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Would You Jump Here?! 😳💦 #boatlife #travel #familyadventure
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Lily took a leap into the stunning Blue Sapphire Hole 💙🌊 Crystal clear water, island adventure, and one brave little jumper living her best Caribbean life. ...

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This Is the Part That Makes You Question It
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We knew this part would be hard. Not the work… not the effort… It’s the responsibility. But then… this. Would you? Follow our journey as we sail as a family ...

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Living Aboard During Cyclone Season in Fiji | Why No One Sails Here
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Welcome back to another episode of WE|Sail. EPISODE 337 Seven years. Over 30,000 nautical miles. We've sailed to some incredible places, and Fiji is ...

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Galápagos Isn’t What We Expected
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We finally made it to the Galápagos after everything it took to get here… but this place feels different than we expected. Raw landscapes, wild encounters, ...

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

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Together | Why We Chose This Life at Sea
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After everything it took to leave… this is what we found out here. No schedules. No distractions. Just time together. This is why we chose this life. ⚓ Follow ...

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LOST? Night Kayaking in St John… Until Captain couldn’t find us! #stjohn #trawlerlife
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🌙 We thought a peaceful night kayak in St John, US Virgin Islands would be a magical experience… and it was—until our captain (Ken) tried to find us with a ...

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What Actually Makes You Question This Life
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Boat work isn’t what makes people question this life. It’s the uncertainty behind it. Not knowing if it’s sustainable. Spending without a paycheck. Wondering ...

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We Dove with BULL SHARKS in Fiji… Here’s What Happened
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Welcome back to another episode of WE|Sail. EPISODE 336 Last week, we dove with black tip reef sharks - curious, peaceful, harmless. This week? Bull sharks. ...

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Arriving in Miami by Sailboat! (At Night 🤯) Ep-210
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This week on Escapade the clock starts working against us! We kick things off by upgrading our guest cabin with a brand new custom mattress from Ship Shape ...

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This Is What It Actually Feels Like Out Here
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This is what it actually feels like once you're out here. After everything it took to leave… this is just life now. Would you be ready for it? ⛵ Follow our ...

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Together. Why We Chose This Life | Sailing Family
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After everything it took to leave… this is what we were chasing. No schedules. No distractions. Just time together as a family, out here on the open ocean. ...

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FROM NAVY BUZZ CUT TO PIRATE HAIR…CAPTAIN KEN’S HAIR DILEMMA #trawlerlife #travelvlog
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In this short clip from our Unanchored Life adventures in the US Virgin Islands, Ken’s long-awaited post-military hair growth takes an unexpected turn… ...

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47 Hours Across the Mona Passage… With Kids 😳
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47 hours. 245 nautical miles. Two overnights. We set sail from the Dominican Republic to Puerto Rico, crossing the Mona Passage—one of the most unpredictable ...

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We Finally Left
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After weeks of waiting, delays, and uncertainty… we finally got what we needed and it was time to go. This is the moment everything shifts — from waiting to ...

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We SOLD everything and moved on a boat
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Hi guys, welcome back to Sailing Clueless Crew! We sold everything and finally moved aboard our Fountain Pajot Astrea 42 catamaran in the boat yard—raw footage ...

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After Weeks of Waiting… We Left
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After weeks of waiting… it finally happened. We got approval. Finished the last things. And then… we left. ⛵ Sailing Big Lost Full story coming. #sailing ...

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Mast Stepped, Boom Installed | We’re So Close to Launch Ep.68 #boatrefit
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After nearly two years without a mast, this is the moment everything finally starts to come back together—we step the mast AND reinstall the boom, and for the ...

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

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Soon… This Will Be Our Reality ⛵
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One moment… but everything about it feels different out here. After weeks of preparation, this is what it’s all leading toward. Not quite there yet… but close. ...

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What 90% of Sailing Actually Looks Like | Days at Anchor in Fiji
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Welcome back to another episode of WE|Sail. EPISODE 335 Here's something most people don't realize about sailing: we spend about 80 to 90 percent of our time ...

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Everything Is Ready… Except One Thing | Pacific Crossing
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We’re officially ready to leave Panama and begin our Pacific crossing… but we’re still stuck. After weeks of preparation, boat work, and planning, everything ...

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This Is What Waiting to Leave Actually Looks Like
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We’re ready to leave Panama and begin our Pacific crossing… but right now, we’re waiting. And waiting doesn’t mean stopping. Boat prep, daily chores, fuel ...

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

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