Sailing Zingaro

The Time My Sail Almost Killed Me

Speaking of dumb things I've done on a sailboat, let's revisit the time the Aruba Coast Guard stayed with us until three in the morning to help me get my sail under control... 📗 Get My Book:

Jul 23, 2026
Language: EN
Play Time: 00:00:42

Sailing Zingaro

I Fell Asleep at the Wheel

While sailing toward Belize, I fell asleep at the wheel and drove my catamaran onto a reef with both daggerboards down. It was a brutal reminder of how quickly fatigue can turn into a serious emergency at sea. 📗 Get My Book:

Jul 22, 2026
Language: EN
Play Time: 00:00:49

Sailing Zingaro

Are Bolted Keels Safe?

I prefer strong attached keels, but I would still sail around the world with a properly constructed bolted keel. What matters most is how the keel is built, supported and attached to the hull. 📗 Get My Book:

Jul 21, 2026
Language: EN
Play Time: 00:00:55

Sailing Zingaro

Some Dinghies are Beyond Saving

I tried to save a dinghy that had spent five years baking in the sun, but the damage and repairs quickly became a money pit. A proper cover may cost a lot upfront, but protecting your gear from UV exposure can save you thousands later. 📗 Get My Book:

Jul 20, 2026
Language: EN
Play Time: 00:00:35

Sailing Zingaro

These Sailboats Were Ridiculously Heavy

Kyle Jachney (Bluewater Yachts) and I talk about how some classic fiberglass sailboats were built with far more material than necessary, resulting in exceptionally heavy designs. They were incredibly strong, but all that extra weight had a major impact on how they sailed. 📗 Get My Book:

Jul 19, 2026
Language: EN
Play Time: 00:00:24

Sailing Zingaro

Broken Rudders, Sunken Boats: The Orcas Are Winning | Sailing Truth Show

Orcas have been ramming rudders and sinking sailboats off Spain, Portugal, and Gibraltar — and tonight we roll the tape. This is a Captain's Breakdown: I pause the footage, judge the crew's decisions in real time, and give the verdict — seamanship, panic, or pure luck. Then I'll tell ...

Jul 18, 2026
Language: EN
Play Time: 01:30:01

Sailing Zingaro

Do I Keep Guns on My Sailboat?

Guns onboard are legal to own but risky to carry abroad. Declare it and you might not get it back, hide it and you're risking prison. This is a personal call with real consequences either way. 📗 Get My Book:

Jul 18, 2026
Language: EN
Play Time: 00:00:47

Sailing Zingaro

Am I Too Old to Start Sailing?

An 80-year-old asks if he's too old to start offshore sailing. I say go for it. Age isn't the dealbreaker, mobility is. Can you climb over the lifelines and pull yourself out of the water? That's what really matters. 📗 Get My Book:

Jul 17, 2026
Language: EN
Play Time: 00:00:41

Sailing Zingaro

Best $50K Monohull for Island Hopping

Catalina 42, Morgan 41, Erwin, Gulf Star, or Beneteau: which mid-size cruiser gets you island hopping on a beer budget? Real talk on what to buy and why. 📗 Get My Book:

Jul 16, 2026
Language: EN
Play Time: 00:00:36

Sailing Zingaro

My Final Video as Sailing Zingaro

After 10 years and 90,000 nautical miles, this is the last video under the Sailing Zingaro name. In 2016 I bought a catamaran, pointed a camera at myself, and made a promise: I'll go, and I'll take you with me. The good, the bad, the ugly. You watched me sail to Ecuador, Easter Island, an...

Jul 16, 2026
Language: EN
Play Time: 00:08:23

Sailing Zingaro

Are All Sailboats Money Pits?

Is a sailboat ever an investment, not just a money pit? The truth about depreciation curves, boat flipping, and why breaking even is the best most owners can hope for. 📗 Get My Book:

Jul 15, 2026
Language: EN
Play Time: 00:00:53

Sailing Zingaro

Cal 40s are Legendary Boats

The Cal 40 is an epic boat. Here's a quick history of Cal Jensen, designer Bill Lapworth, and why Jensen-era hulls are still the ones to hunt for. The company didn't survive after Jensen sold it, but the boats he built before that are still considered ahead of their time. 📗 Get My Book:

Jul 14, 2026
Language: EN
Play Time: 00:00:48

Sailing Zingaro

Can You Steer With a Drogue Out?

Yes, you can still steer with a drogue out. A drogue is purely a drag device that slows the boat down; it doesn't take away your steering control. It's strictly an emergency setup, so knowing your attachment points before you need them makes all the difference. 📗 Get My Book:

Jul 13, 2026
Language: EN
Play Time: 00:00:38

Sailing Zingaro

Aerorigs are Cool, However…

The Aerorig is a cool idea, but articulating anything on a boat isn't for me. When it breaks, simple wins. Stick, hole, glue, sail. Everything on a boat eventually fails, so the fewer moving parts you have to fix offshore, the better. 📗 Get My Book:

Jul 12, 2026
Language: EN
Play Time: 00:00:45

Sailing Zingaro

Are Junk Rigs Actually Worth It?

Junk rigs are custom builds, which makes them great for tinkerers who love fixing their own boat but tough for anyone who needs outside help. They're similar to synthetic rigging in that learning to splice it can make you a better sailor. Both come with a real learning curve, so they're be...

Jul 11, 2026
Language: EN
Play Time: 00:00:48

Sailing Zingaro

The Smallest Boat I’d Take Across the Pacific

What's the smallest bluewater boat you'd trust for a Pacific crossing? Flicka 20s, Nor'Sea 27s, and anything drawn by Lyle Hess are small boats that punch above their weight. They're built strong and shaped for real offshore conditions, not just coastal cruising. 📗 Get My Book:

Jul 10, 2026
Language: EN
Play Time: 00:00:34

Sailing Zingaro

I’m Quitting Sailing.

📕 GET THE BOOK: Be The Captain. Winner of the 2026 Eric Hoffer Award. 25 years of offshore decisions in one book → 🔓 FREE: The Captain's Locker. Printable watch schedules, pre-departure checklists, delivery tools → It’s time to have an honest conversation. I’ve spent nearly two decades li...

Jul 09, 2026
Language: EN
Play Time: 00:00:00

Sailing Zingaro

The Brutal Truth About Cruising on a Budget & Surviving Storms at Sea

In this video, I’m tackling a list of questions collected from our recent live streams! From the best pocket cruisers for a Pacific crossing to the raw reality of catamarans vs. monohulls in bad weather, we cover it all. I’m also diving into storm tactics (heaving to vs. running with a drogue), wh...

Jul 09, 2026
Language: EN
Play Time: 00:41:24

Sailing Zingaro

They Told Us to Turn Around….

Four miles out, Bermuda radio called us back. Bracing for a paperwork problem, we instead found a kid trying to cross the Atlantic with no ride. So we made dinner and took him along. You really can't make this stuff up... 📗 Get My Book:

Jul 09, 2026
Language: EN
Play Time: 00:00:36

Sailing Zingaro

Lying Ahull: A Last Resort

Lash the wheel to windward, drop the sails, and the boat sits sideways to the weather. It buys a pause, but it leaves you broadside to breaking waves with a real chance of rolling. Save it for when nothing else is left. 📗 Get My Book:

Jul 08, 2026
Language: EN
Play Time: 00:00:38

Sailing Zingaro

His Captain Got Mad at Him for Doing This?!

He signed on as crew, everyone got seasick, and when a squall hit at forty knots the captain refused to leave his bunk. The crew member brought the boat back to port alone. A captain who won't stand his watch in weather isn't one to sail with twice. 📗 Get My Book:

Jul 07, 2026
Language: EN
Play Time: 00:00:45

Sailing Zingaro

🚩 RED FLAGS: How I Spot the Lemon Boats on Yacht World 🚩

Vetting a boat on Yacht World isn't just about finding something in your budget; it's about knowing how to spot the hidden warning signs before you lose your shirt. In this video, I’m breaking down 9 very different boats currently listed online to show you exactly how I analyze them thro...

Jul 06, 2026
Language: EN
Play Time: 00:39:19

Sailing Zingaro

Don’t Fight with the Storm

A hundred miles out, he fixed on Bermuda, sure that land meant safety. But closing a reef-strewn coast in big seas is harder than the open water behind you, and no one's coming out in eighty knots. With sea room, you turn and run with the storm. 📗 Get My Book:

Jul 06, 2026
Language: EN
Play Time: 00:00:58

Sailing Zingaro

We Refit the Boat for our Atlantic Crossing

Before crossing the Atlantic, we refit the whole boat: new bimini, repaired dodger, fresh lines, new autopilot. Problems still came, but they were small because the work was done. 📗 Get My Book:

Jul 05, 2026
Language: EN
Play Time: 00:00:34

Sailing Zingaro – Page 4

Watch Sailing Zingaro's Latest Videos

The Time My Sail Almost Killed Me

I Fell Asleep at the Wheel

Are Bolted Keels Safe?

Some Dinghies are Beyond Saving

These Sailboats Were Ridiculously Heavy

Broken Rudders, Sunken Boats: The Orcas Are Winning | Sailing Truth Show

Do I Keep Guns on My Sailboat?

Am I Too Old to Start Sailing?

Best $50K Monohull for Island Hopping

My Final Video as Sailing Zingaro

Are All Sailboats Money Pits?

Cal 40s are Legendary Boats

Can You Steer With a Drogue Out?

Aerorigs are Cool, However…

Are Junk Rigs Actually Worth It?

The Smallest Boat I’d Take Across the Pacific

I’m Quitting Sailing.

The Brutal Truth About Cruising on a Budget & Surviving Storms at Sea

They Told Us to Turn Around….

Lying Ahull: A Last Resort

His Captain Got Mad at Him for Doing This?!

🚩 RED FLAGS: How I Spot the Lemon Boats on Yacht World 🚩

Don’t Fight with the Storm

We Refit the Boat for our Atlantic Crossing

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