Watch Sailing & Boating Adventures Around the World – Page 2 of 12

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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We Bought The Catamaran! …And About To Give Birth! | Sailing Sunday Vlog 322
Sailing Sunday

We Bought The Catamaran! …And About To Give Birth! | Sailing Sunday Vlog 322

🎀⬇️Amazon Baby Registry⬇️🎀 After 3 months apart, Ryan is finally back in Canada, Brittni is about to give birth and we can officially say it… We bought a catamaran! The 48ft Fountaine Pajot Salina 48 is ours! In this sit down we answer the questions you’ve all been asking in the comments of our l...
Eastern Caribbean Was NOT What We Expected
Finding Our Isla Sailing

Eastern Caribbean Was NOT What We Expected

This was NOT the Caribbean we expected. Sailing south through the Eastern Caribbean brought us to Guadeloupe—and what we found completely surprised us. After leaving St. Kitts and Nevis and making a quick stop in Montserrat, we sailed Isla into Deshaies, Guadeloupe, ready to get off the boat and e...
We Got LOST in the Pirates of the Caribbean Indian River! E398
Wildly Intrepid Sailing

We Got LOST in the Pirates of the Caribbean Indian River! E398

We set out to explore Dominica’s famous Indian River… but somehow managed to lose the trail! What followed turned into one of those adventures that makes Dominica so incredible. We wandered through thick jungle, crossed the river and found ourselves surrounded by huge twisted roots that looked str...
Broken Engine, Big Waves Episode 8
Sailing Banana Pancakes

Broken Engine, Big Waves Episode 8

We thought our biggest problem was a broken dinghy… until one of our engines refused to start and a massive wave came crashing through the front door of our boat. After six hours troubleshooting the engine in the Florida heat, Steve finally got us moving again. But our first real day sailing north ...
ROUGH Sail to Dominica But it’s WORTH IT E397
Wildly Intrepid Sailing

ROUGH Sail to Dominica But it’s WORTH IT E397

We say goodbye to Guadeloupe and set sail for Dominica, but it definitely isn't the smooth Caribbean sail we were hoping for! The day starts with a bad feeling in my gut before we head out into a rough, lumpy sea for the crossing to Dominica. 🌧️⛵ It isn't our most comfortable passage, but...
Stranded in a Lightning Storm…Then Our Hair Stood Up Episode 7
Sailing Banana Pancakes

Stranded in a Lightning Storm…Then Our Hair Stood Up Episode 7

Our dinghy died miles from our sailboat as darkness closed in and a massive lightning storm rolled toward us. Then our hair began standing straight up—the terrifying warning that lightning could strike at any moment. What was supposed to be a simple family sailing trip from Miami to Key Largo for k...
Hidden Hot Springs & Sailing life of a family in Guadeloupe E396
Wildly Intrepid Sailing

Hidden Hot Springs & Sailing life of a family in Guadeloupe E396

Sailing Guadeloupe with the family ⛵ Another beautiful stretch of Caribbean cruising! We start out anchored in Malendure, where it’s time to tackle one of the less glamorous parts of boat life — the grocery run! With the boat stocked up, we jump into the clear Caribbean water for another incredible...
We Almost Quit Sailing
Finding Our Isla Sailing

We Almost Quit Sailing

What was supposed to be a manageable overnight sail from the USVIs to St. Martin turned into one of the hardest passages we’ve experienced as a sailing family. The forecast said one thing. The ocean gave us something completely different. We found ourselves beating directly into the wind and waves...
New episode is up on our channel! ⛵️ #sailing #sailingadventures  #funny
Sailing Banana Pancakes

New episode is up on our channel! ⛵️ #sailing #sailingadventures #funny

One of the questions we get all the time: where do you put all your food?! A little look inside our galley, how we organize food, and where we manage to fit everything when your kitchen also has to survive life at sea.
Our 4-Year-Old Started DIVING in the Caribbean! E395
Wildly Intrepid Sailing

Our 4-Year-Old Started DIVING in the Caribbean! E395

Our 4-year-old Coral is taking her underwater adventures to a whole new level! 🤿🌊 We explore the incredible Réserve Cousteau in Guadeloupe, where the water is crystal clear, the reef is full of life, and Coral starts diving below the surface all on her own. Watching her confidence grow underwater a...
Will She Fit? | Docking Our 50 ft Cat & Provisioning Our Sailboat Ep.5
Sailing Banana Pancakes

Will She Fit? | Docking Our 50 ft Cat & Provisioning Our Sailboat Ep.5

We bought a Leopard 50 catamaran, moved our family of six aboard—and immediately discovered our new home wouldn’t even fit at the dock. This is the chaotic reality of becoming a full-time sailing family. After saying goodbye to everything familiar and catching a one-way flight to Florida, it was fi...
There’s No Going Back Now Episode 4
Sailing Banana Pancakes

There’s No Going Back Now Episode 4

We actually did it. We sold almost everything we own, said goodbye to our home, our cabin, our cars, our pets, our friends and the life our kids have always known… and boarded a plane to Florida to begin our new life sailing around the world. This episode is the end of one chapter for our family—an...
“Pour Yourself a Glass of Wine…”  7 to 33 Knots E394
Wildly Intrepid Sailing

“Pour Yourself a Glass of Wine…” 7 to 33 Knots E394

One last adventure at Grande Anse, one of the most beautiful beaches we’ve found in Guadeloupe before making the short hop to Deshaies. There we enjoy some delicious local treats and cool off with a swim in the river. Then it’s time to keep sailing south along the coast of Guadeloupe. The condition...
The Greatest Gift My Parents Gave Us Wasn’t a Thing
Finding Our Isla Sailing

The Greatest Gift My Parents Gave Us Wasn’t a Thing

Sometimes the greatest gifts aren't things—they're the lessons and memories that stay with you forever. ❤️ This week aboard Isla, Nana and Gogo join our family to celebrate my 40th birthday, and what started as a family visit became one of our favorite weeks of boat life. We waste no tim...
We Found Guadeloupe’s Most Beautiful Beach! | Grand Anse by Sailboat E393
Wildly Intrepid Sailing

We Found Guadeloupe’s Most Beautiful Beach! | Grand Anse by Sailboat E393

Anse Leroux, Guadeloupe is perfect, with crystal-clear water, a close by beach and fantastic snorkeling just a short ride from the boat. From there, we take a long dinghy ride to the colorful village of Deshaies, where we wander the charming streets and discover an amazing local bakery serving deli...
We Never Expected to Find Family Here
Sailing Big Lost

We Never Expected to Find Family Here

Following an offshore passage to Moorea, Sailing Big Lost anchors with SV Kaikoa to hike Magic Mountain, swim with rays and sharks, and say goodbye ahead of cyclone season.
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...
Sailing to Moorea Was Hard, The Reward Made It Worth It
Sailing Big Lost

Sailing to Moorea Was Hard, The Reward Made It Worth It

Facing rough seas and seasickness during an overnight passage from Tikehau to Moorea, the crew aboard SV Big Lost completes 178 nautical miles before reprovisioning, clearing trash, and reuniting with cruising friends.
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...
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 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 Thought Success Looked Like This    We Were Wrong
Sailing Big Lost

We Thought Success Looked Like This We Were Wrong

Connor and the crew aboard Big Lost experience the Fakarava grouper spawning dive, tour a black pearl farm, and sail 165 nautical miles to Tikehau in French Polynesia.
We hit Rocks at six knots! Distracted by phone!!
The Cruising Kiwis

We hit Rocks at six knots! Distracted by phone!!

Captain Checked his Phone then We Crashed into Rocks What should have been a short, routine sail between two anchorages in Antigua turned into one of our most expensive mistakes. A moment of distraction, the captain checking his phone, saw Javelot ran onto rocks, causing damage to both hulls and ca...
Our First Overnight Sail as a Family
Finding Our Isla Sailing

Our First Overnight Sail as a Family

Our first overnight sailing passage took us from St. Martin to the U.S. Virgin Islands aboard our Lagoon 450 catamaran—and honestly, it wasn't what we expected. As a family of six living aboard full-time, sailing through the night with our kids was one of the biggest milestones of our journey....
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