If you’ve already been sailing for a while on a friend’s or a family member’s sailboat, then you probably have a good idea of what you want and what to look for. But if you’re relatively new to the sport and shopping for your first used sailboat, it can be a daunting task. There are a lot of used sailboats on the market and their condition runs from one extreme to the other, with corresponding price tags.

How do you know what to avoid that can cost you dearly to repair? What it is reasonable to expect for an aging sailboat? And what marks a well-preserved pocket yacht?

Before I continue, a bit of legal housekeeping. This post contains affiliate links. That means I receive a small commission if you make a purchase using those links. Those commissions help to pay the costs associated with running this site so that it stays free for everyone to enjoy. For a complete explanation of why I’m telling you this and how you can support this blog without paying more, please read my full disclosure.

Start by curbing your enthusiasm

Emotion is a big danger in shopping for a used sailboat. You’re excited about the prospect of sailing more or less at your convenience, you’re hoping to make great family memories together, and new adventures beckon you to get started quickly.

But the best place to start is by curbing your excitement for a while so that you can evaluate your choices rationally. You’ll have to live with the consequences of your choice for a long time and with your wallet, so it pays to be objective. There will be time for excitement later.

To help you make a well-informed decision with practical realities in mind instead of emotion, I offer the following tips to help you pass over the money pits and find a solid, serviceable, sailboat that you can start sailing right away.  One that won’t require a lot of work before you can put it in the water (a project boat) but that you can personalize with upgrades and improvements over time at your own pace and budget.

Take these tips for what they are, the opinions of a guy who’s already been down the road that you’re taking, nothing more, nothing less. Many of these are lessons learned from poor choices I made when first starting out. I’m not a professional marine surveyor, so you get what you’re paying for. You’re free to disagree with me and you won’t have to look far to find somebody who does.

Be realistic

Unless you’re willing to pay top dollar for a used sailboat and you’re not worried about taking a financial loss on it down the road when (not if) you sell it, resolve yourself to the fact that you’re not going to find a hidden diamond out there. Banish from your mind the illusion that you’re going to find a perfectly preserved sailboat in some grandma’s garage and she just wants to get rid of it as you happen to come along.

Instead, realize that the vast majority of the used sailboats you’re going to look at have been poorly maintained, overall. They might have been somebody’s prized possession at one time but few are anymore. The heydays of sailing yacht manufacturing, sales, and ownership are gone. Luxury motor yachts and comfort-first pontoon boats are where it’s at now. You’re more likely to rescue a neglected sailboat from winding up in a landfill. There are exceptions, but you’ll have to hunt hard for them.

Don’t forget to factor in the ongoing cost of owning a sailboat. Besides the repairs, upgrades, and improvements that you’ll want to make, there’s also involuntary costs, some of them annual:

• Insurance premiums
• Motor fuel
• Use fees at launch ramps or launch/haul-out fees if you can’t launch it yourself
• Mooring fees if you don’t dry-sail or storage fees if you can’t park your sailboat at home
• Trailer, boat, and (in some US states) outboard motor registration fees
• Invasive aquatic species control taxes (in some US states)
• Sail and rigging replacement
• Periodic engine, bottom paint, and brightwork maintenance
• Yacht club membership fee (optional)

Making the initial purchase is just the jumping off point to your own hole in the water into which you’ll throw money, lots of it.

With all that in mind, let’s dive in.

Don’t fret over the fiberglass

Unless you’re a perfectionist like me (recovering, if you please), don’t make a big deal out of the condition of the hull and interior fiberglass. If you’re buying a used boat, it will be faded, worn, and have normal defects. That won’t affect your use of the boat much. It’s only an aesthetic issue. If you want perfect fiberglass, buy new.

If you like a shiny finish, don’t assume that you’ll need to paint it unless it’s already painted and the paint has failed. You can recondition dull, chalky, and scratched fiberglass with cutting compound and a power buffer with amazing results. Watch this site for a future article about that.

If a sailboat that you’re considering has excellent fiberglass, that’s a great sign that the owner has taken good overall care of the boat and it’s one that you should pay extra attention to.

In any case, do look for signs of obvious major repairs but you probably won’t find many unless they were done by an amateur, in which case you should be extra careful. For a sense of how expensive just a little bit of damage can be (in the picture above), see Storm Damage to Summer Dance Repaired.

Don’t get decked by a soft deck

Deck areas that feel soft or sag slightly when you step on them are a sign that water may have seeped into the wooden core and it’s rotting. Test for it by tapping with a hard object around all deck penetrations such as chain plates, stanchions, mast tabernacle, cleats, and other fittings. You should hear consistently sharp sounds, not dull thuds. Pay extra attention if you see rust stains around fasteners. Look for cracks that are deeper than the typical, harmless “spider web” cracks found in the gelcoat of many older sailboats.

Small and few areas of decay aren’t cause for alarm and can be repaired relatively easily by “potting” the penetrations with epoxy and rebedding the hardware with butyl tape. But large areas such as the foredeck, cabin roof, or cockpit sole are reason enough to stop looking at a boat. There are plenty of solid boats to choose from. Don’t waste your time on a soft boat unless its a gift. Even then, have a detailed plan for the repairs or it could wind up costing you to dispose of a useless hull.

Be a leak hunter

Ideally, the inside of the hull should be bone dry and unstained by standing water or rust. You’ll be lucky to find that. Rather, you’re likely to find signs of old or current leaks. Know the cause of every one before you buy someone else’s problems.

Start looking on the inside of the boat from the top downward. Examine all deck penetrations for stains that indicate loose fittings and possible decay (see the previous heading). Check around all portlight and hatch frames and seals. The joint between the deck and the hull is a common source of leaks in many older sailboats and indicates failed sealant that should be replaced.

As you scan down the hull, inspect all hull penetrations, particularly through-hull fittings, valves, clamps, and hoses for cracks and leaking. At the bottom of the hull, open all bilge areas and note how much water has been there in the past or is still there. If you haven’t discovered the source yet, it’s still a problem. Keep looking or press the owner for an explanation.

Minor leaks aren’t deadly but they’re more than just unsightly. Moisture inside the boat causes mold, mildew, and corrosion. The first two are smelly and can be a health hazard to some people. The latter is the enemy of every material the sailboat is made of and can lead to catastrophic gear failures. For a REALLY close look, see Beware of Galvanic Corrosion!

Get to the bottom of the bottom paint

Unless a used sailboat has spent its life around fresh water and has been dry-sailed, it’s probably going to have antifoul bottom paint. That’s okay but the real issue is what condition it is in.

Antifoul bottom paint is expensive and if it hasn’t been maintained, it can cause underlying damage that is even more difficult and expensive to repair than just a coat of paint. It’s not a job that you want to have to do in your first couple years with any sailboat, so look for a well-maintained bottom. You should not be able to see any cracks, flakes, blisters, or bare fiberglass showing through. The paint should be uniform in color and application, not a series of haphazard band-aids. If you can’t tell the condition of the paint because there’s a lot of marine growth, ask the seller to have it cleaned so that you can take a closer look.

For a look at a typical bottom paint project, see What to Expect From a Professional Bottom Paint Job.

Find a cool keel

How is a sailboat like an iceberg? The part under the water is at least as important as the part above the water. Without sails and a keel, it’s just another boat. The keel plays a critical role in how a sailboat handles and performs. Don’t ignore it as a useless appendage like your appendix. Keels do fall off and with disastrous results.

Regardless of the type of keel: full, shoal, fin, wing, or swing, focus your inspection first on its attachment points. All hardware should be in excellent condition or else it will be your first repair project if you decide to buy the boat. For fin and wing keel sailboats, inspect the hull joint for cracks and separation that are common with some makes and models. If you discover a problem, find out how serious it is for that particular model before you consider buying it. Know what material the keel is made of and its maintenance requirements.

Swing keel sailboats need extra consideration. Besides the attachment hardware, the winch and all its attached parts should also be in good condition with a clear maintenance history. If the keel is made of cast iron, it will require conscientious maintenance to prevent excessive loss to rust and oxidation.

Start with Refinish Your Swing Keel for Best Performance, Part 1: Removing and read all five parts for what a full swing keel restoration entails.

Don’t choke over cabin cushions

Unless you intend to camp in your sailboat regularly, don’t be overly discouraged by missing, worn, dirty, or dated cushions. That’s the norm. They’re very expensive to replace relative to the value of most used trailerable sailboats and recovering them is an advanced DIY project for any stingy sailor to take on. If you do plan to anchor out often, the best you can hope for is a complete set in serviceable condition.

If you’d welcome the challenge of sewing new cushion covers, you can learn more in How to Sew Cabin Cushion Covers.

Look into the outboard motor

Don’t overestimate the condition of any outboard motor that’s included with a sailboat you’re considering buying. Repairing or replacing one can be the biggest expense you can have after the initial purchase so avoid it like a colonoscopy.

Ask the owner for the motor’s history, maintenance records, and repair receipts. Inspect the motor oil for age, smell, and fill level. Examine the lower unit oil for metal particles and water. Remove the spark plugs and inspect the electrode gap and condition. Look for bent or chipped propeller blades. Test a swing-up motor mount for smooth operation with little effort.

Don’t buy an outboard motor sight unseen. Insist on a true cold start test and also for an on-water test. Check for easy starting, smooth shifting, and full power control. You should see a steady, strong discharge of water coming from the water pump. You’re going to need a reliable motor so accept nothing less without a plan to compensate for the problems and corresponding price reduction.

For a preview of what it takes to maintain an outboard motor properly, see 15 Outboard Motor Maintenance Blind Spots You Can’t Afford to Miss.

Don’t sail past the sails

New or nearly new sails on a used sailboat are as rare as hen’s teeth. The cost of replacing sails is a major factor in many sellers’ decision to sell their sailboats instead of keep them. Don’t let them pass it on to you. Expect to pay at least $1000 USD for a new mainsail and headsail.

Carefully and thoroughly inspect all sails for fabric condition, stitching, and construction. There should be at least a standard mainsail, standard working jib (110), and a 135 or 150 genoa. They should be reasonably clean, have all battens and caps, tack and clew grommets in good condition, and minor or no repairs. The crisper the fabric, the better. Hoist each sail and look for wrinkles that are a sign that it may be blown out or it has a shrunken bolt rope.

Ask for a price reduction to cover any necessary repairs or replacements. Pay particular attention to the mainsail. It gets the most use (and abuse) and is the most expensive to replace. In addition to the standard suit of sails, a light air drifter or spinnaker with the corresponding rigging is a significant plus.

For ideas on how to get the most out of used sails, see these projects.

Standing rigging that you can stand

Replacing the standing rigging is another reason some owners choose to sell their sailboats rather than repair them. Get as much background history on the rigging as you can. Look for bent, missing, mismatched, and overly rusted hardware. Feel every cable for broken wires and inspect all fittings for cracks and corrosion.

Ask the owner if there are any spare parts onboard or upgrades that have been made like new chain plates or turnbuckles. Find out if the sailboat includes mast stepping gear such as a mast crutch or a gin pole. Compare the gear or lack of it with How to Step a Mast Single-Handed With or Without Using the Boom as a Gin Pole.

If you’re a performance enthusiast, look for an adjustable backstay and a rigging tension gauge. If you plan to keep the sailboat in a slip most of the time, you’re going to want a headsail furler. Otherwise, it can be more of a burden than a benefit.

Don’t let questionable standing rigging be a show-stopper for you. It doesn’t have to be an expensive repair, as I describe in How to Replace Your Standing Rigging for Less.

Run through the running rigging

Running rigging isn’t generally a big expense but many small issues can ring up a big price tag. Every sailboat should include the minimum control lines: mainsail halyard and sheet, jib halyard and sheets. Other rigging that you might find include: main sheet traveler, topping lift, mainsail outhaul, Cunningham or boom downhaul, boom vang, mainsail reefing lines, headsail downhaul, or spinnaker halyard and sheets.

Look for excessive wear, age, and general condition. Note whether any popular upgrades have been done, such as leading the control lines aft to the cockpit, conversion of cable halyards to all line, internal halyards,  racing modifications, etc.

Inspect all of the hardware that the lines run through: the blocks, sheaves, and fairleads for smooth turning without cracks and chips.

For ideas on upgrades to look for or to consider adding, see these projects.

Avoid electrical system sticker shock

One system on a sailboat that is deceptively expensive for how small and simple it is, is the electrical system. Basic sailboat electrical systems are about as complex as a motorcycle. But if you aren’t familiar with marine electrical systems and their unique standards, forget most of what you know about automotive electrical systems if you’re a DIY’er.

That’s because the marine environment makes higher demands on virtually everything compared to automotive systems. The basic circuit theory is the same, but the practical applications are significantly different and that means a different price tag too. Most products with the words boat or marine in their name are about twice the price of their automotive counterparts.

When evaluating a potential sailboat purchase, check the quantity, type, and age of the batteries and whether a charger is included. Inspect the breaker panel for lack of corrosion (as in the picture above), working breakers and clear labeling. Test all circuits for function and look for tidy and professional looking installation of all wiring and connections.  Insist on working navigation lights. Electrical accessories like a VHF radio, music system, chart plotter, autopilot,  and depth and knot meters are icing on the cake but not required.

If you see a rat’s nest of incomprehensible wiring in an easy to access space, assume the same exists in the hard to reach places or there’s obsolete, original wiring and that you will need to rewire the entire sailboat. Most boat fires are caused by faulty wiring so this is an important checklist item.

For an example of what it takes to upgrade an electrical system, see How to Completely Rewire Your Sailboat.

Happy trails start with a happy trailer

The single biggest advantage of owning a trailerable sailboat is the freedom it gives you to sail anywhere that you can tow it. Having a solid, reliable trailer to get you there makes trailer-sailing easier and more relaxing.

The trailer should tow straight and steady behind your tow vehicle and not “fish tail.” For that, you need 5%-10% of the gross trailer weight on your hitch.  Less than that, and the trailer could become uncontrollable at highway speeds.

Road test any sailboat/trailer combination that you’re considering buying just as you would a car. The location of the bunks, winch stand, or axle in relation to the sailboat might need to be adjusted to achieve the best balance.

Don’t only consider how fast you can go with the load but also how fast you can stop it. Many states have laws that require trailer brake systems over a certain gross weight (for example, 3000 lbs) or when the weight exceeds a percentage of the weight of the tow vehicle (for example, 40%).

If a trailer you’re considering already has brakes installed, inspect them carefully. Look inside the fluid reservoir for low, dirty, or rusty fluid. Pull one wheel off and examine the drum and shoes or the rotor and pads for uneven wear and remaining lifespan. If the system is so old that it doesn’t have a breakaway actuator, it should probably be replaced. Most trailers can be retrofitted with brake systems. For an idea of what’s involved, see Do it Yourself Trailer Surge Brakes.

Also inspect the size, wear, load rating, and age of the tires. While you’re there, check the springs for broken leaves or worn shackles and bushings. Check that all of the lights are in working order, of course. If the trailer doesn’t have a tongue extension, be sure you find out how the owner launched without one.

It’s common for boat trailers made from steel to have a little surface rust but it shouldn’t be extensive. If you find flaking rust, the structural integrity of the trailer may be questionable. With the owner’s permission, dig through the rust until you know how bad it is or pass on it and find a package in better condition.

Buying a new trailer for an old trailerable sailboat isn’t cost-effective and used ones for sale that will fit a particular sailboat and that are in good condition are hard to find. It’s not impossible, though, as I describe in Sometimes It’s Better to Replace Your Trailer than Repair It.

Dive deeper

For a more in-depth look at evaluating used sailboats, I recommend reading Don Casey’s Inspecting the Aging Sailboat.

Good luck shopping!

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Photo credit: Zach Frailey (Uprooted Photographer) via RemodelHunt / CC BY-NC-ND