in our sailing infancy when we started looking at boats on Craigslist just to dream.  We couldn’t believe our eyes. $3400? We had thought sailing was only for rich people. A few short months into taking up the hobby, we realized that it was within our financial reach to buy a 22-foot boat which would ensure we had no excuse not to sail every weekend.

We found ourselves in an aircraft maintenance hangar, looking at an old (but immaculately maintained) C-22 called the Storm Petrel.  

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Catalina 22 drawing

Where to look

To start dreaming about your sailboat adventures, we recommend looking at Craigslist, Sailboat Listings, or Boat Trader. After you start zeroing in on your dream, you should do some reading on the specific boat you are considering - the operating and maintenance manuals should be available on Google.  Some rules are true across the board though, and you should familiarize yourself with the basics.


The Previous Owner

This was the first lesson in buying a sailboat – the person we bought it from was an aircraft mechanic, so we knew he had taken good care of it. He actually owned the whole aircraft maintenance business. The whole hangar was “dress right, dress” as they say in the US Army and it was clear very quickly that this man took care of everything he owned. The boat was even parked under a roof, so she was doing well. He had told us lovely stories about him and his wife learning to sail in this boat and surely we were feeling better and better about buying from him. He also impressed us by knowing the whole history of the boat. Apparently, a naval officer had commissioned it and it was delivered to Adak, Alaska back in 1979! This girl has got some experience, we thought!

So ask the current owner about the boat’s history. Does he take time to explain it? Does he speak of it highly? Did he cherish the time with his boat? Where did he sail it? Is he a novice or experienced sailor? Has the boat been in any accidents? It becomes obvious when someone gives you half-ass answers or is BSing their way through. Keep an eye out for that.

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Catalina 22

Buying a sailboat: first meeting with Storm - our soon to be Catalina 22.


Hull and Fittings

A Google search provided us with some checklists of items to look at before buying.  Hull integrity and fittings are certainly the most important, and it’s usually fairly evident when there are problems.  You need to come prepared to look at every inch of the hull, inside and out. This means crawling under the boat, sticking your head into lazarettes, and opening the bilge.  Diligent work is required here, don’t stop until you have seen every inch! Make sure you bring along a flashlight, or better yet, get yourself a waterproof solar-powered battery charger to live on your new boat.  Trust us, this will come in handy.

Damage to fiberglass typically doesn’t take an expert to identify - it’s usually glaring.  Less obvious fiberglass cracks can look like little black spider-webs, and amateur fiberglass repair is easy to spot.

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Fiberglass cracking

Buying a sailboat: Check for fiberglass cracks

As far as the through-hull fittings go (places where an instrument goes through the hull, like a depth sounder or drain), damage can be a bit harder to find.  Sometimes you won’t be able to access or remove the fitting to inspect it as closely as you would like. For these items, we recommend putting your hands on all the sea-cocks (valves inside the through-hull fittings) so you know where to go to shut it in right away if something is leaking upon launch.

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Through hull fittings

Buying a sailboat: through-hull fittings are an integral part of the boat. If you can't check them, check the sea-cocks.



To some people this guide is about buying a sailboat, to others, it is about buying a second home and they want it all: a couple of lazy boys, a lounge chase, and a California king inside. Thus, this one is a subjective area and it depends how fancy you want to be. A few questions to ask yourself:

  • How many births do you need?
  • Do you need a marine head (pooper)?
  • Do you want to cook inside?
  • How much room do you need to move around?
  • Do you want to spend the nights inside the boat? (That is super fun and kids love it!!)

Do make sure the inside doesn’t have mold. That could mean that the previous owner didn’t store the boat properly during the winter, on the offseason, or in between sailing sessions. It could also mean that there is a leak somewhere on deck and the water could have been dripping through. Combine that with improper storage and voila, you’ve got mold.  


Rigging and Sails

Rigging and sails shouldn’t be a showstopper for a starter boat, but it’s certainly nice to have confidence in your lines.  Losing a halyard as a novice sailor can wreck your day pretty fast, so you should make sure you put eyes on the whole length of every line on the boat.  For instance, part of the halyards may be run inside the mast. It would be a pain to take them out, but the part inside the mast could be taking the greatest beating, so it’s advisable to do your due diligence.

What kind of sails does it have? You’ll need different size jibs and a mainsail of course. Does it have a spinnaker? Not required, but kinda cool if it does, so you can cruise nicely downwind. You need to make sure that the sail sheets are in good order as well.

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Rigging and sails considerations

Buying a sailboat: internal halyards run through inside of the mast. Mast wiring is usually located there as well.



Electrical systems are one of the most important things you should look at when buying a sailboat.  Electrical failure is the number one cause of fires at sea - a devastating and dangerous outcome. While you may not have access to each wire and electrical component, make sure all the lights, sounders, radios, and other systems are functioning and the power supply is not flickering.  Look for excess heat coming from electrical systems, and check the battery for corrosion and buildup.

If you will only be doing daytime lake sailing for your first season, then maybe you can let some electrical work sit on the back burner.  However, if you are putting your boat in the ocean, in a high traffic area, or are planning on sailing at night, you MUST confirm that your lighting is working and coast guard compliant.  Remember also that the rules have likely changed since your boat was manufactured, so have a look at the current state of the law here

In any event, don’t forget to pull your battery out of the boat and give it a good charge before setting sail!

Ours also came with a radio already installed. That is a nice perk if you’re considering sailing it in the ocean.

 Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Sailboat proper lighting


The condition of the keel is sometimes difficult to ascertain by looking, and it’s a scary component to have problems with.  There are many types of keels (swing keels, wing keels, etc) with different designs and issues. Look for corrosion and rust in the metal components, confirm the presence and condition of the zincs, and ask the seller for a history of keel maintenance.  Make sure you compare this with the manufacturer’s manual for the boat.  If they can’t remember the last time they maintained the keel, it’s probably time to do it.  The Storm Petrel features a swing keel, for which we replaced the cable (see below) after a couple of seasons sailing.

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. Swing keel cable on a Catalina 22.

Buying a sailboat: keel cable and other keel hardware should be replaced per manufacturer's recommendation every so often. Get your eyes on these components.


Outboard motor

So, ok...Buying a sailboat is all fun and games, until you realize that it doesn’t come with an engine. A lot of the boats get sold without an outboard and that’s where the extra cash is needed. The outboard is used to get the boat off the dock, back to the dock, when there is no wind, in an “oh shit” situation like the bottom being very close to the keel or just when you want to. The good news is that there are lots of outboard engines available on Craigslist and chances are you also know people that may have one for sale.


Outboard reliability

Brand spanking new ones are nice, but also spendy. If you find a used one, make sure it is reliable and the pull cord works well as to not get you stranded...unless you like beaucoup paddling. You gotta also figure out the horsepower required for your boat and for the conditions. We bought a 4.1 hp super old relic Johnson and it worked great on a small lake on a Cat 22. Although truth be told, one of us (not Linda) pulled the cord completely out while starting it in the middle of the lake….. Men, try to use less guns on this maneuver and you only need to pull the cord out a bit for it to start. You can also let your lady handle this. :)

Note: if you’re buying a bigger boat, it will have an internal diesel engine. And that’s a whole new ball game.



The best scenario here is that the boat comes with a trailer and the trailer is in good condition. Some owners make post-factory modifications to their trailers (as ours did). For example, our trailer came with special steps you can use to climb into the boat when the boat is hitched and trailered. That makes a huge difference when you’re standing the mast up, rigging down on land, or fixing the boat and you have to go up and down a lot.

Trailers can cost quite a bit and if your proposed dreamboat doesn’t have one, you’ll need to factor that into the total cost. Having a trailer is a huge plus. You can be zipping with your boat all over the place and sailing it wherever you want to. Additionally, the trailer is its home for the winter, if you live in a place like Alaska. :)



You will also want to make sure that the trailer has the proper lights if you ever transport the boat in the dark (chances are you will)  and registration to be state compliant. One big note on the transportation - MAKE SURE the keel gently rests on the trailer as to not wear out the keel hardware. You do not want your keel rattling around as you drive as that causes damage to the hinge pin. That’s no bueno to say the least.

If you don't have a truck to pull your boat, you can borrow from friends/family as we did in the beginning. We also rented a U-Haul truck once in a bind. ha!


Odd and Ends

Safety Gear

Safety gear should go without saying, but sometimes it’s hard to remember with all the information coming at you.  So to be absolutely sure, check out the safety equipment requirements on the Coast Guard website, and make sure you have everything you need.  While you are at it, pick up some gear to make your voyages safe for your stuff as well.  We recommend a set of dry-bags, which you can never have enough of when the rain comes out of nowhere. This waterproof sports pouch is also a very handy thing on the boat:


Tips and tricks

Do you know who should have all the tips and tricks of your boat? Bingo - the previous owner. Get as many best-practices for your specific boat from the seller as possible. They will have years of expertise in sailing your new baby, and you shouldn’t have to start from square one!  Ask the best way to raise the mast, what sails to use in what conditions, how high it can point, maintenance history, and everything you can think of. They should be more than happy to tell you stories. If they’re not, well, maybe that’s a red flag… Some owners will even take the boat out on the water with you. You never know until you ask!


Now hold on to your britches, because the day you buy your first sailboat will an exciting part of your life.  Welcome to the next chapter of your great adventure!


If you haven’t read the first part of the learn to sail series, check it out here.  

Learning to Sail, Part 2:  Your First Time Buying a Sailboat. A Catalina 22 on a trailer.

Buying a sailboat: And voila! Hard work pays off. We bought our first boat!

Now, you see, there ain't nothing to it. Go forth and carp this diem.

Damn Skippy!

From all the @Coastal_Salties at DSW

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    unlogue on

  • Well wishe on your new adventures and all those in the future!!! I has just started looking for my future livaboard. Your article is inspiring.

    Kimberly K Ferrell on

  • Hello from Astoria, Oregon. Took great interest in reading your post, I’m still looking, have been looking. However, I’m still nervous about getting into a 22’ or 28’
    As I have talked to some locals around the area here in Astoria, I get mixed reviews because of the bar, here on the mighty Columbia River. I haven’t given up on the idea of buying a boat but I’m getting excited. I’ll keep on looking around here.
    We’ve talk about going up to Bellingham, Wash. Spend a weekend there and check things out. Providing this virus allows us to go up there. Enjoyed reading your adventure with your pursuit of getting into your boat. Wishing you both good sailing weather all the way. Jorge…

    Jorge Garcia on

  • I just purchased my first sailboat this year as well after completing a couple ASA courses. MacGregor Venture 2-24. So far so good. I enjoyed the blog and feel you are spot on. Happy sailing!

    Jeremy on

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Linda Janes - Co-founder of Damn Skippy Wear - Your Seaside and Beach Outlet

 Imagine your perfect day...

Cold dock under your feet, as you watch the sunrise and listen to the waves lapping.

Comfy t-shirts and well fitting flip flops. The crackle of fresh whitefish on a beachside fire, over the cooing of a friend's ukulele. 15-knot winds at beam reach. Tanned skin, with legs dangling overboard. Laughing.

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Welcome to the family!!!"

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We are veteran owned and woman-led, and we are from Anchorage, Alaska!

We have so much coastline... so much ocean.  We encourage you to visit Alaska. It is both vast and understated. While here, you can get yourself into any imaginable sport, activity or a way of life. Who knows, your next epic adventure could be waiting for you here, unbeknownst...

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