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Bad Sailboats – What NOT to Buy (And How to Spot Them Before It’s Too Late)

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The Harsh Truth About Cheap Old Sailboats

If you’ve been scrolling through YachtWorld or Craigslist and stumbled across a sailboat that looks “too good to be true,” there’s a good chance it is. In this post, we’re diving into the world of bad sailboats—the kinds of boats you probably shouldn’t buy, no matter how romantic their lines or tempting their price tag.

After years of experience owning and working on sailboats (and making my own regrettable purchase), I’m here to break down the red flags you should know before wasting time—or worse, money—on the wrong boat.

Wet Deck Core – The Soft Spot That Sinks Dreams

Walk the deck. If it feels spongy or soft, walk away.

Wet or rotted deck cores are a common issue in fiberglass sailboats from the 70s, 80s, and 90s. Moisture seeps in through improperly sealed fittings or cracks, saturating the balsa or plywood core. This leads to delamination, structural weakness, and a repair bill that could easily reach $10,000–$50,000 if done professionally.

Telltale signs:

  • Soft spots underfoot
  • Water stains around fittings
  • Mildew or rot around headliners
  • Streaks from hardware fasteners

If someone tells you it’ll “dry out” on its own, run.

Blisters – Boat Pox That Can Bite Hard

Those little bumps on the hull? They’re not just cosmetic.

Blisters—caused by water penetrating the fiberglass and forming osmotic bubbles—are another major red flag. Some are harmless, but deep structural blisters can lead to hull failure and thousands in repairs.

Here’s how to tell the difference:

  • Small (1/16”–1/8”) blisters in gel coat? Maybe okay.
  • Large, bulging, or weeping blisters? Walk away.

Fixing them means stripping the gel coat, drying the hull for months, and reapplying barrier coats. It’s labor-intensive and expensive.

Keel Bolts and Hull Joints – Rust Never Sleeps

Peek inside the bilge. If you see rust-streaked keel bolts or cracks at the hull-to-keel joint (often referred to as “Catalina smile”), take note.

Keel bolts are critical for keeping your keel attached to the boat (kind of important!). Rust may indicate corrosion, weakening, or prior grounding.

What to avoid:

  • Rusty keel bolts or bolts painted to cover rust
  • Cracks where the keel joins the hull, especially with rust stains

Repairs can be done, but often they’re expensive and not worth it unless everything else on the boat is pristine.

Rotten Bulkheads, Chainplates, and Compression Posts

These are the bones of the rigging system. If they’re compromised, so is the entire mast structure.

Bulkheads support chainplates that anchor your standing rigging. If they rot from leaks (common around chainplates), you risk losing your mast.

Signs to watch for:

  • Water stains under chainplates
  • Varnish peeling from bulkheads
  • Sagging headliners
  • Floor indentations around compression posts

Again, these are all fixable—but only worth the trouble if the rest of the boat is rock solid.

Poorly Done DIY Repairs – Sloppy Work, Bigger Problems

Many boat owners try to save money by doing their own repairs. Unfortunately, not everyone has the skill—or patience—to do things properly.

What to look out for:

  • Bad paint jobs (two-tone decks, worn gel coat)
  • Hardware mounted on crooked pads or without backing
  • Home-grade plywood replacing marine materials
  • Spray foam or duct tape where proper seals should be

If the visible work is sloppy, imagine what’s hidden behind the bulkheads.

My Worst Purchase Ever – A Seafarer 31

I once bought a Seafarer 31 that looked like a mini-Hinckley. On paper, it was a dream. In reality? A damp, outdated mess.

The interior hadn’t been touched since the 1970s. The cushions were water-stained burlap. A shag carpet was being used as a tablecloth. It was every kind of wrong, and I knew it. But I bought it anyway thinking, “I can restore this.”

I couldn’t. I used it a few times and then sold it. Lesson learned: Don’t fall in love with the idea of a boat. Fall in love with the right boat.

Final Thoughts – Every Boat Has Issues, But Some Are Just Trouble

No used boat is perfect. But there’s a huge difference between a boat that needs updating and one that needs rescuing.

Good bones matter.

If the hull, keel, rigging, and structure are solid, everything else is fixable. But if the boat has been neglected or repaired poorly, it’s probably not a project—it’s a punishment.

Don’t let a low price or pretty lines fool you. Ugly boats with big problems aren’t deals. They’re money pits.

Your Dream Boat Is Out There—Just Don’t Rush It

Take your time, ask questions, get a survey, and walk away when your gut says no.

And if you’ve got your own horror story, drop it in the comments. Let’s help each other avoid those “what was I thinking?” moments.

Until next time—happy hunting, and I’ll see you out on the water.

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