Watch Sailing & Boating Adventures Around the World – Page 4 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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“50 years of history GONE in a second…” | Sailing Sitka Ep 162
Sailing Sitka

“50 years of history GONE in a second…” | Sailing Sitka Ep 162

Jay and Kenna are in Shelter Bay Marina, fixing some minor and major problems they've encountered while transiting the Panama Canal, on top of that they do some routine and periodic maintenance to make sure their 50 year old sailboat is ready to sail her way toward the desolate and world-renown...
Why We Anchored In The Rolliest Anchorage Yet [Ep. 179]
Sailing Sweet Ruca

Why We Anchored In The Rolliest Anchorage Yet [Ep. 179]

In this episode, we anchor in the rolliest anchorage we’ve encountered yet. With unpredictable conditions and tricky navigation, will our decision pay off? Join us as we face the challenges of the North Pacific and adapt on the fly! Plus, an impromptu man overboard drill keeps us on our toes. #sail...
Episode 241- Exciting week SAILING WITH THE KIDS IN CHARGE! part 1
Sailing Pickle Family

Episode 241- Exciting week SAILING WITH THE KIDS IN CHARGE! part 1

So much fun this week guys, we leave the kids in charge! They've done lots of research and planning and now they get to put it all into action and sail us towards our destination! Which was a great opportunity for the weather to teach them some valuable lessons, with big winds unpredicted from ...
Episode 240 – Sailing the World with a Wakeboarding Champion! 🤪
Sailing Pickle Family

Episode 240 – Sailing the World with a Wakeboarding Champion! 🤪

This week is so frustrating.... AND exciting!!! After crummy chores and trekking miles running errands we finally get to have some fun Wakeboarding! Oh my gosh was it frustrating!!! We were sooo bad, I started obsessing, until...... We got to try again, and wow was it a different story!! It's a...
Episode 239 – Will I lose my bikini being pulled behind the boat? Sailing from Sardinia to Corsica!
Sailing Pickle Family

Episode 239 – Will I lose my bikini being pulled behind the boat? Sailing from Sardinia to Corsica!

Great Sails this week guys from Sardinia to Corsica, and along the beautiful Corsican coast too, where we have loads of fun being pulled behind the boat whilst sailing! 😃 We visit some very beautiful locations and have fun playing in the huge sand dunes on this fabulous soft white sandy beach. Than...
Episode 238 – Nudist while Sailing Sardinia!
Sailing Pickle Family

Episode 238 – Nudist while Sailing Sardinia!

After an extremely fun sail tacking up the channel with a zillion other boats we finally drop anchor in a fabulous spot with a huge group of nudists. But that doesn't stop us having a fantastic time celebrating Bears birthday! Thank you to our wonderful patrons, you are really helping to mak...
Episode 237 – Swimming with Dolphins and Exploring the UnderWater World!
Sailing Pickle Family

Episode 237 – Swimming with Dolphins and Exploring the UnderWater World!

What an amazing experience! We swim with dolphins guys!! These dolphins turn up everyday, several times a day in this particular anchorages, so we took a chance dived in and the experience was fantastic! They were so friendly, so inquisitive and extremely beautiful, graceful creatures! We spent a lo...
Episode 236 – Boat Life – Busy Day Aboard Pickle!
Sailing Pickle Family

Episode 236 – Boat Life – Busy Day Aboard Pickle!

Come and join us exploring guys, it's just another day living life on a sail boat! We do everything from provisioning, exploring new cities, docking in new marinas and town walls, swimming with dolphins in isolated anchorages and watching awesome sunsets with sun downers... can Boat life get an...
Episode 235 – Nicky and the Kids Leave Chris alone Aboard Pickle! Boat Life
Sailing Pickle Family

Episode 235 – Nicky and the Kids Leave Chris alone Aboard Pickle! Boat Life

Nicky and the kids leave Chris and Buddy on a mooring buoy in Sardinia and fly back to the UK for some medical appointments, flying back with more crew for Pickle, as Ben, Beaus boyfriend joins us for the summer! Within a day of being back onboard we are out exploring again, and enjoying the beautif...
Episode 234 – Skinny Dipping Off Our Sail Boat!
Sailing Pickle Family

Episode 234 – Skinny Dipping Off Our Sail Boat!

Easy episode this week guys, We swim with dolphins and play a little game of pass the seaweed before a lovely sail to another beautiful anchorage, where we go and explore with the dog and finish our day off with a amazing nighttime swim... butt naked of course! 😃 Thank you to our wonderful patron...
Getting tattooed on a classic sailboat in Costa Rica | Sailing Sitka Ep 154
Sailing Sitka

Getting tattooed on a classic sailboat in Costa Rica | Sailing Sitka Ep 154

Jay and Kenna have sailed their 41 foot sailboat from Canada to Costa Rica of the period of 2 years. Such an adventure does not come without obstacles including trial and errors. During their travels in Central America, they also met a fellow offshore sailor who happened to be a tattoo artist and on...
Episode 233 – Naked Sailors!
Sailing Pickle Family

Episode 233 – Naked Sailors!

Naked Sailor this week guys! Anyone else out there cook naked? we have lots of fun this week, free diving, hiking, sailing, exploring and hanging out on our beloved Pickle... Welcome aboard! Thank you to our wonderful patrons, you are really helping to make all this possible! Don't forget to p...
Episode 232 – The Italian Boatyard Wrecked Our Boat!!!!!
Sailing Pickle Family

Episode 232 – The Italian Boatyard Wrecked Our Boat!!!!!

This week guys we will show you all the damage the Italian Boat Yard in Crotone did to our beloved Pickle! It's shocking, these guys are major scammers and bodge artists!!! And we are left thousands out of pocket and with major works to now fix! Pickle is literally worse than when we took her i...
Separate Boats, One Love: Tips from a Woman Sailor #lovers #buddyboats #sailing #endlesstravel
Japan Solo

Separate Boats, One Love: Tips from a Woman Sailor #lovers #buddyboats #sailing #endlesstravel

"Don`t have a man on board unless he is your lover, your father or your brother" is just one of the tips Evelyne gives based on 40 years at sea as an endless traveler" Meet Evelynne Revallier, a lifelong voyager who set sail from France 40 years ago and never looked back. She’s esta...
Episode 231 – We’re Running Out of Water on our Sail Boat and have a Wild Beast Onboard!
Sailing Pickle Family

Episode 231 – We’re Running Out of Water on our Sail Boat and have a Wild Beast Onboard!

This week guys we are on the search for water, which isn't always easy to get whilst sailing the world! Some countries are easier than others, but this week we sail to a couple of different marinas in search of water and finally get some at a big fuel dock with a bit of fuel. All the while we g...
Episode 230 – Streaking Around Naked on my Sail Boat!
Sailing Pickle Family

Episode 230 – Streaking Around Naked on my Sail Boat!

I Love Sardinia! We are having so much fun guys!!!! So many beautiful anchorages to check out, so many white beaches to hang out on, and so many turquoise waters to swim in! AND its so hot and so chill who needs any cloths... Not ME! 😅 Thank you to our wonderful patrons, you are really helping to...
Episode 229 – Boat-Life! Sailing Adventures in Sardinia, Deserted Beaches and Isolated Anchorages!
Sailing Pickle Family

Episode 229 – Boat-Life! Sailing Adventures in Sardinia, Deserted Beaches and Isolated Anchorages!

Chris is back and we are heading out to explore some of these fantastic anchorages in Sardinia! We check out beautiful white sandy beaches, isolated coves and have calm lovely sails between these fab bays. Come and join us for this week's fun and adventures! Thank you to our wonderful patrons,...
Episode 228 – Final Week Sailing the World Alone with My Kids!
Sailing Pickle Family

Episode 228 – Final Week Sailing the World Alone with My Kids!

Epic sails to beautiful locations, enjoying sailing solo for our last week of freedom before Chris flys back into Sardinia after his successful hernia operation and joins us again for more fun and giggles 🙌 We experience lots of weird and wonderful weather this week, with the thickest fog I've...
Getting our boat ready for our next offshore passage in Costa Rica! Sailing Sitka Ep 148
Sailing Sitka

Getting our boat ready for our next offshore passage in Costa Rica! Sailing Sitka Ep 148

On this episode of Sailing Sitka, we get our Cheoylee sailboat offshore ready by provisioning fr food, water, fuel and some extra fixings by making do with what we got. This is the reality of cruising sometimes and making sure your boat is ready to hit the high seas. Subscribe to join the journey an...
Episode 227 – Chris left! I’m Sailing Solo with the kids!
Sailing Pickle Family

Episode 227 – Chris left! I’m Sailing Solo with the kids!

Its all about the sailing this week guys! Sailing, sailing and more sailing, I am a Sailing Solo Mumma this week with the kiddos, they are actually getting to learn to set sails, lift anchor, navigate and do all the fun jobs with me as I sail us up the Sardinian east coast towards Olbia. It is sooo ...
Episode 226 – Chris is Leaving the Sailing Pickle Family!
Sailing Pickle Family

Episode 226 – Chris is Leaving the Sailing Pickle Family!

This week guys, in this fabulous Sardinian anchorage, Chris and Beau go on a very long hike to find some data. We do some cool little sails to new anchorages checking out these amazing turquoise waters, Chris LEAVES the Pickle family!!!! And I finally get my Man badge for killing a fish... very begr...
I Love a Great Hookup Ep156
Sailing Intermission

I Love a Great Hookup Ep156

Leaving paradise and heading north for winter. It seems a little backwards. We've been in the Florida Keys for quite some time and needed a change. Before leaving we checked out systems, safety gear, and more. Smooth sailing north and decided to stop at Ft. Lauderdale for some additional fuel...
SDA165 Beach Day and the Ray
Sailing Dark Angel

SDA165 Beach Day and the Ray

In this episode of Sailing Dark Angel we hit the beach at Shroud Cay before saying a reluctant good-bye. A short trip to Norman's Cay is made longer by needing to go around the shallows, but a flock of feeding birds entertains us along the way. We anchor outside of Norman's Cay for the fir...
Episode 225 – 3 Day Sail Vulcano to Sardinia! Encounters with Whales and we catch Tuna & Mahi Mahi!
Sailing Pickle Family

Episode 225 – 3 Day Sail Vulcano to Sardinia! Encounters with Whales and we catch Tuna & Mahi Mahi!

Super sail from Vulcano stopping off at another little island for fuel then carrying on for three days to Stunning Sardinia! We see dolphins, Whales, catch Tuna and Mahi Mahi!! Then reach the beautiful deserted anchorage and explore our new surroundings! With amazing turquoise waters and sandy beach...
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