Watch Sailing & Boating Adventures Around the World – Page 3 of 31
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Our New Boat Finally Hits The Water – Ep. 275
After weeks of preparation, stress, and problem-solving, our new Fountaine Pajot Venezia 42 finally goes back in the water for the very first time. In this episode, James prepares the boat for launch day, checks the systems once she splashes, and attempts the first proper move to a new marina… even...
We Didn’t Think We’d Make It
After weeks of rough weather, Christmas winds, storms, and learning how to sail in real time… we finally make it to Saint Martin. But getting there was far from easy. In this episode, we leave Martinique and continue battling our way north through the Caribbean. Along the way we experience incredi...
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
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 ...
Sailing Blind | Season 1, Episode 8
In this episode, we leave Le Marin and continue sailing north toward beautiful Saint-Pierre. What started as one of our most peaceful and enjoyable sails yet quickly changed when we suddenly lost critical electronics onboard Isla. Our charts, depth readings, wind instruments, and navigation system...
The Reality of Getting This Boat Ready – Ep. 274
After 13 months away from sailing, stepping back into boat life has been a lot more intense than expected. In the last episode, we shared our return to YouTube after selling our Beneteau Oceanis 43 and buying an older boat in hopes of building a more sustainable future on the water. But the realit...
CREW CHANGE – A Caribbean sailing adventure
CREW CHANGE - A Caribbean sailing adventure Love your life. Take pictures of everything. Tell people you love them. Talk to random strangers. Do things you're scared to do. Take your life and make it the best story in the world. Don't waste that shit. Welcome back aboard in Sint Maarten,...
Why St. John Feels Nothing Like St. Thomas E381
🌴 Island hopping through the USVI brought us from the busy streets of Charlotte Amalie on St. Thomas to the wild beauty of St. John… and what an adventure it turned into. We wandered the steep chaotic roads of Charlotte Amalie (definitely not the most pedestrian-friendly place 😅), got rescued with ...
We Disappeared For 13 Months…Then This Happened – Sailing Zephyr – Ep. 273
After 13 months away from Youtube and life at sea, we are finally back.....and heaps has changed. We didn't plan to be gone this long, yet stepping away from sailing has turned into a much bigger pause than expected. Over the past year we sold out Beneteau Oceanis 43, stepped back from life...
We Didn’t Expect THIS in the US Virgin Islands… E380
Our sail from Puerto Rico to the US Virgin Islands started off absolutely perfect… warm winds, beautiful seas, and another unforgettable Caribbean passage aboard SV Wildly Intrepid. But once we arrived in St. Thomas, things got interesting fast. We explored the abandoned tunnels of Fort Segarra on ...
We Fixed One Thing… And Broke Another | Boat Life in Martinique
Welcome back to Finding Our Isla. In this episode, we continue settling into life in Le Marin while waiting out strong winds and tackling a long list of boat repairs and projects. From fixing our steering cable and unclogging the toilet… to provisioning the boat, homeschooling, laundry days, and ex...
From Chaos to Paradise: Sailing Vieques → Culebra → Puerto Rico E379
What started as a simple sail turned into a full-on emergency… As we left Vieques, a hose clamp suddenly snapped—dumping all our engine coolant in seconds. With no engine and two little ones onboard, we had no choice but to drop anchor fast and figure things out. From there, we sail on to Culebra—...
Good & Bad News from 2 continents | Together, apart | Extraordinary dolphin moment!!!
Caribbean sailing life | Together, apart This week's episode takes us across oceans from the Caribbean Islands to England, as life on and off the boat unfolds in very different ways. While Rob and the boys sail north, along the west coast of Guadeloupe, they are treated to an unforgettable en...
We Thought It Was Seasickness… It Was Dengue
Welcome back to Finding Our Isla. In Season 1, Episode 6, we leave Bequia and continue our sail north toward the breathtaking Pitons. Along the way, we continue battling the powerful Caribbean Christmas Winds while dealing with more boat repairs at sea. With calmer water along the coast of Saint V...
SHE’S LEAVING
SHE'S LEAVING This week set sail we continue our sailing adventure, sailing north from Martinique to Dominica, but what began as a simple passage quickly became something very different and everything changed. This episode is a reminder that while sailing is about freedom and adventure, life ...
We Found the BRIGHTEST Bioluminescent Bay on Earth! Vieques (Family Sailing Caribbean) E378
Not every stop is planned… and sometimes those are the best ones. We dropped anchor in Puerto Patillas, Puerto Rico and were blown away. A peaceful anchorage, a waterfront park with a playground (perfect for homeschooling days), live music, and even iguanas roaming around—it quickly became one of t...
Sailing Family Sails into Big Seas: Did We Make a MISTAKE?
Welcome back to Finding Our Isla. In Season 1, Episode 5, we leave Saline Bay and continue sailing north toward Bequia — still without a working steering cable. As we push forward, we sail straight into the powerful Caribbean Christmas Winds and battle rough seas, strong winds, and multiple squall...
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 LOST CONTROL of Our Boat… (Our Biggest Scare Yet) Season 1, Episode 4
In this episode of Finding Our Isla, we continue sailing north through the Caribbean as a family of six learning how to sail along the way. We leave Ronde Island and make our way to Sandy Island and Chatham Bay on Union Island — soaking in some of the most beautiful spots in the Grenadines. What s...
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...
THE DEADLIEST VOLCANO YOU’VE NEVER HEARD OF
THE DEADLIEST VOLCANO YOU'VE NEVER HEARD OF This week we continue exploring the beautiful island of Martinique, but beyond the beaches and rainforest lies a much darker history. One of the most devastating events in Caribbean history, the 1902 eruption of Mount Pelée. With the volcano still ac...
The Night I Almost Lost the Keel (and Why I Quit Deliveries)
In 2014, I delivered a Beneteau First 47.7 from the Bahamas to Cartagena. Somewhere in the Caribbean, 150 miles offshore, I found myself ankle-deep in water, crew vacuuming the bilge in the dark, batteries dead, no GPS, no autopilot. I didn't know at the time how close we were to losing the kee...
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...