My Advice for Your First Sailboat (It's Not What You Think)

Stop trying to buy a "circumnavigation boat." Buy an "education" boat. I recently received an email from Simon, an 18-year-old sailor with a tight budget and a big dream. He said something that most beginners miss: "Ugly is fine. Stuck in a boatyard is not." Buying your first sailboat is where most sailors make their most expensive mistakes. They buy the boat that looks good on Instagram, not the boat that teaches them how to be a Captain. In this video, I’m sharing the advice I wish I had when I started. We’ll talk about: * Why your first boat shouldn't be your "forever" boat. * The trap of the "Perfect Boat" vs. the "Right Boat." * How to build "Dangerous Competence" before you ever cross an ocean. This philosophy is the core of my book, Be The Captain. It’s a field manual for sailors who want to move beyond internet checklists and build real offshore confidence. If you’re serious about seamanship—and want to avoid burning money on the wrong vessel—grab a copy here: 👉 https://bethecaptain.com/ Chapters 00:00 The 18-Year-Old Sailor with a Big Dream 00:44 Stop Thinking About Circumnavigation 01:38 The "Education Boat" Strategy 02:18 Why Your First Boat Shouldn't Be Your Forever Boat 03:07 Understanding IOR Sailboat Designs (The "Kalik 33" Problem) 04:39 Why Racing Boats Make Difficult Cruisers 06:15 The Danger of Old Teak Decks & Water Damage 07:54 Checking Bulkheads for Rot 08:36 What You Should Actually Buy (The Best First Sailboat) 09:28 Why Smaller Boats Make You a Better Sailor 10:31 The "Ugly Boat" Rule 11:19 Building Dangerous Competence 11:44 Be The Captain (Conclusion)