How to Inspect an Aging Sailboat (Before You Fall in Love)

Based on “Inspecting the Aging Sailboat” by Don Casey

Buying a used sailboat can feel like love at first sight—but before you’re swept off your feet by a classic hull or cozy cabin, it’s essential to dig beneath the surface. Don Casey’s classic guide, Inspecting the Aging Sailboat, is a must-read for anyone considering a secondhand boat. Here’s a simplified breakdown of his process—perfect for those shopping on a budget or dreaming of fixing up a classic cruiser.

Whether you're a DIY sailor or planning to hire help, here's how to look at a used sailboat with clear eyes and a sharp flashlight.

️ 1. First, Ask Yourself: Is This Boat Worth the Trouble?

Older boats are tempting—they’re often cheaper and full of character. But boats don’t age like wine. They rot, rust, and leak. You’ll need to look past the polish and evaluate the structure, not just the cosmetics.

Key mindset:

• You’re not trying to confirm your love.

• You’re trying to find the deal-breakers.

2. Do a Full Walk-Around: The Quick First Impression

Start with an overall view. Walk around the boat slowly and take notes.

Look for:

• Obvious damage or repairs

• Any signs of neglect

• Smells (musty = mold, diesel = leak, sharp = battery issues)

If the boat seems too clean and perfect—it might be hiding something.

3. The Hull: Blisters, Cracks, and Core Trouble

Check the hull for:

• Blisters: Small bubbles under the paint or gelcoat. A few aren’t a big deal. Many could mean expensive repairs.

• Cracks: Around chainplates, thru-hulls, or under high-stress areas.

• Coring: Many decks and hulls are cored with balsa or foam. Tap (use a plastic mallet) to hear if it’s solid. A dull thud = wet core = $$$

Tip: Pay extra attention around fittings. Water intrusion often begins where hardware was installed improperly.

4. The Deck: Where Water Sneaks In

Soft decks are a bad sign. Walk around in bare feet—feel for flex or “give.”

Inspect:

• Deck fittings (cleats, winches, stanchions): Any movement here means the core may be damaged.

• Signs of past leaks: Water stains below deck, sagging headliner, or moldy smells.

5. The Rig: Mast, Standing Rigging, and Chainplates

A neglected rig can be dangerous and expensive to replace.

Check:

• Mast step: Any signs of corrosion or movement?

• Standing rigging (shrouds and stays): Look for rust, broken wires (especially at the terminals).

• Chainplates: These connect rigging to the hull. Check for leaks, cracks, or movement. A hidden rot here can sink your dreams.

6. The Keel and Rudder: Deep Trouble Below

Inspect:

• Keel bolts: Rust streaks? Movement? Electrolysis?

• Rudder: Look for cracks, swelling, or leaks. If it’s weeping water or oil—it might be compromised.

• Evidence of grounding: Cracks at keel/hull joint or impact marks.

7. The Engine: Love It or Leave It

Engines on older boats are often neglected or overdue for replacement. Don Casey’s advice: if you’re buying a boat for the engine, you’re buying the wrong boat.

Look for:

• Engine mounts rusted or loose

• Corroded exhaust system

• Belts and hoses cracking

• Oil leaks or coolant stains

• Hours on the meter (but service records matter more)

Pro tip: Start it cold. Does it start easily? Does it smoke?

8. Electrical System: Usually a Mess

Electrical systems on older boats are often DIY nightmares.

Check:

• Condition of wiring: brittle, mismatched, or melted?

• Battery installation: secured properly? Corroded terminals?

• Fuse panels: marked or a spaghetti mess?

Fixing electrical is time-consuming—and usually necessary.

9. Plumbing, Tanks, and Head

Look for:

• Leaking freshwater tanks

• Bad smells from the holding tank

• Old hoses that feel brittle or soft

• Water pump operation (check for pressure)

A smelly head can ruin morale on an otherwise solid boat.

10. Leaks: Every Old Boat Has Them

Bring a flashlight below and inspect every corner.

Look for:

• Water stains around hatches and ports

• Moisture under the cushions

• Mold behind the panels

A dry bilge is a very good sign. A soggy boat is your future full-time job.

11. Cosmetics: Don’t Get Distracted

Shiny varnish and pretty cushions might win your heart, but they can hide serious problems. Look deeper.

You’re buying the bones—not the upholstery.

12. What to Do Next

After your first inspection, ask yourself:

• What’s the worst-case scenario?

• Am I ready to fix what I just saw?

• Would I still want this boat if I had to replace the engine and the rig?

If the answer is “no,” walk away. There are so many boats out there.

Final Thoughts: Be Ruthless Before You’re Romantic

Don Casey reminds us: inspecting a boat isn’t about confirming your dream—it’s about protecting it.

Aging boats can be beautiful, soulful, and seaworthy—but they require brutal honesty. The best boat is one that won’t sink your wallet or spirit before you ever leave the dock.

Inspired by: Inspecting the Aging Sailboat by Don Casey
Recommended reading if you're serious about evaluating used sailboats—especially before hiring a surveyor.

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