With so many different boats out there, how do you find the right one? Where do you start? There are thousands of online forums asking the same question. I’m no sailboat oracle capable finding the perfect boat for you. But, I can talk about our boat-buying experience, and hopefully you’ll learn a thing or two — including a few things not to do!

1. How do You Plan to Use the Boat?

Sailors tend to have big dreams. Why wouldn’t they… The thought of casting off your worries and sailing away to distant shores is an extremely enticing idea. It’s very important to be honest with yourself at this stage, to be realistic with your goals, your intentions, and the reality of how you intend to use your boat.

Before worrying about the size, style, construction material, equipment lists, budget, etc., having an honest conversation about your sailing plains will make every other decision in the boat buying process significantly easier.

Will you be day sailing on inland lakes? Do you plan to take the occasional weekend trip with an overnight stay? Coastal cruising for a couple weeks at a time a few times per year? Do you envision living aboard at the dock and sailing occasionally? All of these are very common scenarios. Not everyone will cross oceans, not everyone needs a ‘bluewater’ sailboat capable of withstanding everything Mother Nature can throw at you.

Our Plan

Our sailing plans hatched like many others, as a dream to cruise to faraway lands. We pictured ourselves traveling long-term and living aboard full-time, or for very extended periods of time (6-12 months).

The Result

We knew we wanted a boat that was robust enough to take us through the Caribbean, and large enough to carry enough creature comforts to feel like ‘home.’ We did not want to feel like we were camping. But at the same time, we didn’t need a bullet-proof tank capable of weathering every storm found on earth, and capable of holding two of everything onboard just in case something breaks. Our travels will not take us to the end of the earth in the next few years.  After that?  Maybe… but not now.

End of a lovely day of #sailing with @kirkberryman #SanDiego #SanDiegoBay

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2. What is Your Budget?

This is the second most important question to answer, which should be thought about in conjunction with your sailing plan, as it really helps to validate your ideas. (Or poke holes in it.) Were you really being honest with yourself?  Or are you still dreaming? 😉

Setting a budget for buying a sailboat can also help create a timeline.  In other words, maybe you really do want to cross oceans, but your current budget doesn’t allow for it. You’re now faced with two options:

  1. Buy a smaller/cheaper sailboat now to get experience on protected waters and more capable boat later.
  2. Continue saving money while chartering and/or sailing other people’s boats until you’ve gained enough experience and saved enough money to make the ultimate dream a reality.

Our Plan

Our plan started over 10 years ago. At that point, we were fresh out of college with minimal sailing experience, and still tens of thousands of dollars in debt from school. We had ZERO budget. This was our reality check, we knew we were still dreaming. There was no way we could afford both a sailboat that could take us where we wanted to go AND a place to live that allowed us to keep our jobs on land (so we could pay off our debts). So, we chose option 2 – continue saving and sail other peoples boats.

The Result

After we paid off our debts, saved some money and developed ways to have a remote income, we agreed upon an all-in budget of $50k.

This happened today. #debtfree #msualumni #bubbly #celebrate #oceanside #oside

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3. What Type of Sailboat Best Fits Your Intended Use?

Up until this point in the decision making process there’s really no reason to be looking at boats other than to marinate your mind with sailing terminology. This is especially true if you do not have much sailing experience. But who am I kidding, anyone who’s had this dream has already been making lists of ‘dream boats’ for ages!

Sailboats can be classified a number of different ways.

  • Intended Use (daysailer, racer, coastal cruiser, offshore/bluewater)
  • Construction Materials (fiberglass, wood, steel, aluminum, etc.)
  • Rigging (sloop, ketch, cutter, etc.)
  • Keel Type (shoal draft, centerboard, full keel, fin keel, etc.)
  • Construction Method (cold-molded, foam-cored, vacuum-bagged)
  • Number of Hulls (monohull, catamaran, trimaran)

It’s hard to pinpoint one method of categorizing sailboats as the ‘best’ way, but for me it goes back to the original question: “How do you intend to use the boat?” Answering this question makes decisions using the other methods of categorization considerably easier.

Our Plan

Once we decided how we were going to use the boat we looked to others who were doing what we wanted to do. We paid attention to the types of sailboats they had, to the names of the manufacturers, and the designers. Then we started looking at the details — what was the boat made out of, what type of keel did it have, how was it rigged, etc. Starting there helped us narrow in quite quickly. But this was only after…

The Result

We began our search the wrong way. We desperately wanted a catamaran and tried to adjust everything else to fit that desire. Once we got honest about our budget and how we intended to use the boat, we realized quickly our budget, intention, and desired type of boat were not compatible.

  1. We didn’t have a good way of drastically increasing our budget, so a $250k boat was not an option.
  2. We needed a boat big enough to live on, so a Hobie Cat was not going to cut it.
  3. The only thing left to do was abandon our search for catamarans and focus on monohulls — where our money would go a lot further.

Once we were realistic with ourselves and our goals, things started to come together much more quickly. We settled on looking at the ‘classic plastic’ era of boats from the 1960’s-1980’s, when fiberglass sailboats were a relatively new construction method. Many of the boats from this era are significantly overbuilt because there was simply a lack of knowledge of just how durable fiberglass really was. The end result is a massive number of ‘aging’ boats with very solid bones, good sailing characteristics that may need some refitting, but are significantly cheaper than their modern-day counterparts.

We looked at hundreds of boats online. We steered away from the big production builders like Beneteau, Catalina and Hunter because… and focused more on the semi-custom builders such as Morgan, Ericson, C&C, Endeavor, Pearson, Islander, Irwin and… Tartan.

4. Condition: Sail Away? or Boatyard Special?

This is a touchy topic. Everyone wants a deal. There are thousands of boats sitting around in boatyards that you can buy for next to nothing. Surely these must be a steal right?!

It’s easy to look at a rough-looking boat that could — after you fix it up — sell for tens of thousands of dollars more than you bought it for, and believe you’ve scored the deal of the century. But, unless you are extremely skilled, have a free place to store the boat while you’re working on it, really love working on old boats, and have a reliable way of buying all the parts and materials to refit the boat at less than retail cost — you will most likely find yourself spending far more money than if you had purchased a sistership that had already undergone a refit and/or was well maintained throughout its life.

Our Plan

We knew that any boat we bought would need some work.  It was up to us to decide what type of work we wanted to learn how to do and how much of it we were willing to do. We were hopeful we could find something that didn’t require much work before we could sail her, and that most of the work and upgrades could be done along the way after we had already moved aboard.

The Result

Going back to our budget, our max was $50k.  This meant we would either buy a boat that was completely cruising ready and needed no work for $50k, or we spent less and money left over for repairs and upgrades. THERE WILL ALWAYS BE REPAIRS AND UPGRADES. Do not underestimate this. We ended up buying our boat for $43k, leaving us with $7k for upgrades and repairs.

5. Location, Location, Location

All else being equal, location can play a major role in which boat to choose. Given two similar boats, one in your neck of the woods and one on the other side of the country, the choice is obvious. But, unlike real estate, boats are not immovable objects, nor is their pricing the same around the world, or even around the country. So while location is important, it’s also wise to keep an open mind in the beginning of your boat search. Once you’ve decided how you plan to use your boat, and narrowed in on the rest of the variables outlined above, you might find that the type of boat you’re looking for is in fewer locations than you originally thought. Or, given your sailing plans, you really need to focus your search into one geographic area. In other words, location isn’t important until you’ve made a number of other decisions.

Our Plan

In the beginning, our search literally spanned the globe.  Sitting on the couch, perusing listings on my laptop, I would yell out to Lauren: “I just found our boat!”

She’d always respond the same way: “Oh ya? Where is it?”




In the beginning, it was fun to think about packing everything up and flying to the other side of the world to start a new life on the ‘perfect’ boat. As we got more and more serious, we narrowed our scope drastically. We spent time looking at sailboats on the west coast of the U.S. We looked at a catamaran in Mexico, then went to see another catamaran in Seattle, and eventually we saw a few sailboats in our backyard, San Diego.  we decided we really wanted to sail the Great Lakes first, we knew we should find a boat in the Midwest.

The Result

We became hyper-focused, looking only for sailboats located on or near the Great Lakes, and more specifically Lake Michigan. This meant we’d be within a few hours’ drive from either of our parents’ houses. This allowed us easy access to people we knew who were into boating, tools, advice, and most importantly, a place to crash if we couldn’t sleep on the boat during our refit.


Boat Buying Dashboard

6. Now it’s Time to Start Looking at Boats

Odds are you’ve already been spending your free time pouring over CraigslistSailboatlistings and Yachtworld in search of the perfect boat. Armed with answers to the questions above and the mountains of data from all the boats you’ve already seen online it’s time to put rubber to the road and see some boats in person. No matter where you plan to use your boat, no matter where you currently are, go find the nearest marina or boatyard and start looking.

Even if you have no plan to sail yet, and none of the boats in the marina are the type of boat you’re interested in, you’ll learn something new. It’s incredibly educational to put your feet on as many boats as possible during the buying process. Talk to anyone and everyone — ask them about their boat, and you’ll get more information than you bargained for. Everyone loves talking about their boat. Ask them if they know of any boats for sale. Go see it, tell the owner you’re in the market and just wanted to pop your head in and take a look. Again, it doesn’t matter if you know this isn’t the boat for you. You’re just gathering data.

Our Plan

Find the perfect catamaran anywhere in the world, quit our jobs, sell everything and go! This was our plan until we came to terms with our budget. With a monohull now in our sights, we started thinking more about where we really wanted to start our sailing journey. We knew, all other variables being equal, that we wanted to spend a few years in the Bahamas/Caribbean first, rather than the West Coast/Pacific. To do, we decided to move out of San Diego and start searching for boats in the Midwest/East Coast.

The Result

Both Lauren and I grew up in the Midwest, and have an affinity for the Great Lakes (and the Bahamas/Caribbean are accessible from the Lakes). After moving out of San Diego and back to our parents’ in the Midwest, we began our search for monohulls. After about 4 months, we found our Tartan 37.

Learning how to live on a boat is a big change. Living on a boat while constantly on the move takes it to a whole new level. Uprooting your lifestyle and moving to a different part of the world/country is a big undertaking. Doing all these at the same time and cutting off your income source is downright scary!

We decided it would be far easier for us if we made these big jumps one at a time. So, while we did move across the country to buy our boat, we stayed with family while we searched, and then we kept the boat at the dock for the first few months. This also made it much easier to continue working our remote jobs to sustain some financial stability. This meant all we needed to focus on was learning about the boat and how to live aboard. We’d tackle the other steps in time.

7. Do You Still Want to Own a Sailboat?

You’ve probably heard the old saying a boat owner’s happiest days are the day they bought their boat and the day they sold their boat. I can’t say I agree with this 100%, but I understand the sentiment. Boat ownership is a TON of work. A boat can also be described as “a hole in the water you throw your money into,” and BOAT stands for Break Out Another Thousand.

But, if those sayings don’t turn you off, and the idea of moving slowly, heading nowhere at great expense, while often being cold, wet and miserable sounds enjoyable, then perhaps you’re ready!

(Some) kidding aside, boat ownership is a fantastic adventure. What many people fail to see until it’s too late is that the dream of sailing is not the same as the dream of boat ownership. Owning a boat requires a commitment to take care of the vessel that will be taking care of you. If this commitment is making you a little anxious about owning, chartering can be a cheaper and much simpler option to get yourself aboard, allowing you to indulge in all the fun and almost zero of the work, for a week to a few weeks (or whatever you can afford) per year.

Our Plan

From the beginning our goal was to live aboard, travel slowly, and immerse ourselves in different cultures. While there are numerous ways to go sailing without owning a boat, it is difficult to live on a boat full-time without owning it. For us, sailing has almost always been a secondary goal. Don’t get me wrong, we love to sail, but our intent from the beginning was to travel slowly, and sailing was a very enjoyable and logical means to this end.

The Result

After all of this, our answer to the question above was still yes. The benefits of owning a boat still far outweighed the costs for us, and we’re OK with the fact that sailing is really just doing boat work in exotic places. At least we will be in exotic places!

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