Watch Sailing & Boating Adventures Around the World – Page 2 of 5

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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Robbed…And It Forced Us To Simplify
Gone with the Wynns

Robbed…And It Forced Us To Simplify

A BIG shift in how we travel and film. Head to to get FREE AG1 & AGZ Travel Packs, Vitamin D3+K2, and an AG1 Welcome Kit when you first subscribe. 📷 Photo & Video Gear 📷 ☝Behind the Scenes, Gear Guides & More 📱Socials INSTAGRAM: FACEBOOK: 📧JOIN THE CREW🍦 🎶 MUSIC for vids...
The Start of Our Next Chapter
Gone with the Wynns

The Start of Our Next Chapter

New boat, new chapter, and all the nerves that come with it. 🛥️ Stay salty! Get your free LMNT Sample Pack with any purchase at ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧JOIN THE CREW🍦 🎶 MUSIC for vids. 2 Months Free: 🎨...
First Sea Trial After 2 Years at the Dock!
Gone with the Wynns

First Sea Trial After 2 Years at the Dock!

After two years sitting still, we got this boat off the dock. But not before discovering why boats don’t like being ignored. Start 2026 with better sleep! Try Beam Dream: and use code WYNNS for up to 40% off - limited time only. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gea...
Our First Christmas Market (& A Thank You)
Gone with the Wynns

Our First Christmas Market (& A Thank You)

Merry Christmas and Happy Holidays! ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧JOIN THE CREW🍦 🎶 MUSIC for vids. 2 Months Free: 🎨 Creative Assets for Vids (SFX, Templates & Presets): - 🎽GET YOUR SWAG ON: -------...
Punta Pulpito, Baja California Sur | Sailing Avocet
Sailing Avocet

Punta Pulpito, Baja California Sur | Sailing Avocet

Sailing to Punta Pulpito in the Sea of Cortez was pure magic! We dropped anchor with @odysseyalternative and @KesselUnderway hiked the iconic volcanic rock, snorkeled the clear turquoise waters, and Peter spearfished fresh fish for the best tacos under the stars. 🌮⛵️ As night fell, the ocean lit up...
Sailing Costa Rica’s Pacific Coast
Sailing SV Indigo

Sailing Costa Rica’s Pacific Coast

After sailing La Paz, Mexico, we head to Costa Rica to sail with friends Nicky and Peter aboard their Beneteau First 50, Resolute. We sail south down the Pacific coast for 8 days to Golfito, before departing to fly back to our boat in Seattle.
Fresno Yacht Club’s High Sierra Regatta | Sailing Avocet
Sailing Avocet

Fresno Yacht Club’s High Sierra Regatta | Sailing Avocet

From Puerto Peñasco to our stomping grounds at 7000 feet, we didn't skip a beat with sailing and were stoked to get back and sail our Victory 21 in the 70th Annual High Sierra Regatta at Huntington Lake! This two-day regatta was packed with wind, competition, and fun with our Fresno Yacht Club ...
Vacation in San Blas, Nayarit | Sailing Avocet
Sailing Avocet

Vacation in San Blas, Nayarit | Sailing Avocet

🌎 Get an exclusive 15% discount on Saily data plans! Use code AVOCET at checkout. Download Saily app or go to ⛵️ We put a pause on our frustrating engine rebuild and took a trip overland to San Blas, Nayarit with our pals from SV Lusty. There we embarked on a jungle cruise through the mangroves wh...
Rebuilding Our Perkins 4.108: the Engine Drop | Sailing Avocet
Sailing Avocet

Rebuilding Our Perkins 4.108: the Engine Drop | Sailing Avocet

In our last video you watched us dissect our Perkins 4.108 diesel after limping back to La Cruz from Isla Isabel, where we discovered our fuel pump had failed... AGAIN. After deciding to move ahead with a rebuild, Chris jumped right in and got his hands dirty, making it happen... even if that meant ...
Sailing BC’s Desolation Sound: Rebecca Spit to Octopus Islands  |  Sailing SV Indigo
Sailing SV Indigo

Sailing BC’s Desolation Sound: Rebecca Spit to Octopus Islands | Sailing SV Indigo

More of our adventures in BC's Discovery Islands. As we sail from Rebecca Spit to Octopus Islands, through Beazley Passage and Surge Narrows, it becomes clear that we're completely unprepared for long term cruising.
Sailing Desolation Sound into Von Donop Inlet  |  Sailing SV Indigo
Sailing SV Indigo

Sailing Desolation Sound into Von Donop Inlet | Sailing SV Indigo

There are times when nothing seems to go your way. As we sail into the Desolation Sound area, a series of constant unexpected challenges started coming as soon as we headed into Campbell River, and then into Von Donop Inlet. But ultimately, it’s not about the challenges, it's how you deal with ...
Are We Moving to Sweden? | The Final Frosty Chapter
Chasing Currents

Are We Moving to Sweden? | The Final Frosty Chapter

Our time in Sweden is coming to a close, we have a decision to make... Join the Chasing Currents family!! If you enjoyed this video, consider buying a coffee on our buyacoffee page - or PayPal- Our Youtube videos aren't real time, if you want real time updates you can check out our Social m...
Leaving Everything to Live on a Small Sailboat.. Sailing the Inside Passage to ALASKA | A&J Sailing
Allison & James

Leaving Everything to Live on a Small Sailboat.. Sailing the Inside Passage to ALASKA | A&J Sailing

Join us this week as we cast our lines, say goodbye to our home port for good and set sail on our greatest adventure yet! THANK YOU for considering supporting our video creations! ►PATREON ►PAYPAL SUBSCRIBE! ► for a new video every Wednesday If you're into outdoor adventures, tiny homes,...
Budget Boat TRANSFORMED with Upcycled Trash! Stainless Galley REVEAL! | A&J Sailing Galley Refit
Allison & James

Budget Boat TRANSFORMED with Upcycled Trash! Stainless Galley REVEAL! | A&J Sailing Galley Refit

Clever DIY Boat Galley Refit using upcycled materials transforms this 53 year old Sailboat Galley on a budget! Stainless steel countertops for FREE, custom made icebox, upgraded design & storage solutions! After a season living full time on our 30ft sailboat cruising the epic coastline of the P...
This Salvaged Trash Transforms our 43 YEAR OLD Sailboat! Clever DIY Galley Refit | A&J Sailing
Allison & James

This Salvaged Trash Transforms our 43 YEAR OLD Sailboat! Clever DIY Galley Refit | A&J Sailing

Big changes are happening on our 53 year old boat! We'll be living full time on our small sailboat while we cruise the PNW to Alaska, but not before we upgrade something that has been bothering us for a while... Join us on the docks this week as we demolish the interior of our sailboat, rip apa...
Winter Came Early.. Are We Ready? Where’s the Boat?! Life Update | Allison & James Off-Grid Life
Allison & James

Winter Came Early.. Are We Ready? Where’s the Boat?! Life Update | Allison & James Off-Grid Life

WE'RE BACK in our tiny home in the woods after months on the water & have been real busy getting ready for winter BUT it surprised us and showed up early.. yikes! Join us this week as we scramble to tackle last minute winterization here in our tiny home in the woods while simultaneously sha...
Action Packed Sailing Tour of Guadeloupe (+ Friends Come to Visit Us!) | Ep. 67
Navika Sailing

Action Packed Sailing Tour of Guadeloupe (+ Friends Come to Visit Us!) | Ep. 67

Hello! This week we sail from Antigua to Guadeloupe, which is one of the French Caribbean islands. We didn't know much about the island before coming but we found there was so much to do and see here! Before setting off, we install our AcuvaTech UV filter tap which we're so glad we went ...
ALL THAT WENT WRONG During our First Year of Sailing.. Learning by Doing | A&J Sailing S1Ep.14
Allison & James

ALL THAT WENT WRONG During our First Year of Sailing.. Learning by Doing | A&J Sailing S1Ep.14

We left it all behind to live out our dreams of exploring the epic coastal waters of the pacific northwest by sail! We found a no-frills sailboat, spent months fixing it up and taught ourselves how to move around with the wind! Steep learning curve, this sailing business! We learned that anything th...
Sailing.. Going Nowhere Slowly, Sometimes Backwards & Always Sideways⛵️A&J Sailing
Allison & James

Sailing.. Going Nowhere Slowly, Sometimes Backwards & Always Sideways⛵️A&J Sailing

POV our home floats and we use the wind to move around. It's usually sideways and moving very slowly (rarely in the direction of our desired destination) but it's constantly.. MOVING. Life aboard a sailboat is tricky, and it can be hard to find balance, especially at first. Things break (...
Our Boat Broke AGAIN! Does Smooth Sailing Exist? | A&J Sailing
Allison & James

Our Boat Broke AGAIN! Does Smooth Sailing Exist? | A&J Sailing

It's all 'smooth sailing'.. until it isn't... and you have to turn on your engine.. and then your engine explodes.. This is the story of how our engine failed close to shore and what we did to fix it! SUBSCRIBE! ► for a new video every Wednesday WHO WE ARE Hi! We're Al...
Living on a Small Sailboat in Canada’s Cruisers Paradise | Off Grid Boat Life in British Columbia
Allison & James

Living on a Small Sailboat in Canada’s Cruisers Paradise | Off Grid Boat Life in British Columbia

FAR from Fancy - our tiny floating home has no refrigeration, we cook on a camp stove and haul our anchor up by hand⚓️ It's not glam, but boat life has been some of our best days to date. Savoring freshly caught seafood🍤soaking up the spectacular mountain vistas and splashing into the warmest c...
ALONE on Anchor in Desolation Sound.. An Emotional Start to a New Adventure | A&J Sailing
Allison & James

ALONE on Anchor in Desolation Sound.. An Emotional Start to a New Adventure | A&J Sailing

Join us this week as we sail thru the towering peaks & deep waters of Desolation Sound!The Pacific Northwest's most iconic (and most popular) cruising destination 🏔 in the beautiful traditional territories of the Klahoose, Tla'amin and Homalco First Nations. ⛵We sail by ancient pictog...
Steering SNAPPED Near Land! Using Emergency Tiller for First Time | A&J Sailing
Allison & James

Steering SNAPPED Near Land! Using Emergency Tiller for First Time | A&J Sailing

After spending a week in incredible Princess Louisa Inlet, we hauled anchor and sailed back towards civilization in order to reprovision. 48 hours and 75nm miles later we were back in the Straight of Georgia, sailing in 20kn winds and surfing down 6-8ft swells when our STEERING FAILED. Suddenly our...
Sail to Summit: An Unforgettable Journey from Sea to Sky in a Remote Fjord | A&J Sailing
Allison & James

Sail to Summit: An Unforgettable Journey from Sea to Sky in a Remote Fjord | A&J Sailing

Looking down at the sea below, our little sailboat⛵️ is a tiny speck, barely visible from the 2100m mountain from which we stand...We sailed 70 nautical miles into the remote reaches of one of BC's most magnificent coastal fjords - Princess Louisa Inlet (Swiwelát) - gazing at glaciers from the ...
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