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)

Everyone asks, "How much does the boat cost?" Almost nobody asks, "How much does the electricity cost?" Tonight on the Sailing Truth Show, we are breaking down the specific boat systems that drain cruising budgets the fastest. It’s not the hull that bankrupts sailors—it’s the upgrades. We’re talking about the "Lithium Trap," the generator nightmare, and why making your boat "too safe" might actually be making it too expensive to sail. I’m also preparing for a massive interview with the legendary Nigel Calder (author of Boatowner's Mechanical and Electrical Manual). I have a list of difficult questions from my Patrons, but tonight, I’m opening the floor to YOU. In this Livestream: The Big 3 Money Pits: Why generators, watermakers, and complex electrics often cost more to own than to buy. Nigel Calder Prep: I’m taking the hardest technical questions from the chat tonight to ask Nigel directly. The "Simple vs. Complex" Debate: Is the era of the simple mechanical diesel officially dead? Drop your questions for Nigel in the chat! Get the Book: 📖 Be The Captain (First Edition Hardcover): [Link to your store] Join the Crew: Patreon: https://www.patreon.com/svzingaro Website: https://bethecaptain.com/ Follow the Journey: Instagram: @sailing_zingaro Facebook: Sailing Zingaro #sailing #boatlife #cruisingcost #nigelcalder #boatmaintenance #offshoresailing #sailingzingaro

Thinking about buying a boat or going cruising? Read this first: https://bethecaptain.com/ Most people think buying the right boat is the hard part. It isn’t. The hardest part—and the part almost nobody slows down enough to think through—is whether this life actually fits who you are. In this Sailing Truth Show, we’re having a serious conversation about the most important question you should ask before you buy a boat, sell a house, or reorganize your life around cruising. This has nothing to do with brands, budgets, or bluewater checklists. It’s about responsibility, temperament, and how you actually respond when things stop going according to plan—which offshore, they always do. If you’re casually curious, this might not be the conversation for you. But if you’re seriously considering cruising—or already deep into the decision—this is one you need to hear before you go any further. I wrote Be The Captain because I kept having this same conversation with people—usually after they’d already spent the money. Watch first. Decide second.

This live stream is built entirely from real questions pulled straight from the comments on recent videos. No slides. No scripts. No armchair theory. We’ll cover real offshore sailing topics—storm tactics, reefing, routing, boat design, fatigue, risk, and judgment—and talk about what actually works at sea, not what looks good in textbooks or marketing brochures. If you’re watching live, drop your questions in the chat. If you’re watching later, leave them in the comments—this series is ongoing. This is about seamanship, margin, and stacking the deck in your favor offshore.

Last chance for the first printing of Be The Captain → https://bethecaptain.com I want to set expectations for this video, because this isn’t a review and it’s not a sales pitch. This was my first time ever stepping aboard a Sirius sailboat. I didn’t come in with a script, an agenda, or any affiliation with the builder. I was at the show when someone from the audience insisted I go see it—and by the end of the tour, I was genuinely impressed by how thoughtfully this boat is put together. What you’re seeing here is a real, unscripted walk-through from the perspective of someone who loves smart design, practical engineering, and boats that are clearly built with purpose. Any excitement you hear is real. I’m not being paid, and no one asked me to say anything nice. A big thank-you to Thorsten for taking the time to walk me through the boat and answer my questions. If you’d like more information about Sirius, you can find them here: 👉 [link to Sirius Yachts website] Grab the first edition of my book → https://bethecaptain.com If you enjoy honest, experience-based sailing content, consider subscribing. I post long-form videos about seamanship, offshore sailing, and boats that are actually meant to be used.

When is it time to give up the sails? This livestream is a reflective conversation about sailing, aging, fatigue, partnership, and changing priorities—not a sail vs power argument. We’ll start with an excerpt from Skip Novak, explore why some sailors transition to trawlers, and look at a few real boats as examples of different philosophies of life afloat. No judgment. No dogma. Just an honest discussion about what we actually want from being on the water.

Most people don’t give up on cruising because of weather, boats, or seamanship. They give up because they can’t figure out the money. In this episode, I break down how people actually make money while cruising—and just as importantly, what doesn’t work once real life at sea gets involved. This isn’t a hype video. There’s no passive-income fantasy here. We talk honestly about: Why chartering is a terrible “backup plan” for most cruisers Why physical labor and boat work often trap people in one place The reality of consulting, freelancing, and remote work offshore Why social media is a long game—not a paycheck How real estate can support cruising only if it’s set up beforehand And why online businesses are one of the few models that consistently survive cruising life when done right This conversation is especially for: People dreaming about cruising but stuck on the financial side Couples trying to make this decision together Anyone who wants the truth, not the Instagram version I’m not promising this will work for everyone. I’m sharing what I’ve seen survive reality—motion, fatigue, bad internet, time zones, broken gear, and stress. If you’re not independently wealthy and you want to understand how people make this life work financially, this one’s for you.

This video took me three years to make. Two sailors lost their lives aboard S/V Escape, and this is a careful, experience-based breakdown of what went wrong to understand the seamanship lessons that matter. Captain’s Locker — FREE DOWNLOAD Gear, checklists, watch schedules, night-reef cards, emergency playbooks, and more that I actually use at sea: https://bethecaptain.com/pages/locker Be The Captain — my book on decision-making, judgment, and seamanship: https://bethecaptain.com Further Reading & Context • Lessons From a Tragedy at Sea — real-world analysis and takeaways: https://www.morganscloud.com/2022/08/22/lessons-from-a-tragedy-at-sea/ • Reefing a Sailboat — a practical primer on reefing techniques that work: https://www.morganscloud.com/2010/11/19/reefing-a-sailboat/ About This Video I was one of the last people to see Karl and Annemarie before they departed Bermuda, and this analysis is grounded in real-world offshore experience. If we learn the right lessons from this, it can help prevent something similar from happening again. If you found this video useful, consider subscribing and sharing your sailing plans in the comments. Chapters: 00:00 Context & Intent 01:09 What Happened to S/V Escape 05:50 Lesson 1: Reef at Sunset 06:54 Lesson 2: Sail at 80 Percent 07:42 Lesson 3: Wind Against Current 08:43 Lesson 4: Reef Off the Wind 09:48 Lesson 5: A Ship Is a Crew Brain 11:26 Lesson 6: Boat Size and Control 12:59 Lesson 7: The First 72 Hours 13:36 Personal Reflection 14:09 The Captain’s Locker (Free Resources) 14:56 Final Takeaways

Want more info? Check out my book - https://bethecaptain.com/ This is the MOST common question I am asked during paid consultations. And most people don’t buy a bad boat. They buy the wrong boat for the life they’re actually going to live. On this week’s Sailing Truth Show, we’re breaking down one of the most common, and expensive, mistakes in offshore sailing: choosing a boat without first being honest about your intended use. High latitudes. The milk run. Adventure routes like Easter Island or the Kimberleys. Or the slow circumnavigation—finding paradise and staying put for months at a time. Each of those lives demands very different boats, systems, and compromises. Problems start when people ask one boat to do all of them. This isn’t brand bashing, and it’s not about money. It’s about alignment. Bring your questions, your plans, and your dream routes. We’ll talk through where the real mismatches happen—and how to avoid buying the wrong boat for the wrong life.

Most people think surviving storms offshore is about having a strong boat. Heavier. Tougher. Overbuilt. It’s not. Offshore seamanship is the art of keeping a boat in balance: aerodynamically, structurally, and mentally. When a boat is balanced, energy stays manageable. When it’s not, energy builds until something breaks… or someone gets hurt. In this livestream, I break down several real-world examples; near misses, fatalities, and structural failures — to show how the same imbalance manifests in very different ways. This isn’t about blaming individuals or reacting for clicks. It’s about understanding force, judgment, and why “adding strength” so often makes things worse instead of better. If you sail offshore, or plan to, this mindset matters more than any piece of gear. If you want to go deeper into offshore judgment, storm tactics, and real-world seamanship, my book Be The Captain was written for exactly that purpose. Book: https://bethecaptain.com

BLACK FRIDAY LIVESTREAM. I’m giving away $1,000 worth of books tonight. One book every five minutes. Stick around, drop your questions in the chat, and let’s talk boats, seamanship, offshore realities, storm tactics, and whatever else you want to throw at me. I’ll be going through your comments from the last few videos, reviewing boats live, and pulling questions straight from the chat. If you’ve ever wanted to ask me something directly, tonight is the night. If you want to grab Be The Captain while the deal is on: FREE worldwide shipping this week only: https://bethecaptain.com If you win a book tonight, DM me on Instagram or email me so I can get your shipping info. Thanks for hanging out, captains. Let’s make this one fun. Much love, James

BLACK FRIDAY BOOK DEAL: FREE WORLDWIDE SHIPPING: https://bethecaptain.com After 90,000 ocean miles, four Pacific crossings, losing a forestay, a knockdown, and a catamaran literally splitting in half… I’ve realized something nobody talks about: Most of the danger offshore doesn’t come from storms or gear. It comes from the mindset mistakes that every sailor makes without realizing it. Today we’re breaking down the 6 hidden fears that quietly sabotage your sailing, wreck your judgment, and stall your cruising dreams before you ever leave the dock. This video is NOT about gear, checklists, or fancy upgrades. This is the stuff that actually matters when everything is going sideways offshore and everyone is looking at YOU. WHAT YOU’LL LEARN IN THIS VIDEO • The six fears that kill more cruising dreams than money or storms • Why you rush when things go wrong (and how to stop it instantly) • The “fight or flight” trap every sailor falls into offshore • Why gear isn’t seamanship — and what actually is • How fatigue rewires your brain and destroys your judgment • My “Law of Compounding Chaos” (L&A January Issue) If you’ve ever wondered why some sailors sail offshore while others stay tied to the dock, these 6 mindset shifts are the difference. GET THE BOOK. BE THE CAPTAIN. My #1 goal with this channel is to help you become the calm, confident, capable captain your crew trusts when it matters most. That’s why I wrote Be The Captain: a field manual for real-world offshore judgment and leadership. Order the First Edition Hardcover + Audiobook: https://bethecaptain.com/products/be-the-captain-first-edition-hardcover Black Friday Deal: FREE Worldwide Shipping this week only JOIN THE LIVESTREAM THIS SATURDAY @ 5:30PM EST We deep-dive real offshore scenarios every week and break down decisions that keep boats and crews safe. Bring your questions — see you there. 👇 COMMENT BELOW What’s the fear that’s held YOU back from sailing offshore? Let’s talk about it, you’re not alone. Fair winds, Jamie / Sailing Zingaro Chapters: 00:00 – Happy Thanksgiving & Introduction 00:25 – The Real Reason Sailors Stay at the Dock 01:00 – FEAR #1: “I Need Everything Figured Out Before I Go” 02:04 – FEAR #2: “I Need to Act FAST — We Only Have Seconds!” 03:26 – How Fighter Pilots Stop Panic (Physiological Sigh) 03:36 – FEAR #3: Over-Dependence on Tech 04:33 – Training Yourself for No-Tech Sailing 07:49 – FEAR #4: “I Need Someone to Tell Me I’m a Captain” 09:28 – FEAR #5: “Fatigue Won’t Break Me” 10:42 – FEAR #6: Forgetting the Law of Compounding Chaos 12:02 – How to Stop Chaos Offshore 12:31 – Why These 6 Fears Matter 12:50 – Get the Book 13:19 – What Fears Hold YOU Back?

If you buy this boat, you'll need this book: https://bethecaptain.com/ Ever dreamed of starting a YouTube channel — and blowing up instantly? This 82-foot abandoned yacht might be the craziest “content cheat code” I've ever seen. Tonight on the Sailing Truth Show we’re looking at a massive Dutch-built aluminium Trintella that’s been sitting unfinished for decades… and heading to auction for $28,000. For 99% of sailors, this is a financial nightmare. For a new YouTuber? This might be the most powerful story engine you could ever buy. In this episode we’re breaking down: ⚓ Why this 82-foot boat was abandoned ⚓ What it would really cost to finish ⚓ Who should take on a project this insane ⚓ Why the story alone could carry a YouTube channel ⚓ What makes big, impossible builds go viral ⚓ How couples and creators use projects to explode their channels ⚓ Why dream projects are also the most dangerous ones If you’ve ever thought about starting a channel — or taking on a big refit — this episode is for you. And if you want the real offshore truth… we’re going deep tonight.

FULL TOUR: ➡️ https://patreon.com/svzingaro Every boat has a story… but this one is on another level. This is the MCP 68 Global Expedition — a 32-ton aluminum yacht that sailed six thousand miles upwind on its maiden voyage, straight into hurricane season… and nothing meaningful broke. Not the rig, not the systems, not the structure. This film isn’t a boat tour. It’s a deep dive into offshore engineering: — Why a ballasted swing keel on an aluminum boat is rare, and enhances performance — Why this hull survived 35 days of upwind punishment — How the raised deck-salon and mid-ship cabins change offshore living — The details most people walk past: triple-purchase mainsheet, alloy structure, access, drains, systems — The decisions that actually matter offshore (and the ones that don’t) Whether you’re a sailor or not, this is one hell of a story. Want to learn everything I teach offshore? ➡️ Be The Captain — https://BeTheCaptain.com Chapters 0:00 – Every Boat Has a Story 0:23 – The Impossible Maiden Voyage 0:59 – How This Boat Survived 1:25 – Offshore Engineering That Matters 4:02 – Centerboards vs. 9-Ton Swing Keel 5:58 – Smart Design You Don’t See at Boat Shows 9:33 – The Downsides You Need to Know 13:00 – What Actually Matters Offshore

Tonight I’m spending your money. We're going BOAT shopping. If you're interested in learning more about sailboats, pick up my book - https://bethecaptain.com/ Chapter two is dedicated to teaching you everything you need to know to pick a gread offshore boat. We’re boat shopping together in real time. Production boats, bluewater cruisers, steel cutters, project boats, dream boats — everything is fair game. We’ll break down: • The best sailboat deals happening right now • What’s worth the money (and what isn’t) • Real offshore capability vs marina queens • Keel, rig, and engine red flags • Deal breakers most buyers don’t even know to look for • The boats YOU send in live • And why some listings are straight-up dangerous My special link for Yachtworld: https://www.yachtworld.com/boats-for-sale/type-sail/make-amel+alubat+baba+baltic+bowman+c-c+cabo-rico+caliber+cape-dory+cape-george+contest+farr+frers+garcia+hans-christian+hylas+islander+kelly-peterson+koopmans+little-harbor+malo+mason+najad+ovni+oyster+pacific-seacraft+passport+pearson+robert-perry+rustler+saga+southerly+southern-cross+ta-shing+tayana+trintella+tripp+valiant+westsail+allures+catana+chris-white+dolphin+dudley-dix+hallberg-rassy+herreshoff+hinckley+hoek+island-packet+kanter+knysna+lerouge+meta+moody+nautor-swan+outbound+outremer+perry+schionning+shannon+spirit+sundeer+van-de-stadt+abeking-rasmussen+alberg+alden+allied+alloy-yachts+alumarine+aluminum-cruiser+bestevaer+bluewater+bluewater-yachts+brewer+bristol-channel-cutter+bruce-roberts+cal+colin-archer+columbia+columbia-yacht+colvin+contessa+corbin+cutter+deerfoot+endeavour+endurance+fuji+gib-sea+gozzard+gulfstar+hank-hinckley+hughes+irwin+lafitte+maple-leaf+morrelli-melvin+neel+nauticat+nor-sea+nordic+norseman+puffin+santa-cruz+slocum+sparkman-stephens+spirit-yachts+sweden-yachts+ta-chiao+ted-brewer+vagabond/ 📘 Grab my book “Be The Captain” https://bethecaptain.com

A Benetti yacht… for twenty-five thousand dollars?! This 61' Benetti steel sailing yacht, designed by Laurent Giles, is heading to auction — and on paper, it looks like the deal of the century. But is it really? In this livestream, I’ll break down everything you need to know: the real costs, the hidden problems, the refit risks, and what it would actually take to turn this classic into a safe, offshore-ready cruiser. We’ll go through: ⚓ What makes Benetti yachts special (and what doesn’t) 🛠️ The steel + aluminum construction — a blessing or a curse 💰 What it’ll really cost to fix and refit 🌊 Why this $25K price tag might be too good to be true If you’ve ever dreamt of finding a “deal” on a bluewater yacht — or you just want to see what happens when a luxury build ends up at auction — you’ll love this one.

Sailing knowledge isn’t centralized — it’s tribal. You learn from old salts, obscure blogs, long-out-of-print manuals, and the people who’ve actually done the miles. But with so much noise online, where do you find information you can actually trust? In this video, I’ll share the best places to learn real sailing — the YouTubers, books, courses, and communities that actually make better sailors — and why I built The Captain’s Locker, a free collection of the best offshore checklists, templates, and guides I’ve ever used. It’s all here — no paywalls, no sponsorships, no BS: 👉 https://www.bethecaptain.com/locker In this video: 00:00 – Why this video exists 00:40 – The question that started it all 01:00 – The Captain’s Locker (free resource) 03:20 – YouTube: The Wild West 05:30 – The Books That Actually Matter 07:00 – Courses & Certifications (What They Don’t Teach) 08:00 – Blogs, Forums & Magazines Worth Reading 09:30 – Experience: The Ultimate Teacher 11:00 – Final Thoughts Mentioned in this video: Lady K Sailing 👉 https://www.youtube.com/c/LadyKSailing Rigging Doctor 👉 https://www.youtube.com/c/RiggingDoctor Sailing Fair Isle 👉 https://www.youtube.com/@svfairisle Practical Sailor Magazine 👉 https://www.practical-sailor.com Peter Swanson’s Loose Cannon 👉 https://loosecannon.substack.com Beth Leonard – The Voyager’s Handbook 👉 https://www.amazon.com/dp/0071437657 Steve & Linda Dashew – Offshore Cruising Encyclopedia 👉 https://setsail.com/free-books/ SailLibra 👉 https://www.saillibra.com John Kretschmer Webinars 👉 https://www.johnkretschmersailing.com/webinars Koru Expeditions 👉 https://www.koru.world Morse Alpha Schedule 👉 https://www.morsealpha.com/2026-sailing-schedule Ocean Passages 👉 https://www.sailoceanpassages.com/sailing-schedule None of these folks are paying me — I just respect what they do. MY BOOK: 📘 Be The Captain – A Field Manual: https://www.bethecaptain.com 🎧 Audiobook + Extras: https://bethecaptain.com/products/be-the-captain-offshore-sailing-audiobook ⚓ Join the Crew (Patreon): https://www.patreon.com/svzingaro 📺 More videos: – My Catamaran Split in Half 100 Miles Offshore. Here’s How We Survived. https://www.youtube.com/watch?v=o__mcZS-jfU&t=117s – Offshore Weather Routing https://youtu.be/MfeWGROLU8s – The WORST Advice for Offshore Sailors https://youtu.be/JCKj882NpRs

Get The Book → https://bethecaptain.com The True Story Behind the Night I Almost Lost Everything—and What It Taught Me About Command at Sea. Two boats. Two oceans. Two mistakes I’ll never forget. This is the night I fell asleep under full sail and ran my boat straight into the reef—twice. It’s not about drama; it’s about what fatigue really does to judgment at sea, and what it means to take full responsibility for your boat and crew. ⚓ Support the Journey Join the Patreon crew for behind-the-scenes stories, uncut footage, and exclusive sailing lessons: → https://patreon.com/BeTheCaptain 🎬 Watch Next – My Catamaran Split In Half: Here’s How We Survived → https://www.youtube.com/watch?v=o__mcZS-jfU – Rescue 2000 Miles Offshore → https://www.youtube.com/watch?v=NTlpurrBV3A Much love, James Evenson Be The Captain | https://bethecaptain.com Chapters 00:00 – I Fell Asleep at the Helm 00:40 – Mexico: The First Boat Crash 02:00 – The Crash 03:30 – Don’t Quit 05:00 – The Aftermath 09:00 – Bahamas: The Second Boat Crash 11:00 – Fatigue Strikes Again 14:00 – Escaping the Reef 18:00 – Lessons Learned

This true story, and dozens more like it, are in my book Be The Captain 👉 https://www.bethecaptain.com This is a true sailing story about what happens when a solo sailor falls asleep offshore. I’ve been through two different boat crashes, both from fatigue, and each taught me hard lessons about seamanship, preparation, and the realities of sailing offshore. If you’ve ever wondered what happens when you fall asleep while sailing, or how to prevent it, this is a story you need to hear. 🗺 About Be The Captain It’s not a sailing book — it’s a captain’s manual for real life at sea. Every chapter is drawn from thousands of miles offshore, from heavy weather to leadership, anchoring, maintenance, and self-reliance. If you connected with this story, you’ll find the whole system in Be The Captain. 📘 Get your copy here → bethecaptain.com

Get 'em while they're signed: https://bethecaptain.com The Captain’s Collector’s Edition books are finally shipping! 4,000 copies signed and stacked, ready to make their way around the world. This is just the beginning of a huge adventure. Thank you for being part of it. Big thanks to those who came to help me: Steven Lindsey Amber Calahan Jon Moga Nikki Moga Yuri MORE FROM ME: 🎥 The Mason 65 Pacific Crossing series: https://www.youtube.com/watch?v=_lo0L22FDq4 https://www.patreon.com/svzingaro https://www.paypal.me/sailingzingaro IG: https://www.instagram.com/sailing_zingaro/