I have advised on the purchase of used vessels for years. I've inspected hulls, reviewed engines, read logbooks and assessed equipment. And in that time I've seen the same story repeat itself over and over: someone buys a sailboat excitedly, without proper inspection, and a few months later the problems appear that nobody detected — or preferred not to see.

This article doesn't exist to discourage anyone. Buying a sailboat is one of the best decisions a sea lover can make. But you have to do it with a cool head and your eyes wide open. Here are the mistakes I've seen most often, in order of frequency.

"A cheap sailboat that needs a lot of work is never cheap. The boat price is just the beginning."

Mistake #1
Not getting an independent hull survey

This is the most costly and most common mistake. The buyer sees the boat in the water, finds it beautiful, and closes the deal. The problem: the hull in the water cannot be inspected. Osmosis blisters, delamination, repaired impacts and structural issues are only visible with the boat out of the water.

I've seen hulls that looked perfect from deck with osmosis blisters all over the bottom — a repair that can easily cost several million pesos and leave the vessel out of service for months.

The solution: Insist that the boat be hauled out of the water before signing anything. A dry survey with a professional costs nothing compared to what it can save you. If the seller refuses, that already tells you something.
Mistake #2
Trusting the price without understanding operating costs

The purchase price is just the entry fee. A sailboat has fixed costs that many buyers don't calculate before signing: berth or haul-out, insurance, annual maintenance, registration, antifouling, Maritime Authority inspections, and an emergency fund for the unexpected.

A 40-foot vessel can cost $80 million pesos and have annual costs of $8 to $15 million, depending on condition and use. That needs to be calculated before, not after.

The solution: Make a projected annual cost sheet before buying. Include berth, insurance, engine (annual service), sails (10–15 year lifespan), safety equipment (batteries, EPIRB, flares), and a 10% contingency.
Mistake #3
Not verifying documentation with the Chilean Navy

In Chile, every larger vessel must be registered with the National Merchant Marine Registry. Before buying, you must verify that the vessel is registered in the seller's name, that there are no maritime mortgages, liens or encumbrances, and that the registration papers are current.

I've known of people who bought vessels with debts attached that the new owner had to assume — or who could never register the vessel in their name due to a legal tangle from a previous seller.

The solution: Request a vessel legal status certificate from the Harbour Master before paying. It's a simple, free process. Without that certificate, don't sign anything.
Mistake #4
Ignoring the state of the engine and electrical system

On a sailboat, the engine is Plan B. But Plan B gets used more often than people imagine — for entering and leaving marinas, for emergency situations, for sailing when the wind fails. A bad engine in southern Chile can be a very serious situation.

The electrical system is equally critical. Modern sailboats have many systems that depend on electricity: chartplotter, VHF, autopilot, navigation lights, fridge. An aging electrical system with poor wiring is a constant source of problems and a fire hazard.

The solution: Run the engine for at least 30 minutes and check temperature, oil pressure and exhaust. Ask for the maintenance history. For the electrical system, bring a multimeter or have an electrician check it before buying.
Mistake #5
Buying without sailing the boat

It seems obvious, but it happens more than you'd think: the buyer sees the boat in the marina, inspects it at the dock, and signs. Never sails it. Never feels how it moves, how the helm responds, whether the rig has problems, whether the mast has proper tension, whether there are strange vibrations from the engine.

A 2 to 3-hour sea trial can reveal problems that no land inspection detects.

The solution: Insist on a sea trial before any agreement. If the seller says conditions don't allow it, wait until they do. No urgency is worth more than sailing the boat before buying it.
Mistake #6
Underestimating the state of the rig

The rig — mast, backstays, shrouds, sheets, blocks, sails — is the part most ignored in inspections by inexperienced buyers. And it's expensive to fix. A new set of sails for a 40-foot sailboat can cost between $5 and $15 million pesos. A new mast, considerably more.

Shrouds and backstays have a service life that depends on use and maintenance. Stainless steel terminals corrode from the inside and can look fine externally while they are about to fail.

The solution: Ask for the installation date of the rig. Visually inspect terminals and fittings for corrosion, wear or deformation. If in doubt, a rigger can inspect the full mast with the boat hauled out for a reasonable cost.
Mistake #7
Buying emotionally, without technical advice

The last mistake is the one that summarizes all the others. Buying a sailboat is an emotional decision — that's completely normal and valid. The problem is when emotion overrides technical judgment. The boat is gorgeous, the price seems fair, the seller is friendly, and you sign without having done any of the necessary checks.

I've seen people spend their entire budget on the purchase and have nothing left for the problems that appeared in the first six months. Enthusiasm is the worst advisor when it comes to inspecting a hull.

The solution: Involve someone technical in the process — a Captain, a marine mechanic, a rigger — before committing. The cost of professional advisory is minimal compared to what catching a problem in time can save you.

"The best time for a technical inspection is before signing. The worst time is after."

The checklist I use for my advisories

Basic checklist before buying
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50-Point Sailboat Inspection Checklist
Printable PDF checklist · Take it to the inspection
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Thinking about buying a sailboat?

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Captain Rodrigo Troncoso
Rodrigo Troncoso Peirano
Merchant Marine Captain with over 30 years of experience. Has advised the purchase and assessment of dozens of vessels in Chile, from cruising sailboats to offshore work boats.

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