Watch Sailing & Boating Adventures Around the World – Page 2 of 8
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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This Clipper 36 Sailboat Is A WINNER! A 1971 Cheoy Lee built Bluewater Cruiser | $45k | FULL TOUR
#bluewatercruiser #cheoyleecclipper36 #sailboatreview #boatfoolssailing **The thumbnail image is a sister ship! The Clipper 36 Sailboat is a Winner! A SWEET 1971 Cheoy Lee built Bluewater Cruiser | $45k | FULL TOUR BoatFools Nation! This week, Canadian Ken couldn’t make the trip — so his body do...
We’re FINALLY Doing It⛵️Catamaran Workshop Conversion
We’re FINALLY doing it! After years of dreaming and months of planning, we’re starting the process of converting our port forward cabin into a functional onboard workshop so we can tackle all the future projects boat life will throw at us. In this episode, we start the demolition and rebuild proces...
I Fell Asleep and Crashed Into the Rocks
Get The Book → The True Story Behind the Night I Almost Lost Everything—and What It Taught Me About Command at Sea. Two boats. Two oceans. Two mistakes I’ll never forget. This is the night I fell asleep under full sail and ran my boat straight into the reef—twice. It’s not about drama; it’s about...
We Traded the Ocean for the Mountains | Our Journey to Minca, Colombia
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. In this episode of Sailing Big Lost, we head inland for a change of scenery—trading the Caribbean coast for the lush mountains of Minca, Co...
Sailing Is Way Scarier Than You Think – Ep 353 – Lady K Sailing
Sailing looks calm, romantic, and free — until it isn’t. In this video, we explore the real-life disasters and accidents that show just how fast things can go wrong at sea — from the 1979 Fastnet Race tragedy to the Cheeki Rafiki and Sydney to Hobart storm, to modern-day survival stories that remind...
Addressing a Serious Safety Issue During Our Catamaran Refit
We’re back on the hard this week, making major progress on our refit and addressing one of the biggest safety concerns for catamarans: escape hatches. In this video, we dive into what makes them so risky, vent a little (okay, a lot 😅), and show the changes we’re making to keep our boat safe. While ...
BIG CHANGES AHEAD: Refitting our Catamaran in New Zealand
We’ve officially hauled Sabado out of the water at Port Whangarei Marine Center in New Zealand, and the refit has begun! In this video, we take you through a day in our new routine: starting the morning at our rental house, commuting to the boatyard, and diving into our first big boat projects. We ...
She Left Me… and Now There’s a Hurricane Coming!! Ep-191
Go to and use code ESCAPADE to get 5% off your Holafly eSIM for your next trip! After 2.5 years onboard, Janaye has flown back to Australia for some much-needed time with family, friends, and the little luxuries of land life — hot showers, delicious food, and even driving a car again! 🇦🇺✨ But whi...
DON’T DO WHAT WE DID‼️Sailing Minerva Reef to New Zealand
After waiting out a storm on anchor in Minerva Reef, we set off toward New Zealand — but a drastic shift in the forecast, rough seas, and a vicious counter-current quickly turned this into one of our most challenging passages yet. With another storm closing in, we were pushed to make tough calls und...
Our Sail South Begins: Tonga to Minerva Reef
Join us on our journey South to New Zealand! In this video we prepare to leave Tonga: stocking up on provisions, triple checking the weather and saying farewell to the local wildlife…🐋🪼🦑 From there, we set off on a 3-day passage to Minerva Reef, facing rough seas along the way and adding a few new i...
Bonaire Bound: Our First Downwind Sail on the Vision 444
After a month of boat work and marina life in Grenada, it’s finally time to say goodbye to friends and set sail west toward Bonaire! This passage is extra special because it’s our first downwind sail on our Vision 444 catamaran, and we’re eager to see how she performs. With the weather on our side, ...
The Ultimate Walk Through
Welcome aboard Moor R & R! Episode 1. In this video, we’re giving you a full walk-through of our Lagoon 450 F — but this isn’t your average catamaran. Over the past two years, we’ve completely transformed this boat into a comfortable, upgraded liveaboard home. From a one-of-a-kind tender lift...
Our Dinghy SANK?! Sailing to Martinique
What started as a smooth sail from Îles des Saintes to Martinique quickly turned into one of our wildest passages yet. As we sailed south through the Eastern Caribbean, we were surrounded by massive mats of sargassum, battled unpredictable gusts near Dominica, and watched fearless kiteboarders tear...![[Ep 18] Last Day in the USA! Sailing Off On Our International Sailing Adventure to Mexico](https://i.ytimg.com/vi_webp/twH8Fuki05Q/mqdefault.webp)
[Ep 18] Last Day in the USA! Sailing Off On Our International Sailing Adventure to Mexico
We’re finally leaving San Diego! After months of boat projects, delays, and anchor life, our engine is fixed and we’re ready to set sail for Mexico. In this episode, we run our final errands and prepare the boat for offshore sailing. We depart in the early morning darkness and make our first interna...
After the Fun in Sint Maarten, We Set Sail for Saint Kitts
After an unforgettable time in Sint Maarten—celebrating Bastille Day, ziplining through the lush hills of Loterie Farm, and soaking up the cruiser-friendly vibes of the lagoon—it’s finally time to hoist the sails again. In this episode, we say goodbye to the comforts and conveniences of Simpson Bay...![[Ep 17] Prepping the Sailboat for Mexico Cruising | Routine Maintenance Threw Us a Curveball](https://i.ytimg.com/vi_webp/ErHsbooskOI/mqdefault.webp)
[Ep 17] Prepping the Sailboat for Mexico Cruising | Routine Maintenance Threw Us a Curveball
After 3 Months in San Diego... We Are Finally Ready to Sail to Mexico 🇲🇽⛵️ In this episode, we finally wrap up most of the projects while staying on anchor in San Diego, before taking off for Mexico. What was supposed to be a quick stop turned into three months of intense boat projects, major engine...
Sailing from Morocco to the Canaries: four days of quiet companionship at sea
After a quick marina repair in Rabat, Morocco, we cast off for a 480 nautical mile offshore sailing passage toward the Canary Islands. With a well-prepped sailboat and favorable weather, we were hopeful—but not fully ready for how physically draining the days ahead would be. This wasn’t a journey f...
Package Delays & Island Days | USVI Boat Life
After our 7-day passage to the USVI, we find ourselves in island time — waiting on delayed packages before we can continue our journey south to Saint Martin for hurricane season. While we wait, it’s a week of boat projects and island adventures! We spend time troubleshooting a radar that won’t acti...
What a Full Day on Passage REALLY Looks Like | VLOG 285 4K
We’re finally back at sea! After months on land, we’re setting sail from Georgia and making our way to the Bahamas — this time as a family of four. With our 7-month-old baby and dog onboard, we navigate a mix of the Intracoastal Waterway and offshore passages, adapting our route with the weather as ...
Why Sailboats Have Two Rudders
Check out my new book, Be The Captain: Ever wondered why so many modern sailboats now have dual rudders? You might think it's about safety or redundancy—but there's actually a deeper story. This video reveals the real reasons behind the widespread adoption of dual rudders on cruising sai...
Sneak Preview of My Book: “Be The Captain”
Get a signed copy while they last → In this video, I’m sharing the story behind Be The Captain—why I wrote it, what I’ve learned from thousands of readers like you, and a preview of what’s inside. Thank you for all the support, encouragement, and energy you've sent my way. I can't wait ...
Near-Death At Sea: What I Learned
Chapter 13 of my book *Be The Captain* is Storm Tactics: This is what I learned the night our catamaran cracked open 100 miles offshore. It wasn’t a rogue wave. It wasn’t one bad call. It was a chain of decisions—some rushed, some careless, some just unlucky. And the truth is, the biggest problem...
OFFSHORE SAIL NORTH: no choice but to take it on the chin – Ep 237
We set sail from the British Virgin Islands on a major offshore passage marking the first leg of our journey north in our new to us custom aluminum expedition sailboat toward remote, high-latitude destinations. This episode is a raw and unfiltered view of roffshore sailing as a couple starting with ...