Watch Sailing & Boating Adventures Around the World tagged “Cheoylee”

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 to Santa Rosalia | Sailing Avocet
Sailing Avocet

Sailing to Santa Rosalia | Sailing Avocet

Join us on our sail from Puerto Refugio to Santa Rosalia, where things got a tad sporty on the water! Luckily, Avocet handed it like a champ as we sailed wing on wing and surfed down waves in front of @KesselUnderway Don't miss out on upcoming sailing ad...
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...
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 h...
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...
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 ...
The real ups and downs of budget cruising | Sailing Sitka Ep 152
Sailing Sitka

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 an...
Cruising Costa Rica on a 41′ Sailboat | Sailing Sitka Ep 151
Sailing Sitka

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.
Feeling the wrath of Mother Nature: Can we catch a break? | Sailing Sitka Ep 146
Sailing Sitka

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...
Can we escape this rolley hell? | Sailing Sitka Ep 145
Sailing Sitka

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 ...
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 ...
We have holes in our masts! Inspecting woodpecker damage… | Sailing Sitka Ep 139
Sailing Sitka

We have holes in our masts! Inspecting woodpecker damage… | Sailing Sitka Ep 139

On this episode of sailing Sitka, we tackle day 2 and 3 in the boat yard here in Chiapas, Mexico. During this time we start diving into our biggest worry yet. While we were away for off season, we got notified that a woodpecker (or more) were attacking our...
WE’RE BACK! Day 1 of Season 3! (Chiapas, Mexico) | Sailing Sitka Ep 138
Sailing Sitka

WE’RE BACK! Day 1 of Season 3! (Chiapas, Mexico) | Sailing Sitka Ep 138

WE"RE BACK and better than ever! Welcome to season 3 of sailing sitka! After 6 months of off season, working away at saving money for our cruising lifestyle, we have finally returned to Sitka here in Chiapas, Mexico. In this episode, we start plugging away...
3 days of RAW boat life at sea. | Sailing Sitka Ep 129
Sailing Sitka

3 days of RAW boat life at sea. | Sailing Sitka Ep 129

3 days of raw boat life footage while sailing at sea. In this episode of sailing sitka, we sail 190 NM from Ensenada Carrizal to Zihuatanejo and show what it is like to spend numerous days sailing offshore the pacific coast of Mexico.
The epitome of cruising! (Ensenada Carrizal) | Sailing Sitka Ep 128
Sailing Sitka

The epitome of cruising! (Ensenada Carrizal) | Sailing Sitka Ep 128

Join the adventures of Jay and Kenna as they uncover the beauty of Ensenada Carrizal, a secluded gem in Mexico. Watch now and experience the stunning snorkeling spots, their journey to Sail 190 nautical miles to Zano, and gain valuable sailing tips from th...
We sailed HERE to explore a 300ft SHIPWRECK | Sailing Sitka Ep 127
Sailing Sitka

We sailed HERE to explore a 300ft SHIPWRECK | Sailing Sitka Ep 127

In this captivating episode of Sailing Sitka, hosts Jay and Kenna share their thrilling adventure exploring a massive 300ft sunken cargo ship near Santiago Bay, Mexico. Discovering remnants from the historic 1959-wrecked San Luiso, they witness how it now ...
“A shocking sight to sail by…” | Sailing Sitka Ep 126
Sailing Sitka

“A shocking sight to sail by…” | Sailing Sitka Ep 126

Sailing Sitka Episode 126: Leaving Barra Manzano & Exploring Shipwrecks - Join Canadian couple Jay and Kenna as they depart from Barra Manzano, Mexico after two weeks spent making new friends, partying, and eating great food. Setting sail for Manzano, 27 n...
Cruising down the Pacific Coast of Mexico on our Sailboat | Sailing Sitka Ep 124
Sailing Sitka

Cruising down the Pacific Coast of Mexico on our Sailboat | Sailing Sitka Ep 124

Join young Canadians, Jay and Kenna from Sailing Sitka, as they set off for an adventure sailing through Mexico's stunning Pacific Coast aboard their boat. Dive into their remarkable experiences navigating water-filled challenges, finding a rare milk sourc...
This is the FURTHEST SOUTH we’ve sailed so far! | Sailing Sitka Ep 121
Sailing Sitka

This is the FURTHEST SOUTH we’ve sailed so far! | Sailing Sitka Ep 121

In this episode, Jay and Kenna from Sailing Sitka share their experience sailing further south than ever before, encountering challenges and joys along the way. Tune in to learn about their latest adventure!
THIS is what makes cruising worth it! | Sailing Sitka Ep 120
Sailing Sitka

THIS is what makes cruising worth it! | Sailing Sitka Ep 120

Join Canadian couple Jay and Kenna in Season 2 of Sailing Sitka as they venture further south with Sitka from Victoria BC, Canada exploring Mexico on their sailboat journey. Witness boat repairs, meet cruisers at the anchorages, and learn valuable lessons ...
Sporty Sailing on an Offshore Passage | Sailing Sitka Ep 119
Sailing Sitka

Sporty Sailing on an Offshore Passage | Sailing Sitka Ep 119

Join Jay and Kenna of Sailing Sitka as they navigate a sporty offshore sailing passage from Los Morros on the Baja side of Mexico to Lac Cruz on the mainland, crossing the Sea of Cortez. Witness their highs and lows while at sea, learning valuable lessons ...
Crossing the Sea (350NM) Pt. 1 | Sailing Sitka Ep 118
Sailing Sitka

Crossing the Sea (350NM) Pt. 1 | Sailing Sitka Ep 118

Jay and Kenna from Sailing Sitka share their epic 350 NM sea journey from Los Morros to La Cruz, Mexico in Season 2 Episode 118. Join them on this offshore sailing adventure with special guest Warren as they navigate the challenges and excitement of crossi...
Passage Mode Activated! Leg 1 of our longest SAIL of the Season. | Sailing Sitka Ep 117
Sailing Sitka

Passage Mode Activated! Leg 1 of our longest SAIL of the Season. | Sailing Sitka Ep 117

Discover the journey of sailing the Sea of Cortez with Sailing Sitka as they cross from La Paz to mainland Mexico, facing autopilot issues and embracing life at sea with friends.
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....
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