Watch Sailing & Boating Adventures Around the World

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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Everything Changed This Year
Roaming Rupps

Everything Changed This Year

A lot has changed lately — some planned, some not. We made a few big decisions, welcomed another tiny human, and found ourselves rethinking what the next chapter looks like for our family. For now, we’re trading slip fees for open roads, slowing things down, and giving the kids time to grow while w...
We are Boatless… NOW WHAT?! | Sailing Sunday Vlog 301
Sailing Sunday

We are Boatless… NOW WHAT?! | Sailing Sunday Vlog 301

With “Sunday” officially sold, we pack up our little family, squeeze into a 5th wheel and hit the road from Florida to the Annapolis Boat Show. It’s our first big trip as boatless sailors. Just us, the baby, the dog and a whole lot of “what now?!” We explore the Boat show, hug our Patreons and Sub...
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...
Boatyard RESCUE + Life Update | We’re Finally Back VLOG 282 4K
Sailing Sunday

Boatyard RESCUE + Life Update | We’re Finally Back VLOG 282 4K

From welcoming our baby boy into the world to hauling an RV across America, these past seven months have been a wild change of pace. Slowing down, soaking up family life, and taking on a whole different kind of adventure was exactly what we needed — but we’ve been counting down the days to get back ...
Are We Really Doing A Reality TV Show? Episode 46
Sailing Banana Pancakes

Are We Really Doing A Reality TV Show? Episode 46

In this episode of Sailing Banana Pancakes, we wrap up our unforgettable time in Martinique, start major sailboat repairs, and head off on an epic sail toward Grenada—complete with a dolphin encounter that blew our minds! After spending weeks sailing through the Caribbean, Martinique gave us a chan...
RV Life Reality Check – When Everything That Can Break… DOES BREAK! | Vlog 278
Sailing Sunday

RV Life Reality Check – When Everything That Can Break… DOES BREAK! | Vlog 278

Last week we got a fresh new paint job on the 5th wheel and it looks amazing, but then everything else started going wrong! In this week’s vlog, we hit the road again after completing the final stage of our 5th wheel renovation, only to face a broken truck and a shattered window in the desert, then ...
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