Watch Sailing & Boating Adventures Around the World tagged “Epic fail”

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What seems to be the problem? (Engine failure diagnostics) raw & extended | Sailing Sitka Ep 171
Sailing Sitka

What seems to be the problem? (Engine failure diagnostics) raw & extended | Sailing Sitka Ep 171

Jay and Kenna sail back to Linton Bay in order to get their engine in top notch after having experienced multiple failures. They spend countless hours over the course of a few days eliminating what could be the culprits while on anchor, but they won't know...
Engine Failure… NOT AGAIN?! Feeling Hopeless in Rough Seas…| Sailing Sitka Ep 170
Sailing Sitka

Engine Failure… NOT AGAIN?! Feeling Hopeless in Rough Seas…| Sailing Sitka Ep 170

Jay and Kenna felt ready—prepared and excited to return to paradise. After a week anchored in Linton Bay, they set sail for what should have been a smooth trip back to the San Blas Islands. But that’s not how things played out.Pounding into relentless ...
Getting delivered boat parts to the edge of civilization (FAIL)  | Sailing Sitka Ep 167
Sailing Sitka

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. ...
Sometimes cruising doesn’t always go according to plan… | Sailing Sitka Ep 166
Sailing Sitka

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 si...
Trouble in Paradise… | Sailing Sitka Ep 165
Sailing Sitka

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 f...
Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164
Sailing Sitka

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 adventu...
Why our engine FAILED while transiting the Panama Canal | Sailing Sitka Ep 161
Sailing Sitka

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 eve...
Engine Nightmare, Breakages & Bad Luck Continues… Panama Canal Day 2 | Sailing Sitka Ep 160
Sailing Sitka

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 d...
Panama Canal Nightmare: Engine Failure, No Sails, Will we make it through? | Sailing Sitka Ep 159
Sailing Sitka

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 alr...
Realities of sailing no one wants to talk about | Sailing Sitka Ep 147
Sailing Sitka

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......
Repairing our damaged masts… (+ splash day)  | Sailing Sitka Ep 140
Sailing Sitka

Repairing our damaged masts… (+ splash day) | Sailing Sitka Ep 140

In this episode of sailing sitka, we take the time to repair our damaged sitka spruce masts from some very destructive holes created by woodpeckers here in Chiapas, Mexico. We are so happy to be splashed and back in the marina, floating for the first time ...
Fijian local left speechless by our gift 🥲  (Episode 281)
Sailing Parlay Revival

Fijian local left speechless by our gift 🥲 (Episode 281)

This week we continue sailing around Fiji, with some very important guests! We sail out to the Yasawa island group, and even get to swim with manta rays! But when glenn goes to give his fish a smooch, he learns that's a bad idea! Get your tickets here if ...
Kiwi scares Kangaroo!
Sailing Parlay Revival

Kiwi scares Kangaroo!

Got the big fella in the bush! SV Parlay is a hurricane damaged Lagoon 450 catamaran, which Colin rebuilt with friends and has started sailing around the world. We found bulkhead damage on their catamaran in Panama, so have fixed her up, and are now saili...
RANDOM DOG JUMPS ON A SHARK!! #sharkvsdog #shark #dogshorts #sharkweek
Sailing Parlay Revival

RANDOM DOG JUMPS ON A SHARK!! #sharkvsdog #shark #dogshorts #sharkweek

Cant believe this random dog did this right in front of our eyes! SV Parlay is a hurricane damaged Lagoon 450 catamaran, which Colin rebuilt with friends and has started sailing around the world. We found bulkhead damage on their catamaran in Panama, so h...
We DRAGGED at anchor… | Sailing Sitka Ep 125
Sailing Sitka

We DRAGGED at anchor… | Sailing Sitka Ep 125

In a recent episode, Sailing Sitka shares their first-ever experience with dragging at anchor. Learn how Jay and Kenna handled the challenging situation and what lessons they took away from it.
We sailed HERE and got STUCK in the jungle! | Sailing Sitka Ep 123
Sailing Sitka

We sailed HERE and got STUCK in the jungle! | Sailing Sitka Ep 123

Jay and Kenna from Sailing Sitka continue their sailing journey, heading 25 miles south to Baja Tenacatita. They face obstacles like shallow waters and unexpected challenges while navigating a jungle mangrove.
Sailing into a Boat Cemetery… (Hurricane aftermath in Mexico) | Sailing Sitka Ep 115
Sailing Sitka

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....
Sailing to an uninhabited island with a stranger! | Sailing Sitka Ep 113
Sailing Sitka

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.
Hand steering in SPORTY conditions (autopilot down)… | Sailing Sitka Ep 108
Sailing Sitka

Hand steering in SPORTY conditions (autopilot down)… | Sailing Sitka Ep 108

Hand steering in sporty conditions. In this episode of Sailing Sitka, we sail from Ballandra to Escondido in 25-30 knots. Once we get there, we dive into two major breakages onboard Sitka... Thanks for watching!
“WE NEED TO LEAVE NOW.” | Sailing Sitka Ep 107
Sailing Sitka

“WE NEED TO LEAVE NOW.” | Sailing Sitka Ep 107

We need to leave now! In this episode of sailing sitka, we sail from Isla Coronados to Loreto so we can provision on food, water, diesel ect. When doing so, things turned for the worst and we had to abort our already-unprotected anchorage in Loreto and b-l...
Leaky boat, no sleep, low batteries… NOTHING can stop us from SAILING on! | Sailing Sitka Ep 105
Sailing Sitka

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 a...
This BAD news changes everything… | Sailing Sitka Ep 104
Sailing Sitka

This BAD news changes everything… | Sailing Sitka Ep 104

This bad news changes everything. On this episode of sailing sitka, we are stuck in a rough anchorage and if that wasn't bad enough, we figure out some dreadful news regarding our boat and our cruising future plans. Sailing and the cruising lifestyle can b...
There is NO going back now… | Sailing Sitka Ep 92
Sailing Sitka

There is NO going back now… | Sailing Sitka Ep 92

There is no going back now... In this episode of Sailing Sitka, we come up with an out of the box solution to our tides marine track problem... Stupid? Maybe... but at this point we have no other option.
Did we just WASTE THOUSANDS $$$ on this? | Sailing Sitka Ep 91
Sailing Sitka

Did we just WASTE THOUSANDS $$$ on this? | Sailing Sitka Ep 91

Did we just waste thousands of dollars on this? In this episode of sailing sitka, we come upon some sad news. After doing some regular maintenance to our wooden masts, we try out our new piece of equitment that will change the sailing game for Sitka... onl...
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