Watch Sailing & Boating Adventures Around the World

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48 Hours Before We Enter the Panama Canal
Sailing Big Lost

48 Hours Before We Enter the Panama Canal

In 48 hours, we enter the Panama Canal. But right now… it still feels like just another work week. Before a major milestone like a Panama Canal transit, life doesn’t look dramatic. It looks like cleaning engine rooms, repairing sails, servicing our dinghy motor, switching Starlink to DC power, and ...
Rained Out in San Blas
Sailing Big Lost

Rained Out in San Blas

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’ve had rain off and on since arriving in Panama, and as we begin exploring the San Blas—now learning their true name, the Guna Yala Isla...
Sailing Into Guna Yala: From Puerto Obaldía to Isla Pinos
Sailing Big Lost

Sailing Into Guna Yala: From Puerto Obaldía to Isla Pinos

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 Tue...
An update you’re not expecting!
Sailing Sitka

An update you’re not expecting!

Thats right! We're starting a private charter business with Sitka in the San Blas Islands!! Click the link here to check out our website and inquire about booking ➡️ Thank you to everyone who watches, supports and has contributed to our journey. We love and appreciate you all.
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 10–14 ft seas on a lee shore, their engine faile...
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 sight, this is all cruising. Thanks for riding...
San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163
Sailing Sitka

San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163

Jay and Kenna depart from Shelter Bay marina after a week straight of boat work and diagnosing problems. Finally, after stopping in Linton bay for one night, they sail to the desolate and world renowned San Blas islands. A dream come true. They've worked hard for years and the hustle has now tu...
“50 years of history GONE in a second…” | Sailing Sitka Ep 162
Sailing Sitka

“50 years of history GONE in a second…” | Sailing Sitka Ep 162

Jay and Kenna are in Shelter Bay Marina, fixing some minor and major problems they've encountered while transiting the Panama Canal, on top of that they do some routine and periodic maintenance to make sure their 50 year old sailboat is ready to sail her way toward the desolate and world-renown...
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 even made it all the way through, they now can ...
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 done with just yet. The bad luck sticks ...
Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158
Sailing Sitka

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
Sailing Sitka

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
Sailing Sitka

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
Sailing Sitka

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!
Did we break a sailboat record!? Completing the Panama Canal at night in only 6 Hours! | Ep 3
Searching for the Edge

Did we break a sailboat record!? Completing the Panama Canal at night in only 6 Hours! | Ep 3

Searching for the Edge Website ➡ Filmed November 2022 6 Days after the closing of sale on the vessel we FINALLY have the travel papers and cruising papers needed to start our journey from Panama City, Panama to Florida! We wrap up the shipyard week with critical repairs and an unexpected haul out...
Solo adventures can be scary 😬 Meeting a crocodile kayaking up the river Cacique – UNTIE THE LINES
WhiteSpotPirates

Solo adventures can be scary 😬 Meeting a crocodile kayaking up the river Cacique – UNTIE THE LINES

⇩ Watch the full movie ⇩ Download the full movie length documentary UNTIE THE LINES at ⇩ Want to support these videos ⇩ ► PATREON ► PAY PAL ⇩ Binge watch from the beginning ⇩ ► Season 1 ► Season 2 ► Season 3 ► Season 4 ⇩ More about Nike & Karl’s journey ⇩ ► INSTAGRAM ► FACEBOOK ► MY ...
Solo sailing to beautiful rugged & remote bays where tourists usually don’t go – UNTIE THE LINES
WhiteSpotPirates

Solo sailing to beautiful rugged & remote bays where tourists usually don’t go – UNTIE THE LINES

⇩ TotalBoat products ⇩ Get 10% off all products on by using TBNike at the check out. ⇩ Watch the full movie ⇩ Download the full movie length documentary UNTIE THE LINES at ⇩ Want to support these videos ⇩ ► PATREON ► PAY PAL ⇩ Binge watch from the beginning ⇩ ► Season 1 ► Season 2 ► Season...
How I nearly ran my friend’s sailboat aground 😬. Tidal anchoring on the edge – UNTIE THE LINES
WhiteSpotPirates

How I nearly ran my friend’s sailboat aground 😬. Tidal anchoring on the edge – UNTIE THE LINES

⇩ Watch the full movie ⇩ Download the full movie length documentary UNTIE THE LINES at ⇩ Want to support these videos ⇩ ► PATREON ► PAY PAL ⇩ Binge watch from the beginning ⇩ ► Season 1 ► Season 2 ► Season 3 ► Season 4 ⇩ More about Nike & Karl’s journey ⇩ ► INSTAGRAM ► FACEBOOK ► MY ...
BOCAS DEL TORO – SwT 41 The best place to spend the Caribbean hurricane season
Sailing with Thomas

BOCAS DEL TORO – SwT 41 The best place to spend the Caribbean hurricane season

Let me take you back to happy days in the exotic region of Bocas del Toro, Panama. In this episode, I'm sharing my experience with Bocas del Toro as one of the best places to spend the Caribbean hurricane season. I am planning to go back there later this spring so I thought it was a good idea t...
Out looking for crocodilios and battling with taking apart my Windpilot Pacific – UNTIE THE LINES
WhiteSpotPirates

Out looking for crocodilios and battling with taking apart my Windpilot Pacific – UNTIE THE LINES

⇩ Watch the full movie ⇩ Download the full movie length documentary UNTIE THE LINES at ⇩ Want to support these videos ⇩ ► PATREON ► PAY PAL ⇩ Binge watch from the beginning ⇩ ► Season 1 ► Season 2 ► Season 3 ► Season 4 ⇩ More about Nike & Karl’s journey ⇩ ► INSTAGRAM ► FACEBOOK ► MY ...
When YouTube channels collide | Racing with Project Atticus | Episode 62
Sailing Parlay Revival

When YouTube channels collide | Racing with Project Atticus | Episode 62

In this episode we race in the 2nd annual regatta in Bocas Del Toro, Panama. Youtube channel Sailing Project Atticus join us for the day as we race our 45ft catamaran with 26 other boats. We then tie up to a real life pirate ship for the after party! Check out some of Project Atticus's videos h...
PANAMA CANAL ON A SAILBOAT – Chase the Story 33
Chase the Story

PANAMA CANAL ON A SAILBOAT – Chase the Story 33

Panama Canal on a Sailboat – Chase the Story 33 Here we come, Pacific Ocean – we’ll be sailing across you soon enough! In this episode we are back in tropical Panama as our catamaran Cheeky Monkey traverses two continents through one of the largest engineering projects ever undertaken in the world,...
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