Watch Sailing & Boating Adventures Around the World – Page 4 of 12

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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3 Fails in 3 Days… Puerto Rico Didn’t Go As Planned E377
Wildly Intrepid Sailing

3 Fails in 3 Days… Puerto Rico Didn’t Go As Planned E377

Not every sailing day goes to plan… and this one REALLY didn’t 😅 We kick things off with a beautiful, calm sail past Cabo Rojo Lighthouse—one of the most stunning coastlines in Puerto Rico. But from there… things start to unravel. We anchor in La Parguera hoping to experience the famous biolumines...
We Left Everything Behind… Was It Worth It?
Sailing Big Lost

We Left Everything Behind… Was It Worth It?

Sailing from Panama across the equator to the Galapagos brings doldrum calms, a broken Code 55 continuous furling line, yellowfin tuna, and biosecurity clearance.
Hours Before We Left… This Happened
Sailing Big Lost

Hours Before We Left… This Happened

Facing last-minute visa delays, a sudden $6,700 chart plotter failure, and heavy rain, Sailing Big Lost departs Panama on an offshore passage toward the Galapagos.
We Survived the MONA PASSAGE (47hrs Nonstop Sail to Puerto Rico) E376
Wildly Intrepid Sailing

We Survived the MONA PASSAGE (47hrs Nonstop Sail to Puerto Rico) E376

After months of life in Luperón, Dominican Republic, it was finally time to move on… and take on one of the Caribbean’s most notorious crossings — the Mona Passage. We set sail for Puerto Rico on a 47-hour, 245 nautical mile passage, pushing through a double overnight sail with little sleep and sea...
Everything Is Ready… Except One Thing | Pacific Crossing
Sailing Big Lost

Everything Is Ready… Except One Thing | Pacific Crossing

Sailing Big Lost prepares for a Pacific crossing from Panama, facing consular deadlines, hull cleaning for Galápagos clearance, and Holy Week holiday shutdowns.
This Was Our Toughest Hike (Isabel de Torres) + Our Final Luperón Days
Wildly Intrepid Sailing

This Was Our Toughest Hike (Isabel de Torres) + Our Final Luperón Days

This one tested us 😅 We took on the steep and slippery climb up Isabel de Torres in Puerto Plata—and it was no joke. Muddy trails, sketchy footing, and a serious leg burn… but the view at the top made every step worth it. Sitting above the city with a mini botanical garden and that iconic statue, i...
We’re Ready… But We Can’t Leave Yet | Pacific Crossing
Sailing Big Lost

We’re Ready… But We Can’t Leave Yet | Pacific Crossing

At anchor in Panama after transiting the canal, Big Lost is fully provisioned and ready to cross the Pacific, paused only for children's visas and wind.
Goodbye Belgium: We made it to FRANCE! ⛵Sailing Britaly⛵
Sailing Britaly

Goodbye Belgium: We made it to FRANCE! ⛵Sailing Britaly⛵

SUBSCRIBE for FREE Goodies! ➜ In this video we leave Dinant and finish crossing the whole of Belgium. We finally made it to the French canals! (Not without some initial drama...) We are taking our 1992 Bavaria 350 sailboat from the UK to the Mediterranean via the rivers and canals of Belgium and F...
WHY WE WENT SAILING – the answer may surprise you!
The Cruising Kiwis

WHY WE WENT SAILING – the answer may surprise you!

WHY WE WENT SAILING Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] This week's sailing vlog we're bac...
Belgium’s Waterways Are UNDERRATED! ⛵ Sailing Britaly ⛵
Sailing Britaly

Belgium’s Waterways Are UNDERRATED! ⛵ Sailing Britaly ⛵

SUBSCRIBE for FREE Goodies! ➜ In this video we continue our journey along the River Meuse, which will take us from Belgium into France. We are taking our 1992 Bavaria 350 sailboat from the UK to the Mediterranean via the rivers and canals of Belgium and France. Belgium has been a wonderful countr...
Choosing the Window | Leaving San Blas & Sailing to Shelter Bay
Sailing Big Lost

Choosing the Window | Leaving San Blas & Sailing to Shelter Bay

The crew aboard Sailing Big Lost departs the San Blas islands, navigating beam seas and commercial canal shipping lanes on passage to Shelter Bay Marina in Colón, Panama.
Making SAILORS OF OUR KIDS – HAND STEERING BRAZIL’S RUGGED COAST
The Cruising Kiwis

Making SAILORS OF OUR KIDS – HAND STEERING BRAZIL’S RUGGED COAST

Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate MAKING SAILORS OF OUR KIDS - HAND STEERING BRAZIL'S RUGGED COAST After two long days of hand steering through la...
Our Tiny Home on Water: THE LAST SAIL | St. Marys, Georgia Vlog: 299
Sailing Sunday

Our Tiny Home on Water: THE LAST SAIL | St. Marys, Georgia Vlog: 299

We have been living aboard for 7 years, sailing half way around the world over 40,000nm and this week we head off shore for our final passage with our tiny home sailing into St. Marys, Georgia, USA to meet the (potential) new owners! But, before anything’s “official,” we arrive and explore the stree...
Sailing Bahamas to USA in September! | Sailing Sunday VLOG 296
Sailing Sunday

Sailing Bahamas to USA in September! | Sailing Sunday VLOG 296

We’ve been living aboard our sailboat for 7yrs and in the Bahamas now for the past three months while Ryan’s been working with the Boy Scouts teaching sailing and running adventures out of the Abacos. But on his final trip, news hit that a Category 5 hurricane was tracking straight for us! With li...
HEARTBREAK AT SEA – FORCED TO LEAVE BRAZIL
The Cruising Kiwis

HEARTBREAK AT SEA – FORCED TO LEAVE BRAZIL

HEARTBREAK AT SEA - FORCED TO LEAVE BRAZIL This was one of the hardest episodes we've ever had to share. We lost our beautiful Mocha overboard, unseen and unnoticed until it was too late. She was part of our crew, and many of you who have followed us for years know how much she meant to us. As...
Boat Work in Paradise: Changing Fuel Filters
Sailing With Phoenix | Oliver

Boat Work in Paradise: Changing Fuel Filters

Just another day in paradise... I mean in the engine cave! In this episode of Sailing With Phoenix, I tackle a long-overdue job: replacing my diesel engine’s fuel filters aboard my sailboat in Hawai'i. It's sweaty, messy, and slightly chaotic, but that’s boat life right? I share thoughts ...
After the Fun in Sint Maarten, We Set Sail for Saint Kitts
Sailing Big Lost

After the Fun in Sint Maarten, We Set Sail for Saint Kitts

Sailing Big Lost navigates Bastille Day festivities in Marigot, rescues stranded kayakers in Simpson Bay, commissions an aluminum GoDu dinghy, and sails past Sint Eustatius to Saint Kitts.
Our First BIG Crossing Back — Sailing USA to the Bahamas!| VLOG 288 0
Sailing Sunday

Our First BIG Crossing Back — Sailing USA to the Bahamas!| VLOG 288 0

This week’s episode is a big one — our first ocean crossing since moving back aboard, and Oakley’s very first offshore sail! We teamed up with friends for the crossing, forming a little convoy as we made the 12-hour run across the Gulf Stream and onto the Bahamas Banks. It was an early start, calm ...
We Bought a Boat! | Vision 444 Catamaran
Sailing Big Lost

We Bought a Boat! | Vision 444 Catamaran

Sailing Big Lost navigates a high-stakes survey day, haulout, travel lift collision, and Gulf Stream sea trial while buying a Vision 444 catamaran in Dania Beach, Florida.
Selling Our Sailboat: Goodbye Banana Pancakes
Sailing Banana Pancakes

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...
SAILING FAMILY’S TOUGHEST Boat work Challenge Yet – FIRST Haul Out!
Sailing Paradise Falls

SAILING FAMILY’S TOUGHEST Boat work Challenge Yet – FIRST Haul Out!

SAILING FAMILY'S TOUGHEST Boat work Challenge Yet - FIRST Haul Out! #sailingfamily #familyvlog #sailingaroundtheworld #familytravelvlog #boatlife #bucketlist #lifestyle #travel #sailboat We are FINALLY back on the boat and haul out for our very first time since owning the boat. Join us as we ...
ESCAPING KNYSNA – SAILING OUT OF SOUTH AFRICA’S MOST FEARED HARBOUR ENTRANCE
The Cruising Kiwis

ESCAPING KNYSNA – SAILING OUT OF SOUTH AFRICA’S MOST FEARED HARBOUR ENTRANCE

ESCAPING KNYSNA - SAILING OUT OF SOUTH AFRICA'S MOST FEARED HARBOUR ENTRANCE After an unforgettable stopover in beautiful Knysna Lagoon, it's time to untie the lines and take om the Knysna Heads once again - only this time, we're heading out. With tide, swell, and timing needing to a...
Meet the Crew | Kelly – From Chaos to Calm: My Journey to Sea Life 💙⚓
Sailing Big Lost

Meet the Crew | Kelly – From Chaos to Calm: My Journey to Sea Life 💙⚓

Waiting on a catamaran survey in Fort Lauderdale, Kelly documents her transition from competitive equestrian arenas and high-stress real estate to full-time family ocean cruising.
SAILING KNYSNA after the SCARIEST WILD HEADS ENTRANCE
The Cruising Kiwis

SAILING KNYSNA after the SCARIEST WILD HEADS ENTRANCE

LIFE ON THE INSIDE - EXPLORING KNYSNA AFTER THAT WILD ENTRANCE After our dramatic entrance through the legendary Knysna Heads, we finally get a chance to catch our breath inside the stunning Knysna Lagoon. In this episode, we explore the calm waters and take a hike up to the East Head lookout, ret...
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