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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When Family Visits Boat Life for the First Time
After discovering an unexpected porcupine stowaway outside Shelter Bay Marina, the crew of Big Lost tackles watermaker leaks and sails east to San Blas with family aboard.
Choosing the Window | Leaving San Blas & Sailing to Shelter Bay
The crew aboard Sailing Big Lost departs the San Blas islands, navigating beam seas and commercial canal shipping lanes on passage to Shelter Bay Marina in Colón, Panama.
We Came for San Blas… and Ended Up in a Rescue | Life at Anchor
When an afternoon squall hits the San Blas Islands, a routine day turns urgent as cruisers unite to rescue a stranded mariner outside the breaking reef.
Boat Electrical Fires in San Blas ⚡ Power Risks Every Cruiser Should Know
Anchored at the Swimming Pool in San Blas, Sailing Big Lost manages power in heavy cloud cover, receives a panga grocery order, and investigates recent boat fires.
We Finally Made it the San Blas “Swimming Pool”
Aboard Big Lost, Connor and Kelly escape no-see-ums in Snug Harbor, haul diesel by hand in Nargana, troubleshoot a starboard raw water pump, and sail into the Swimming Pool anchorage in San Blas.
Rained Out in San Blas
Sailing catamaran Big Lost navigates heavy rain and seven-foot swells through Guna Yala, exploring the shallow Sugandi River before finding shelter in Snug Harbor.
From Dreamy Anchorage to Pirate Drama | Sailing Sitka Ep 180
Jay and Kenna were about a week into a postcard-worthy anchorage—spending their days lounging on the beach, sipping cocktails, surrounded by friends and fellow sailors, soaking up the beauty of the sailing lifestyle. But with all that beauty comes a bit of chaos. The truth is, common sense isn’t so ...
Sailing Into Trouble: The Day Our Anchorage Was a Crime Scene | Sailing Sitka Ep 179
Jay and Kenna lift the hook and set sail from Green Island toward the stunning Holadaze Cayes, one of the most picture-perfect anchorages in all of the San Blas Islands. But just when we thought we’d found paradise, we suddenly found ourselves—and Sitka—in the middle of an active criminal investigat...
3 Years Offshore Cruising: Here’s What We Really Think (raw update) | Sailing Sitka Ep 175
Jay and Kenna are currently anchored in the beautiful San Blas Islands, soaking in the cruising lifestyle — though, as always, the highs come with their fair share of lows. After weeks of battling persistent engine troubles, this week they think they've finally tracked down the culprit. It’s be...
The Man who built a 75ft Wooden Catamaran and Sailed the World | Sailing Sitka Ep 168
Jay and Kenna along with their pal Derek @ontongjava5441 the man who built a 75ft wooden catamaran on a beach with his own bare hands! He shared with us some stories, details on his boat, lessons learnt and favourite place in the world! Apart from that memorable encounter, Jay and Kenna sailed to L...
Trouble in Paradise… | Sailing Sitka Ep 165
Jay and Kenna, along with their friends from Canada and the crew from @SailingSVBully sail their sailboat from Holandes Caye to Salaradup in the San Blas Islands. While enjoying everything that paradise has to offer, they run into some weather that makes for a chaotic situation. Thanks for watching ...
Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164
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 through the San Blas islands. We are sailing off-grid between sand spit islands in search for adventure, wind and good times. Check it out and su...
VAN vs BOAT: 7 Reasons BOATLIFE Is Too Hard For You
Is Vanlife better than Boatlife? Go to for 4 extra months of Surfshark I love Boatlife, but Vanlife was my 1st love. But which one's actually better? We compare our Vanlife roadtrip across America to a Boatlife passage we did to the San Blas Islands. Vanlife crushes it in most of the categori...
Crossing the Pacific and STOPPING in GALAPAGOS – Is it WORTH IT? Ep 57
We've been checking out the beautiful islands of Galapagos. But now, our looming Pacific crossing is taking up most of our time and attention. We are refueling, provisioning, cleaning the hull, and trying to fix what's broken. Stick around to the end of our video to see the answer of i...
Starting to Wonder if It’s Worth the EXPENSE – SAILING the GALAPAGOS ISLANDS Ep 56
We have jumped through all the hoops and have officially made it to the beautiful Galápagos Islands! We leave San Cristobal and all the sea lions behind and make our way to Floreana then eventually back to Santa Cruz. Thank you for watching and subscribing! To God be the GLORY! All music provided...
INTRUDER on the BOAT in GALAPAGOS – Sailing FAMILY – SAILING AROUND THE WORLD – 🎥 Episode 55
We have jumped through all the hoops and have officially made it to the beautiful Galápagos Islands! We check out Santa Cruz and sail over to San Cristobal where we get close and have some interesting interactions with the sea lions. Thank you for watching and subscribing! To God be the GLORY! ...
REALITY of crossing the PANAMA CANAL on our SAILBOAT – SAILING FAMILY with SAILDRIVE FAILURE! (51)
It's our canal transit day and we are hoping to make it to the Pacific Ocean! We have to grab our line handlers and our advisor and make it through - but it's not without some steerage issues! Did we lose our propeller, we have no idea. We are trying to make it across Gatun Lake as quic...
Salt & Tar: Ep.279- Embrace the Journey
It's not always easy to embrace the journey when the destination is so seductive. Sailing has taught me to slow down and enjoy the here and now. Currently, now that we're in the tropics, I don't care where the boat's going just that I'm on it! Thanks for watching! p.s. I t...
Ep. 454 Eating the genitalia of a #$&*#$. Who would do that? She must be crazy !
CHARTERS ON THE CATAMARAN "TOO SHORT" with Deren and Crystal You will have a blast on a charter with these 2 great people. I had the pleasure of being with them for many weeks and out of all the people I have met on my adventures they are 2 of the very few people that I have truly clicked ...
Ep. 453 FOUR girls on the boat “TOO SHORT”, the clash of YOUTUBE channels
Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: Want more? Became our patron and get access to exclusive content. If you would like to support with single donations click here - Check out some gear we have on the boat: Inverter handheld radio (A...
Ep. 452 Party time with Parlay Revival
Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: Want more? Became our patron and get access to exclusive content. If you would like to support with single donations click here - Check out some gear we have on the boat: Inverter handheld radio (A...
Ep. 451 Beach BBQ with Parlay Revival
Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: Want more? Became our patron and get access to exclusive content. If you would like to support with single donations click here - Check out some gear we have on the boat: Inverter handheld radio (A...
The signing
Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: Want more? Became our patron and get access to exclusive content. If you would like to support with single donations click here - Check out some gear we have on the boat: Inverter handheld radio (A...