Watch Sailing & Boating Adventures Around the World – Page 5 of 51

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 the Mediterranean: Wild Weather after Cape Malea on a Family Catamaran
Sailing Bluefish

Sailing the Mediterranean: Wild Weather after Cape Malea on a Family Catamaran

Rounding Cape Malea in Greece then up to Monemvasia the weather changed fast. 45+ knots, waterspouts, and one of the wildest days we’ve had aboard our Lagoon 42. Full episode on Sailing Bluefish. #sailing #sailinggreece #catamaran #lagoon42 #sailingfamily #mediterraneansailing #boatlife
Sailing from Bermuda to New Hampshire. 822 miles offshore!
Sail Stillwater

Sailing from Bermuda to New Hampshire. 822 miles offshore!

What’s it really like to crew on an offshore sailing passage across the North Atlantic? Join Brian aboard Sailing Vessel Kleos as he sails 822 miles from Bermuda to New Hampshire on a 5-day offshore passage. From standing watch in the middle of the night to cooking meals underway, this video gives ...
We Didn’t Expect St John to Be THIS Beautiful E383
Wildly Intrepid Sailing

We Didn’t Expect St John to Be THIS Beautiful E383

This week aboard SV Wildly Intrepid we continue exploring the stunning island of Saint John! We sail from beautiful Waterlemon Bay to the world famous Trunk Bay with its crystal clear turquoise water and perfect white sand beach. A tropical rain shower clears the crowds and leaves us almost alone i...
The Best Affordable Sailboats Nobody Talks About (With Kyle Jachney) | Sailing Truth Show
Sailing Zingaro

The Best Affordable Sailboats Nobody Talks About (With Kyle Jachney) | Sailing Truth Show

Everyone chasing the cruising dream gets pointed at the same handful of "name" boats — and most of them are priced out of reach for a first-timer. So today Kyle Jachney and I are talking about the ones nobody puts on a list: the older, affordable fiberglass cruisers from the 70s and 80s th...
This One-of-One Wooden Yacht Costs Just $95K | FULL TOUR
BoatFools Sailing

This One-of-One Wooden Yacht Costs Just $95K | FULL TOUR

#boatfoolssailing #sailing #woodenboat #liveaboard #bluewatersailing #sailboattour This One-of-One Wooden Yacht Costs Just $95K | FULL TOUR This 49' Modern Wooden Cutter Left Us Speechless... Welcome back BoatFools Nation! Today Canadian Ken and I step aboard something truly extraordinary —...
S1E49. I FOUND the Source of the NASTY Boat Smell… 🤢 | DIY Shower Sump Install
Sailing UV ( UltraViolet )

S1E49. I FOUND the Source of the NASTY Boat Smell… 🤢 | DIY Shower Sump Install

🚨 THE BOAT FINALLY DOESN’T SMELL LIKE A SWAMP… 🚨 This week aboard Sailing UV, we tackle one of the nastiest problems we’ve had living on the boat… the shower draining straight into the bilge. 🤢 Turns out, shower water + bilge funk = absolutely disgusting. So in this episode, we rip into the boat ...
LAND at Last – Arriving in COLOMBIA After a WILD Passage | Day 15
Leading the Escapade

LAND at Last – Arriving in COLOMBIA After a WILD Passage | Day 15

The final stretch to Colombia… and after everything this passage threw at us, the wind completely disappears. After battling storms, big seas, a shredded headsail, and days offshore, we spend the entire night drifting slowly toward Cartagena at just 2–3 knots. If we’d had enough fuel, we could have...
Wet, Exhausted & Hanging On – 50 Knot Caribbean Storm | Day 13 & 14
Leading the Escapade

Wet, Exhausted & Hanging On – 50 Knot Caribbean Storm | Day 13 & 14

Day 13 & 14 of our offshore passage from the USA to Colombia… After days at sea, the weather forecast suddenly shifts for the worse. What was meant to be manageable conditions turns into a long-lasting storm stretching across the entire Caribbean Sea — leaving us with nowhere to run and no way...
The Raw Reality of Offshore Sailing – Torn Sail, No Fuel & Wild Weather | Day 12
Leading the Escapade

The Raw Reality of Offshore Sailing – Torn Sail, No Fuel & Wild Weather | Day 12

Day 12 of our sail from the USA to South America… and this is where the crossing starts to get rough. After finally reaching stronger winds out in the Caribbean Sea, the conditions quickly deteriorate and our headsail completely shreds offshore. With over 30 knots of wind, building swell, and no fu...
Crossing the Pacific Changed Our Family
Sailing Big Lost

Crossing the Pacific Changed Our Family

After months of preparation and 24 days at sea since leaving Panama, we finally crossed the Pacific Ocean and arrived in Nuku Hiva in the Marquesas Islands of French Polynesia. This crossing pushed our family physically and mentally in ways difficult to explain. Interrupted sleep, endless sail chang...
The Last Glimpse of Land Before South America | Day 11
Leading the Escapade

The Last Glimpse of Land Before South America | Day 11

Day 11 of our sail from the USA to South America… and today feels like a real turning point. The last glimpse of land disappears behind us as we head further offshore with nothing but ocean ahead. After barely any wind and carefully watching our fuel levels, we finally start to feel the conditions ...
This sailing technique saved my butt (Why does nobody teach this?)
Sailing Zingaro

This sailing technique saved my butt (Why does nobody teach this?)

1,800 miles from the nearest road, my autopilot exploded into pieces on my lap. Three and a half days into an 18-day crossing from Ecuador to Easter Island, on a light catamaran with small rudders and no displacement, the wheel pilot's ring snapped, the belt cut itself in four places, and the b...
I was Fine…till I Wasn’t!! Tough times Sailing the Caribbean
The Cruising Kiwis

I was Fine…till I Wasn’t!! Tough times Sailing the Caribbean

I Was Fine... Till I Wasn't - Sailing the Caribbean Welcome back aboard for another Caribbean sailing adventure. This week our patrons our patrons Greg and Gideon experience their very first offshore sailing passage, on our live aboard catamaran, departing Saint Martin for Saint Barts. Its a...
We Found the PRETTIEST Island in the Caribbean E382
Wildly Intrepid Sailing

We Found the PRETTIEST Island in the Caribbean E382

This week aboard SV Wildly Intrepid we explore what might be the most beautiful island we’ve visited all season… 🌴🇻🇮 Sailing the US Virgin Islands with our buddy boat, we explore St John Island and hike the incredible trail from Francis Bay while discovering the crystal clear waters of Francis Bay ...
The Best kind of Fixes on a Boat! –  Sailing the Scottish Highlands – Ep 272
Sailing Jibsea

The Best kind of Fixes on a Boat! – Sailing the Scottish Highlands – Ep 272

Join us as we continue sailing through Scotland as we make our way north to Norway for the cruising season. We explain how we fixed our marine electronics and how we tackled more equipment failure while cruising and exploring Oban, Plockton and the Scottish Highlands NEW VIDEOS EVERY SUNDAY! Pleas...
WE FINALLY BACK on our 450 Lagoon … After 5 Months Away From Sailing We’re Back Ready To Head North
Sailing Moor R & R

WE FINALLY BACK on our 450 Lagoon … After 5 Months Away From Sailing We’re Back Ready To Head North

Welcome back aboard Moor R & R! Episode 28 We’re finally back aboard Moor R & R after 5 months away and ready to set sail north again! ⚓🌊 After untying the lines, our first stop is The Narrows at Maria Inlet, where we spend our very first night back onboard floating once again. From there,...
Six Boats. One Atlantic Dream. Why He Chose a Cape Dory 36.
BoatFools Sailing

Six Boats. One Atlantic Dream. Why He Chose a Cape Dory 36.

#boatfoolssailing #capedory36 #bluewatersailing #atlanticcrossing #sailboattour Six Boats. One Atlantic Dream. Why He Chose a Cape Dory 36. Welcome back BoatFools Nation! This one is a little different—and exactly the kind of story we love. Back in February, Andrew flew all the way from Norway t...
We Fixed the Sail… But Now the Rigging Might Fail | Day 8
Leading the Escapade

We Fixed the Sail… But Now the Rigging Might Fail | Day 8

We Fixed the Sail… But Now the Rigging Might Fail | Day 8 We fixed the sail and set off again… but now we’re worried the rigging might fail. After tearing our sail on our first attempt to leave the Bahamas, we finally get it repaired and feel ready to try again. We haul anchor, hoist the sails, an...
Our Sail Tore in 40 Knots…10 Minutes Into the Crossing | Day 7 Continued…
Leading the Escapade

Our Sail Tore in 40 Knots…10 Minutes Into the Crossing | Day 7 Continued…

We use Airalo to stay connected when we land in new countries — super easy eSIMs with no physical SIM needed. Try it here: Code: LEADING Day 7 continued of our sail from the USA to Colombia… and this is not how we imagined it going. After days of waiting in the Bahamas for the right weather wind...
The Easiest SELF-FLYING DRONE We’ve Ever Used on a Boat – HoverAir X1ProMax Review
Sailing Jibsea

The Easiest SELF-FLYING DRONE We’ve Ever Used on a Boat – HoverAir X1ProMax Review

The HOVERAir Memorial Day Sale is live! Get up to 30% off from May 20 to May 26 SELF-FLYING DRONE HoverAir X1PROMAX NEW VIDEOS EVERY SUNDAY! Please subscribe and share our videos - every bit of support is much appreciated, keeps our journey going and the content coming! IF YOU'D LIKE TO S...
Boat Life in the Remote Bahamas Hits Different | Day 6-7
Leading the Escapade

Boat Life in the Remote Bahamas Hits Different | Day 6-7

Still tucked away in the Ragged Islands, we’re waiting on the right weather window to make our next big move south to Colombia… but life out here doesn’t exactly slow down. While we wait, it’s time to get a few jobs ticked off. We break out the sewing machine onboard and get to work repairing our...
Somehow… This Became Normal | Pacific Crossing
Sailing Big Lost

Somehow… This Became Normal | Pacific Crossing

Two weeks into our Pacific crossing and something unexpected started happening… Life out here began to feel normal. The watches, the meals, the routines, the exhaustion, the quiet moments in between — somewhere along the way the Pacific stopped feeling so unfamiliar. In this episode we share what da...
The Ragged Islands Are Pure Paradise! | Day 4-5
Leading the Escapade

The Ragged Islands Are Pure Paradise! | Day 4-5

We finally get a moment to breathe… After a wild crossing from Miami and getting hit with way more wind than expected, we wake up in the remote Ragged Islands in the Bahamas — and honestly, it feels like paradise. With the next weather window not quite ready for our push down to Colombia, we slow ...
Fast forward to the START OF A NEW ADVENTURE! (& what we’ve been up to behind the scenes) – Ep 271
Sailing Jibsea

Fast forward to the START OF A NEW ADVENTURE! (& what we’ve been up to behind the scenes) – Ep 271

Join us as we begin a new adventure sailing offshore with our sights on a very exciting destination! During our sail, we recap how we spent winter in the United Kingdom, what we got up to, including travel, boat projects and sailing plans ahead. NEW VIDEOS EVERY SUNDAY! Please subscribe and share o...
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