Your First Sailboat: No BS Advice for New Sailors
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)
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)
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 "Your First Sailboat: No BS Advice for New Sailors", 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
Your First Sailboat: No BS Advice for New Sailors
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 no...
Do You Know The 10 Essential Knots? 🪢 #sailing #knots
"If you can't tie knots, tie lots" is terrible advice offshore. 🚫 This is your last chance to grab the first edition of my new book Be The Captain → https://bethecaptain.com
Sailing Truth Show: The Systems That Bankrupt Cruisers
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 ban...
Sailing Truth Show: The MOST Important Question Before You Buy a Boat
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 whethe...
Sailing Truth Show: Real Offshore Sailing Questions – Answered
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...
I Didn’t Expect This… Sirius Might Be the Smartest Sailboat I’ve Toured
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...
Sailing Truth Show: When Is It Time to Give Up the Sails?
Interested in sailing offshore? Here's what you need to know: https://bethecaptain.com/ 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...
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?...
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.