Watch Sailing & Boating Adventures Around the World – Page 10 of 30
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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Sailing North: Navigating New Waters to an ICONIC Island – Ep 241
Sail with us from through New England as we leave Martha’s Vineyard behind and head for the fog-shrouded shores of Nantucket aboard our rugged aluminum sailboat. Navigating in dense fog and unfamiliar waters, we arrive in one of the most iconic destinations of a New England summer, Nantucket Island....
Package Delays & Island Days | USVI Boat Life
After our 7-day passage to the USVI, we find ourselves in island time — waiting on delayed packages before we can continue our journey south to Saint Martin for hurricane season. While we wait, it’s a week of boat projects and island adventures! We spend time troubleshooting a radar that won’t acti...
This Was NOT Part of the Plan…INJURED while Anchoring | VLOG 286
👇 Drop a comment: This week we're cruising down the ICW with Oakley and Jackson onboard, weaving through narrow channels and shifting sandbanks. Just when we thought we were in the clear, storms rolled in—and to top it off, I managed to injure myself while anchoring. Classic. ⛵️ KEEP UP WITH...
BUILDING MORE USABLE LIVING SPACE on our SAILBOAT before Sailing to the Arctic! – Ep 238
Join us as we tackle one of our biggest DIY boat projects yet: sewing and installing a full canvas enclosure on our custom aluminum sailboat! In this episode, we walk you through the entire process — from choosing the right marine-grade materials to patterning, sewing, and installing our cockpit enc...
Our First Sail on our NEW Vision 444 Catamaran – Finally!
After weeks of stress and setbacks at Harbour Towne Marina, the moment we've been waiting for is finally here—we're pulling the dock lines and setting sail for the very first time aboard our brand new 2023 Vision 444 catamaran! Our destination: Xquisite Marina in Freeport, where the rest ...
Finally Sailing Again! Night Passage from St Martin to Guadeloupe
As the Caribbean hurricane season approaches it's time to start heading south! The episode begins with a surprise storm slamming the St Martin anchorage; high winds, rough seas, dragging boats - not good for someone who went out the night before! 😳 It's a quick insight into how unexpecte...
Beach BBQ & Engine Service – Living With The Tide
In this episode of Living with the Tide, we dive into some essential boat work —servicing our trusty Beta Marine engine, replacing our tired fridge, and tackling a much-needed repair on our heads (yes... the toilet drama continues!). To top it all off, we take a trip over to beautiful Mount Edgecum...
From Sailing Dreams to Surgery: Our Biggest Challenge Yet | Episode 303
Welcome back to WE|Sail... Life threw us a curveball that we weren't expecting. In this episode, we're sharing the real, unfiltered story of how we're navigating this challenge - from the initial diagnosis to the decision to have surgery at Steamboat Orthopedics. While I'm de...
Another Bad Week In The Shipyard
This week hit hard. After being told the marina would cover the damage they caused during our haul out—damaging our sail drive and prop—we got a call no boat owner wants: the general manager overruled the previous decision. Now, we're left with the full bill. Another crushing blow in what’s fel...
UNEXPECTED DISASTER: Torn Achilles Leaves Our Sailing Plans in Jeopardy | Episode 302
Welcome back to WE|Sail... Our sailing life just took an unexpected turn that NO ONE saw coming! After months of non-stop travel through New Zealand and hosting back-to-back charter weeks in the Caribbean, we were finally returning to VA for some much-needed boat projects. But then disaster struck ...
Shipyard Setbacks & Small Wins | One Step Closer to Sailing Again
We’ve made it through another challenging week in the shipyard — and let’s just say, it hasn’t been smooth sailing. Between two hit-and-runs, a broken sail drive, and a pile of unexpected invoices, it’s felt like for every few steps forward, we take one back. 😅 But finally... we’re seeing a light a...
Solo Sailing After 6 Months Land Locked – First Voyage Back!
Support on Patreon: After 6.5 months locked down in Oreoi, Greece, I finally set sail again — solo. This episode follows the nerves, the boat prep (rigging, anchor, propeller issues), the tough upwind beating to Skiathos, and the mindset lessons of overcoming challenges at sea. Watch as I shake off...
Back to Boat Life; The Transition from Wheels to Waves | Episode 301
Welcome back to WE|Sail.... where we start sailing again!!!! This week we transition back to the boatlife. Our time has come to an end with the Vanlife tour around New Zealand and it's time for us to get to work on Va, but first we have to switch gears again and get ready for our patreon Saili...
Accident After Accident — Our Toughest Week Yet!
It’s been an incredibly challenging and frustrating week for the crew of Big Lost. After all the excitement and anticipation of finally closing on our brand-new Vision 444 ES, we were ready to set sail on the adventure of a lifetime. But instead, we’ve been hit with one unfortunate event after anoth...
Time’s Ticking – One Week to Go #sailing #japan #bluezone
Only one week left to pre-order A Journey Beyond the Blue Zone — my 10th and most personal book yet. From the deck of my sailboat in Japan’s Blue Zone to cherry blossom-covered castles in the mountains, I’ve spent the past year chasing the secrets of healthy aging. This book weaves together stories...
The ONE Question That Changes Everything About Buying a Boat
Want a signed copy of my book? Limited time: Buying your first sailboat? There’s ONE question you must ask before you spend a dime—or you’ll end up with a floating disaster that doesn’t match your life at all. In this video, I break down the six real-world sailing archetypes—and exactly what kin...
Better off Naked?! Rash ending to final days of Boat Life in Paradise – Ep 236
Get an exclusive 15% discount on Saily data plans! Use code JIBSEA at checkout. Download Saily app or go to Sailing the British Virgin Islands as our last stop in the Caribbean before we set sail for the high latitudes for our next big adventure on our new to us custom aluminum sailboat. In this ...
Pit Stop in Malta – Sailing Helios Season 3 Episode 3
After two seasons of Mediterranean cruising, we’ve come to know Malta well. This visit feels more like a pit stop than a sightseeing adventure, as we gather supplies, collect parcels, and prepare for the next leg of our journey. But even a functional stop in Malta has its perks – our timing couldn’t...
A Peaceful Eveing in a Remote Bay #japan #sailing #boatlife
A peaceful evening in Buren Bay aboard Wahine. After a shower and supper, I take a quiet 360° look around the anchorage—glassy water, Mitsu’s boat, a generous loaned tender, and my inflatable paddleboard. Sometimes, it’s these calm, ordinary moments that remind us why the journey matters. Sleep well...
This Scared Me More Than Sailing | Nevis Bungy Jump | Episode 300
🎉 EPISODE 300 CELEBRATION! 🎉 Welcome back to WE|SAIL and our 300th EPISODE!!!! It's a little surreal that we have been adventuring and sailing for almost 7 years now and sharing with you the adventures in 300 episodes. To mark this incredible milestone, we're jumping off of New Zealand�...
Meet Conor | Sailing Big Lost Captain
From the snowy mountains of Idaho to the turquoise waters of the Caribbean, Conor’s life has always been about chasing adventure. Dirt bikes, skiing, waterskiing, hunting, and sailing — his childhood was packed with energy, freedom, and a growing love for the outdoors. In this video, Conor shares h...
The ULTIMATE New Zealand View | Mt. Cook to Milford Sound | Episode 299
Welcome back to WE|Sail! Join us for a jaw-dropping adventure in New Zealand's Southern Alps! In this episode, we tackle the stunning Hooker Valley Track at Mt. Cook, then surprise helicopter rides take our adventure to new heights - literally! From breathtaking glacier views to an unexpected ...
Selling Our Sailboat: Goodbye Banana Pancakes
We set sail from Martinique to the breathtaking Grenadine Islands, passing the iconic Pitons of St. Lucia with a rainbow over the island—talk about a postcard moment! After anchoring next to our friends on Twin Flame in Union Island, the adventures kicked off: hiking, sailing lessons, dolphins, work...