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How People ACTUALLY Make Money While Cruising (No BS)
Sailing Zingaro

How People ACTUALLY Make Money While Cruising (No BS)

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 is...
What Went Wrong — Lessons from S/V Escape
Sailing Zingaro

What Went Wrong — Lessons from S/V Escape

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, emerge...
Sailing Truth Show: How to Choose the RIGHT Boat for Your Sailing Plans
Sailing Zingaro

Sailing Truth Show: How to Choose the RIGHT Boat for Your Sailing Plans

Want more info? Check out my book - 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 bein...
Sailing Truth Show: Why Balance Beats Strength on a Sailboat
Sailing Zingaro

Sailing Truth Show: Why Balance Beats Strength on a Sailboat

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 ...
Sailing Truth Show — $1,000 Book Giveaway (Every 5 Minutes!)
Sailing Zingaro

Sailing Truth Show — $1,000 Book Giveaway (Every 5 Minutes!)

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 fro...
Why You’re Failing at Sailing
Sailing Zingaro

Why You’re Failing at Sailing

BLACK FRIDAY BOOK DEAL: FREE WORLDWIDE SHIPPING: 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 t...
Sailing Truth Show — The $28k Boat That Could Make You A YouTube Star
Sailing Zingaro

Sailing Truth Show — The $28k Boat That Could Make You A YouTube Star

If you buy this boat, you'll need this book: 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...
Every Boat Has a Story… You’re Not Gonna Believe This One
Sailing Zingaro

Every Boat Has a Story… You’re Not Gonna Believe This One

FULL TOUR: ➡️ (Uploading... Give it 60 minutes...) 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. N...
LIVE: Let Me Spend YOUR Money — Sailboat Deals NOW!
Sailing Zingaro

LIVE: Let Me Spend YOUR Money — Sailboat Deals NOW!

Tonight I’m spending your money. We're going BOAT shopping. If you're interested in learning more about sailboats, pick up my book - 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 ...
I Found a $25K Benetti Yacht for Sale… Here’s Why It’s So Cheap
Sailing Zingaro

I Found a $25K Benetti Yacht for Sale… Here’s Why It’s So Cheap

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, t...
Where to Find REAL Sailing Information
Sailing Zingaro

Where to Find REAL Sailing Information

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 lea...
I Fell Asleep and Crashed Into the Rocks
Sailing Zingaro

I Fell Asleep and Crashed Into the Rocks

Get The Book → 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...
The Night I Fell Asleep and Hit the Rocks — Twice
Sailing Zingaro

The Night I Fell Asleep and Hit the Rocks — Twice

This true story, and dozens more like it, are in my book Be The Captain 👉 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 th...
I Never Thought I’d Be Signing 4,000 Books…
Sailing Zingaro

I Never Thought I’d Be Signing 4,000 Books…

Get 'em while they're signed: 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:...
Signing 4000 books!!! #bethecaptain
Sailing Zingaro
Full Tour of the Bluewater 56 | Kevlar Offshore Yacht
Sailing Zingaro

Full Tour of the Bluewater 56 | Kevlar Offshore Yacht

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 →...
Live @ the Cannes Boat Show
Sailing Zingaro

Live @ the Cannes Boat Show

Experience the Cannes boat show with Zingaro! Grab the first edition of my book → 📗 Book (ends July 31st): MORE FROM ME: 🎥 The Mason 65 Pacific Crossing series: IG:
Link for the livestream: https://www.youtube.com/live/5XVu1ThpACk?si=XxPCbJGUogRQ_ffp
Sailing Zingaro
Captain’s Log: Atlantic Crossing (Day 1) (Patron-only)
Sailing Zingaro

Captain’s Log: Atlantic Crossing (Day 1) (Patron-only)

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: Get the Collector’s Edition of my new book 'Be The Captain' →
My $80K Sailboat Shortlist
Sailing Zingaro

My $80K Sailboat Shortlist

🛑 SALES END JULY 31ST – Don’t Miss This. This is your last chance to grab the first edition of my new book Be The Captain → $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’...
Which Rig Is BEST for Bluewater Sailing?
Sailing Zingaro

Which Rig Is BEST for Bluewater Sailing?

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 surprisin...
DO NOT BUY These 5 Sailboats (And 5 You SHOULD)
Sailing Zingaro

DO NOT BUY These 5 Sailboats (And 5 You SHOULD)

Preorder my book “Be The Captain”: In this video, I break down 10 real offshore sailboats — 5 that I think are smart, seaworthy buys... and 5 that raise red flags. These boats are all for sale right now, and I’ll walk you through what I look for in an offshore cruiser, what makes or breaks a good ...
Why Sailboats Have Two Rudders
Sailing Zingaro

Why Sailboats Have Two Rudders

Check out my new book, Be The Captain: Ever wondered why so many modern sailboats now have dual rudders? You might think it's about safety or redundancy—but there's actually a deeper story. This video reveals the real reasons behind the widespread adoption of dual rudders on cruising sai...
Sneak Preview of My Book: “Be The Captain”
Sailing Zingaro

Sneak Preview of My Book: “Be The Captain”

Get a signed copy while they last → In this video, I’m sharing the story behind Be The Captain—why I wrote it, what I’ve learned from thousands of readers like you, and a preview of what’s inside. Thank you for all the support, encouragement, and energy you've sent my way. I can't wait ...
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