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/

Full in-depth walkthrough of the Bluewater 56 — a Kevlar/Twaron-reinforced offshore sailboat designed for real bluewater passagemaking. This isn’t just a quick deck shot; it’s a detailed 90-minute tour filmed after I spent six weeks commissioning this yacht in Mallorca. 📕 My book: Be The Captain → https://bethecaptain.com. In this video, you’ll see: - German Frers’ design choices for offshore safety and performance - Kevlar/Twaron hull construction — stronger than aluminum or steel? - Deck layout and sail-handling systems for shorthanded passagemaking - Interior layout, tankage, and systems access for serious liveaboard use - My candid thoughts from commissioning the boat before she hit the water 🔗 Bluewater Yachts: https://www.bluewateryachts.com/ Support the channel: Patreon: https://www.patreon.com/svzingaro PayPal: https://www.paypal.me/sailingzingaro Instagram: https://www.instagram.com/sailing_zingaro/

Experience the Cannes boat show with Zingaro! Grab the first edition of my book → https://bethecaptain.com 📗 Book (ends July 31st): https://bethecaptain.com 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/

The real captain's log from the Atlantic Crossing of sailing vessel 'Aequus'. True story, read by the author: Captain James Evenson. Want the WHOLE Captain's Log series? Go here: https://www.youtube.com/watch?v=aUJiKty_7zY&list=PLYK_-XEJdbbRoa8JEF-vt5NVATSTkCfPI Get the Collector’s Edition of my new book 'Be The Captain' → https://bethecaptain.com

🔴 LAST CHANCE – Signed Books Disappear July 24. Get the Collector’s Edition of Be The Captain™ before it’s gone → https://bethecaptain.com $80,000. It’s one of the most overlooked price points in the cruising world—and also one of the most interesting. You’re not quite scraping the bottom of the barrel, but you’re not shopping turnkey either. You’re in the middle: smart buyer territory. In this video, I give you my personal shortlist of 8 bluewater sailboats over 40 feet that I’d actually trust offshore—and 5 that show up all the time but aren’t what they seem. Whether you’re looking for your first liveaboard or downsizing for long-term cruising, this list is for you. 👇 Boats looked at in this video: 👇 Offshore-Capable Picks (My $80K Shortlist): Corbin 39 (1980): boats.com listing Shannon 38 (1979): YachtWorld listing Hallberg-Rassy 41 (1978): YachtWorld listing Najad 390 (1993): YachtWorld listing Valiant 40 (1982): YachtWorld listing C&C Landfall 40 (1986): YachtWorld listing Jeanneau Sun Odyssey 40 DS (2003): YachtWorld listing Tayana 42 (Vancouver) (1980): YachtWorld listing 🚫 Boats to Be Wary Of (Popular, But Not Offshore-Ready)🚫 Caliber 40 LRC (1998): YachtWorld listing Morgan Out Island 41 (1974): YachtWorld listing Hunter 45 Center Cockpit (2006): YachtWorld listing Moody 422 CC (1987): Port Navy Service listing Formosa 41 (1974): YachtWorld listing 📍 Chapters: 00:00 - THE BIG SHORT (list) 01:11 - How to LOOK at a boat 02:40 - Boat #1: Corbin 39 05:08 - Boat #2: Shannon 38 07:19 - Boat #3: Hallberg Rassy 41 09:12 - Boat #4: Najad 390 10:13 - Boat #5: Valiant 40 13:26 - Boat #6: C&C Landfall 40 14:45 - Boat #7: Jeanneau Sun Odyssey 40DS 17:20 - Boat #8: Tayana 42 19:16 - Warning #1: Caliber 40 LRC 20:32 - Warning #2: Morgan OI41 21:33 - Warning #3: Hunter 45 22:43 - Warning #4: Formosa 41 24:10 - Warning #5: Wauquiez Pretorien 40 25:15 - Be the Captain 26:00 - Special Announcement 📘 Want to go deeper? My book Be The Captain breaks down the entire anatomy of an offshore cruising boat—how to choose it, how to fix it, and how to sail it. Preorder now → https://bethecaptain.com ☕️ Support these videos and get behind-the-scenes access: 📍 Patreon.com/svzingaro

🔴 LAST CHANCE – Signed Books Disappear July 24. Get the Collector’s Edition of Be The Captain™ before it’s gone → https://bethecaptain.com In this video, I break down the real-world pros and cons of masthead rigs vs fractional rigs for offshore sailing. This isn’t just theory—I’ve sailed almost 100,000 nautical miles on both, in storms, trade winds, and dead calms. You’ll learn: Which rig performs better offshore—and why The surprising history behind these designs Why racing boats went one way and cruising boats went the other And what I personally trust on ocean crossings If you're choosing a boat, refitting a rig, or just want to understand what’s really going on up there, this one’s for you. Thanks for watching—let me know in the comments what rig you prefer, and why. #bluewater #bluewatersailing #offshorerescue #sailing #sailboat #sailboatlife #howto #education Chapters 00:00 - The Question 00:53 - A History of Sailboat Rigging 3:03 - Technical comparison: Fractional vs Masthead 6:16 - A note on Baby Stays 7:05 - Chainplate configuration 9:36 - Race and performance boats 11:51 - When fractional rigs still make sense offshore 12:40 - My Opinion 16:40 - "Be the Captain" THANK YOU