It's a dirty situation—literally, the vibe is off, and she’s just not feeling it. In this Sailing Episode we show what life really looks like behind the dreamy ...

In this episode, Jay and Kenna welcome aboard their friends from Canada and give them the full tropical, sailing experience by island hopping and cruising ...

Jay and Kenna depart from Shelter Bay marina after a week straight of boat work and diagnosing problems. Finally, after stopping in Linton bay for one night, ...

You Wanna know the Dirty Secret after the failure? Join us this week in another episode of boat life unfiltered #boatlife #sailing *Want to support us?" ...

In this episode we reminisce about our first year living aboard, the endless projects, and the mysterious leak that had our bilges flooded for a few months. ...

Jay and Kenna are in Shelter Bay Marina, fixing some minor and major problems they've encountered while transiting the Panama Canal, on top of that they do ...

This is why I love Sailing Around The World. Join us in our latest sailing episode as we share a glimpse into our life at sea and exactly why we love sailing ...

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: ...

Panama Canal Day 2: Engine nightmare & bad luck continues, Atlantic awaits... In this episode jay and Kenna (along with @SailingSVBully ) continue their ...

This is what boat life is all about! In this episode you get to see the real life of sailing around the world and how we live full time and living off-grid ...

Join us on an epic journey across the Caribbean as we track down the last true sailors—masters of the sea, tradition, and adventure. Don't miss. Follow us ...

Join me on an epic adventure as I embrace the ocean nomad life, sailing to a hidden island paradise! 🏝️🌊 Crystal-clear waters, untouched beauty, and pure ...

Jay and Kenna share some real thoughts and info as they prepare to transit the Panama Canal from the pacific to the Atlantic. But not before they enjoy some ...

Hey Everyone! We've been busy sailing and having a lot of fun with new friends these past couple weeks, including new sailing kids that Ricci has been loving ...

Secure your privacy with Surfshark! Go to http://www.surfshark.com/sailingsv for an extra 4 months Follow us every week in our real life sailing adventure, as ...

Jay and Kenna embark on a 3 day passage sailing from the tiny village of Bahia Honda to the concrete jungle of Panama City. This sail happens to be their last ...

In this episode we take you for a wild ride as we start with a beautiful tallship anchored in our backyard, then venture on a daring dinghy ride far into a ...

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: ...

Jay and Kenna sail further into Panamanian waters only to discover a hidden gem of a village which was completely stuck in time. Join us on this special 3 year ...

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: ...

Living on a boat can be idyllic, but it also comes with unexpected challenges. This video explores some surprising hurdles faced by those who choose to live ...

In this video of sailing sitka, jay and Kenna sail to their first port in Panama from Golfito, Costa Rica. They anchor in front of a desolate little island ...

Join us for the epic final episode on this stunning island! From crazy boat life fun to unexpected blasts, we end the adventure with a bang! Don’t miss it!" ...

Jay and Kenna sailed off from Victoria BC, Canada two years ago and have been sailing south ever since. Now, in the luscious lands of Costa Rica, they ...