He's Built 400 Boats. The Cheap Used Sailboats He'd Buy in 2026

A 40-year boatbuilder and former charter-fleet operator breaks down which cheap, used cruising sailboats are actually worth buying, and which ones will eat your savings and your dream. If you are shopping for a first bluewater boat on a budget, watch this before you wire a deposit. Kyle Jachney has over 40 years in the boat business, grew up in one of the first charter operations in the Caribbean (a thousand charters a year at its peak), and has had his hands on close to 400 Hylas builds. I commissioned his boats, and this is the conversation I wish every first-time buyer could sit in on. We cover the builders worth your money from the 70s, 80s, and 90s, the ones to admire from the dock and walk away from, the keel-bolt panic YouTube got wrong, why high engine hours don't scare him, the plumbing job everyone skips, and the brutal math on the "needs TLC" bargain boat. This episode also finishes the livestream; our internet cut off, so the back half is your Q&A, answered one question at a time. GET THE BOOK Be The Captain, a no-BS offshore field manual from 90,000+ miles at sea, and winner of the 2026 Eric Hoffer Award for best self-published book. Order it, and you unlock 10% off at Defender Marine and 20% off PredictWind. Get the book and claim both discounts: https://bethecaptain.com CONNECT Patreon: https://patreon.com/svzingaro Instagram: @sailingzingaro Web: https://sailingzingaro.com Boats by Kyle: https://www.bluewateryachts.com/ RECOMMENDED GEAR & STORES Defender Marine has been outfitting boaters since 1938, with trusted brands, expert advice, and everything you need for maintenance, upgrades, and refits. Shop Defender Marine: https://defender.com/en_us/ Get 10% off your next Defender Marine order when you purchase a copy of Be The Captain through the link below. Get the book and claim your discount: https://bethecaptain.com/ CHAPTERS 0:00 Meet Kyle: 40 years, 400 boats, 1,000 charters a year 2:26 Quick news: the book, the Eric Hoffer Award, and your discounts 3:18 What actually makes a cheap old cruiser worth buying 4:45 Inside a Caribbean charter fleet, and what it taught him 5:30 Irwin: built for space, not the open ocean 8:20 Why use a partial (60%) skeg rudder 9:12 Hydrodynamics matter more than your rig 10:49 How to stage a passage south (the Bermuda trick) 12:36 Buy for when you screw up, not for speed 14:32 The hard truth: you'll pour money into ANY boat you buy 15:39 The builders worth your money: Bristol, Tartan, Gulfstar 17:20 Why 14,000 engine hours don't scare him 18:13 The job everyone skips: plumbing and tanks 19:30 The high end: Alden, Hinckley, Little Harbor 21:06 The Tartan 34 he stole for $22,000 22:01 Raising a family aboard a 27-foot boat 23:22 Q&A: the questions the livestream cut off 23:41 Should you fear lead-bolted keels? 27:06 The best 30 to 40 footer to refit 31:46 Are 1985 boats really uninsurable? 35:03 A Hylas 44 for $18,500... worth it? 37:52 What happened to Camper & Nicholson? 40:27 Is a Catalina 30 a good starter boat? 42:10 The Cheoy Lee Clipper 48 46:08 Is a Moody 30 enough for offshore? 47:08 Should we keep making these? Leave a comment! Now tell me in the comments: are these hour-long boat talks worth doing, and which boats should Kyle and I pull apart next? #sailing #liveaboard #bluewatersailing #boatbuying #cruising