HOW TO: 6 best steps to buying a used sailboat and sail around the world

Or in our case… buying a 20-year-old ocean-ready sailboat!

When we bought Adhara in July of 2020, she was the first boat we ever bought. She is a Contest 48CS build in the Netherlands in 1998 by the Conyplex yard. She is very solid and has a center cockpit, her in-mast furling main sail and furling genoa and jib allow us to adjust all sails from her safe cockpit. 

Many of you ask us about our decision-making progress and tipps what to look out for when buying a boat. In this post, I will tell you how and why we bought this boat, and also what we would do differently with what we know today.

Adhara when we first saw her in Plymouth

1. “How Much did you pay for your boat?

Obviously your favorite question. But to be completely honest we think it’s irrelevant. If you really want to fulfill your dream then the only thing that matters and the very first thing you have to set for yourself is your budget. I think it is the most decisive factor and will give you a good idea on what you can get for your money. This might seem easier than it actually is because comparing boats can get very confusing very quickly once you go into the specifications and consider all the different options some boats have and some don’t. This might be a good place to state that I am solely talking about boats that you want to live on for large portions of the year, take across oceans, and live on comfortably off-grid for weeks or even months at a time. The decision-making becomes completely different if you are looking for a boat to spend your holidays on in the Mediterranean for example. (Quick disclaimer here: there is never THE perfect boat, just a perfect boat for what you want to do with her). 

For a liveaboard, ocean-going boat you will want a few things that you might not need if you are only spending a few weeks on board each year. Ideally these are lots of solar, big batteries, a watermaker, big fuel and water tanks, and a good autopilot (maybe even two). The list goes on and on and retrofitting these items can be very expensive if you didn’t consider it in the first place. From what we have heard and experienced it is always more expensive to fit new gear on a boat than to buy a boat that is already fitted out. The labor cost of installing all the new gear is often more expensive than the gear itself and yards tend to give you estimates that are on the low side but in our experience, it always ends up being more expensive. On the other hand, you could argue that it makes more sense to look for a cheaper boat and buy everything new. I guess that also depends on your time span. If you are planning on keeping the boat for 5 years or more then buying new might make sense. We were always planning on traveling on our boat for 3 years, so we tried to find a boat, which was already fitted out, enabling us to set off right away. 

2. Mono vs Catamaran vs Trimaran?

Ha! This is great – boat people’s favorite topic Nr.2! So next, you have to make the decision on whether you want a mono – or multi-hull boat. This is where you’ll be banging your head against a brick wall. If you ask 10 different cruisers you will probably get 11 different opinions about the subject but here is our experience and why we chose to buy a monohull. I grew up sailing small dinghies from Optimist to lasers and 470s on the Baltic Sea. I have spent some holidays on sailboats of different sizes and all were monohulls. I have never been on any multi-hull until a week-long Catamaran charter in Croatia a few years back on a pretty beat-down Lagoon 400. We put up sails once during the week and while it was a comfortable and stable platform we really did not like the atmosphere on this big piece of white plastic. Okay, you could say that this Lagoon is not the pinnacle of multihulls but with all I knew and had experience in plus what was realistic within our budget, we very quickly decided to look for monohulls. 

3. Old vs. New

So for us and within our budget, we had to decide whether to look for a newer more modern monohull (eg Beneteaus, Hanse, etc) or go a bit older and look for more prestigious makes such as Hallberg Rassy, Najad, Amel, or Contest. There are definitely arguments for both kinds of boats but we decided that the second category was what we wanted and here is why: While newer boats usually have bigger cockpits and sail better due to new hull forms and lighter constructions, older boats from yards like the one mentioned above have the advantage that they are well over specced and built like tanks (think Mercedes from the 90s). That makes them heavier of course but on the ocean that rather becomes an advantage as the motion becomes more predictable. For us, safety was a big factor and having the center cockpit which we rarely have to leave makes us feel more protected especially when it is just the two of us. To be honest, even though Adhara is quite heavy at 18,5 tons (add 750 liters of water and 600 liters of fuel) we are not that much slower than newer monohulls of the same length, especially in the stronger trade winds of the Caribbean. 

Furthermore, the build quality of these older boats is just fantastic. Our woodwork inside is a piece of art that would be crazy expensive to reproduce today. These boats were very expensive when new so all the gear was top-notch. Even though most of it has been replaced over the years people usually go for the same quality again. And then there is style. You just can’t compare the flair and feeling of the older boats to the more economically built boats from today. We sometimes compare it with living in an old nice building with stucco on the walls and 3 meter ceilings to newer compartment complexes. While the newer flat might be more convenient at times, nothing gives you the feeling and atmosphere of old structures.

Things we were looking for:

  • Solid boat construction
  • 2-3 cabins
  • 42 – 50 ft
  • Center cockpit
  • Water maker
  • Big water and fuel tank
  • Newish electronics (with AIS, Radar, Plotter, etc)
  • Newish rigging
  • Big batteries
  • Good autopilot
  • Strong engine

The list actually goes on and on and while not all of these items were mandatory it eliminates quite a few boats right away. We started looking at different boats from Hallberg Rassy, Moody and Contest in Denmark, Spain and Holland. I guess in our case what really made a big difference was when we visited the Contest yard in Holland where Adhara was built. We could see the quality and detail that goes into each of their boats. We looked specifically at a Contest 43, a 44CS, and a 48CS. The really awesome part of the 48CS (and 44CS as well) is the raised salon. It makes a huge difference coming down inside and you never really get that going “below” into a dark cellar kind of effect. Also, the layout with the gally alongside on port and the nice owner’s cabin aft with a central double bed are perfect (on a side note: I don’t understand why so many of the HR have split single berths in the aft cabin).

The problem was that actually, the boat was a bit above our budget. We made offers but could never quite reach the final step, which meant looking further. It was around the time when Covid hit hard and nobody really knew if the world was going down tomorrow. I was constantly looking on when I saw that Adhara had been reduced in price. She was not at the yard in Holland but in the UK, in Plymouth. The travel restrictions in Europe were still very much intact which meant that we could not go and see her. However, having visited the Contest yard twice and likely driving the brokers close to crazy with our questions (sorry Thom) we knew that we loved the boat, build quality and layout. Another bonus was that Adhara was refitted to great detail in 2018 and we therefore decided we could make an offer which was subject to a survey. Now, you could say that it is a bit naïve but in our case, we felt comfortable for a few reasons: First we knew her sister boat really well and loved the general arrangement but more importantly we knew that we as Newbies would probably not find anything on her that a good surveyor would not detect. It also gave us some emotional distance which I believe helped us in being stronger in the following negotiations. We clearly stated at the beginning what we could afford and if the seller would not agree that we would have to walk away (which was true). We had been in contact with a surveyor in Spain for a boat that did not work out so we asked him if he knew anyone in the south of England. He recommended Tom Hustler from Seaworthy Services ( ) and after a few video calls we felt confident that Tom was our man. We explained that we could not be there for the survey or the sea trial so he would have to make a few extra pictures and put himself in our shoes. 

We were very excited when we received the very detailed report of 55 pages and 750 pictures. To be honest at first, we did not really know what to do with it. However, after a few calls with Tom, he reassured us that there are no major things like Osmosis, engine, or rigging problems. We also conducted a test on the engine fluids and had an engineer go over the vital parts to be sure. Two things that were a bit concerning were that during seatrial the generator did not start and the main sail got stuck in the furling mechanism. The main was an easy fix and we never had any problem with it again. The generator however turned out to be broken, which started to become a bit of a problem. Usually what happens after a survey is that you go back to the broker or owner and tell them what the surveyor found. You then try to find a middle ground and agree on a sum which is then deducted from the previously agreed price. Makes sense to me. However, in our case, the previous owner became very hard to deal with. I think one reason might have been that it became clear by now that Covid wouldn’t kill us all so it seemed that he suddenly had second thoughts about selling and also, I think he wasn’t totally honest with the condition of some of the items (eg generator) on board. It took a lot of effort by the broker to convince him that we need to agree on a new generator (the brokerage firm even forewent on some of its commission) to make the deal happen. In the end the relationship between us became so bad that we never actually met the previous owner which made it a lot harder to get to know all the different systems and quirks that are normal for a boat of this age and size. I am still a bit upset on how the whole process went but in the end it all worked out and on July 10th(my mother’s birthday 2020 we officially moved onboard Adhara.

Here you can find some of the specs of Adhara

Upgrades we’ve added:

  • New main sail
  • 15hp outboard engine for dinghy
  • 600 amp Lithium-Ion battery bank
  • 710 watts of solar on the stainless arch (we used the generator for 2 hours last season) 
  • Iridium Go satellite phone
  • New and bigger alternator
  • New engine shaft
  • Installed inspection hatches in diesel tank
  • All new safety equipment (new Epirb, handheld radio, VERY comprehensive grag bag, new rescue sling, etc)

Right now, we feel Adhara is very well equipped. The only thing we are changing for the new season is adding more shade to the aft deck (that Caribbean sun is strong!). If we were to go on across the pacific, I would maybe think of a second autopilot and a hydro generator for long passages. 

So, what did we learn from our experience? First of all, if we were to buy a boat again for the same journey under the same circumstances but with what we know today we would definitely buy Adhara again. We would definitely put emphasis on different items today but in a way I guess we also got a bit lucky and went with our intuition and gut feeling (great advice I know. We do sometimes talk about the benefits of a catamaran but the budget for a quality fast catamaran is more than we can afford right now. 

After cruising full-time for the past two years we can still say: Adhara is the right boat for us!

Our takeaways:

  • buy a well-equipped boat if you can find one (rather than buying everything new)
  • buy a well-used boat or even liveaboard –> things break on boats if you don’t use them 
  • find a good broker you can trust
  • do a survey! You will get your money back in the negotiations for sure
  • try and meet the owner
  • we would still go for a quality older boat than newer big production but that is a personal preference. Most boats are safe to do ocean crossings on if you equip them properly

Often times we talk to other cruiser friends about their boats and how they decided on the right boat. Stories vary a lot but budget mostly constrains you to a certain category. You can then make decisions on going older vs newer and at a certain point, (budget) speed (meaning quicker passages) becomes a thing to consider. I don’t think I know anyone though who isn’t checking online from time to time dreaming about the next little bit quicker, bigger, or more comfortable boat. Like I said: There never is THE perfect boat…

All the best to you all, a nice start into the summer and fair winds!


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