Watch Sailing & Boating Adventures Around the World

Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.

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We Made an Offer on This HUGE Catamaran | Sailing Sunday Vlog 320
Sailing Sunday

We Made an Offer on This HUGE Catamaran | Sailing Sunday Vlog 320

We just sailed four days to reach this huge catamaran in search of our new floating home! We had previously put an offer in to buy this boat, sight unseen and only now are we discovering what we may have agreed to buy… Once the survey is complete, we continue our journey delivering our old boat wit...
HOT TAKE – Stupid Anchoring Mistakes
Lady K Sailing

HOT TAKE – Stupid Anchoring Mistakes

Lady K Swag!!! Right here: Need a consult? Click here to drop a message: Want to help support Lady K Sailing? Click here to become a Patron: Or here to make a one time donation: Follow Lady K on Facebook: Or Instagram:
Shopping for a Secondhand Sailboat? Which 1980’s “LUXURIES” Are STILL worth YOUR Investment?
Secondhand Sailors

Shopping for a Secondhand Sailboat? Which 1980’s “LUXURIES” Are STILL worth YOUR Investment?

In episode 75 of Secondhand Sailors, we answer the question on the mind of potential liveaboard cruisers who are searching for the sailboat they can call home-What features from the 1980's era sailboat are keepers and which are weepers? If you are looking for your sailing home, then you want ...
Don’t Get Fleeced-How to Buy a 2ndhand Sailboat Without Wasting $MONEY$
Secondhand Sailors

Don’t Get Fleeced-How to Buy a 2ndhand Sailboat Without Wasting $MONEY$

Are you thinking about buying a boat? See the reality behind online listings and the practical challenges of starting your sailing journey. In episode 74 of Secondhand Sailors, we walk you through the step by step process that we used to buy our secondhand sailboat, SV Daisy Mae. Buying a used boat...
The Sailboat With No Wires Holding Up the Mast
Lady K Sailing

The Sailboat With No Wires Holding Up the Mast

Thinking about buying a 30-foot sailboat, liveaboard cruiser, weekend sailboat, or easy singlehanded cruising boat? The Nonsuch 30 is one of the strangest and smartest used sailboats on the market. With no standing rigging, no shrouds, no forestay, no headsail, one huge sail, a freestanding mast, an...
The Best Canadian Sailboat You’ve Never Heard Of  | Sailing Truth Show
Sailing Zingaro

The Best Canadian Sailboat You’ve Never Heard Of | Sailing Truth Show

📕 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 → She's a 1996 Gozzard 44, built by one family in a small Ontario shop th...
We Finally Fixed the Worst-Looking Part of Our Boat Ep. 277
Sailing Zephyr

We Finally Fixed the Worst-Looking Part of Our Boat Ep. 277

After months of projects, upgrades, and hard work, Zephyr 2.0 is finally starting to become the boat we’ve always dreamed of. This episode takes us to the Bahamas where James tackles one of the biggest transformation projects yet. Out goes the tired old lazy bag and in comes a beautiful new custom ...
Hans Christian 43T is NOT for Everyone
Lady K Sailing

Hans Christian 43T is NOT for Everyone

Is the Hans Christian 43T a great bluewater sailboat, or is it the wrong boat for the way most people actually cruise today? In this episode, we look at the Hans Christian 43T as a serious ocean crossing sailboat, a classic double-ended bluewater cruiser, and a tempting option for anyone searching f...
We Somehow Made It To The Bahamas…Then The Boat Work Started – Ep.276
Sailing Zephyr

We Somehow Made It To The Bahamas…Then The Boat Work Started – Ep.276

In our last episode we splashed the boat and moved her to a new marina… and now somehow we’re already in the Bahamas?! Things moved fast after that. My dad flew out to help James bring our new catamaran all the way from a freezing North Carolina down to the Bahamas. Unfortunately the cameras didn’t...
Our New Boat Finally Hits The Water  – Ep. 275
Sailing Zephyr

Our New Boat Finally Hits The Water – Ep. 275

After weeks of preparation, stress, and problem-solving, our new Fountaine Pajot Venezia 42 finally goes back in the water for the very first time. In this episode, James prepares the boat for launch day, checks the systems once she splashes, and attempts the first proper move to a new marina… even...
The Reality of Getting This Boat Ready  – Ep. 274
Sailing Zephyr

The Reality of Getting This Boat Ready – Ep. 274

After 13 months away from sailing, stepping back into boat life has been a lot more intense than expected. In the last episode, we shared our return to YouTube after selling our Beneteau Oceanis 43 and buying an older boat in hopes of building a more sustainable future on the water. But the realit...
We Disappeared For 13 Months…Then This Happened – Sailing Zephyr – Ep. 273
Sailing Zephyr

We Disappeared For 13 Months…Then This Happened – Sailing Zephyr – Ep. 273

After 13 months away from Youtube and life at sea, we are finally back.....and heaps has changed. We didn't plan to be gone this long, yet stepping away from sailing has turned into a much bigger pause than expected. Over the past year we sold out Beneteau Oceanis 43, stepped back from life...
Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384
BoatFools Sailing

Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384

#sailing #boatfoolssailing #morgan384 #boatwork #boatprojects #sailboat Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384 Canadian Ken and I are back aboard our “new-to-us” Morgan 384 as we race to get her ready for charter season in Maine… but like every old sailboat, she has a few opinio...
Robert Perry: The Greatest Cruising Boat Designer?  | Sailing Truth Show
Sailing Zingaro

Robert Perry: The Greatest Cruising Boat Designer? | Sailing Truth Show

Is Robert Perry actually the greatest cruising boat designer of all time, or is the "Perry Legend" just clever marketing from the Taiwan boat era? Today, I am putting my 18 years of living aboard and 60,000 miles of Navy submarine navigation experience to the test to judge the "Sailin...
How to Buy (and Sell) a Sailboat | Sailing Truth Show
Sailing Zingaro

How to Buy (and Sell) a Sailboat | Sailing Truth Show

🏆 AWARD NEWS: Be The Captain is officially a finalist for the Eric Hoffer First Horizon and Foreword INDIES Awards! Grab your award-nominated copy here: Most people buy the wrong boat for the wrong reasons, and they get buried in the paperwork they didn’t see coming. In today’s "Sailing Truth...
Buying a Sailboat Without This Plan Will Destroy Your Dreams
BoatFools Sailing

Buying a Sailboat Without This Plan Will Destroy Your Dreams

#boatfoolssailing #IsSailingDead #sailing #boatbuying How To Buy A Sailboat - The Right Way: What You Need To Know BEFORE Buying a Boat! From the empty docks and rising costs, it can feel that sailing is dead - or at at least impossible to break in to. But sailing isn’t dead — access to sailing ha...
BIG ANNOUNCEMENT + We Almost Bought a Dismasted Sailboat! EP 201
Leading the Escapade

BIG ANNOUNCEMENT + We Almost Bought a Dismasted Sailboat! EP 201

Big sailing announcement! In this episode, we share a long-overdue life update and explain why we almost bought a dismasted sailboat. It’s been a while, so we’re catching you up on everything we’ve been working on behind the scenes and what’s coming next for us and the channel. We talk through a r...
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...
We Reviewed 31 Sailboats This Year. 17 Sold. Here’s What Happened
BoatFools Sailing

We Reviewed 31 Sailboats This Year. 17 Sold. Here’s What Happened

#boatfoolssailing #sailboatreview #sailingboat #boattalk What Sold, What Sat, and Why. A Wild Year in Sailboats! (BoatFools 2025 Review) 2025 was a BIG year for BoatFools Sailing. Canadian Ken and Tris take a hard look back at the sailboats we profiled, the ones that sold, the ones that surprised...
I SOLD My Sailboat! (Teaching The New How-To Use It)
Adventureman Dan

I SOLD My Sailboat! (Teaching The New How-To Use It)

My sailboat is SOLD! After seven amazing years of adventures on the high seas, I've sold my beloved sailboat Adventureborne. This video isn't just to say goodbye to Adventureborne. It's to give you a complete top to bottom “how-to-use” sailboat instructional video. Perfect for anyon...
From Superyacht to Hurricane Wreck: Boat Shopping in the US | Sailing Sunday Vlog 303
Sailing Sunday

From Superyacht to Hurricane Wreck: Boat Shopping in the US | Sailing Sunday Vlog 303

This week we're shopping for our new boat in USA. As leave New York City behind, we point the 5th wheel all the way back down to Florida to the warmer weather as the next boat hunt officially begins! First stop is Charleston to catchup with our mates to do some quick repairs and have a few lau...
We Bought the Boat We Reviewed! Meet Our Morgan 384
BoatFools Sailing

We Bought the Boat We Reviewed! Meet Our Morgan 384

#boatfoolssailing #morgan384 #classicsailboats We Bought the Boat We Reviewed! Meet Our Morgan 384. If you want to see the full tour of this boat, watch this: Guess what? We did it again. Canadian Ken, Green Mountain Josh, and I just bought a second sailboat — a 1986 Morgan 384… the very same b...
A RUGGED World Cruiser! Inside a $75,000 Sailboat Tour. The Intrepid 40!
BoatFools Sailing

A RUGGED World Cruiser! Inside a $75,000 Sailboat Tour. The Intrepid 40!

#boatfoolssailing #sailboatforsale #sailboattour ONLY 8 Ever Built! $75,000 Chuck Paine Intrepid 40 Sailboat | Full Tour This week, Canadian Ken, Captain Kew, and I climb aboard one of the rarest Chuck Paine designs ever launched: the 1986 Cape Dory Intrepid 40 — hull #7 of only 8 ever built. If ...
Don’t Buy a Sailboat Until You Watch This – 5 Costly Mistakes New Sailors Make
Practical Sailor

Don’t Buy a Sailboat Until You Watch This – 5 Costly Mistakes New Sailors Make

Quiet Power: Electric and Hybrid Propulsion at Annapolis: Thinking of buying your first offshore sailboat? Before you hand over your life savings, watch this video. In it, we break down the 5 biggest mistakes new sailors make when buying their first cruising boat — and how to avoid them. From fal...
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