We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. ...

We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. ...

Not every week is turquoise water and perfect anchorages. This week in Grenada, heavy rain, canceled plans, and marina life kept us tied to the dock — and gave ...

Jay and Kenna finally breathed a sigh of relief after securing a new propeller for their outboard—a mission that took a grueling 9-hour sail to complete. With ...

From the snowy mountains of Idaho to the turquoise waters of the Caribbean, Conor’s life has always been about chasing adventure. Dirt bikes, skiing, ...

Every journey has a beginning—and an evolution. In this episode, we take a trip down memory lane to share how we got here, from dreaming of life on the water ...

Experience a new perspective on travel by joining Holly and Ray for an enlightening discussion about the transformative power of sailing trips. Compare sailing ...

Join Jay and Kenna of Sailing Sitka in episode 122 as they explore Punta Perula, Mexico, after sailing from Shamea Bay. Enjoy a glimpse into their daily ...

The Gambier Islands are a group of islands located in French Polynesia, offering untouched beauty, fascinating culture, and unparalleled human spirit.

Welcome back to Season 2 of Sailing Sitka! In this latest video, Jay and Kenna are anchored in La Paz, Mexico. They're prepping their sailboat, Sitka, for an ...

Sailing into a boat cemetery...On this episode of Sailing Sitka, we sailed from Esiritu Santo to La Paz but little did we know the destructive mess we would be ...

In this episode of Sailing Sitka, join Canadian couple Jay and Kenna as they discover a deserted anchorage in Mexico on their journey around the world. ...

In the latest episode of Sailing Sitka, Jay and Kenna set sail to explore an uninhabited island near La Paz. Join them as they face challenging winds, make a ...

Our favourite anchorage yet! We spent a few days anchored in Bahia Agua Verde where we swam, ate and snorkelled our way through it all! This protected, ...

All boat projects start off with the best of intentions and highest of hopes. But sometimes, when you're deep enough to a project to see it for it will really ...

Being Alone on Turtle really puts into perspective quite a few things. One, safety of being alone on the boat on a new island really comes to light and I make ...

This is what we live for! On this episode of Sailing Sitka, we sail from San Jaunico to Isla Coronados which turns out to be a glorious down wind sail. Our ...

Between the leaky boat, lack of sleep and our drained batteries... our boat and our cruising life has been stressful... but nothing can stop us from sailing ...

The last time we tried this, it was a a disaster ending with the navy/armada of the Dominican Republic dragging us back into DR! This time is different. While ...

This week we take you through what its like as full-time liveaboards trying to head south in USA. Right now we are in North Carolina in winter headed to ...

Last week traveling through the beautiful waters along the Intracoastal waterway we hit a 65' bridge! Undeterred, we continue this week navigating south ...

This week is an epic reality of what life is like living on a boat sailing around the world! It's just fun in the sun, cocktails and bikinis, we get to take ...

This week on Sailing Sunday we head south in the Chesapeake Bay in what was meant to be a beautiful calm peaceful sail turned into chaos making us abort ...