An Idiot’s Guide to Buying a Sailing Boat

Choosing a boat to buy

Buying a sailing boat isn’t as easy as it sounds.   When you are a sailing novice and a boat buying newbie, the choices can be overwhelming.  This is a quick idiot’s guide to how we narrowed down our search and bought a sailing boat.  If you’re thinking of buying a sailing yacht for a world-wide sailing adventure, read on.

The many, many sailing boat options

We’re buying a sailing boat.  This is an important part of our ‘sailing round the world with kids’ plan.  We have a couple of inflatable kayaks but I just don’t fancy circumnavigating in those.  We’ll need to buy a proper offshore sailing yacht for our sailing adventure!  So we started researching sailing boats….

Who knew there were so many options?  

Do you want…

  • A racer or a cruiser or a racer/cruiser or a cruiser/racer? 
  • Monohull or multihull? 
  • Bluewater cruiser or coastal cruiser? 
  • Older or newer? 
  • A wineglass shaped hull or a flatter bottom? 
  • Two cabins?
  • Three cabins? 
  • Aft cockpit or centre cockpit? 
  • Skeg hung rudder?  
  • Deck saloon or coach saloon? 
  • Sloop rig? 
  • Cutter rig? 
  • Ketch rig? 
  • Fully battened slab reef mainsail or in-mast furling? 
  • Fin keel, wing keel or bilge keel? 
  • 35 foot, 45 foot or 50 foot?  What size boat is right for you??

We set about educating ourselves.  We have been reading and researching for months.  We’ve asked many, many boat buying questions of many boaty people.  We have asked questions on boat forums and Facebook groups.  We have spent ages trawling through specifications on and  

Choosing a boat is very time consuming when you’re a newbie.  Not only do you have loads of different types of boats to learn about, but you also have to learn a whole new language! 

sailing boat passage bunks. Buying a sailing boat.

The boys won’t fit in these passage bunks.

What type of sailing boat do WE need to buy?

It’s important to narrow down your options right at the start.  Compromise is all-important when it comes to selecting the right sailing boat.  For us, I think it’s pretty unlikely that we’ll find any boat in our price range that exactly meets all of our requirements, but we want to buy a sailing boat that’s right for us and for the type of sailing that we hope to do.  We’ll have to be flexible and keep an open mind if we want to find a safe and comfortable offshore sailboat that suits us –  a family of four from the UK, with two more-or-less teenage boys, who plan to sail across the Atlantic and, hopefully, sail around the world. 

We narrowed our main requirements down to:

A boat that we can live aboard comfortably (ish)

Our sailing boat will need all the things a home should have – beds (bunks), a functioning kitchen (galley), toilets (heads), a comfortable living and dining space (saloon), enough storage for our stuff, heating or maybe air conditioning, and entertainment and tech gadgets (this isn’t the time of Christopher Columbus after all).

And that’s another problem – sailing involves learning another language.  I still don’t know what ‘splice the main brace’ means.  Anyone??

A boat large enough for four big people

Sam is 14 years old and as tall as me.  Evan isn’t far behind him.  As they approach their grumpy, unreasonable teenage years, they will need their own space.  Also, with two smelly, hormone-ridden boys on a sailing boat with limited washing facilities…. I’ll need my own space too. 

A boat that can easily be sailed by two people

Despite the boys being almost the size of adults, they are actually still children.  I’m sure they will be very useful crew members (they are fully qualified RYA Competent Crew) but we have to presume they won’t be.   So we need to buy a sailing boat that can easily be handled by two people, with modern navigation equipment and all lines leading back to the cockpit, at the very least.  I don’t want to buy a sailing yacht that we can’t sail without hiring crew! 

A boat capable of sailing across oceans

Who knew this question could be so contentious?  It turns out that there are many strong opinions about what makes a good bluewater cruiser,  from all sides of the boaty community.  As one forum member informed me, “Opinions are like a*seholes.  Everybody has one”.  And she’s definitely right there! 

I’ve been told many times that there is no such thing as the perfect boat and every boat has it’s compromises.  But enquire as to whether a particular make of production-made sailing boat is a bluewater boat suitable for offshore sailing and crossing oceans and all hell breaks loose.  Calm down, people! 

A boat that isn’t so old that things will break all the time

Yes, yes, I know!  All boats are a constant repair project.  Cruising the world on a sailing boat is often described as “boat repair in exotic places”.  But surely a boat built in 1983 is going to break more often than a boat built in 2002?  Isn’t it??  

Well, yes, probably.  Unless the boat has been meticulously maintained and loved and had constant money spent on it, then lots of parts will be old.  On a thirty year old boat, lots of things will be thirty years old and some of them will be nearing the end of their life span.  However, a thirty year old GRP boat will likely have a thicker hull and may be better built.  We have been told many times that in the era of computer aided design and budget cuts, GRP hulls got thinner and thinner almost to the point of being too thin.   In any budget, you’ll get more ‘old boat’ than you will ‘new boat’, but would ‘old boat’ be better?

A boat that is within our budget

Our budget has had to change since we started the boat buying process.  Needless to say, the budget hasn’t gone in a downward direction.  Buying a sailing yacht is never going to be cheap.  Whatever your budget, keep a hefty chunk of cash aside for all the unexpected expense after you’ve bought the boat.  

Boat toilet

The obligatory ‘pump as you dump’ marine toilet. What’s not to love?

And so to the dilemma….

How do we make sure we buy the right type of sailing boat for us?

Older, heavier boats with a narrower wine glass shaped hull cut through big waves but don’t generally have a lot of space inside.  Some of the older boats that we have looked at reminded us of dark, dingy old man pubs with dark wood, low ceilings and yellowing head linings.  Now, I love an evening at our local dark and dingy pub, but I wouldn’t want to live in it.

The newer production-made boats make the most of the internal space and feel like modern apartments inside, but have flatter bottoms and are lighter, making them much less comfortable in heavy seas.   They also tend to have much thinner hulls as they have been designed to within an inch of their lives by computers.  Our knowledgable boat builder friend descried them as ‘bendy toys’.  When asking the ‘safety in big seas’ question, I’ve been told many times that the modern production boats are quite capable of crossing oceans but if caught in a storm they would much rather be in a heavy, bluewater cruiser.   Even yacht brokers trying to sell me said ‘bendy toys’ have told me this.

To add to the dilemma, some say modern boats may have thinner hulls but are made with more modern techniques and have more modern hull designs. 

Relaxing on a yacht in Los Gigantes

OK, so trying out boats hasn’t been all bad. We introduced the boys to sailing and did some training in the Canary Islands on a Hanse 400.

Sailing boats = a floating compromise

It soon became apparent that a boat of the size we want and the age we want, with the internal space we want and with the ability to safely cross oceans…… doesn’t actually exist.  Well, it does.  But not within our budget.   

There really is no such thing as the perfect boat for our family sailing adventure.  At least not without a substantial lottery win.

Something has to give.  There has to be a compromise. 

We can have size and bluewater capability, but it has to be off of the 1980s with limited living space and a resemblance to the Black Hole of Calcutta.  Or we can have size and space and a much newer and more modern boat, but we might all die in the middle of the Pacific.  It’s a toughie!

choosing a family sailboat isn't easy. Buy sailing boat.

Boat research in the UK – not quite so glamorous.

We keep going round and round in circles.

“We’re going to spend 99% of our time sailing around the coast or chilling on anchorages, so we want to buy a yacht that we can comfortably live on as a family with lots of room.  Ah, but we are going to cross oceans hopefully so it has to be safe and sturdy.  We can’t get safe and sturdy within our budget without going for something much older though.  So do we need to buy a newer bendy boat with lots of lovely space and mod-cons but maybe not so safe in big seas…… or an old, properly built, solid hulled sailing boat with the internal dimensions of a small wardrobe.  Oh FFS.”

We haven’t even mentioned the monohull/multihull argument.  Or the option of buying a cheap project boat and making it your own.  Or the option of buying a sailing boat in another country, like the US, where there is a lot more choice than here in the UK. 

The Bogey Problem

To add to the rational, sensible, well thought out and researched arguments between the different types of boats, we have the issue that I just can’t bring myself to buy a boat that I don’t love.  

It has to feel right

Is that wrong??

We have a 17 year old Mazda Bongo campervan called Bogey.  Bogey isn’t really suitable as a campervan for a family of four.  He’s too small, very slow, very cramped and drinks so much fuel that you can almost see the fuel gauge dropping as you drive.  And he smells a bit.  But we love him, so it doesn’t matter.  I want to buy a boat that we love as much as Bogey.

Our campervan

Bogey – he’s not perfect but we love him.

Then there is the well known saying amongst boaties…

“There’s no such thing as bluewater boats, only bluewater sailors”.


The Big Decision – Which boat did we buy?

I think by now you can see our problem.  I think the key to choosing the right sailboat for your family is to figure out what your requirements are. Narrow down your search.  View loads of boats.  Sail different boats.  If possible, spend a night on different boats.  And be patient. Don’t rush into anything but also don’t take too long about it.  Buying a sailing boat takes time,  I’m pretty sure you could spend years searching for the perfect boat and I don’t think it exists.

For those of you who know about these things, we have looked at Bavarias, Hanses, Westerlys, Moodys, Beneteaus, Hunters and Oysters.  We’ve looked at boats from 39’ to 46’ (that’s about 12 metres to 14 metres).  The oldest boat we have viewed was built in 1983 and the newest in 2004. 

And finally, after months of researching, learning and searching, after hours of obsessively sifting through, after sailing on different boats and viewing loads more…..  we have found our sailing boat!   

She’s an Oyster 435.  Cutter rigged.  Built in the UK in 1990.

We have changed her name to SV Fat Susan.


We have learned a lot since buying our sailing boat.  We have also made a lot of mistakes.

Other posts your might be interested in….

The mistakes we made when buying a sailing boat – there were lots of them!

How we bought our boat and some of the mistakes we made – so you don’t have to…

Why we had to buy a new mast for Fat Susan.


Follow us on Instagram or Facebook to see where we are now.


An idiot's guide to choosing a sailboat, family sailing adventure

Buying a sailing boat?  Proper boat buying books.

Of course, this is just a brief wander through the thought-processes of a peri-menopausal mum trying to buy a very specific boat for a very specific purpose.  We are boat buying numpties so don’t take our word for it.    There are some pretty good books about how to buy a boat.  Most are available as a Kindle Edition.

If you’re completely new to this, like us, ‘The Ultimate Guide to Buying a Boat‘ will walk you through the basics of buying a boat from the decision to the survey to closing the deal.  I wish I’d read this a bit earlier, to be honest.  It’s a Kindle edition so you can just download it to your phone.  And it doesn’t cost much.

How NOT to Buy a Cruising Boat‘ is an honest and entertaining look at the boat buying process and how it can go wrong.  Highly recommended.

And while you’re at it, if you are thinking of jumping on a boat indefinitely with your kids and going on a family sailing adventure, get ‘Voyaging with Kids‘.  It’s fab.

Buying a yacht is a complicated, frustrating process that takes lots of time and patience.  As a first time boat buyer, there are so many obstacles to stumble over, so many mistakes to make.  Hopefully our experience helps to make your boat buying adventure a little easier.  Good luck with buying a sailing boat!


13 Comments on “An Idiot’s Guide to Buying a Sailing Boat

  1. Is there a country where they cost less than others in general? A better place to buy, lower prices, less taxs, lex fies etc.?

    • I don’t think there is a ‘cheapest’ country. From our (limited) boat buying experience, it seems that there are pros and cons to buying close to home or buying abroad. We are in the UK. We searched for boats in Europe and boats in the US, by trawling through The taxes to import the boat into the UK and the cost of getting it back here put us off. But that is because we want to sail in the UK for a couple of seasons. it depends on your needs. I think if you are willing to start your sailing adventure from the country you are buying from, then that would work. I have heard that you can get bargains in the Caribbean where people have fully kitted up their sailing boats for cruising and then realised that it’s not the life for them. And there are always lots of cheaper ex-charter boats in Croatia and Greece at the end of the season.

    • USA, but then tax is not paid and it might need some work. UK, Italy, France, Spain & Netherlands have some good ones but have the patience to shop around for a while.

    • I have read there is a good selection of inexpensive blue water boats in the Philippines. Folks cross the Pacific then sour on the complexities of continuing west or circling back through the northern Pacific.

  2. I’ve been saying that I’ve never had to work so hard to spend money. We’ve been trying to buy a boat since February. Flew down to Florida a couple times and have spent a TON of hours driving around locally (another 3 hour trip each way?) to look at different boats. A week from today we will be surveying a second boat – first one failed. But, we aren’t as excited as we thought we’d be. I mean we are a little bit. So many months, so many disappointments. I think we just don’t want to get our hopes up again. No one told us this is was what could happen or how hard it would be – just pure exhaustion. It’s got to be better on the other side, right?

    • That’s so true! I’ve had lots of ‘What the hell are we doing??!” moments too. We mostly didn’t have to travel far, unlike you. It is exhausting to travel for hours just to find the boat is wrong. None of the boats we looked at were right. But, to be honest, neither was the one we bought, she just felt better and we were running out of time and patience! I know exactly what you mean about not wanting to get excited. It’s a frustrating process. There’s light at the end of the tunnel though. Don’t give up! it will still be frustrating and hard work when you have bought the boat too, but at least you will be on the way to an adventure. Good luck with the survey! Let me know how you get on! Fingers crossed. x

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  4. Lovely article.

    Clicked your affiliate link (ultimate guide to buying a boat) – better a few pennies in your pockets than amazons! 🙂

    But it didn’t work, I got an error ‘too many redirects’.

    Please feel free to delete this comment – it was only a note to you 🙂

    • Hi Paul! Thanks for letting us know! I’ve been neglecting our website a bit since we left to UK. I seem to be quite busy :o) and internet access is often tricky. I’ll update the links and get more stuff on the website soon. Big love, Floss

  5. Buying a sailboat is easy compared to finding a place to moor it. Mooring can soon outrun the cost of a sailboat, a factor that’s killing the dream of most aspiring sailors and the sailing bussiness.
    Unless you permanently sail (away from the UK) it will not be affordable or with reasonable cost and most of the time you’ll be dropping anchor in the Med, Azores or Bahamas (at no or very little cost)
    Keeping a boat moored in the UK, is not for the average person who earns a salary.

    • Absolutely completely agree, Johannes! We bought a boat to sail away on. We couldn’t justify the cost of mooring a boat in the UK. The cost of keeping a boat in a marina came as quite a shock to us non-sailors. We managed to find a cheapish (but massively inconvenient) mooring with reductions for NHS employees. That’s a whole different blog post. Thanks for commenting.

  6. I came across your pages very recently and thoroughly enjoyed your beautifully written and entertaining Pacific crossing blog. We bought our first boat very recently and had all of the same issues and questions. We looked at only a few (well, we looked at hundreds of adverts) and bought a 1980’s Cobra 1050 variously described as ‘a capable blue water cruiser’ and ‘not a blue water cruiser’. It fitted our limited budget and we liked it and in the end that’s why we choose it. We’ll learn to sail this summer and set off next year on an as yet unplanned adventure.

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