Watch Sailing & Boating Adventures Around the World – Page 37 of 300
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 anchored near a forgotten island in the Northern Sporades and discovered an abandoned monastery once inhabited by Byzantine monks… and later, political exiles. What we found inside shocked us — beds still made, shoes untouched...
Here she is! – we bought a sailboat! Meet Flying Freedom ⛵️, our new floating home and the start of our biggest adventure yet. In this video, we’ll give you a full first look and tour of our 40ft Freedom 40/40 sailboat, showing you around every corner before we start the work to get her ready for li...
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...
We sail more than 400 nautical miles across open ocean, leaving the Bahamas behind and heading back to the U.S. coast — destination: Charleston, South Carolina. The weather throws us some surprises, the seas don’t make it easy, and morale is tested. But the crew pulls through — especially Jennifer, ...
Episode 277 | Sailing and exploring Ilhabela. Watching a regatta, chasing waterfalls, scuba diving and more!
💌 I’ve created a newsletter to share the moments the camera missed, the untold stories, behind-the-scenes moments, and little things that don’t make it into the videos. Sign up here: (it...
This week’s episode is a fun one — we officially move into our new rental here in the Bahamas, take a day trip to the (in)famous Nippers Beach Bar with friends, and head out for a relaxed sail with the crew from SV Escapade.
No big drama, just a little slice of what life’s looking like right now — ...
What was meant to be a quiet stop for small waves and simple boat life turned into an unforgettable showdown. When an unexpected intruder slithered aboard—not once, not twice, but three times—we had no choice but to face it head-on.
From surf sessions to one very determined snake, this episode has ...
Living Off-Grid Dawn Hunters Style on sailing catamaran!
📺 THIS IS DAWN HUNTERS SEASON #4 EPISODE 15 ➡️ S4E15
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Welcome back to WE|Sail!
The finish line is finally in sight! After what feels like endless boat projects, we're so close to getting Va back out on the open water where she truly belongs. But just when we thought we'd have to tackle the final stretch alone, something incredible happened.....
Beautiful Jennifer rejoins the crew just in time for one last unforgettable beach day in the Bahamas! We sail up to stunning Spanish Cay, soaking in the final days of sunshine, clear blue water, and tropical vibes before setting our course back to the USA. It's peaceful, a little bittersweet, a...
Hello hello! Sailing adventures resume as my brother joins me in Hawai’i. We set sail from Waikiki Yacht Club into 30+ knot headwinds, bound for the stunning sandbar in Kāne‘ohe Bay, Oʻahu.
What should have been a scenic day sail quickly turned stressful: wind advisories, towing mistakes, and hitti...
Sailing really slows down time and time is not a commodity you have when you are still working in the rat race. But we all found a week where we can go pretend like time doesn't matter to explore what we can. But first we must tackle the to-do list and get some of the stuff done on the boat s...
Episode 432 :
Hello Friends,
On this episode I wake anchored 2.5 miles off shore in remote Borneo after a 435NM passage from Lombok. I have a very wet passage of unforecasted weather to anchor in a peaceful anchorage just inside the mouth of the Kumai River. After a few days rest, I nervously mad...
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We have been on a difficult journey for years now. It is a subject a bit different from our usual sailing adventures, but sharing the highs and the lows is all part of telling our true story. Life at sea isn’t always sm...
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In today’s adventure, we set sail to the stunning, uninhabited island of Nissos Prasso, one of Greece’s most remote and beautiful locations. With no permanent residents, this hidden gem offers pristine beaches, crystal-clear waters...
This week’s video is a raw, unfiltered look at what sailing really looks like when a storm rolls in out of nowhere — and you’re trying to make it to safe harbour with a baby onboard.
It's the kind of moment that reminds us why preparation matters… and also why sailing with a baby adds a whole ...
Sailing Long Island to Port Jefferson, we decided to have a little chat about our new view on sailboat travel.
*Sorry it's been a while since we posted - life happens, responsibilities and all, but we're glad to share this one with you!! Thanks for watching.
Jay and Kenna have been off the grid, not setting foot on land for over a week while sailing through the San Blas Islands. While anchored at Green Island, they took it slow to ride out some intense winds. With no working outboard and a less-than-reliable paddleboard, getting to shore has felt more l...
Sailing solo through the stunning Abacos, I make my way from Great Guana Cay up to Green Turtle Cay in the Bahamas. But along the way, I spot something totally unexpected — a yacht, wrecked and abandoned on the beach with no one in sight.
Curiosity gets the best of me, so I anchor Nauti Dogs nearby...
Episode 276 | Sailing 250 nautical miles north to Ilhabela in rough seas
📡 *Starlink* made a huge difference for us doing our trip. We could check the forecast in real-time, video-call our families, talk to our friends, share our location live with patrons and even stay entertained. If you would li...
What started with confusion over anchoring fees quickly turned into something more familiar — finding our family rhythm in a brand new spot. After dealing with paddling locals, unclear payments, and a bit of drama, we finally settled into daily life: school, work, afternoon surfs, and chats about sc...
Welcome back to WE|Sail...
This sail free week we again dive into boat projects, with the fiberglass barbecue and cooler once again taking the lion share of attention. Also we check in with Erica and her surgery from tearing her achilles tendon. WE are starting to feel the pressure and struggle wi...
With our catamaran safe and secure on the hardstand there's boat work happening every day! This episode we're replacing a critical part of the anchor windlass, upgrading the interior with DIY boat curtains, and getting some things done on our tender, an unusual dinghy which is designed to ...
We complete our loop; Antigua, Sint Maarten, British Virgin Islands, USVI, St Croix, and Guadeloupe.
This trip is always bittersweet, given that it marks our return home to Antigua. We love Antigua, and it’s our home base, but it means the adventure sailing is coming to an end. Soon it’ll be summe...
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The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
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