You know this anchor, you see in tattoos, pictures, decorations, but never on a boat! This anchor goes by many names: Fisherman’s Anchor, Admiralty Anchor, ...

We had a great time exploring around Little Farmers Cay! It truly is a beautiful spot. We have now made it to George Town which is an awesome spot. Thank you ...

There’s a common scam that has effected many boaters recently and we are going to tell you all about how to recognize and avoid it! Patreon: ...

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 ...

Witness a real stick up. Windover and her crew leave the comfort of Waterford and make their way to the Hudson River and to the Hudson Boat Club to put the ...

On the boat and ready to explore. WE have lifted the sails and started to practice navigating the shores of Grenada. Took some time waiting around for just a ...

Herby prepares Wisdom for Hurricane Helene! After the storm, he continues working on the boat. The project on the menu is to remove the rotten wood from the ...

Our THROWBACK THURSDAY video! Just to give a little insight into where we have been in the past! Last year we spent the holidays on the beach in FIJI! It was ...

Patreon: https://www.patreon.com/riggingdoctor Shirts: https://teespring.com/stores/rigging-doctor Instagram: https://www.instagram.com/riggingdoctor ...

Leaving Nassau we head to the Exuma's! Allen's Cay, Normans Cay and Warderick Wells! All beautiful spots! The exumas truly are amazing! Thank you to everyone ...

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 and Maddie are finally ready to haul out and leave Wisdom on the hard while they return to the states. They have a chance to explore Angra do Heroísmo, a ...

It is so much fun to be able to sail our home from one destination to another! Had a great time exploring the southern end of the Berry Islands. Next stop ...

Paper charts are the most reliable and important form of navigational information that you can carry on your boat. They not only tell you where you are, but ...

Herby and Maddie leave Horta, Faial, and set sail for Angra do Heroísmo, Terceira. The winds were more favorable than predicted and we managed to sail the ...

We made it! Now it’s time to get off the boat and start exploring! Come along with Herby and Maddie as they hike, eat, and explore the town of Horta, the ...

After crossing the Atlantic, Herby and Maddie discuss their general thoughts of the voyage, and what is next to come! Patreon: ...

We had a great weather window and made the crossing from Miami Florida to Bimini in the Bahamas! Only one issue along the way but we made it and it is ...

Herby and Maddie talk about the gear they used while crossing an ocean. What worked, what broke, and what was worthless! Some of the major talking points are ...

Hey hey crew! As I write from La Rochelle, I have a confession to make. I’ve been saving a treat for you! I was holding this for when I knew we would likely ...

Herby and Maddie discuss their tactics for storm avoidance while crossing the Atlantic. They discuss the gear they used and how they used it to better predict ...

Sailing across an ocean means sailing 24 hours a day. How do you sleep and still stay safe? In this video, Maddie and Herby discuss what worked for them as ...

Health while sailing across an ocean is a very important and an often overlooked aspect of sailing. You need to eat to stay healthy and strong because if you ...

When you set off on your cruising yacht to cross an ocean, should you have crew? Herby and Maddie discuss what they have learned from their own personal ...