Watch Sailing & Boating Adventures Around the World – Page 3 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 49-72 of 91 results
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...
Practice Makes Perfect! | Sailing Wisdom Ep 55
Rigging Doctor

Practice Makes Perfect! | Sailing Wisdom Ep 55

Herby and Maddie head to their final destination in the Chesapeake before heading out to Bermuda. Maddie practices reefing in the calm weather and Morty gets a treat of his very favorite food. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Maddie
Sailing overnight down the Bay, sculling into the slip
How to Sail Oceans

Sailing overnight down the Bay, sculling into the slip

A vlog entry on sailing south down the Chesapeake Bay; installing a cheap (and easy) chart plotter; negotiating another narrow harbor entrance under sail, and moving the boat into the travel lift slip with sail and oar.
What’s on Tangier Island?! | Sailing Wisdom Ep 54
Rigging Doctor

What’s on Tangier Island?! | Sailing Wisdom Ep 54

We Spend the day on the beautiful Tangier Island. Maddie takes you on a small biking tour of the town and gives a brief history of its inhabitants. You learn that there are a few things that make this island very special and unique, but it's in great danger. Support us on Patreon: Follow us ...
Trapped For A Day! | Sailing Wisdom Ep 53
Rigging Doctor

Trapped For A Day! | Sailing Wisdom Ep 53

We visit Tangier and realize its beauty as the sun sets over a great day, but the following day isn't nearly as ideal. A storm hits and we become trapped in Wisdom, unable to make it to shore in Tooth. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music pr...
How Oysters are Farmed! | Sailing Wisdom Ep 51
Rigging Doctor

How Oysters are Farmed! | Sailing Wisdom Ep 51

We are surprised by kind Reedville Residents and friends by a road trip to their son's oyster farm! We learn all about the oyster growing process and even muster the courage to try slurping some picked straight from the water. And the verdict is.......... SAPIDUS FARMS Michael Manyak Sapidus...
What’s in Reedville? | Sailing Wisdom Ep 49
Rigging Doctor

What’s in Reedville? | Sailing Wisdom Ep 49

Maddie and Herby spend the day exploring the beautiful, quiet town of Reedville. The day includes a museum tour, a peak at some of the Victorian homes, and ice cream to top it off. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
In the Great Wicomico | Sailing Wisdom Ep 48
Rigging Doctor

In the Great Wicomico | Sailing Wisdom Ep 48

We are forced to wait out the storms in the Great Wicomico River but we make the most of the situation! Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
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
Fun With Friends | Sailing Wisdom Ep 45
Rigging Doctor

Fun With Friends | Sailing Wisdom Ep 45

Maddie and Herby host two good friends for the weekend and have a fabulous time "showing them the ropes!" Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Pets On A Boat | Sailing Wisdom Ep 43
Rigging Doctor

Pets On A Boat | Sailing Wisdom Ep 43

We find a marina in st. Mary's where we are able to do some work and talk about important things like what it's like to have pets on a boat. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
A Perfect Day | Sailing Wisdom Ep 42
Rigging Doctor

A Perfect Day | Sailing Wisdom Ep 42

We drop anchor in St. Mary's river and pack a picnic. It's a rough dinghy ride over to the beach, but it's well worth it! We spend a perfect day relaxing and swimming before rowing back to raise the sails and continue on. Support us on Patreon: Follow us on Instagram: Check out o...
Rough Seas and Following Storms | Sailing Wisdom Ep 41
Rigging Doctor

Rough Seas and Following Storms | Sailing Wisdom Ep 41

We start with some cool shots of beating through big seas. Maddie continues to battle seasickness and then a beautiful storm decides to pass over us in the middle of the night... ASupport us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Monitor Windvane Explained! | Sailing Wisdom Ep 40
Rigging Doctor

Monitor Windvane Explained! | Sailing Wisdom Ep 40

Herby drills some holes in our new oars and does some varnishing before his parents head out and we begin our sail to St. Mary's river! On the way, Maddie struggles with seasickness and Herby discusses the Monitor Windvane. Support us on Patreon: Follow us on Instagram: Check out our websi...
Fun on Solomons Island | Sailing Wisdom Ep 39
Rigging Doctor

Fun on Solomons Island | Sailing Wisdom Ep 39

We explore Solomons Island on our bikes! We visit the Calvert Maritime Museum and find out about the fossils we found on the cliffs and grab some wine before heading to a delicious dinner! Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensoun...
Wine Tasting and Fixing the Stove | Sailing Wisdom Ep 38
Rigging Doctor

Wine Tasting and Fixing the Stove | Sailing Wisdom Ep 38

It's a rainy day so Maddie goes wine tasting while Herby fixes the stove. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
SLEEP IS FOR THE WEAK! | Sailing Wisdom Ep 37
Rigging Doctor

SLEEP IS FOR THE WEAK! | Sailing Wisdom Ep 37

We were thrown around so much at our terrible anchorage that neither of us had gotten any sleep when we set sail once again towards Solomons. We got there in good time, but there was a lot to be done upon our arrival! Support us on Patreon: Follow us on Instagram: Check out our website: Musi...
Summer Sail and Pickle Tasting | Sailing Wisdom Ep 34
Rigging Doctor

Summer Sail and Pickle Tasting | Sailing Wisdom Ep 34

We run aground again (thanks for your help, Andrew), fill our tanks, get sailing south, discuss synthetic life lines, and taste test our pickles! It's a good time. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Sailing Wisdom: A Day in a Life | Ep 30
Rigging Doctor

Sailing Wisdom: A Day in a Life | Ep 30

We jump to just before the past week. Herby starts up early in the morning as we slowly ghost out of West River. It's a simple day, but they arrive in their new marina with plenty of daylight to spare and they feel safe leaving the boat for the week of the family reunion. Support us on Patreo...
Sailing Wisdom: Magical Forest Island | Ep 29
Rigging Doctor

Sailing Wisdom: Magical Forest Island | Ep 29

Maddie and Herby explore a beautiful forest island and sail to a restaurant in West River for dinner. They will be on vacation for a week with no more videos until their return! Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Thomas Point | Sailing Wisdom Ep 27
Rigging Doctor

Thomas Point | Sailing Wisdom Ep 27

The sail has arrived! Maddie and Herby finally set sail for a gem of a destination in the Chesapeake Bay. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Laundry on a boat! | Sailing Wisdom Ep 26
Rigging Doctor

Laundry on a boat! | Sailing Wisdom Ep 26

Herby puts finishing touches on the dinghy rack and Maddie cooks lunch. They do laundry aboard and give Morty a much needed bath before letting him roam ashore. Support us on Patreon: Follow us on Instagram: Check out our website: Music: Music provided by Bensound
Being Green/Self-Sufficient | Sailing Wisdom Ep 25
Rigging Doctor

Being Green/Self-Sufficient | Sailing Wisdom Ep 25

It's a rainy day and the sail still hasn't come in. Herby organizes his clothes, they collect tons of rain water and use it to wash dishes, and they go for a bike ride to grab some hair dye. They then discuss all of the various ways in which their lives have turned out to be very earth-fri...
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