Watch Sailing & Boating Adventures Around the World – Page 4 of 5

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 73-96 of 102 results
Red Sky In Morning, Sailors Take Warning (MJ Sailing – EP 92)
MJ Sailing

Red Sky In Morning, Sailors Take Warning (MJ Sailing – EP 92)

Volcanic craters, hurricanes barreling down, and a bumpy ride with the most beautiful sunset we have ever seen. THIS...was an interesting few weeks for us. We start out by trying to spend a few nice days at anchor next to a simply stunning sunken volcano. We wake up the morning after arriving, rea...
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...
Would You Swim in Coffee Colored Thermal Springs? (MJ Sailing – EP 91)
MJ Sailing

Would You Swim in Coffee Colored Thermal Springs? (MJ Sailing – EP 91)

SUBSCRIBE and hit the bell for weekly videos! In the heart of Furnas São Miguel is the Parque Terra Nostra with iron rich thermal springs, which give it a nice coffee color. Would you take a dip in this milk chocolate goodness? Back at the boat Matt is hard at work installing our new Autonnic ...
CALL THE AMBULANCE! | Sailing Wisdom
Rigging Doctor

CALL THE AMBULANCE! | Sailing Wisdom

Maddie recounts the events that put her in crutches and discusses what it’s like to be injured in a foreign country. Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected] Amazon: Hotel Booking: Thanks to our sponsors: Audible: Sun Oven: Aleader Watersh...
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...
Can We Extend Our EUROPEAN VISA to 12 Months? (MJ Sailing – EP 89)
MJ Sailing

Can We Extend Our EUROPEAN VISA to 12 Months? (MJ Sailing – EP 89)

This week's episode brings us back to the harbor of Angra where we visit the immigration office to see if we can extend our 90 day visa to 12 months. Since we haven't been finding the winds we need to get north we thought, why not winter here? That weekend we travel around the island of ...
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...
FAILING At Cooking Fish Cakes – Even The Cat Won’t Eat Them  – (MJ Sailing – EP 88)
MJ Sailing

FAILING At Cooking Fish Cakes – Even The Cat Won’t Eat Them – (MJ Sailing – EP 88)

Getting ready for a large festival in Urzelina, us and s/v Calico Skies move our boats down from Velas. The wind seems pretty non-existant, but that's a good thing for us once we drop anchor. Because there were no sandy patches and we anchored on rocks, the chances of dragging went down and w...
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...
What’s the Deal With SPREADERS? | Sailing Wisdom
Rigging Doctor

What’s the Deal With SPREADERS? | Sailing Wisdom

Ever wonder why sailboats have spreaders? And why some have many while others only have one? In this video, Herby and Maddie explain what spreaders are for and how they work. They also go into detail about keel stepped vs deck stepped masts, as well as typical single and double spreader setups. #s...
AZORES: The Untouched Island of São Jorge (MJ Sailing – EP 87)
MJ Sailing

AZORES: The Untouched Island of São Jorge (MJ Sailing – EP 87)

Although not known as a destination spot in the Azores, Sao Jorge should be near the top of everyone's travel list for untouched and unspoiled beauty. While immensely enjoying our time in Sao Jorge, our dragging anchor causes us to move ourselves and burn out the engine starter in the process....
How Rigging Doctor Began | Sailing Wisdom
Rigging Doctor

How Rigging Doctor Began | Sailing Wisdom

Ever wonder how your favorite Youtube Channel started? How it came to be? Herby and Maddie take a look down memory lane to talk about how they started Rigging Doctor! #Riggingdoctor #travelvlog #vlog Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected] Amazo...
Chop it up into little pieces | Sailing Wisdom [S3 Ep24]
Rigging Doctor

Chop it up into little pieces | Sailing Wisdom [S3 Ep24]

Herby and Maddie continue tearing out the old head to make room for the head refit they are doing. They also take a break from the work to visit the sulfur pits on the island of Terceira, Azores. #Azores #boatwork #refit Patreon: Shirts: Instagram: Facebook: Website: Paintings: artisticeyes...
We Have a Dirty Little Secret | Sailing Wisdom [S3 Ep23]
Rigging Doctor

We Have a Dirty Little Secret | Sailing Wisdom [S3 Ep23]

We are living in squalor and celebrate São Martinho and eat whole sardines. Herby finished the closet reconstruction while Maddie does the laundry at a friends house. The boat painting continues as the floor project gets completed. Herby also works with foam core to build the chimney base. A powe...
Bend and Snap | Sailing Wisdom [S3 Ep22]
Rigging Doctor

Bend and Snap | Sailing Wisdom [S3 Ep22]

While Wisdom is being repainted, Herby and Maddie explore the island of Terciera, Azores! They venture off the beaten path to find a side of the Azores rarely seen (like a geothermal power plant). The wood finally arrives at the boat so that they can begin the galley refit! The plan is to build sep...
We Got Off To A Bumpy Start…  (MJ Sailing – EP 84)
MJ Sailing

We Got Off To A Bumpy Start… (MJ Sailing – EP 84)

Finally tearing ourselves away from Faial, it was time to hit open waters again. Getting to them was not very easy though. After not being able to shove off the dock due to a strong current pushing us in, the marina had to bring out their tender to pull us off. But from there we had an amazing m...
The Worst Part of the Boat | Sailing Wisdom [S3 Ep21]
Rigging Doctor

The Worst Part of the Boat | Sailing Wisdom [S3 Ep21]

Herby and Maddie explore the island of Terceira, Azores, and decide to undertake some projects inside of the boat as well as outside! Galley refit! Did we mention Halloween in the Azores? Scott also loans us his car which gives us the freedom to drive around and get amazing footage of the island. Pr...
BUCKET LIST Sailing Destination: Faial, Azores (MJ Sailing – EP 83)
MJ Sailing

BUCKET LIST Sailing Destination: Faial, Azores (MJ Sailing – EP 83)

Of all the far flung destinations to sail to in the world, Faial Azores should be near the top, for it's beauty, diversity, and sometimes surreal atmosphere.
You Just Licked That. What’s Wrong With You?! | Sailing Wisdom: S3 Ep20
Rigging Doctor

You Just Licked That. What’s Wrong With You?! | Sailing Wisdom: S3 Ep20

Herby and Maddie suffer from the confusing effects of jet lag after returning to Terceira, Azores, to work on the boat. While on the island, they are given a tour of the sights and scenes of the land in the middle of the Atlantic. Panic ensues when they lose all of their memory cards, but thankfully...
AZORES: Pico – The Island No One Ever Sails To (MJ Sailing – EP 82)
MJ Sailing

AZORES: Pico – The Island No One Ever Sails To (MJ Sailing – EP 82)

One of the most noticeable islands the Azores have, for housing Portugal's highest point, is also the one that gets nearly the fewest visitors by sailboat. Without many good harbors, we find another way to get to neighboring Pico. Hopping the ferry for the four mile trip across from Horta, ...
Project Problems | Sailing Wisdom: S3E18
Rigging Doctor

Project Problems | Sailing Wisdom: S3E18

We finally make it onto the next flight back to the United States, which then leads to family time and a random video for you to enjoy (DH Mountain Biking)! Herby returns to the Azores to work on the boat and runs into a series of road blocks that seem to halt any attempts at making progress. While...
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