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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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...
LOST? Night Kayaking in St John… Until Captain couldn’t find us! #stjohn #trawlerlife
UNANCHORED LIFE

LOST? Night Kayaking in St John… Until Captain couldn’t find us! #stjohn #trawlerlife

🌙 We thought a peaceful night kayak in St John, US Virgin Islands would be a magical experience… and it was—until our captain (Ken) tried to find us with a spotlight and things got slightly ridiculous. In this clip from our Unanchored Life adventure aboard our Kadey Krogen 55 trawler, Elsa and I he...
24 HRS OF BOAT LIFE: Day in the Life & Tropical Escape – Ep 222
Sailing Jibsea

24 HRS OF BOAT LIFE: Day in the Life & Tropical Escape – Ep 222

Ever wondered what it’s like to live on the open water, exploring hidden islands, and embracing a minimalist, off-the-grid lifestyle? In this video, we take you on a journey through 24 hours aboard our custom aluminum sailboat, showcasing life in a tiny floating home in the stunning Caribbean. We&...
Exploring Virgin Islands National Park (St. John) | SAILING THE CARIBBEAN
Holly and Ray

Exploring Virgin Islands National Park (St. John) | SAILING THE CARIBBEAN

This week we explored the Virgin Islands National Park (St. John) while Holly’s parents were aboard! We snorkeled Henley Cay, Lovango Cay, Waterlemon Cay, and Maho Bay. There was healthy coral and diverse marine life- we even got to see a small nurse shark and a turtle! We spent a day enjoying the L...
Vacation on St. John after our Bareboat Charter | Boating Journey
Boating Journey

Vacation on St. John after our Bareboat Charter | Boating Journey

In episode 148, we spend our last few days of our bareboat charter trip in St. John, USVI. We rent a condo at Grande Bay Resort, explore fantastic restaurants and shops. We also rented a Zodiac to go and swim with the turtles, but Mother Nature had other plans for us. Be sure to tune in to find out...
Exploring the Ruins on St John | Boating Journey
Boating Journey

Exploring the Ruins on St John | Boating Journey

In episode 113, we explore the sugar mill ruins and plantations on St John, USVI with a private guide named Tony. This was a great way to see the ruins up close without being in a large tour group. What we didn't expect was a mode of transportation! It was also cool to see how close we actually...
Cruising St. John by Dinghy | Boating Journey
Boating Journey

Cruising St. John by Dinghy | Boating Journey

In episode 111, we explore St. John's beaches, including Caneel Beach by dinghy. We rented a dinghy from Wharfside Watersports in Cruz Bay for the day. Links: www.wharfsidewatersports.com www.chillaxincharters.com Follow our blog at www.boatingjourney.com. You can also follow us on social @B...
We found DIAMONDS & GOLD and can stop JUMPSTARTING the Boat – Ep 37
Sailing Jibsea

We found DIAMONDS & GOLD and can stop JUMPSTARTING the Boat – Ep 37

We strike gold! And diamonds! We’ll sort of lol. We also have a starter issue with the engine so we’re changing the solenoid. Then we explore St. John, USVI where we get our hike on! We explore an old guesthouse, sugar plantation and hike up to a popular look out. WHERE WE DROPPED ANCHOR/MOORED -...
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