Cheap Sailboats: The Dream, The Deal, and The Disaster

Mon, 15 Jun 2026 13:56:10 +0000

Cheap sailboats are still everywhere if you know where to look. In this episode, I went online and found 50 real sailboats for sale under $15,000, including older fiberglass boats like Catalina 22s, Catalina 25s, Catalina 30s, C&C sailboats, Pearson 30s, Hunters, O’Days, Islanders, Cals, Mirages, Tanzers, and other affordable used sailboats from the 1970s, 1980s, and 1990s. If you’re searching for cheap sailboats for sale, used sailboats under $10,000, used sailboats under $15,000, best first sailboat, affordable cruising sailboat, trailerable sailboat, small sailboat with a cabin, or a cheap liveaboard sailboat, this video is the reality check before you buy.

The big lesson is simple: when you buy a cheap sailboat, you’re buying a to-do list. Some old sailboats only need cleaning, lines, bottom paint, an outboard, or basic upgrades. Others have serious problems like wet deck core, soft decks, bad keel bolts, keel joint damage, rotten bulkheads, worn-out sails, old standing rigging, dead inboard engines, bad wiring, and years of deferred maintenance. We’ll talk about what matters most when buying a cheap used sailboat, which problems are normal old-boat projects, which problems should make you walk away, and why the best cheap sailboat is not always the lowest-priced boat. It’s the boat with the right to-do list.

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