Watch Sailing & Boating Adventures Around the World – Page 5 of 125

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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After 8 Years…It’s Time to Say Goodbye
The Cruising Kiwis

After 8 Years…It’s Time to Say Goodbye

After 8 Years...It's Time to Say Goodbye And just like that...a chapter comes to a close. After eight years of live aboard sailing around the world, where Declan and Ivan have grown from boys to capable, adventurous young men, they are jumping ship, bound for Mexico to join a 106 year old sail...
Things aren’t going to plan Sailing across the Pacific Part 2 Episode 501
Sailing Catalpa

Things aren’t going to plan Sailing across the Pacific Part 2 Episode 501

Cheers everyone for watching!! Subscribe @SailingCatalpa Become a Patron For a discount on Mudwtr www.mudwtr.com/catalpamud or use Discount code CATALPAMUD For a discount with Sky & Sol or use the code SAILINGCATALPA To contribute to the creation of theses videos For more on our fami...
Goodbye Saba… A 3-Day Caribbean Sailing Adventure to Guadeloupe E392
Wildly Intrepid Sailing

Goodbye Saba… A 3-Day Caribbean Sailing Adventure to Guadeloupe E392

Leaving Saba was one of the hardest departures yet. It quickly became one of our favorite islands in the Caribbean, but the weather had other plans. With stronger winds on the way, it was time to keep heading south. Our original plan was to spend a few days exploring St. Kitts and Nevis, but the an...
The MOST INTRIGUING ISLAND we have EVER Visited! Saint Helena Island… Ep 451
Sailing Nandji – Frothlyfe

The MOST INTRIGUING ISLAND we have EVER Visited! Saint Helena Island… Ep 451

To learn more about Keane Insurance and to seek your bespoke boat policy check them out here 👉 🫡 Here we are, anchored in the middle of the South Atlantic Ocean at the tiny volcanic island of St Helena. After two weeks at sea, dropping the anchor into crystal-clear water, surrounded by an abundance...
I finally discovered what makes me sea sick |  Family of 4 living aboard
A Life Awry Sailing

I finally discovered what makes me sea sick | Family of 4 living aboard

Some days on the water remind us exactly why we chose this life. This week, we set off before sunrise on a 70-nautical-mile sail to our next destination. With calm weather, a beautiful day ahead, and 13 hours on the water, we settle in for another family adventure. Like any journey, there are a fe...
We Didn’t Know If We Could Keep Going…  | EP144 HD 1080P
Motherload sailing

We Didn’t Know If We Could Keep Going… | EP144 HD 1080P

For the past few weeks, we’ve questioned everything. After disappointment, uncertainty, and wondering if Motherload Sailing had reached its end, we honestly weren’t sure what came next. Sometimes life doesn’t give you a clear course—it simply asks you to keep moving forward. Then something unexpecte...
Our Visa Extension Was Rejected… Cape Town Had Other Plans | S5 E29
Sailing with six

Our Visa Extension Was Rejected… Cape Town Had Other Plans | S5 E29

📨 Join our newsletter: Our visa extension was rejected. After driving five and a half hours from Hout Bay to George to collect our decision in person, we got news we weren't expecting — and had to figure out how to pivot fast. We turned a stressful day into an opportunity, joining a half mar...
Our Family Sailing Adventure Wasn’t Supposed to End Like This
The Cruising Kiwis

Our Family Sailing Adventure Wasn’t Supposed to End Like This

Family Sailing Adventure Wasn't Supposed To End Like This After safely sailing our damaged catamaran south from Antigua to Guadeloupe, we make one final stop in the breathtaking archipelago of Les Saintes, home to one of the Caribbean's most beautiful natural harbours and the best baguett...
Sailing 4000nm across the Pacific Ocean PART ONE Episode 500
Sailing Catalpa

Sailing 4000nm across the Pacific Ocean PART ONE Episode 500

Our 500th episode and the start of our Pacific crossing from Panama to French Polynesia Cheers everyone for watching!! Subscribe @SailingCatalpa Become a Patron For a discount on Mud/Wtr www.mudwtr.com/catalpamud or use Discount code CATALPAMUD For a discount with Sky & Sol or use the ...
Our FINAL Day on Saba | The Caribbean’s Most Incredible Island? E391
Wildly Intrepid Sailing

Our FINAL Day on Saba | The Caribbean’s Most Incredible Island? E391

Saba completely stole our hearts, and saying goodbye wasn't easy. 🌋❤️ Before setting sail, we squeezed every last adventure out of what has become our favorite island in the Caribbean. Our final day starts with one last spectacular hike from The Bottom to Windwardside via the beautiful Crispee...
FORCED to Leave Europe And Sail To Africa! One Last Mediterranean Adventure | S2 – EP9
The Runa Life

FORCED to Leave Europe And Sail To Africa! One Last Mediterranean Adventure | S2 – EP9

If you've ever wondered what the everyday looks like when you quit your job and live on a sailboat, this is it 😀 Last week, we began our sailing journey down Sardinia's stunning west coast as we head south towards Africa. With our time in Europe coming to an end, we're being forced t...
Why We Chose Boat Life (And What It Really Costs)
A Life Awry Sailing

Why We Chose Boat Life (And What It Really Costs)

Why did we choose a boat over a house? And what does it really cost to live on a sailboat? These are two of the questions we get asked the most, so in this week's episode we're sharing the honest answers. When we first bought our sailboat back in 2019, it was all about adventure. But ove...
We Crashed Fiji’s MOST Exclusive Resorts by Sailboat
Sailing Machete

We Crashed Fiji’s MOST Exclusive Resorts by Sailboat

Come with us to explore FIJI by sailboat. This week we are seeing some of the most beautiful resorts of the Coral Coast of Fiji. To God be the glory! #sailingfamily #familyvlog #boatlife #familytravelvlog #youtubekids #sailingaroundtheworld #outdoors #bucketlist #fiji #paradise #sailing #laugro...
50 Knots and a Growing Job List: Preparing Happy Days for the Atlantic | S5 E28
Sailing with six

50 Knots and a Growing Job List: Preparing Happy Days for the Atlantic | S5 E28

Before we could leave South Africa behind for good, Happy Days needed to be ready for everything the Atlantic could throw at her. What followed was days of running rigging failures, 50-knot winds in the marina, and a job list that seemed to grow faster than we could tick it off. This episode we...
We CRASHED our SAILBOAT….NOW WHAT?
The Cruising Kiwis

We CRASHED our SAILBOAT….NOW WHAT?

We CRASHED our SAILBOAT....NOW WHAT? What do you do after crashing your sailboat into rocks? With holes in our catamaran and only temporary repairs completed, we set sail from Antigua to Guadeloupe, in the Caribbean, hoping our temporary fixes will hold. abut this episode isn't just about re...
This Didn’t End the Way We Hoped… 🎣💔
Finding Our Isla Sailing

This Didn’t End the Way We Hoped… 🎣💔

What started as an exciting fight turned into a tough lesson. Krew and I battled a huge barracuda in rough seas, but the hook was swallowed too deeply. We did everything we could to safely release it, but we don’t think it survived. Moments like this remind us that fishing isn’t just about the exc...
Sailing to Saba: The Caribbean’s Hidden Jurassic Island E390
Wildly Intrepid Sailing

Sailing to Saba: The Caribbean’s Hidden Jurassic Island E390

Saba completely blew us away. 🤯 After waiting for the perfect weather window, we finally sailed to one of the least-visited islands in the Caribbean—and it instantly became one of our favorites. Towering straight out of the sea, Saba looks more like something from Jurassic World than the Caribbean...
WE SAILED to one of the MOST REMOTE ISLANDS in the WORLD! St Helena Island… Ep 450
Sailing Nandji – Frothlyfe

WE SAILED to one of the MOST REMOTE ISLANDS in the WORLD! St Helena Island… Ep 450

To learn more about Keane Insurance and to seek your bespoke boat policy check them out here 👉 🫡 After more than 1,800 miles and two weeks at sea, we have arrived to a small patch of land, in the middle of the South Atlantic Ocean… the tiny island of St Helena. And wow... it feels good to be here. ...
We Finally Rounded the Bottom of Africa | S5 E27
Sailing with six

We Finally Rounded the Bottom of Africa | S5 E27

📨 Join our newsletter: Leaving Knysna was always going to be one of the biggest milestones of our South African adventure… but it didn’t come without a few heart-racing moments. After soaking up our final days exploring the beautiful Knysna Lagoon and sneaking in one last family surf at Victoria ...
We’ve Reached Our Breaking Point… What Happens Next..? | EP143 HD 1080P
Motherload sailing

We’ve Reached Our Breaking Point… What Happens Next..? | EP143 HD 1080P

Friends arrive in paradise, the waves are firing, and it’s Mom’s birthday—a recipe for unforgettable memories. But behind every smile is a reality we’ve struggled to hide. Living aboard with five growing boys isn’t always sunsets and anchorages. The pressure of parenting, maintaining a boat, creatin...
Safety Upgrades we made to SAIL across the PACIFIC OCEAN Episode 499
Sailing Catalpa

Safety Upgrades we made to SAIL across the PACIFIC OCEAN Episode 499

This episode we share some of the safety upgrades we made before we set sail across the Pacific Ocean. ⏱️ CHAPTERS 00:00 Intro — why AIS & VHF matter [00:42] Life Raft [01:02] Life jackets [02:18] Life Sling [03.25] Our Grab bag [06:18] Communications on the ocean 🛠️ GEAR from West Marine ...
Can We Repair our Sailboat After Crashing into Rocks?
The Cruising Kiwis

Can We Repair our Sailboat After Crashing into Rocks?

Can We Repair our Sailboat After Crashing into Rocks? Welcome back aboard, you join us this week in Antigua where we are assessing the damage to our sailboat, after accidentally crashing her into rocks at 6 knots. We are repairing what we can, and hoping to get our floating home seaworthy enough to...
We Hiked a Volcano with a 2 & 4 Year Old! | Mount Scenery, Saba E389
Wildly Intrepid Sailing

We Hiked a Volcano with a 2 & 4 Year Old! | Mount Scenery, Saba E389

After finally finding the perfect weather window, we arrive in spectacular Saba and check in by sailboat to one of the most unique islands in the Caribbean. Our adventure begins with a ride along the legendary "Road That Couldn't Be Built"—an engineering marvel carved into impossibly...
We dreamed of this life but its harder than we expected
A Life Awry Sailing

We dreamed of this life but its harder than we expected

Life on a sailboat isn't always sunshine and perfect anchorages. This week we're anchored at Pancake Creek, where we set off on a family walk to the lighthouse before the weather has other plans. After a few days stuck onboard with two young kids, we start questioning whether this lifesty...
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