Watch Sailing & Boating Adventures Around the World tagged “Sailing vlog” – Page 9 of 265
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Fast Sailing to Poros & Finding a Private Paradise in Greece!
On our next-to-last day sailing in Greece with Sailing Miss Lone Star, we had some of the best moments of the trip! 🌊⛵ We pushed the boat hard in brisk winds on the way to the beautiful Greek town of Poros, flying across the water under sail. The fol...
ONLY in SOUTH AFRICA would this be a PROBLEM! | Simon’s Town… Ep 415
Use the codeword: sailingnandji at the checkout, put the blades in your cart and get 100 for free! 👉https://hensonshaving.com/sailingnandji After months of calling the breathtaking town of Knysna home, we finally exited through the legendary and notori...
Sailing to Andros: Ancient Bridges, Caves, and Crystal Seas | Greece
Try Captain's Salve — handcrafted skin balm for the wild life: https://captainssalve.com Sailing to Andros, Greece, we expected wild winds — but instead we motored across glassy seas through one of the windiest passages in the Aegean. Along the way, we...
Sailing Liberty- I am Sailing Away in Florida Keys on Beneteau 50
https://gofund.me/978c8696 Help Helen to get refurbished editing computer to get the shows coming faster. Sailing Liberty Wish List: https://www.amazon.com/hz/wishlist/ls/20TZMXKIDADA2/ref=nav_wishlist_lists_1 SUPPORT US ON PAYPAL: SailingLibertyProject@...
Toga Party in Greece! Sailing, BBQ, and Plate Breaking
Join us for a short but beautiful downwind sail from Aegina to Agistri, where things get interesting as I attempt a creative (and slightly unusual) mooring. After some relaxing beach time, we head to the Jamaica Yacht Club for an unforgettable Greek BBQ an...
Live from Langkawi, Malaysia – August 2025 – Realtime Update about Future, Past and Refit
This live stream followed the premiere of this video: https://youtu.be/KsrkoRLuL5c - I will be doing a live stream following the premiere of my latest long format sailing film; “Quiet Sailing, Life At Sea” that covers my two and a half day sail from...
ANTI CLICKBAIT? Quietly Sailing to the South China Sea Alone On A 30ft Boat, No Troubles Just Peace
Episode 436 : A Peaceful 2.5 day sail 235NM / 53 hours of sailing and only 2 hours of motoring. Hello Friends, On this episode we hauled up and said farewell to Borneo and pointed our bow West for the island of Belitung. After I finished editing this fi...
LIVE UPDATE: Hurricane Season In The Bahamas | Sailing Sunday Vlog 295
👇 Drop a comment and let us know what you think! Hurricane season is here in The Bahamas and this week we found ourselves right in the middle of it as hurricane Erin passed right by us in the Abacos. 🌪️⚓ While most people dream of crystal-clear ...
Paradise Isn’t Always Gentle | S4 E27
From a moody outboard to unexpected wipeouts, life at sea doesn’t always run smoothly. In this episode, we discover a pristine spot that quickly became one of our favourites — with epic waves, underwater surprises, and a black eye that proved paradise ...
Our last sail | Sailing Sitka Ep 182
After two unforgettable months in paradise, Jay and Kenna lift anchor and set sail on a short 9-hour passage from Chicheme to Linton on Panama’s mainland. Along the way, they take in every last moment of beauty that this sailing lifestyle has to offer. B...
We Sailed into a Town That was Built to Flood — Sailing Yabá 280
Episode 280 | Sailing to the magical town of Paraty, a place frozen in time where every sailor dreams of visiting. ⛵ *Hop aboard & follow our journey* → SUBSCRIBE https://bit.ly/3dI3hBn 💙 *Support the adventure:* 📖 *Grab our book* → https...
Greek Island Adventure Ends in Trash Avalanche!
We continue our Greek island adventure with Sailing Miss Lone Star as we sail from Vathy to Aegina. Along the way we stumble across something unusual on the cliffsides… but the day finishes in true Mediterranean style — with a dip in crystal-clear wate...
Boat tour – A Surfers Dream Catamaran
Living Off-Grid Dawn Hunters Style on sailing catamaran! 📺 THIS IS DAWN HUNTERS SEASON #4 EPISODE 15 ➡️ S4E15 ⛵WANT TO KEEP VIDEOS COMING? SUPPORT OUR PRODUCTION HERE: If you’d like to help with this production please consider supporting us ...
Ep 178 Some Of What We Do To Put The Boat Away | Kevin & Wendy
Picture this; Waking up at dawn to find the marina about as quiet as it ever gets. Water barely rippling and no wind at all. Dew on the decks and sun brightening the eastern horizon. Then fixing some coffee and taking sips between setting up fenders and tr...
Clothing Optional Sailing in Greece! | 25+ Knot Winds on a Lagoon 38
We’re back sailing in Greece with Miss Lone Star aboard a Lagoon 38 catamaran! 🌊⛵️ With the wind blowing over 20 knots, we reefed down twice and still flew along at 8 knots on our way from Aegina to one of my favorite harbors in the Saronic Island...
Is this Hidden Gem of a Greek Island My Favorite? | Skyros
🔥 Support the journey and get the salve I use daily in the sun, sea, and wind: https://captainssalve.com We set off to explore one of the most underrated Greek islands — Skyros. What started as a peaceful scooter ride quickly turned into a breakdown s...
Fiji or Bust: The Most BRUTAL Ocean Crossing EVER!!!! | Episode 310
Welcome back to WE|Sail! This was supposed to be another beautiful Pacific crossing to Fiji. Instead, it became the most terrifying, difficult passage of my sailing career. Without Erica by my side for the first time in 7 years, I had to captain VA and ou...
YOUTUBE LIVE : REALTIME UPDATE FROM LANGKAWI MALAYSIA Following Video Premiere ⛵️📹
I will be doing a live stream following the premiere of my latest long format sailing film; “Quiet Sailing, Life At Sea” that covers my two and a half day sail from Borneo to the island of Belitung. I will be on the live chat during the premiere. Onc...
Getting Food & Water in Remote Borneo, Battling the Engine and Trying to Repair the Broken Autopilot
Episode 435 : Hello Friends, On this episode I stock up on Food, Water and Fuel in the town of Kumai in Borneo and battled the engine to get it started. I then head down river to wait for a weather window to sail to Belitung. While I am waiting I get ...
Botched Cutlass Bearing & Prop Shaft Install and Here’s How We Fixed It – Ep 247
Join us as we continue with the replacement of our prop shaft and cutlass bearing on our custom aluminum sailboat while hauled out in Conception Bay South, Newfoundland. Rather than a how-to DIY, we show you what not to do and the challenges we faced and h...
Baby on Board! Sailing from Athens to Aegina with Miss Lone Star
We’re in Greece! 🇬🇷 In this episode, I fly into Athens to meet up with fellow YouTuber Sailing Miss Lone Star! @SailingMissLoneStar our very first collaboration. We chartered a beautiful catamaran and set sail on our maiden voyage together. Joinin...
The End of an Incredible Chapter | Sailing Sitka Ep 181
And just like that, Kenna and Jay reach their final stop in the San Blas, savoring every last drop of paradise. Between lazy island days and exploring a beachside shipwreck on a neighboring isle, they make the most of their tropical farewell. With the seas...
Exploring the ONLY Tropical Fjord in the World… by Sailboat — Sailing Yabá 279
Episode 279 | Sailing to the only tropical fjord in the world: Saco do Mamanguá. But we not only sail there. We went from climbing mountain tops to exploring the mangroves and finding the calmest anchorages. It's safe to say it's been our favorite place s...
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