Watch Sailing & Boating Adventures Around the World – Page 2 of 9
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Getting delivered boat parts to the edge of civilization (FAIL) | Sailing Sitka Ep 167
While cruising through the San Blas Islands, Jay and Kenna unfortunately broke the propeller on their outboard motor. Given the remote nature of the islands, where services like Amazon Prime are unavailable, obtaining replacement parts can be challenging. However, there are local services that deliv...
Sometimes cruising doesn’t always go according to plan… | Sailing Sitka Ep 166
Jay and Kenna navigate the harsh realities of cruising. There are both challenges and benefits to sailing and both can rock your world. From fixing broken systems, to installing new ones and reaching for the medical kits with no healthcare facilities in sight, this is all cruising. Thanks for riding...
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...![[Ep 5] The WORST Start To Our Sailing Adventure: 29 Hours Of Nonstop Misery!](https://i.ytimg.com/vi_webp/stEumbBkEzs/mqdefault.webp)
[Ep 5] The WORST Start To Our Sailing Adventure: 29 Hours Of Nonstop Misery!
This is it! Years of planning and we’re finally ready to cut the dock lines (metaphorically, not literally cause dock lines are expensive), leave Monterey, make that sharp left and start our sailing adventure. We’ll take you along on our last minute preparations, our departure from Monterey, and the...![[Ep 4] First Year Living on a Boat: Water in the Boat, Endless Projects, We Quit!](https://i.ytimg.com/vi_webp/DTYszJbcrWg/mqdefault.webp)
[Ep 4] First Year Living on a Boat: Water in the Boat, Endless Projects, We Quit!
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. Finally, we rip the band-aid and quit our jobs as the final step in preparation for taking off from Monterey and starting our life as full-time...
Why our engine FAILED while transiting the Panama Canal | Sailing Sitka Ep 161
Jay and Kenna are now tied along a dock in Shelter Bay marina after undergoing two of the most stressful days of their lives. While transiting the Panama Canal, their Yammer 56 engine failed several times in the worst possible scenarios. Surprised they even made it all the way through, they now can ...
CHASING BUBBLES around the Virgin Islands! ⛵️ Let’s Bring Her Back WITH A BANG! 🎉 l ep.61
Get your free LMNT Sample Pack with any purchase at Also try the new LMNT Sparkling — a bold, 16-ounce can of sparkling electrolyte water. Join the Next Chasing Bubbles Regatta HERE (APRIL 9th, 2025)- You can charter a boat or sail in a vessel of your own...For more information and to keep up wit...
Engine Nightmare, Breakages & Bad Luck Continues… Panama Canal Day 2 | Sailing Sitka Ep 160
Panama Canal Day 2: Engine nightmare & bad luck continues, Atlantic awaits... In this episode jay and Kenna (along with @SailingSVBully ) continue their unexpected adventure through the Panama Canal with their unreliable engine. Their troubles aren't done with just yet. The bad luck sticks ...
Panama Canal Nightmare: Engine Failure, No Sails, Will we make it through? | Sailing Sitka Ep 159
Engine Failure in the Panama Canal: Will we make it or get Fined? In the very exciting episode of Sailing Sitka, Jay and Kenna ( along with their pals @SailingSVBully ) embark on their most stressful journey yet. The Panama Canal is an emotional strain already but adding an unreliable and untrustwor...
Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158
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 time enjoying the city life in Casco Viejo. Thanks for watching and subscribe if you enjoy. Stay tuned for next episode as it will be the one w...
Our last sail on the Pacific Ocean | Sailing Sitka Ep 157
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 the Pacific Ocean as they get ready to cross the Panama Canal into Atlantic waters. Thank you for watching and please subscribe if you enj...
Sailing to a remote, timeless village on Panama’s pacific coast | Sailing Sitka Ep 156
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 anniversary episode as we sail to Bahia Honda on Panama's pacific coast and learn to live slowly as we discovery the simplicity and bea...
Sailing to Panama | Sailing Sitka Ep 155
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 consisting of nothing but tall standing palm trees and white sandy beaches. Thanks for watching and subscribe if you do!
Getting tattooed on a classic sailboat in Costa Rica | Sailing Sitka Ep 154
Jay and Kenna have sailed their 41 foot sailboat from Canada to Costa Rica of the period of 2 years. Such an adventure does not come without obstacles including trial and errors. During their travels in Central America, they also met a fellow offshore sailor who happened to be a tattoo artist and on...
Journey to the most protected bay in Costa Rica | Sailing Sitka Ep 153
In this episode of Sailing Sitka, Jay and Kenna sail the squally and sloppy seas from Quepos to Golfito, down the pacific costa of Costa Rica. After having numerous encounters with rolley anchorages, we finally make landfall in a bay that is often mistaken for a lake, thats how protected it is. Some...
The real ups and downs of budget cruising | Sailing Sitka Ep 152
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 experience both the highs and lows that come with sailing and cruising offshore.Thank you for watching and subscribe if you enjoy!
Cruising Costa Rica on a 41′ Sailboat | Sailing Sitka Ep 151
In this episode of Sailing Sitka, Kenna and Jay sail from Bahía Ballena to Quepos on the pacific coast of Costa Rica.
THIS is why we sail offshore. | Sailing Sitka Ep 150
In this episode of sailing sitka, we sailed to Bahía Ballena here on the pacific side of Costa Rica. After some squally and rough seas, we were more than grateful to be anchored in such a postcard worthy anchorage. It really puts it into perspective exactly why sailors sail offshore... to arrive and...
Realities of sailing no one wants to talk about | Sailing Sitka Ep 147
In this episode of sailing sitka, we escape the wet and wild anchorage of Playa Del Coco to sail to a much more secluded and calm bay here in Costa Rica. We discuss the truths behind boat life and just how difficult the sailing lifestyle can be at times... subscribe if you agree and let us know some...
Feeling the wrath of Mother Nature: Can we catch a break? | Sailing Sitka Ep 146
In this episode of Sailing Sitka, we can't seem to catch a break when it comes to anchorages or the forecast of Central America. We sail to Playa Del Coco to officially check into the beautiful country of Costa Rica, which was a long but free process. Coco's left a mark on us but not one I...
Can we escape this rolley hell? | Sailing Sitka Ep 145
In this episode of sailing sitka, we are anchored in San Jaun Del Sur, the southernmost port in Nicaragua. As much as this anchorage was suggested by multiple friends, it turned out to be the second rolliest anchorage we've ever experienced on the pacific coast. In order to sail to Costa Rica w...
Sailing Central America | Sailing Sitka Ep 144
In this episode, we sail from Marina Puesta Del Sol at the northern tip of Nicaragua to San Juan Del Sur at the southern point of Nicaragua. During this sail we got to fly our drone, have visitors, sail with continuous wind and experience the crazy/wet squalls that Central America has to offer. Than...