Watch Sailing & Boating Adventures Around the World

The Language of Traveling | Sailing Wisdom

International travel brings about a bunch of different experiences. One of them is going to be language! Learning a language by immersion is a very effective way to become proficient, and it also opens doors to new and wonderful opportunities while you are there! Patreon: Shirts: Instagram: Fa...

May 02, 2019
Language: EN
Play Time: 00:10:45

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...

Apr 23, 2019
Language: EN
Play Time: 00:09:22

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...

Apr 21, 2019
Language: EN
Play Time: 00:19:45

Have you heard?? | Sailing Wisdom

Have you heard?? Because chances are, we haven't! Taken aback by the tragic news of the burning Notre Dame in Paris, we discuss our experiences with cruising and how it effects our ability to receive news in other countries. Patreon: Shirts: Instagram: Facebook: Website: Paintings: art...

Apr 16, 2019
Language: EN
Play Time: 00:09:20

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,...

Apr 14, 2019
Language: EN
Play Time: 00:14:27

Surprise Taxes! | Sailing Wisdom

Ever planning on cruising in Portugal? If so, you will want to be prepared for these hidden taxes! In this video, we detail the taxes levied on visiting boats. Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected] Amazon: Hotel Booking: Thanks to our spon...

Apr 09, 2019
Language: EN
Play Time: 00:09:23

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...

Apr 07, 2019
Language: EN
Play Time: 00:17:38

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...

Mar 31, 2019
Language: EN
Play Time: 00:19:57

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...

Mar 24, 2019
Language: EN
Play Time: 00:14:57

Sailing the Flat Earth

We just watched the documentary “Behind the Curve” and respond with our experiences. Please for the love of everything, WATCH THE END! Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected] Amazon: Hotel Booking: Thanks to our sponsors: Audible: Sun Oven: ...

Mar 19, 2019
Language: EN
Play Time: 00:10:06

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: ...

Mar 17, 2019
Language: EN
Play Time: 00:17:51

Gunboat vs Outremer Catamaran Battle!

Gunboat vs Outremer - who will win!?!? It's not a fair fight. The Gunboat is 66 feet, has 12 foot daggerboards, a much higher mast, larger sail area and carbon fiber reinforced. The Outremer is 51 feet, has 3 foot daggerboards and is made of fiberglass. Let's not even mention the price d...

Mar 16, 2019
Language: EN
Play Time: 00:03:55

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...

Mar 14, 2019
Language: EN
Play Time: 00:07:01

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]...

Mar 12, 2019
Language: EN
Play Time: 00:10:06

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...

Mar 10, 2019
Language: EN
Play Time: 00:18:53

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...

Mar 05, 2019
Language: EN
Play Time: 00:08:02

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...

Mar 03, 2019
Language: EN
Play Time: 00:15:35

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...

Feb 26, 2019
Language: EN
Play Time: 00:05:41

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...

Feb 24, 2019
Language: EN
Play Time: 00:19:13

What YOU Need to Know About Schengen | Sailing Wisdom

Have you ever heard of Schengen? Most Americans haven’t! If you ever intend to travel to Europe, you need to watch this video. We will help prepare you for what we were not prepared for. Schengen makes travel through Europe seamless, as long as you are only traveling for a short period of time. T...

Feb 19, 2019
Language: EN
Play Time: 00:09:50

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...

Feb 17, 2019
Language: EN
Play Time: 00:21:24

Should You Stay in School Before Living the Dream? | Sailing Wisdom

You decide you want to live the simple life and travel instead of getting a 9 to 5 job. Maybe you want to go cruising full time! There is no college major for “cruising” so why go to school? In this video, Herby and Maddie talk about their thoughts on education and if it’s worth it if you want to li...

Feb 12, 2019
Language: EN
Play Time: 00:06:15

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...

Feb 10, 2019
Language: EN
Play Time: 00:20:52

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...

Feb 05, 2019
Language: EN
Play Time: 00:06:43

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