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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Sailing Cartagena to Panama (Rosario Islands Stop!)
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. After a month in Colombia—soaking in the historic charm of Cartagena and cooling off in the lush mountains of Minca—we finally had the boat...
We Traded the Ocean for the Mountains | Our Journey to Minca, Colombia
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. In this episode of Sailing Big Lost, we head inland for a change of scenery—trading the Caribbean coast for the lush mountains of Minca, Co...
A Week That Didn’t Go to Plan | Rain & Marina Life in Grenada
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 us a real dose of the cruising lifestyle. Between endless boat chores, a soggy anniversary outing, sewing a DIY bow shade, and watching our...
Light at the End of the Tunnel… Or Was It? | Sailing Sitka Ep 169
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 that crucial task checked off, they took time to regroup in Linton Bay, refueling, stocking up, and tackling laundry and water runs. For a mo...
Meet Conor | Sailing Big Lost Captain
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, waterskiing, hunting, and sailing — his childhood was packed with energy, freedom, and a growing love for the outdoors. In this video, Conor shares h...
Sailing Big Lost: Our Story & Goodbye
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 to making it a reality. We say goodbye to Big Lost, our first catamaran, as we close escrow and hand her over to her new owners. But don’t wo...
“Now THIS is the life!” (Punta Perula, Mexico) | Sailing Sitka Ep 122
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 routines aboard their boat, including meals, maintenance, and local explorations.![What We Found In This Remote Island Will Change Your Mind About Humanity [Ep. 156]](https://i.ytimg.com/vi_webp/KoppBpMkKC0/mqdefault.webp)
What We Found In This Remote Island Will Change Your Mind About Humanity [Ep. 156]
The Gambier Islands are a group of islands located in French Polynesia, offering untouched beauty, fascinating culture, and unparalleled human spirit.
Prepping our SAILBOAT for our longest passage of the Season! | Sailing Sitka Ep 116
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 extensive passage across the Sea of Cortez. The couple shares insights on boat maintenance and ownership as cruisers.
Sailing into a Boat Cemetery… (Hurricane aftermath in Mexico) | Sailing Sitka Ep 115
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 sailing into... 6 month ago La Paz got hit by Hurricane Norma and left a catastrophic aftermath... we got some of it on film. If you enjoyed...
Exploring a desolate anchorage in Mexico (with unexpected company😳) | Sailing Sitka Ep 114
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. Encounter unexpected marine life and enjoy the breathtaking beauty of unexplored waters in paradise!
Sailing to an uninhabited island with a stranger! | Sailing Sitka Ep 113
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 daring dinghy rescue, and encounter breathtaking sunsets along the way.
A perfect anchorage in Mexico! | Sailing Sitka Ep 111
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, beautiful bay is full of everything a cruiser could ever want. Check out this weeks episode and if you enjoy please subscribe and comment to let us ...
Sometimes the Best Thing To Do Is To GIVE UP! – Sailing Turtle⛵
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 be, you have to be ready to walk away. --------- We are Dev (pronounced Dave he/him) and Spandana (pronounced Spun-The-Nuh she/her), a ...
Being ALONE On The Boat! – Sailing Turtle⛵
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 some needed changes about that. Second, everything takes SO much longer without a partner to help you! --------- We are Dev (pronounced Dav...
“THIS is what we live for!” | Sailing Sitka Ep 106
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 1976 Cheoylee Offshore 41 sailboat LOVES sailing wing on wing and we are reminded exactly why we do this crazy life in the first place! We hope ...
Leaky boat, no sleep, low batteries… NOTHING can stop us from SAILING on! | Sailing Sitka Ep 105
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 on! In this weeks episode we "escape" the rolley, exhausting and windy anchorage of Punta Pulpito and sail further south. If you enjo...
We LEAVE DOMINICAN REPUBLIC!! Let’s Try This Again! – Sailing Turtle⛵
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 a full bash was expected as we take part in the last part of the thorny path, we are in a for a BIG SURPRISE! --------- We are Dev (pronounc...
Full-Time Liveaboard life | Sailing Sunday Vlog 236
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 Florida before crossing to the Bahamas. Follow our travel vlog with myself Ryan, Brittni and our rescue pup Jackson as we travel the world on our...
Surrounded By Land Through The Outer Banks | Sailing Sunday Vlog 235
Last week traveling through the beautiful waters along the Intracoastal waterway we hit a 65' bridge! Undeterred, we continue this week navigating south through the Oter Banks racing against time to outpace an approaching storm! As we continue our travel, we face the challenge of passing under ...
Paying Off Our Debts! | Sailing Sunday Vlog. 232
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 you back 4 years ago and reminisce on times back in Greece, Turkey and crossing the Atlantic ocean this week bringing you to why we stoppe...
Unpredictable Winter Sailing in the Chesapeake Bay | Sailing Sunday Ep 231
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 mission in the middle of the night. Follow our travel vlog with myself Ryan, Brittni and our rescue pup Jackson as we travel the world on our sai...
Home For The HOLIDAYS! – Sailing Turtle⛵
FINALLY! We are BACK on Turtle! After being away for 6 LONG months we finally find ourselves home on our sailboat in the Dominican Republic. Finding her safe after having had no hurricanes touch her through out the season, we set to getting her back on her feet so to speak. We also have many many ...