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 179 results
Which are the SCARIEST Bridges?! | Sailing Wisdom [S5 Ep32]
Rigging Doctor

Which are the SCARIEST Bridges?! | Sailing Wisdom [S5 Ep32]

▸ AMAZON WISHLIST: ▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: We loved our time in Charleston, SC but now we will continue our sail north! 0:00 Intro ↓BIN...
Sailing the DREADED Mona Passage! | Sailing Wisdom [S4 Ep16]
Rigging Doctor

Sailing the DREADED Mona Passage! | Sailing Wisdom [S4 Ep16]

▸ 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: It’s 1000 miles to our next destination: Florida...
How We Prep for a 10 Day Passage! | Sailing Wisdom [S4 Ep15]
Rigging Doctor

How We Prep for a 10 Day Passage! | Sailing Wisdom [S4 Ep15]

▸ 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: While Puerto Rico has been amazing, it's ti...
Herby Breaks Down in Tears | Sailing Wisdom [S4 Ep14]
Rigging Doctor

Herby Breaks Down in Tears | Sailing Wisdom [S4 Ep14]

▸ 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 most beautiful snorkeling in Puerto Rico con...
Swimming Naked in the Bio Bay | Sailing Wisdom [S4 Ep13]
Rigging Doctor

Swimming Naked in the Bio Bay | Sailing Wisdom [S4 Ep13]

▸ 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: For generations, Herby's family would play ...
Girls Like to Walk Around NAKED on Boats | Sailing Wisdom [S4 Ep12]
Rigging Doctor

Girls Like to Walk Around NAKED on Boats | Sailing Wisdom [S4 Ep12]

▸ 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 meet up with @Bumsonaboat in Guanica, PR near...
Which Hull Material is BEST: Fiberglass | Sailing Wisdom
Rigging Doctor

Which Hull Material is BEST: Fiberglass | Sailing Wisdom

▸ @MJSailing: ▸ 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: This is the 5th in a 5 Part Seri...
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...
Sailing into the Sunset! | Sailing Wisdom [S4 ep58]
Rigging Doctor

Sailing into the Sunset! | Sailing Wisdom [S4 ep58]

We set sail to the west for the first time in our entire 3 year journey, but first, Herby explanes our headsail setup. This includes how to reef our jib and staysail. Join us for our final run in the Mediterranean towards Gibraltar! Integrated Soft Shackle: Regular Soft Shackle: Patreon: Merch...
Peaceful Boat Cabin Fireplace [30 minute ASMR]
Rigging Doctor

Peaceful Boat Cabin Fireplace [30 minute ASMR]

Longing for a peaceful fireplace on these cold wintry days? The warm feeling of a wooden interior with the diesel flames flickering? Curl up in a blanket and enjoy this long video of our fireplace in action, bringing the cozy interior of our sailboat into your home! Patreon: Shirts: Instagram: ...
The Ultimate Cruising Yacht? | Sailing Wisdom [S3 Ep49]
Rigging Doctor

The Ultimate Cruising Yacht? | Sailing Wisdom [S3 Ep49]

It’s time to compare a Pogo 12.50 to our Plastic Classic Morgan 45! A friend has invited us to come sailing on a racer cruiser. It’s a very different experience from what we are used to! In this video, we include footage of our adventure on the Pogo while we reflect on the differences between racers...
Instagram Hot Spring in Real Life! [Azores] | Sailing Wisdom [S3 Ep48]
Rigging Doctor

Instagram Hot Spring in Real Life! [Azores] | Sailing Wisdom [S3 Ep48]

The island of Sao Miguel is famous for its hot springs, and we tried them out! Come along as we test out the different hot springs, each with its own water qualities. We also explore how tea is made on the islands largest tea plantation, Cha Gorreana! #Azores #Hotspring #Travel Patreon: Shirts: ...
Why We Can’t Get Enough of São Miguel | Sailing Wisdom [S3 Ep47]
Rigging Doctor

Why We Can’t Get Enough of São Miguel | Sailing Wisdom [S3 Ep47]

We continue our trip through the beautiful island of São Miguel beginning with a visit to the town of Ribeiriño Grande. We visit a liquor famous liquor distillery and sample the goods before we say goodbye to Maddie’s mom and continue our journey by hiking an amazing trail through nature where we di...
On to São Miguel! | Sailing Wisdom [S3 Ep45]
Rigging Doctor

On to São Miguel! | Sailing Wisdom [S3 Ep45]

With a slight hiccup in leaving Terciera, we head over to Sao Miguel where we begin exploring this magical wonderland! We stay at the Azorean Urban Lodge and visit Sete Cidades. Maddie' mom is still with us on this amazing introduction to what São Miguel has to offer. #Azores #SaoMiguel #Trav...
This is the BEST Rudder! | Sailing Wisdom
Rigging Doctor

This is the BEST Rudder! | Sailing Wisdom

They are one of the most important parts on your boat, yet often the least thought about: Rudders! In this video, we look at different design characteristics and the particulars imparted from these different designs. Patreon: Shirts: Instagram: Facebook: Website: Paintings: artisticeyestudio...
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