Watch Sailing & Boating Adventures Around the World – Page 6 of 143
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 just sold our boat… So why are we going back onto the boat we just sold?
After racing across America on our road trip in our last travel vlog, plans changed as soon as this little sailing family arrived and we found ourselves heading straight back to our boat on sailing sunday.
In this episode...
📍 Sea of Cortez, Mexico
Bahía de los Ángeles → Ensenada Quemado → Isla La Ventana
We wrapped up our time in Bahía de los Ángeles thinking we were ready to move on… but not before one last surprise.
After a stingray encounter, we set off and spent hours trying to make our way through the channel ag...
Follow us in this episode as we dodge shallows and reefs, sail to a deserted island and get our first glimbse of the 2nd largest barrier reef in the world.
Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country to country discover...
It really is about the journey as much as the destination. Get an exclusive 15% discount on Saily data plans! Use code WYNNS at checkout. Download Saily app or go to
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☝Behind the Scenes, Gear Guides & More
🎬 Produced, Filmed and Edited by: Jason & Nikki...
After walking away from Sailing Sunday, we thought this would be a new exciting chapter looking for our new boat, our new home, to continue this sailing life we live, traveling around the world full time off grid. But after numerous let downs, overpriced boats and months of searching we become quite...
#sailing #sailboat #pearson35 #sailboatsforsale #sailboattour
$100K Spent on This 1974 Pearson 35 — Offered at $29,500 | FULL TOUR
$100,000 was spent refitting this Pearson 35… and it’s listed for $29,500.
We went to see if it actually lives up to the numbers.
This week we’re in Warwick, Rhode I...
Today I am solo sailing through the aegean sea to the island of Patmos, Greece. This single-handed sailing adventure is about 40 nautical miles beating to windward and a rough sail.
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Did I just say my Boat Life sucks right now? No, but I SHOULD HAVE... because everything on my sailboat keeps breaking! 😤⚓ One expensive repair after another, this is the raw, unfiltered reality of liveaboard sailing life in 2026. If you're dreaming of boat life or already living it, you have s...
Cheers everyone for watching!!
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It's time to go...but the boat isn't ready! Struggling with sleep? Dream changed the game for me. Visit and use code WYNNS for up to 40% off—limited time only!
☝Behind the Scenes, Gear Guides & More
🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn
⚓️ Our Explorer Yacht ⚓️...
Join us for a day on our life at an island in Panama 🇵🇦
Cheers everyone for watching!!
To purchase anything for our pacific crossing on Amazon this is our Wishlist
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use code CATALPA2
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Boat life isn’t always turquoise water and smooth sailing… sometimes it’s project after project 😅
In this episode, we tackle a long list of upgrades and repairs—finishing our epoxy countertop, varnishing the fridge top and installing a new gasket, making new dinghy cushions, repairing our headsail,...
This episode we enjoy a tropical paradise together, share how our son earns a living and say goodbye as he is off on a big adventure ✈️
Cheers everyone for watching!!
Tajs website www.tajrice.com
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Join us as we settle into the beautiful marina life in Cartagena, Spain! After weeks at sea, we’re finally tied up in this historic Mediterranean port, soaking up the warm autumn sun and the lively energy of the city. Cartagena feels like one endless party right now — with cruise ships lining the ha...
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In this episode we pick up where we left off in San Francisquito, also known as “The Slot”.
After exploring more of this remote Baja anchorage, including abandoned buildings and a close encounter with a not-so-friendly bull, we settled into life at anchor on Cosmo and give you a little “day in the ...
Our first time breaking ice with a boat! 🌎 Get an exclusive 15% discount on Saily data plans!
Use Our Code "WYNNS" at checkout. Download
Saily app or go to
☝Behind the Scenes, Gear Guides & More
🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn
⚓️ Our Explorer Yacht UN...
After two months away visiting family in Canada, we finally return to our sailboat in Luperón, Dominican Republic. Leaving your boat unattended in the tropics is always a gamble, so we were relieved to find her looking surprisingly good when we arrived back.
Of course, boat life means there’s alway...
This episode we arrive in Panama 🇵🇦 and sail to a beautiful group of islands in the pacific side of Panama.
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After days offshore, the real challenge begins. Changing winds, large swells, and the isolation of the open sea test us and SV CUBA. In this episode, you’ll experience the raw reality of offshore sailing, from dodging squalls and boat life routines to the unique things that only sailors experience. ...
After months in the Caribbean, we head back to Canada for some much-needed family time and a full taste of fall and winter.
Our trip starts in La Beauce, where we spend time with Mamie surrounded by incredible fall colours. The kids soak up the crisp autumn air while we enjoy quiet family moments b...
Cruising Scotland by sailboat, we dropped anchor beside some of the most iconic castles in the Hebrides, including Eilean Dolan Castle and Castle Tioram. From biking in the highlands to exploring tidal islands this stretch of coastline has stunning scenery and unforgettable anchorages. Join us as we...
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