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.

Showing 1-24 of 42 results
Storms Don’t Sneak Up On You: Heaving-to at Anchor | Sailing Wisdom [S5 Ep42]
Rigging Doctor

Storms Don’t Sneak Up On You: Heaving-to at Anchor | Sailing Wisdom [S5 Ep42]

▸ MATERIALS NEEDED FOR OUR PROJECTS: ▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Herby and Maddie sail 28 miles to make it to Swansboro, NC where they get to ...
BEST or WORST Cruising Boat??! | [S5 Ep6]
Rigging Doctor

BEST or WORST Cruising Boat??! | [S5 Ep6]

▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ PHOTOGRAPHY FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: The bottom is clean allowing us to truly test out our new LiFePO4 batteries powering our electric motor. Do they work? Do we...
Why We FAILED the First Lithium Battery Test | Sailing Wisdom [S5 Ep5]
Rigging Doctor

Why We FAILED the First Lithium Battery Test | Sailing Wisdom [S5 Ep5]

▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ PHOTOGRAPHY FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: The Lithium Batteries are built and it's time to test them! But first, we need to clean our bottom because it is covere...
THIS was the Reason We Went CRUISING! | Sailing Wisdom [S4 Ep11]
Rigging Doctor

THIS was the Reason We Went CRUISING! | Sailing Wisdom [S4 Ep11]

▸ PAINTING COMMISIONS: [email protected] ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: Back in 2017, we set off to go cruising on a 9 m...
Can we TAKE DOWN A MAST at Anchor?! | Sailing Wisdom [S4 Ep10]
Rigging Doctor

Can we TAKE DOWN A MAST at Anchor?! | Sailing Wisdom [S4 Ep10]

▸ PAINTING COMMISIONS: [email protected] ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: We sail from Culebrita to Culebra where we help ...
What Would You Do on a Private Island? | Sailing Wisdom [S4 Ep9]
Rigging Doctor

What Would You Do on a Private Island? | Sailing Wisdom [S4 Ep9]

▸ PAINTING COMMISIONS: [email protected] ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: The USVI has been a sailing dream come true but ...
Make YOUR BOAT BETTER For CHEAP? | Sailing Wisdom [S4 Ep8]
Rigging Doctor

Make YOUR BOAT BETTER For CHEAP? | Sailing Wisdom [S4 Ep8]

▸ PAINTING COMMISIONS: [email protected] ▸ THE VIEW: Joy of Life Villa, St. John: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: Join H...
Sailing in the USVI | Sailing Wisdom [S4 Ep7]
Rigging Doctor

Sailing in the USVI | Sailing Wisdom [S4 Ep7]

▸ PAINTING COMMISIONS: [email protected] ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: What is it like to cruise in the USVI, the sailo...
What’s WRONG With Our Electric Motor?! | Sailing Wisdom [S4 Ep6]
Rigging Doctor

What’s WRONG With Our Electric Motor?! | Sailing Wisdom [S4 Ep6]

Subscribe directly with us so you never miss an episode: We are off to another island in the Caribbean! But first we need to figure out what the problem is with our motor. Herby is a lot of things, but he’s not an electrician, which makes trouble-shooting an electric motor a bit tricky. Can we fix...
Where Can You Swim With SEA TURTLES!? | Sailing Wisdom [S4 Ep5]
Rigging Doctor

Where Can You Swim With SEA TURTLES!? | Sailing Wisdom [S4 Ep5]

Subscribe directly with us so you never miss an episode: What makes a particular cruising area a "Sailing Paradise"? Is it awesome sails to new and beautiful coves, or excellent protection from the wind and seas? Maybe its white sandy beaches with incredible snorkeling once you arrive at...
Can You SINGLE HAND a Big Sailboat? | Sailing Wisdom [S4 Ep4]
Rigging Doctor

Can You SINGLE HAND a Big Sailboat? | Sailing Wisdom [S4 Ep4]

▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: How big is too big when it comes to solo sailing and single handing a sailboat? Herby accepts the challenge of single handing and solo sailing Wisdom, a Morgan 45 from 1968, from one mooring ball to another in the St. John National Park, i...
Electric Motor Range Test and Setting a Swell Bridle | Sailing Wisdom [S4 Ep3]
Rigging Doctor

Electric Motor Range Test and Setting a Swell Bridle | Sailing Wisdom [S4 Ep3]

In the beautiful waters of the US Virgin Islands, we had a swell coming in from the side making our anchorage miserable! Herby sets up a swell bridle to point the bow into the wave and stop the horrible rolling motion. 0:00 Intro 0:40 Setting Sail 2:20 Grabbing a Mooring Ball 4:00 Swell Bridle 5:18...
Why You Should Sail to the USVI | Sailing Wisdom [S4 Ep2]
Rigging Doctor

Why You Should Sail to the USVI | Sailing Wisdom [S4 Ep2]

After a delightful sail around the southern coast of St. John, we anchor near Cruz Bay to enjoy and explore the main town on this nature island. What better way to finish up the day than to go for a nice swim in crystal clear waters! 0:00 Intro 0:15 Sailing around St. John 3:13 Two Anchors Deploye...
OMG! Our Boom FELL OFF!! | Sailing Wisdom [S3 Ep38]-
Rigging Doctor

OMG! Our Boom FELL OFF!! | Sailing Wisdom [S3 Ep38]-

As we near the end of our Atlantic Crossing, our BOOM FALLS OFF! Can we make it into the river safely? 0:00 Intro 0:20 Map 0:30 Morning Sailing 1:24 What color is the water today? 1:40 Light air sailing 2:27 The smell of land 3:42 Food supply after a crossing 4:20 Cooking on a passage 5:00 THE BOOM...
What Smells so BAD after 26 Days at Sea? | Sailing Wisdom [S3 Ep37]
Rigging Doctor

What Smells so BAD after 26 Days at Sea? | Sailing Wisdom [S3 Ep37]

After 26 days at sea, something is really starting to smell! 0:00 Intro 0:18 Map 1:04 Morning Sailing 1:45 Sails going up 2:30 Where's the land? 3:21 What Color is the Water Today? 3:35 Electric Motoring off of Solar Power 4:06 The Smell 6:07 Herby's Sleep Time 7:10 Sun is setting 7:54 Wi...
WEIRD SURPRISE at Sea! | Sailing Wisdom [S3 Ep36]
Rigging Doctor

WEIRD SURPRISE at Sea! | Sailing Wisdom [S3 Ep36]

Our Drifter has ripped yet again, but in a different place! Herby does an effective fix and we think seriously about our plans when we get to the Suriname River. Excitement is building! Patreon: Merchandise: Instagram: Facebook: Website: Paintings: [email protected] Amazon: Musi...
We Haven’t Seen Any Other People for 23 DAYS | Sailing Wisdom [S3 Ep35]
Rigging Doctor

We Haven’t Seen Any Other People for 23 DAYS | Sailing Wisdom [S3 Ep35]

Patreon: Merchandise: Instagram: Facebook: Website: Paintings: [email protected] Amazon: 0:00 Intro 0:18 Map 0:26 No Wind 1:48 Breakfast on a boat 2:30 Cleaning up 4:38 Navigation Changes 5:40 Guiana Current 6:38 Maddie's excitement 9:35 Peaceful Sailing 13:20 Dropping the Dr...
Why DON’T we Have RADAR?!? | Sailing Wisdom [S3 Ep34]
Rigging Doctor

Why DON’T we Have RADAR?!? | Sailing Wisdom [S3 Ep34]

We wake to a very calm day on the ocean but soon find ourselves changing sails to keep up with the changing weather conditions as we approach the Amazon River. 0:00 Intro 0:18 Map 0:23 Morning Update 1:03 Why we don't have radar 1:20 How to tell strong winds are coming 2:03 Excitement happens ...
BROKEN Mast Track! | Sailing Wisdom [S3 Ep33]
Rigging Doctor

BROKEN Mast Track! | Sailing Wisdom [S3 Ep33]

The winds get light and we see boobies in the distance! It's time to act like you aren't looking while you stare at the boobies that are passing by. 0:00 Intro 0:18 Progress Map 0:23 Morning at sea 1:54 Gybing in the Ocean 2:29 Laundry on the High Seas 2:59 Celestial Navigation 3:53 Sail ...
More of a CHALLENGE than I Thought | Sailing Wisdom [S3 Ep32]
Rigging Doctor

More of a CHALLENGE than I Thought | Sailing Wisdom [S3 Ep32]

The generator is running and it’s interrupting our perfect day of sailing! Herby discusses the unexpected challenges of using a sextant for navigation and shows our planned route into Suriname. Maddie talks about the strangeness of being in the middle of the Atlantic while history is made back home....
STOWAWAYS: Atlantic Crossing | Sailing Wisdom [S3 Ep33]
Rigging Doctor

STOWAWAYS: Atlantic Crossing | Sailing Wisdom [S3 Ep33]

Dive down and see the world from beneath the waves. A pod of dolphins escorts us across the Atlantic Ocean while blessing us with their charm and grace. 0:00 Intro 0:18 Map 0:20 Amazing Dolphin Show 0:53 Dive Down with Dolphins 4:04 Flying Fish Procedure 4:39 Water Usage 5:20 Battery Problems 6:04 ...
Look What we Found!!? | Sailing Wisdom [S3 Ep32]
Rigging Doctor

Look What we Found!!? | Sailing Wisdom [S3 Ep32]

It's an odd day at sea. The winds are squirrely and the currents are forcing us southward. We are in the midst of an election, but being so removed puts everything into perspective. Herby is able to find beauty and wonderment at sea no matter the conditions, but he still has to fix a sail an...
BROKEN Hatch and DEAD Batteries in the Atlantic | Sailing Wisdom [S3 Ep31]
Rigging Doctor

BROKEN Hatch and DEAD Batteries in the Atlantic | Sailing Wisdom [S3 Ep31]

It's been a long crossing and stuff keeps breaking! Herby is on the repair process while Maddie changes sails for the new ocean weather. Can Herby fix the battery woes that have been plaguing Wisdom? 0:00 Intro 0:18 Progress Map 0:21 Repairs while sailing 1:20 Hydrogenerator problems 2:30 Gene...
IT’S HAPPENING: Exciting Moment | Sailing Wisdom [S3 Ep30]
Rigging Doctor

IT’S HAPPENING: Exciting Moment | Sailing Wisdom [S3 Ep30]

It’s time to gybe! We are less than 900 miles from Suriname, and accurate navigation is becoming increasingly important as we near the currents around South America. 0:00 Intro 0:18 Progress Map 0:22 Maddie's Morning Thoughts 1:38 Weather Forecast at Sea 2:09 Underwater View of the Boat 2:40 K...
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