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 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.
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.
Sailing Zingaro
Over the last 7 years, Sailing Zingaro has been to some of the most remote areas on the planet in search of Adventure and experiences of a lifetime. Follow along with Captain James as he sails around the world, documenting the whole time...
Channel Information:
Social Media Links:
Note of Recognition for Sailing Zingaro
At WeBoating.com, we profoundly acknowledge the unwavering dedication that Sailing Zingaro and other creators invests in crafting each and every video. Their passion for delivering exceptional content shines through every frame, and it's a labor of love that deserves your attention.
We invite you to watch their captivating videos and actively engage with their content, including their social media links above. Liking, commenting, and sharing their work goes a long way in fueling their creative fire.
We're also inviting you to explore any sponsorships and partnerships highlighted in the video description of "How People ACTUALLY Make Money While Cruising (No BS)", or directly on YouTube. By considering their offerings or purchasing services and items, you not only support Sailing Zingaro but also the brands and collaborators they're associated with.
If you have any feedback, corrections, or additional information about Sailing Zingaro or their videos, please use the comment form below to share your thoughts with us.
Thank you for being a part of our community and supporting the creators we cherish. Your time and support truly matter!
Sailing Zingaro Lastest Videos
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’...
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, check...
Sailing Truth Show: How to Choose the RIGHT Boat for Your Sailing Plans
Want more info? Check out my book - https://bethecaptain.com/ 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, an...
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...
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...
Why You’re Failing at Sailing
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 ...
Sailing Truth Show — The $28k Boat That Could Make You A YouTube Star
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 Sa...
Every Boat Has a Story… You’re Not Gonna Believe This One
FULL TOUR: ➡️ https://patreon.com/svzingaro (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 i...
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 - https://bethecaptain.com/ Chapter two is dedicated to teaching you everything you need to know to pick a gread offshore b...
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 e...
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 trus...
I Fell Asleep and Crashed Into the Rocks
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 ...
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 👉 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 f...
I Never Thought I’d Be Signing 4,000 Books…
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 f...
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 thi...
Live @ the Cannes Boat Show
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?...
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: https://www.youtube.com/watch?v=aUJiKty_7zY&list=PLYK_-XEJdbbRoa8JEF-vt...
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 → https://bethecaptain.com $80,000. It’s one of the most overlooked price points in the cruising world—and also one of t...
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: Whic...
DO NOT BUY These 5 Sailboats (And 5 You SHOULD)
Preorder my book “Be The Captain”: https://www.bethecaptain.com 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 ...
Why Sailboats Have Two Rudders
Check out my new book, Be The Captain: http://bethecaptain.com 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 beh...
Sneak Preview of My Book: “Be The Captain”
Get a signed copy while they last → http://bethecaptain.com 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 s...
Something AWESOME is coming!
Be the FIRST to know⛵
Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!
We don’t spam! Read our privacy policy for more info.