Watch Sailing & Boating Adventures Around the World – Page 2 of 4

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 25-48 of 79 results
Introducing Oscar and the Finished Galley | Sailing Wisdom [S3 Ep38]
Rigging Doctor

Introducing Oscar and the Finished Galley | Sailing Wisdom [S3 Ep38]

The galley refit is finished! Maddie gives the new galley a test run in our new sink surrounded by the mahogany butcher block counter top. Herby also gets to work on some other boat projects as the clock ticks away at their time on the hard. Maddie experiences the European healthcare system as she s...
Sailor girl: Acrylics on Canvas
Rigging Doctor

Sailor girl: Acrylics on Canvas

16x20 acrylics on canvas time lapse painting video Instagram: artistic_eye_studio Website: For Commissions: [email protected]
Building the Galley | Sailing Wisdom [S3 Ep37]
Rigging Doctor

Building the Galley | Sailing Wisdom [S3 Ep37]

Herby gets to work on building the galley out of Sapele Mahogany. The plan is to make an edge grain butcher block counter top that will be strong and beautiful, and build a useful storage solution beneath it. Boat Work! Maddie does a commissioned portrait and also finds time to help brainstorm the s...
Why the Azores?
Rigging Doctor

Why the Azores?

We have just finished up our sailboat refit in the Azores. We are frequently asked why we didn't do all of this work in the United States before we left. This video answers those questions and better explains how we found ourselves here on these magical islands for almost a full year! Patreon...
Galley DESTRUCTION | Sailing Wisdom [S3 Ep36]
Rigging Doctor

Galley DESTRUCTION | Sailing Wisdom [S3 Ep36]

The head refit is coming to an end as we begin painting the first coat of deck paint. The galley destruction begins as we make way on the "other" "next project" and begin the galley refit. Our time on the hard is running out and we need to get back into the water to continue wit...
Painting Quinn with Acrylics on Canvas
Rigging Doctor

Painting Quinn with Acrylics on Canvas

#timelapsepainting #dog #art A time lapse of Maddie’s painting process while she does a pet portrait commission. Painting Commissions: [email protected] Website: Music: FLY AWAY – THEFATRAT Music: TheFatRat - Fly Away feat. Anjulie FLY AWAY (INUKSHUK REMIX) – THEFATRATMusic: Th...
How to Apply Decal Stickers on a Boat or Car | Sailing Wisdom
Rigging Doctor

How to Apply Decal Stickers on a Boat or Car | Sailing Wisdom

Need to install the name on your boat or graphics on your car? This video will show you how to do a graphics install from start to finish. This video demonstrates the installations of a logo on the bow of a bo Patreon: Shirts: Instagram: Facebook: Website: Paintings: artisticeyestudio@gmail....
The Closer We Get… | Sailing Wisdom S3 Ep35
Rigging Doctor

The Closer We Get… | Sailing Wisdom S3 Ep35

It feels like these projects are never going to end! As we finish one, the next project is staring us in the face! Herby is finishing the head Refit and finally is applying varnish to the wood. Maddie sands the entire deck in preparation for the primer that is to follow. Boat work is a lot of work,...
Paddles Needs a Home!
Rigging Doctor

Paddles Needs a Home!

[email protected] Email with bids starting at $300 to give Paddles a new home! 16x20 acrylics on canvas Email before April 16th, 2019
The Police Come Knocking! | Sailing Wisdom [S3 Ep34]
Rigging Doctor

The Police Come Knocking! | Sailing Wisdom [S3 Ep34]

The police come banging on our hull early in the morning with guns and all! Our blue binder comes to the rescue and we explain why it’s so important to stay organized! We’ve got some unexpected payments to make, which is a bummer. Maddie deals with the struggles of having a sprained ankle in the boa...
Want to See my Seacock? | Sailing Wisdom [S3 Ep33]
Rigging Doctor

Want to See my Seacock? | Sailing Wisdom [S3 Ep33]

The head refit is coming along nicely! The old seacock is removed, the wood paneling gets installed, and most importantly: Maddie sprains her ankle! Maddie is out of commission for the next several days as she waits for her ankle to heal while Herby keeps working on the head refit. Time is running o...
Alaska: Acrylics on Canvas [Painting Time Lapse]
Rigging Doctor

Alaska: Acrylics on Canvas [Painting Time Lapse]

Maddie paints another portrait of a lovely couple in Alaska. Enjoy as her time lapse speed painting brings this canvas to life! Instagram: artistic_eye_studio Website: [email protected] Paintings Commissions: [email protected] Music: HER REQUIEM – SHANNI SHANNI - Her Requiem Listen...
No Reservations | Sailing Wisdom [S3E32]
Rigging Doctor

No Reservations | Sailing Wisdom [S3E32]

Valentines Day! Herby and Maddie celebrate in their own “special” way. Also, Herby does a bunch of head work and the planning phase for the reconstruction begins! Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected] Amazon: Hotel Booking: Thanks to our sp...
[How to] Install a New Halyard | Sailing Wisdom
Rigging Doctor

[How to] Install a New Halyard | Sailing Wisdom

Either your old halyard fell out of the mast or you want to install a brand new additional halyard in your mast, how do you do it? How do you feed it through the spar? Watch this video and I will show you the tricks to feeding a brand new halyard through your mast with internal halyards! Patreon: ...
So Much Head…Refit Work | Sailing Wisdom [S3 Ep31]
Rigging Doctor

So Much Head…Refit Work | Sailing Wisdom [S3 Ep31]

We start off with a phone call to Lady K Sailing ( where we discussed rigging options for his boat. Herby continues the head refit, but instead of tearing out, he finally gets to start installing it back in! Watch as the new and improved shower design comes to life! Patreon: Shirts: Instagram: ...
Diesel VS Gas Generator?! | Sailing Wisdom
Rigging Doctor

Diesel VS Gas Generator?! | Sailing Wisdom

Which generator do we prefer: diesel or gas? We have both, but we have to get rid of one. Which will it be and WHY? Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected] Amazon: Hotel Booking: Thanks to our sponsors: Audible: Sun Oven: Aleader Watershoe...
The Struggle is REAL | Sailing Wisdom
Rigging Doctor

The Struggle is REAL | Sailing Wisdom

Ever wonder what goes on behind the scenes of your favorite sailing vloggers? This video gives you an insight into the struggles and work that goes on behind the scenes with Sailing YouTubers and Vloggers. Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected]...
This is why the hard hats | Sailing Wisdom [S3 ep30]
Rigging Doctor

This is why the hard hats | Sailing Wisdom [S3 ep30]

The day has finally come! The topsides are getting painted which means we need to evacuate the boat! We hike Monte Brazil where we see the cutest deer and make friends with a cat. We’ve met some fellow Americans at a restaurant who happened to be staying at the fort hotel behind our boat, so we deci...
NASTY Boat Surprise | Sailing Wisdom [S3 Ep 28]
Rigging Doctor

NASTY Boat Surprise | Sailing Wisdom [S3 Ep 28]

Herby and Maddie return to Wisdom in the Azores and discover some nastiness! Herby also gets some major work accomplished in the head refit. They also set off and explore the beautiful wonders of the island of Terceira. Patreon: Shirts: Instagram: Facebook: Website: Paintings: artisticeyestu...
Kindness is Still Out There! | Sailing Wisdom
Rigging Doctor

Kindness is Still Out There! | Sailing Wisdom

Ever wonder how kind people are in foreign countries? What about to foreigners in their country? Herby experienced first hand just how kind people are to cruisers that are visiting their country. #travel #vlog #hope Patreon: Shirts: Instagram: Facebook: Website: Paintings: artisticeyestudi...
Do you have an appointment? | Sailing Wisdom [S3 Ep 27]
Rigging Doctor

Do you have an appointment? | Sailing Wisdom [S3 Ep 27]

Herby and Maddie return to the states to visit their family and pets for the holidays. While back in the states, Herby works full time as a dentist to earn money which allows them to go cruising. They also begin the process of getting their residency visas in Portugal in hopes that this would then a...
Whaling Where Waterfalls UP! | Sailing Wisdom [S3 Ep26]
Rigging Doctor

Whaling Where Waterfalls UP! | Sailing Wisdom [S3 Ep26]

The second half of our Flores side trip where we continue to explore the island and experience first hand the immense power of the wind! Waterfalls up! Powerful hurricane force winds fall on the island and alter reality! Up is down, down is up, and nowhere is safe from the wind. #flores #azores #t...
Dog Portrait Painting Time lapse
Rigging Doctor

Dog Portrait Painting Time lapse

#timelapsepainting #dog #art A time lapse of Maddie’s painting process while she does a pet portrait commission. Painting Commissions: [email protected] Patreon: Shirts: Instagram: Facebook: Website: Amazon: Thanks to our sponsors: Audible: Sun Oven: Aleader Watershoes: O...
Flores, Azores: The Most Beautiful Place in the World | Sailing Wisdom [S3 Ep25]
Rigging Doctor

Flores, Azores: The Most Beautiful Place in the World | Sailing Wisdom [S3 Ep25]

Herby and Maddie take a vacation from the boat work and venture off to the magical land of Flores (pronounced Floresh) where the encounter untouched natural beauty in the westernmost point of Europe and the most western Portuguese Colony. Herby and Maddie saw Flores in the distance as they entered t...
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