Head Over Keels in Love - Choosing a Cruising Sailboat

"Peace is not found in a calmer storm, it's found in a better boat." - Travis Meadows

I don't know what Yachtworld.com's web traffic stats are, but I'm guessing they pull huge numbers from both keel kickers and serious buyers trying to answer one basic question: What sailboat should I purchase for cruising? There's already been a lot written on the topic by sailors far more accomplished than me. For starters, I can't recommend these enough: Charlie Doane's The Modern Cruising Sailboat, John Kretschmer's Sailing a Serious Ocean and Beth Leonard's The Voyager's Handbook.

So I'm not going to reinvent the wheel with this post nor am I going to try to create the definitive source of information about choosing a cruising sailboat. Instead, I'm going to share a few simple tips I've picked up through reading, sailing, purchasing 5 boats of my own, and interacting with online sailing communities and some old salts on the dock.

My pride and joy, s/v Bearly-A-Wake

Ignore engine hours. If you're considering a diesel engine, don't get turned off by the engine hours. It's far more common for a marine diesel to die from neglect or outright abuse than to ever simply just wear out. So, what's far more important than the engine hours is knowing and verifying that the maintenance schedule has been followed. Also, carefully consider how easy it is to access common service points for tasks such as oil changes/checks, impeller changes, anode replacements, etc. This is particularly important if you intend to maintain the engine yourself. The better access you have to the engine, the more likely you (and any previous owner/s) are to keep up with maintenance.

Rule out what you don't want. After you've done your own research and are ready to start looking for the perfect cruiser (Here's a tip - They don't exist!), a good first step is to make a list of things that are deal breakers. Some of these might include your preference between catamaran or mono, aft or center cockpit, rig types (sloop, cutter, ketch, yawl, etc.), and hull material (FRP, metal, wood, etc.). Most the things on your deal breaker list should be things you can't change. For example, you might really want davits for your dinghy, but you can always add them to almost any boat for a fairly reasonable cost so they shouldn't be a deal breaker.

Don't get too up or down over electronics. While upgrading to a new complete electronics package for the helm can be expensive, electronics are also often outdated within just a couple of years, so don't put too much value on a shiny new chart plotter. And don't forget how powerful mobile phones, tablets and laptops have become for cruising. There's a growing array of excellent navigation, communication, weather and planning apps available that can supplement just about everything you need to safely operate your craft and make you feel like you have new electronics.

Fall in love. After all is said and done, I strongly feel a personal attraction to your sailboat is an important ingredient. She might have all the bells and whistles for globe trotting, but if you don't like the way she looks and feels, the dream can whither long before it becomes a reality. You want a boat that inspires you to keep her maintained. You want a boat that beckons one more glance back as you walk down the dock or putt-putt away on the dinghy. I'm not saying your friends and other sailors need to think she's the most beautiful or best sailing boat in the anchorage, but I am saying your boat should stir YOUR emotions.

Our first sailboat, s/v Hannibel. And yes, I fell hard from day one.

Turnkey boats aren't. Sailboats reflect their owner's personality, so even a dock queen isn't likely to be set up the way you'll want it or need it even if it's in pristine condition. Besides, if you've ever owned a boat before, you already know you never finish the maintenance list, you just simply start back over at the top again. So like I said, turnkey boats aren't turnkey.

Some features do add value. Good sails, a reliable motor, a quality autopilot, wind vane steering, an electric windlass and a reasonably speedy dinghy can be important assets for cruising. Some or all of these items can be added (at varying costs), but the point is that these are some of the features I think add actual value to a cruising boat, unlike a fresh coat of wax, newly painted topsides, air conditioning, or a new flat screen TV hung on the salon bulkhead.

Consider the resume. Find a boat that has already done the kind of voyaging you have in mind or was at least equipped to do so. If you're planning a milk run through the South Pacific, a sailboat that's already done that might have good downwind sails and rigging and extra tankage for reserve fuel and water (or even a watermaker). Similarly, if your adventurous spirit is leading you to high latitudes, a boat that's already cruised there could have a diesel heater installed or insulation added to the interior hull sides. A lot of the extras are expensive and depreciate very quickly, so it's a bonus if you can get a quality hull/motor/sails with life left in options that are on your upgrade list anyway.

Condition trumps age. It's often said, but is worth repeating - Condition and quality are much more important than how old a boat is. That's good to remember for resale too. Regardless of how old your boat is, if you keep her in good condition, you'll flatten the depreciation curve considerably.

Ask the pros. If you're still lost in a sea of sailboats to choose from and want professional advice, consider consultation from Bob Perry ($500) or John Neal ($750).

Our second sailboat, s/v Island Bound

The Sailboat Reviews page here at SFLF has tons of free, useful information and articles on sailboat design (rigs, keels, hull shapes, hull materials, etc.) from heavyweights like Bob Perry, Ted Brewer and Chuck Paine. Give them a read. At the very least you'll be entertained and more than likely gain some new knowledge.

If you've found a boat you're ready to seriously consider or want to make an offer on, you'll find some help in this post: Sailboat Inspection Tips for Prospective Buyers

Ready to browse cruising sailboats for sale? Here's a shameless plug for our grassroots sister website, SailFarYachts.com, where "we make your dreams float".

I know many of you are already veteran cruisers and have a wealth of knowledge and more importantly, experience to share. Feel free to do so by dropping me an email or simply leaving your thoughts in the comments below. I'll do my best to keep this post updated with new information as it comes in from the cruising community.


  1. Thank you so much. I found this post incredibly valuable, really. There were some points here that I hadn't even thought of to look at.


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