WORST Sailboats to Buy in 2025

Some sailboats look great on paper—and turn into endless problems offshore. In this video, I break down a list of boats I would personally avoid for bluewater and serious cruising, and explain why. These aren’t hot takes or internet pile-ons—they’re lessons learned from real-world design tradeoffs, maintenance realities, and offshore use. We’ll talk about boats like the Formosa 41, which often ends up more “pirate movie prop” than practical cruiser, as well as IOR racer-cruisers like the Catalina 38 and C&C 40 that can create long-term headaches when pushed beyond what they were designed for. If you’re shopping for a cruising boat, knowing what to avoid is just as important as knowing what to buy. This video is about saving you time, money, and frustration—before commitment sets in. Boats discussed in this video 00:00 – Intro 01:07 – Formosa / CT41 02:13 – Morgan Out Island 41 03:23 – CSY 44 Walkover 04:33 – Catalina 38 06:02 – Gulfstar 37 (early production) 06:27 – Hunter 37 Legend 07:38 – Columbia 45 08:09 – Endeavour 37 09:07 – Choy Lee Offshore 38 09:38 – C&C 40 📘 Be The Captain — Offshore Captain’s Field Manual This video shows the symptoms. In Be The Captain, I lay out the full framework for evaluating boats—design intent, structure, systems, fatigue, and failure modes—so you can spot problems before they become your problem. First Edition hardcover + audiobook available here: 👉 https://bethecaptain.com 👇 Join the discussion What boats do you think belong on this list—and why? Drop a comment. Good examples (and bad ones) help everyone learn. Hashtags #SailboatsToAvoid #BoatBuying #BluewaterSailing #CruisingLife #OffshoreSailing #Seamanship