Watch Sailing & Boating Adventures Around the World – Page 3 of 24

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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From Dreamy Anchorage to Pirate Drama | Sailing Sitka Ep 180
Sailing Sitka

From Dreamy Anchorage to Pirate Drama | Sailing Sitka Ep 180

Jay and Kenna were about a week into a postcard-worthy anchorage—spending their days lounging on the beach, sipping cocktails, surrounded by friends and fellow sailors, soaking up the beauty of the sailing lifestyle. But with all that beauty comes a bit of chaos. The truth is, common sense isn’t so ...
Sailing Into Trouble: The Day Our Anchorage Was a Crime Scene | Sailing Sitka Ep 179
Sailing Sitka

Sailing Into Trouble: The Day Our Anchorage Was a Crime Scene | Sailing Sitka Ep 179

Jay and Kenna lift the hook and set sail from Green Island toward the stunning Holadaze Cayes, one of the most picture-perfect anchorages in all of the San Blas Islands. But just when we thought we’d found paradise, we suddenly found ourselves—and Sitka—in the middle of an active criminal investigat...
NEW Anchorage = NEW Home!!! —– (Day 41/100 Water World Challenge)
Adventureman Dan

NEW Anchorage = NEW Home!!! —– (Day 41/100 Water World Challenge)

Moving my anchor means, moving my home! This is what I LOVE, 1hr of work, and a whole new view! Also, check out these adventures on Nicole's channel: www.youtube.com/@SailingArtha _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help ...
Episode 258 –  We’re Gel Coating Our Boat! And Bear’s gone Coconuts!
Sailing Pickle Family

Episode 258 – We’re Gel Coating Our Boat! And Bear’s gone Coconuts!

After months of bent stainless steel solar arch on the back of our catamaran, we finally get in fixed by a really great company who actually look like they know what they're doing! We have now officially started GelCoating our entire boat, it's a huge job... but we're going to do it! ...
Are We DONE Solo Sailing?  ——–   (Day 36/100 Water World Challenge)
Adventureman Dan

Are We DONE Solo Sailing? ——– (Day 36/100 Water World Challenge)

An important question gets brought up and discussed...... are we done solo sailing? We're both feeling exhausted from what we do each day. These problems are the beginning of new ideas and new adventures! Also, check out these adventures on Nicole's channel: www.youtube.com/@SailingArtha ...
3 Phase Sail Away…………………………………(Days 34 & 35/100 Day Water World Challenge)
Adventureman Dan

3 Phase Sail Away…………………………………(Days 34 & 35/100 Day Water World Challenge)

Goodbye to the South coast of Great Inagua. And hello to the Western most, Man O War bay! Also, checkout these adventure on Nicole's channel: www.youtube.com/@SailingArtha _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support ...
Episode 254 – Boat Yard Dirty Boat Work… At least we have Hot Showers!
Sailing Pickle Family

Episode 254 – Boat Yard Dirty Boat Work… At least we have Hot Showers!

We've finally got back to our beloved catamaran Pickle and we are getting on with lots of boat work, including sanding and grinding! We have some shocking discoveries guys! You won't believe it until you see it, so join us this week guys to see some crazy bodge jobs the Italian boatyard pr...
Episode 253- Shore Time! Final week in the UK exploring Cornwall before returning to our Sail Boat!
Sailing Pickle Family

Episode 253- Shore Time! Final week in the UK exploring Cornwall before returning to our Sail Boat!

Hour Long Movie for you this week guys! We love making these big episodes for you, it's also nice to sometimes share our shore time with you guys and explore some amazing places with you as we go on our final adventure in Cornwall UK before we head back to our catamaran in Spain, its a great tr...
Our Most Beautiful Anchorage Yet 👙💙 You Have to See This! | Ep.145 Sailing SV CUBA
Sailing SV CUBA

Our Most Beautiful Anchorage Yet 👙💙 You Have to See This! | Ep.145 Sailing SV CUBA

In 5 years of Sailing around the World, THIS has to be THE BEST anchorage we ever sailed to. What we found in this anchorage is pretty unique.
What seems to be the problem? (Engine failure diagnostics) raw & extended | Sailing Sitka Ep 171
Sailing Sitka

What seems to be the problem? (Engine failure diagnostics) raw & extended | Sailing Sitka Ep 171

Jay and Kenna sail back to Linton Bay in order to get their engine in top notch after having experienced multiple failures. They spend countless hours over the course of a few days eliminating what could be the culprits while on anchor, but they won't know if they solved it until they put it to...
Episode 250 – Annapolis Sail Boat Show with The Sailing Pickle Family!
Sailing Pickle Family

Episode 250 – Annapolis Sail Boat Show with The Sailing Pickle Family!

We attend the Annapolis Boat Show guys... And it's so much fun!! 🤩 After a bit of a rush to get Pickle lifted out the water in Spain for well needed boat work in a few weeks, we have the usual crazy road trip back to the UK, where we leave Buddy with my eldest daughter Bryony and Fly out to Am...
Episode 249 – Last Sunrise at Anchor Guys before we tackle Major Boat Repairs!
Sailing Pickle Family

Episode 249 – Last Sunrise at Anchor Guys before we tackle Major Boat Repairs!

Hello my most favourite people in all the world! It's my last sunrise at anchor on our gorgeous little catamaran Pickle, then we sail into the lifting dock and get Pickle put on the hard so we can tackle some MAJOR repairs due to a accident and bodged repair done by an Italian boatyard!!! But n...
Light at the End of the Tunnel… Or Was It? | Sailing Sitka Ep 169
Sailing Sitka

Light at the End of the Tunnel… Or Was It? | Sailing Sitka Ep 169

Jay and Kenna finally breathed a sigh of relief after securing a new propeller for their outboard—a mission that took a grueling 9-hour sail to complete. With that crucial task checked off, they took time to regroup in Linton Bay, refueling, stocking up, and tackling laundry and water runs. For a mo...
Offshore Sailboat Prep: Essential Systems & Tips for Long Voyages | Captain German Exploring
Captain German Exploring

Offshore Sailboat Prep: Essential Systems & Tips for Long Voyages | Captain German Exploring

Planning a long-distance offshore passage on your sailboat? 👉 Want to join our adventures? Subscribe now: In this detailed guide, Captain German Exploring shares his essential tips and real-life experience on how to properly prepare a sailboat for offshore sailing. Discover crucial insights on wha...
Episode 248 – Sailing Life… We’re just Winging it! Storms in Southern Spain!
Sailing Pickle Family

Episode 248 – Sailing Life… We’re just Winging it! Storms in Southern Spain!

As you may know we have some standing rigging issues and our Genoa was damaged in a storm along with breaking our furling system track so we are still sailing under reduced sails, but it's ok we are dodging storms, taking refuge when necessary and exploring the quaint little places along the so...
S1E7 Stuck in Ohio .
Sailing UV ( UltraViolet )

S1E7 Stuck in Ohio .

Still " stuck in ohio " . in this weeks episode we pick up right where we left off last week . building stuff , cleaning up around the property , and adding finishing touches to the van . The snow comes and locks us down . hope you enjoy the video . ...
Episode 247 – Accident while Sailing in a Storm in Formentera, Ibiza!
Sailing Pickle Family

Episode 247 – Accident while Sailing in a Storm in Formentera, Ibiza!

We Sail happily from Mallorca to Formentera, a little island just off the coast of Ibiza, we explore ashore and snorkel in a beautiful anchorage full of wonderfull sea life, until we are taken unawares in the early hours of the morning, when a unpredicted storm hits and we find ourselves being pushe...
Episode 246 – Caught Out in a Unpredicted Storm at Sea!
Sailing Pickle Family

Episode 246 – Caught Out in a Unpredicted Storm at Sea!

Sailing from Sardinia, Italy to the Balearic, Spain we are caught in a unpredicted storm which blows up to nearly 50 knots so quickly and as we try and reef our sails the furling line for our Genoa (headsail) snaps and the full 140% headsail bellows out and sets our boat onto a cause we did not plan...
Episode 245 – Hundreds of Miles from Land in all Directions!
Sailing Pickle Family

Episode 245 – Hundreds of Miles from Land in all Directions!

The experience of Sailing in the middle of nowhere is wonderful, free from land and all its stresses, free from mobile signals and social media, what a fantastic experience! Come along this week guys as we take you from beautiful Sardinia, Italy towards Balearics, Spain. We do some very light wind s...
Trouble in Paradise… | Sailing Sitka Ep 165
Sailing Sitka

Trouble in Paradise… | Sailing Sitka Ep 165

Jay and Kenna, along with their friends from Canada and the crew from @SailingSVBully sail their sailboat from Holandes Caye to Salaradup in the San Blas Islands. While enjoying everything that paradise has to offer, they run into some weather that makes for a chaotic situation. Thanks for watching ...
Episode 244 – Naked Boat Maintenance and we go Climbing in Sardinia!
Sailing Pickle Family

Episode 244 – Naked Boat Maintenance and we go Climbing in Sardinia!

Great few days sailing the east and north coast of Sardinia, with a few water intake problems on our engine along the way. We arrive at the most fabulous anchorage in all the Mediterranean, and whilst waiting for a weather window to sail to the Balearics, we get to hang out in tranquility and explor...
Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164
Sailing Sitka

Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164

In this episode, Jay and Kenna welcome aboard their friends from Canada and give them the full tropical, sailing experience by island hopping and cruising through the San Blas islands. We are sailing off-grid between sand spit islands in search for adventure, wind and good times. Check it out and su...
Episode 243 – Sailing Corsica to Sardinia and finding some Awesome Caves!
Sailing Pickle Family

Episode 243 – Sailing Corsica to Sardinia and finding some Awesome Caves!

We find some awesome caves and one has this amazing open top like a giant sink hole! The dog and kids play freely in this beautiful isolated tranquility, then we have some cool sails from Corsica to Sardinia and work our way back to a favourite anchorage to swim with dolphins again! Come and join us...
Episode 242 – Extended Ep – Part 2 of Kids in Change of the Sail Boat! Plus underwater adventures!
Sailing Pickle Family

Episode 242 – Extended Ep – Part 2 of Kids in Change of the Sail Boat! Plus underwater adventures!

Epic episode this week guys, we had so much fun making this for you! Firstly it's the second part of the kids in charge! They sail us along the east coast of Corsica and we moor up at the beautiful town of Bonifacio, this historic town boasts dramatic cliffs, beautiful medieval streets, and pan...
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