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.

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Maiden Voyage Of A Lifetime! New Boat, First Trip! Sailor Barry & Hailly
SailorBarry

Maiden Voyage Of A Lifetime! New Boat, First Trip! Sailor Barry & Hailly

Support: Patreon: PayPal: Sailor Barry & Hailly Season 2 is HERE! And this is the crazy story of how we got Thunder Child! Part One: - Barry - Hailly
Sailing the ICW | Sailing Wisdom Ep 74
Rigging Doctor

Sailing the ICW | Sailing Wisdom Ep 74

SHIRTS: To donate yarn: [email protected] We finally get moving! In this video, we enter the ICW for the first time and run aground three times. It's not the most graceful trip, but we make it to an anchorage by the end of the day. Support us on Patreon: Follow us on Instagram: ...
Preparing for the Storm and How to Heave To | Sailing Wisdom Ep 60
Rigging Doctor

Preparing for the Storm and How to Heave To | Sailing Wisdom Ep 60

Two more sunny days allow plenty of time to enjoy the sail and prepare for the storm to come. We gain some new passengers (3 birds and a butterfly). Herby takes you through a tutorial of how to properly heave to in a storm and explained why it is so important to do so. Support us on Patreon: Foll...
Into the Ocean! | Sailing Wisdom Ep 59
Rigging Doctor

Into the Ocean! | Sailing Wisdom Ep 59

We finally make it out into the ocean and are visited by a whole pod of dolphins! We have a beautiful ocean sail and see more dolphins! Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Surprise Destination | Sailing Wisdom Ep 58
Rigging Doctor

Surprise Destination | Sailing Wisdom Ep 58

We prepare our food for travel and reveal our new destination! We set out for the Atlantic Ocean and Herby gives a tour of the deck. It's a slow pace, but our excitement doesn't stop building! Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music by Madd...
Hurricane Jose | Sailing Wisdom Ep 47
Rigging Doctor

Hurricane Jose | Sailing Wisdom Ep 47

Plans to go to Smith Island are once again thwarted by the weather and we end up turning South into the Great Wicomico River. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Hammock, Shower, and Departure! | Sailing Wisdom Ep 46
Rigging Doctor

Hammock, Shower, and Departure! | Sailing Wisdom Ep 46

Maddie rigs up the Hammock and relaxes before sharing how we take warm showers on the deck! They then set off for Smith Island despite the looming weather. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
All About the Solar | Sailing Wisdom Ep 44
Rigging Doctor

All About the Solar | Sailing Wisdom Ep 44

Herby explains the solar panels and how they are tied into our electrical system. He also gives some pointers about cooking on a fixed stove while sailing and underway. #solar Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected] Hotel Booking: Thanks to o...
Shark Teeth and Boat Yoga | Sailing Wisdom Ep 36
Rigging Doctor

Shark Teeth and Boat Yoga | Sailing Wisdom Ep 36

Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Fair Winds and Corgi Snuggles | Sailing Wisdom Ep 35
Rigging Doctor

Fair Winds and Corgi Snuggles | Sailing Wisdom Ep 35

We continue the trek north toward Solomons. Maddie reads, Morty is in an extra adorable mood, we talk about boat decks, and almost get hit by a tug in the dark!! Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound Music: Music provided ...
Sailing Wisdom: Cruiser Projects | Ep 21
Rigging Doctor

Sailing Wisdom: Cruiser Projects | Ep 21

Maddie Herby take down, flake, and drop off their mainsail for maintenance. Herby does some work on Tooth III, and Maddie reveals her secret for combatting seasickness! Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Sailing Wisdom: Full Sail, Full Day! | Ep 20
Rigging Doctor

Sailing Wisdom: Full Sail, Full Day! | Ep 20

Herby and Maddie give each other onboard haircuts before they set sail for an anchorage further up the river. They are then able to visit their other sailboat on the hard and pump him out. www.patreon.com/riggingdoctor Follow us on Instagram: Check out our website: Music: Music provided by B...
Sailing Wisdom: The Chesapeake Bay | Ep 2
Rigging Doctor

Sailing Wisdom: The Chesapeake Bay | Ep 2

Maddie and Herby make their way through the Chesapeake Bay as they head to Worton. Follow us on Instagram: Check out our website: Music: Music provided by Bensound
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