What to Look For - When Buying a Used Sailboat

What To Look For When Searching For A Used Sailboat


When I think about all the boats I have been aboard in my lifetime of sailing, it amazes me what a brief inspection around a boat, even a quick glance, brings to mind. I have been very lucky to have sailed with a man, Andy Wall, who was totally absorbed in making and keeping his boat in perfect condition, always. It did not matter if we spent long months at a dock or anchorage, or made a long ocean passage, the boat always had to look and be in perfect running order. The old saying, "Shipshape and Bristol Fashion" was Andy's idea of what all sailing vessels should be.

I came to believe that as well, and as a part-time yacht broker, it became even more important for me to point out what I thought might be a suitable boat for individuals searching for their "perfect" boat. I would need to understand what they wanted, where they intended to go with the boat, and, of course, what their budget was for purchasing and getting their boat ready to set off. And how much they knew of the inevitable maintenance issues of a floating home.

I soon realized that many of the wonderful friends I made by helping them find the right boat, knew very little about any of it. It became my great pleasure to help them with the process and help them understand what they were getting into.

One such very intelligent and alert young woman asked me to go aboard a boat she really liked. We spent some long hot hours together going over this seemingly lovely boat that had captured her imagination. While I did not want to discourage her, it was important to point out a lot of things I saw while going over the deck, the rig, and below.

After our day together, she wisely asked me to put together a list for my observations, and what I had already pointed out to her. She wanted to show the list to her husband, so they would be better prepared to continue their search.

While this list is by no means complete, and certainly does not substitute for a professional survey, perhaps it will help you in your search for a good boat that fits your plans. At the very least, It will get you thinking deeper than a simple walk through as you step aboard a potentially "perfect" sailboat.

Down Below

Look at the windlass installation and chain locker to inspect chain for rust and condition under the deck under the windlass.


Inspect the headstay chain plate and if there is an inner forestay make sure there is a chainplate to hull.

Look at all thru hulls, including head intake and discharge output, sink intake and output. Check all thru hulls and hose clamps.

Check chain plates for rust and fatigue, look at all fastenings.


Inspect the bottom of the mast and electrical wiring that comes out of it at the bottom. Also check where the mast goes through the deck to make sure it is waterproofed.

Look at the electrical panel, open it if you can to see the condition of the wiring and connections. How does it look? Are the wires neat and orderly and terminals don't have multiple wires ganged on any single terminal?


Check all bilge pumps and make sure they work. Are there bilge alarms?

Under the galley sink, check the check valve (if present), seacock, and all hose clamps.

Check out the water pressure system and hot water, look at hot water heater and hoses to the engine.

Look in the bilge. Is there standing water, or oil and dirt and loose hardware?


Inspect the general condition of the engine and generator. How accessible are they? Is there a fuel filter off engine, does it have a vacuum gauge? How easy/difficult will it be to change the oil? Note the engine hours, check all hoses and hose clamps, overall inspection (oil leaks, rust, engine mounts, where to check engine oil as well as transmission level).


Check where the prop shaft goes through the hull for leakage, stuffing box, wear of cutless bearing.

Check the steering system, look for rust, worn wire or cable or fittings. 


Do all electronics work and how well are they wired? If they need to be updated, how difficult will it be for proper placement and installation.

In the galley, is there a solenoid for the propane stove and does it work?

Under floorboards, inspect all water, fuel, and holding tanks, wiring, hoses, bilge pumps, traces of water or oil, general condition.

Check the batteries for age, how well they are secured, and wired properly.

Properly secured battery bank.jpg

Check that the refrigerator and freezer work properly.

Check lee cloths, hatches, toilets not leaking (if replacing, suggest Raritan Elegance toilet)


Check sinks and thru hulls, foot pumps and electric water pressure pumps.

Is there a watermaker? What kind, how old, does it work?

Check the condition of the overhead liner.


Check roller furling genoa, and condition of the Sunbrella sail cover and stitching. Check the roller furling system, the drum, make sure there is a double-jaw toggle in the turnbuckle of the headstay (link plates would be good too). This should also be done if there is an inner forestay and staysail.


Windlass condition and chain and lead to anchors, foot switches up and down, what kind of anchors, anchor snubber (such as 35 feet of half-inch three strand nylon and use a rolling hitch on the chain).


Running back stays for the staysail, track, car, condition (can replace wire and tackles with T-900 line)

Liferaft, and think about placement of tender to be stowed on davits or on deck.

Downwind pole, stowed on track on mast is best.

Condition of Lexan, glass, and metal fittings on all hatches and ports, or whatever they are made of and name of manufacturer for replacement parts.


Condition of mast. Is the surface chalky, or are there corrosion bubbles and peeling? Pay particular attention to any stainless steel fasteners on an aluminum mast. If necessary, replace and use Tef-Gel when installing new fasteners.

Mast steps should not be attached with rivets, only machine screws with Tef-Gel.

Check all leads to cockpit for fair runs, with no chafe, with fair leads around or through them to cockpit. Check all rope clutches in cockpit to make sure they work. Check all running rigging for condition, if faded or chafed, or very stiff, they will have to be replaced.


Check all wire rigging for rust or cracking, check wire for rust and barberpoling, and check turnbuckles and cotter pins in turnbuckles, and chain plates on deck. If there are covers on the turnbuckles and shrouds check for corrosion.


Check the spreaders and make sure they are set at the proper angle. They should have a slight upward positioning on upper shroud.

Check running lights for working and corrosion. Consider replacing older fixtures with LEDs.

Check lifelines, wire terminals, and condition of the wire and gates and stanchions where fastened to the deck (rust).

Check steering pedestal, compass, outside instrumentation, hatch boards, MOB equipment, outboard bracket and hoist, steering wheel and lock, condition of winches (if Lewmar check the top cap, if gray instead of black is probably deteriorating). See if self-tailing or open, does autopilot work, engine controls in cockpit, remote Ram mic for VHF, manual bilge pump and handle, cockpit table, boarding ladder on the stern or lifeline gate, condition of the deck and cockpit sole.

Does the depth sounder work and is it easy to read?

Evaluate the condition of the bimini top and dodger.

If the boat is in the water, look at the waterline for cleanliness, no grass or barnacles.