How to Inspect a Second Hand Sailboat Before Buying

November 22, 2025 Mike Ventura Buying Boats 0


How to Inspect a Second Hand Sailboat Before Buying (Without Missing the Big Problems)

Standing on the dock looking at your maybe-future boat is exciting. It’s also when a lot of buyers make expensive mistakes.

They fall in love with cushions and woodwork… and completely miss the soft deck under the mast, the dying engine, or the rigging that should’ve been replaced 10 years ago.

You don’t need to be a pro surveyor to do a smart first inspection of a second hand sailboat. You just need a plan, a basic toolkit, and the right mindset: you’re there to find problems, not to confirm your dream.

This guide walks you step-by-step through how to inspect a second hand sailboat before buying so you can spot big red flags early and decide if it’s worth moving to a survey and sea trial.

1. Before you even step aboard: mindset & basic tools

Your mindset

When you’re buying used, your job at inspection is to answer:

“Is this boat structurally sound and realistically fixable for my budget?”

You are not trying to decide if the upholstery is your favourite colour.

You’re allowed to like the boat—but for this stage, try to be deliberately picky. The more problems you find now, the more informed (and safer) your decision will be.

Simple tools to bring

Nothing fancy:

  • A bright flashlight (headlamp is ideal)

  • A small plastic or rubber mallet (or the handle of a large screwdriver)

  • A flat screwdriver (for gently probing soft spots, not prying)

  • Notepad or phone for photos and notes

  • Old clothes—you’ll be crawling into bilges and lockers

If possible, bring a knowledgeable friend. A second pair of eyes is invaluable.

2. Start outside: hull, keel, and rudder

If the boat is ashore, start with the hull. If it’s in the water, inspect what you can and plan to see it out later if you get serious.

Hull

Walk slowly around the boat and look for:

  • Cracks or impact damage

    • Around the bow, waterline, and transom

    • Around through-hulls and fittings

  • Weird bulges or flat spots

    • May indicate previous grounding or bad repairs

  • Osmosis / blisters on GRP hulls

    • Small “pimples” under the paint or gelcoat

    • Light, scattered blistering on an older hull isn’t instant doom, but heavy, large blisters over big areas can mean serious work later

Ask yourself:

“Does this hull look structurally honest, even if it’s ugly?”

Cosmetic ugliness is fine; structural weirdness is not.

Keel

The keel is a big deal – literally and figuratively.

Check:

  • The keel/hull joint – look for cracks, weeping stains, or distortion

  • Signs of serious grounding – bent keel, gouges, or plate damage

  • On fin keels: rust streaks or movement around the keel bolts (inside, in the bilge)

Hairline cosmetic cracks are common; open, rusty, or wide cracks are a red flag.

Rudder and steering

Look for:

  • Excessive play in the rudder (side-to-side movement)

  • Cracks around rudder stock entry points

  • Signs of water ingress – swelling or bubbling on the rudder blade

Turn the wheel or tiller and feel:

  • Is it smooth or notchy?

  • Any tight spots or grinding sounds?

A slightly stiff system might just need maintenance; clunks and grinding can mean worn bearings or alignment issues.

3. Deck and hardware: soft spots & leaks

Now move topsides.

Deck

Walk the entire deck, including:

  • Around the mast step (especially on deck-stepped masts)

  • Around chainplates, stanchion bases, and deck fittings

  • Along side decks and around hatches

As you walk:

  • Gently bounce your weight

  • Feel for softness, flex, or crunching sounds

Soft areas can signal rotting core (balsa or plywood) under the fibreglass. That can be very expensive to fix.

Deck hardware and rails

Check:

  • Stanchions and lifelines – are stanchions solid or wobbly? Corroded bases?

  • Cleats and winches – secure, no obvious cracks around their bases

  • Hatches and portlights – crazed, cracked, or clearly leaking?

Look inside later for water staining under these fittings. Outside + inside clues together tell the story.

Second hand sailboat

4. Rigging: standing and running

The rig is one of the most expensive parts of a sailboat. You can’t ignore it just because it’s up in the air.

Standing rigging (shrouds, stays, terminals)

Ask the owner:

  • “How old is the rigging?”

  • “Do you have any invoices or records of replacement?”

Then inspect what you can:

  • Terminals and swages – look for cracks, rust weeping, or broken wire strands

  • Chainplates – check where they pass through the deck and where they attach inside

  • Turnbuckles and bottlescrews – bent, badly corroded, or severely seized?

If the rigging is obviously ancient or in poor condition, assume it needs replacing and factor that into your budget.

Running rigging (ropes & control lines)

Look at:

  • Halyards, sheets, reefing lines, control lines

  • Are they stiff, furry, badly worn, or starting to fail?

Old, tired running rigging isn’t the end of the world; it’s relatively cheap to replace and a very common first-year job. But it’s still a cost.

5. Sails: condition and practicality

You’re unlikely to get brand-new sails on a second-hand boat unless the price reflects that. But you want usable, safe sails, not rags.

Hoist or unroll what you can (or at least spread them out):

Look for:

  • Tears, patches, or big repairs

  • Delamination on laminate sails

  • Stretched-out shapes – deep belly where there should be a nice aerofoil shape

  • UV covers on genoas – shredded, cracked, or intact?

Ask:

  • What sails are included? (Main, genoa, jib, spinnaker, storm sails?)

  • Roughly how old are they?

Tired but usable sails are fine for coastal cruising and learning. Just don’t mentally treat them as “like new.”

6. Engine and propulsion: heart of the hidden costs

Even on a sailboat, the engine matters a lot—for docking, manoeuvring, and safety.

You might find:

  • Outboard on a bracket

  • Inboard diesel (common on 25ft+ boats)

  • Occasionally a petrol inboard (more common on older, smaller boats)

Visual inspection

Check:

  • General cleanliness – oily swamp or reasonably kept?

  • Hoses – cracked, swollen, or perished?

  • Fuel lines – secure and not leaking

  • Exhaust – any obvious leaks or black mess

  • Belts – cracked or slack

Start and run the engine (from cold)

Ideally:

  • Start it cold – a previously warmed engine can hide starting issues

  • Check how quickly it fires and how it idles

  • Observe smoke (colour and amount) and unusual noises

  • Engage gear (forward and reverse) and listen for clunks or grinding

If in the water, run under load briefly (within reason). If on the hard, you’re limited—but even a short run on a hose can reveal obvious problems.

You don’t need perfection, but a motor that barely runs, knocks badly, or belches smoke is a serious cost factor.

7. Interior and structure of a second hand sailboat: beyond pretty cushions

This is where many buyers get distracted by woodwork and forget to check the bones.

Structural areas

You care about:

  • Mast step – look for compression, rot, or cracking in the surrounding structure

  • Chainplate attachment points – any rot, delamination, or water damage around them?

  • Bulkheads and structural members – cracked tabbing (fibreglass that bonds them to the hull), separation, or movement

  • Bilge – standing water, strong diesel/oil smells, structural cracking around keel bolts

Use your flashlight. Get down low. Look into the awkward corners; that’s often where problems hide.

General interior condition

Look for:

  • Water stains and mildew on liners and panels

  • Soft or delaminated floorboards

  • Rotten wood around windows, hatches, or in lockers

  • Smell: strong damp or mould odours can indicate persistent leaks

Cosmetic issues can be fixed over time. Structural rot and water ingress are much more serious.

8. Systems: electrics, plumbing, and gas

You’re not trying to do a full survey, but you want to know how bad (or good) the systems are.

Electrics

Check:

  • The battery bank – type, age (if labelled), and condition

  • Cable runs – neat and supported, or spaghetti chaos?

  • Corrosion on terminals and junctions

  • Operation of basic items: lights, bilge pump, instruments (if powered up)

Messy electrics can be a DIY tidy-up job or a reason to plan a partial rewire. It’s about scale and your comfort level.

Plumbing

Look at:

  • Fresh water system – tanks, pipes, pump operation

  • Seacocks and hoses – can you turn the seacock? Are hoses double-clamped? Any cracks?

  • Condition of toilet (head) and any associated hoses (smell matters here…)

Hoses and clamps are cheap; hidden seacock corrosion and seized valves are more serious.

Gas (if present)

Take gas safety seriously.

  • Where are the bottles stored? Proper gas locker or just rolling around?

  • Are lines flexible hose, copper, or a mix?

  • Any obvious cracking, bodged joints, or worrying smells?

If a gas system looks sketchy, plan on having it professionally checked or replaced.

9. Paperwork, history, and “story”

A second hand sailboat isn’t just fibreglass and rigging; it has a history. The more you know, the better.

Ask for:

  • Ownership documents / title / registration – is everything clear and in the seller’s name?

  • Maintenance records – invoices for engine work, rigging replacement, major repairs

  • Any previous surveys – even if old, they give clues about what’s been repaired or ignored

  • Reason for selling – listen for consistency (moving, health, upgrade, lack of time, etc.)

Be wary if:

  • Ownership is vague or not clearly documented

  • The seller can’t answer basic questions about how things work or how old major items are

  • The story keeps changing

You’re not a detective, but your gut feel about the “story” is part of the decision.

10. Sea trial: watching the boat behave under way

If the boat passes your basic inspection and you’re seriously interested, the next step (often alongside or after a survey) is a sea trial.

During the sea trial:

  • See how the engine starts and runs under real load

  • Note how the boat behaves under sail:

    • Balance (does it round up violently or behave predictably?)

    • How sails set and trim

    • Any alarming noises from rig or hull when heeled

  • Test basic gear in action:

    • Winches, clutches, traveller, steering, autopilot (if fitted)

    • Windlass (if any), anchor handling

    • Instruments (if powered)

A sea trial is your chance to confirm that this second hand sailboat actually does what you want it to do on the water—not just at the dock.

11. When to bring in a professional surveyor

Even a thorough DIY inspection doesn’t replace a survey, especially for bigger or more complex boats.

You almost certainly want a professional survey if:

  • The boat represents a significant chunk of your savings

  • You’re new to boats and unsure what you’re seeing

  • You’ll be insuring the boat for a decent value (many insurers require a survey)

  • You’ve found potential issues you don’t fully understand

A good surveyor will:

  • Confirm or challenge your impressions

  • Find issues you’ve missed

  • Provide a written report you can use to renegotiate price—or walk away

Think of it as a relatively small investment to avoid a very large mistake.

12. Second Hand Sailboat red flag checklist: when to walk away

Sometimes, the best decision is to thank the seller and leave.

Strong reasons to walk away from a second hand sailboat (especially for new, budget-conscious buyers):

  • Badly soft decks around mast or key fittings

  • Major rot or delamination in bulkheads, mast step, or structural areas

  • Severely neglected or failing engine with no service history

  • Clearly ancient, corroded standing rigging and no budget to replace it

  • Multiple serious leaks, mould everywhere, and no sign of care

  • Ownership or paperwork confusion that can’t be clearly resolved

You’re not just avoiding hassle—you’re protecting your future enjoyment (and bank account).

Key takeaways: how to inspect a second hand sailboat before buying

When you go to inspect a used sailboat, remember:

  • Arrive with a plan and tools, not just excitement.

  • Prioritise structure, rigging, engine, and leaks over cosmetics.

  • Look closely at hull, keel, rudder, deck hardware, and interior structural areas.

  • Understand the difference between fixable wear (old cushions, tired lines) and major problems (soft decks, rotten bulkheads, dead engines).

  • Use a sea trial and, ideally, a survey to confirm your impressions before handing over money.

  • Be ready to walk away if the problems are bigger than your budget—or your appetite for projects.

Do this, and you dramatically increase your chances of ending up with what you actually want: a safe, honest, second hand sailboat that fits your budget and lets you spend your time sailing, not regretting.