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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Who is Tasha (Chase the Story)?
Chase the Story

Who is Tasha (Chase the Story)?

Hi Everyone! This is not a video episode but really just the story of who I am and what is to come in the future on this channel. I haven't posted a new video in 6 years since I left Cheeky Monkey and it's been a long journey back to myself and to making videos again. I hope this explain...
🔴 [LIVE] Surgery update, Adventures to come, MARCH YouTube Growth and a BIG announcement…
Daniella :-)

🔴 [LIVE] Surgery update, Adventures to come, MARCH YouTube Growth and a BIG announcement…

If you liked this video, I recommend watching my last sailing trip with John: Surgery update, Adventures to come, YouTube Growth and a BIG announcement... Join my YT growth newsletter: ****** SUPPORT THE PRODUCTION: 🤲 Consider supporting this channel on Patreon: 💪1-time contribution: 🔱Amazon:...
Solo Female Hikes OVER 25 KM to Remote Hot Springs!
Daniella :-)

Solo Female Hikes OVER 25 KM to Remote Hot Springs!

Solo Female Hikes OVER 25 KM to Remote Hot Springs! | S03E11 Sailing Pivo If you liked this video, I recommend watching the series from the beginning! In this video, I hike over 25km to the remote Kaitoke Hot Springs on Great Barrier Island off the East Coast of New Zealand! Join my YT growth n...
Something has changed for me.
Daniella :-)

Something has changed for me.

Something has changed for me. | S03E06 Sailing Pivo If you liked this video, I recommend watching this one, where my personal growth journey begins: In this video, my patrons and I meet up at Rocky Bay on the South side of Waiheke Island, New Zealand for our first ever "Sail In". We enj...
Would you try this? The Extreme Sports of Indonesia – Sailing SE Asia Ep.61
Sailing Yacht Florence

Would you try this? The Extreme Sports of Indonesia – Sailing SE Asia Ep.61

We experience the extremes in Sumbawa, Indonesia. From swimming with the WORLDS LARGEST SHARK to competing in the BUFFALO RACING WORLD CHAMPIONSHIPS. Extreme sports are alive and well in Sumbawa, water buffalo racing is all the rage and we turned up to the world championships, believe it or not, the...
Surviving The Middle: Ocean Racers Adventure Documentary Film
Ocean Racers

Surviving The Middle: Ocean Racers Adventure Documentary Film

An extraordinary, exciting and at times hazardous experience, in 2018 we pulled together a young sailing team to taken on the challenging 50th Anniversary Rolex Middle Sea Race on our Pogo 12.50, Hermes. From becalming seas to electrical storms, the team faced the fierce Mediterranean Sea head on....
18-06_Meet Tyler Bradt – extreeme is understatement (sailing ZERO)
sailing ZERO

18-06_Meet Tyler Bradt – extreeme is understatement (sailing ZERO)

Ahoy, What's the best thing about sailing around the world? It's definitely meeting so many different awesome people in so many different awesome spots. And their stories are breathtaking, jaw dropping and inspiring and I think there is nothing better. Having that said, I met Tyler Bradt. ...
I DARE YOU TO!! Jumping off a bridge | SMLS
Sailing Miss Lone Star

I DARE YOU TO!! Jumping off a bridge | SMLS

👇 BEHIND THE SCENES VIDEO👇 👀 Watch the DAILY VLOG here: Instagram😉 Guess WHAT?!! I have a new Podcast😎 It's FREE: SUPPORT THE FILMS: Camera Gear Small camera Big Camera Go-to Lens Sound Everyday tripod Favorite Sailing books Must Read! My all-time Favorite Inspiring Read C...
Surviving a TIGER SHARK! – S2:E53
Sailing Doodles

Surviving a TIGER SHARK! – S2:E53

Diving in tahiti with Tiger Sharks! Wow This was the best dive ever! Enter the giveaway here: Tiger Shark Dive Tahiti House of Happiness Air Bnb This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron Donate Via Paypal to ...
Big-Ass Boat to the Rescue – Fakarava – Chase the Story 49
Chase the Story

Big-Ass Boat to the Rescue – Fakarava – Chase the Story 49

Hey Everyone! I realize it’s been over a year since you’ve seen any action on this YouTube Channel and there is a good explanation for this — Ryan and I split up a year ago in French Polynesia and we are in the process of getting a divorce. If you watch to the end of the video, you’ll see a little...
The SECRETS of being a LIVEABOARD Sailor | SMLS S6E17
Sailing Miss Lone Star

The SECRETS of being a LIVEABOARD Sailor | SMLS S6E17

👇 BEHIND THE SCENES VIDEO👇 👀 Watch the DAILY VLOG here: Instagram😉 Guess WHAT?!! I have a new Podcast😎 It's FREE: SUPPORT THE FILMS: Camera Gear Small camera Big Camera Go-to Lens Sound Everyday tripod Favorite Sailing books Must Read! My all-time Favorite Inspiring Read C...
Rock Climb Newfoundland [Flatrock]
Wildly Intrepid Sailing

Rock Climb Newfoundland [Flatrock]

Ever wanted to try rock climbing on the "ROCK" or Newfoundland? Join us as we travel to the East coast of Newfoundland near St. John's to the small community of Flatrock. There we sport climb alongside minke and humpback whales and watch icebergs with friends. Rock climb Newfoundland ...
Exploring Fakarava & Challenging the Ping Pong Champ – Chase the Story 48
Chase the Story

Exploring Fakarava & Challenging the Ping Pong Champ – Chase the Story 48

WANT A CHEEKY MONKEY T-SHIRT?! Check out our NEW merchandise shop here for all kinds of fun goodies: Hey Everyone! It's taken a long time to upload this video in the South Pacific, but it's finally here! This video has a little of everything -- fixing our broken dinghy engine in the mid...
Sailing the Dangerous Archipelago! Chase the Story 47
Chase the Story

Sailing the Dangerous Archipelago! Chase the Story 47

Story 47 -- Tahuata to Fakarava: Sailing the Dangerous Archipelago Hey everyone! First of all, here's a link to the Cruiser's Handbook of Fishing I mentioned: And if you buy it using this link, we get a little kickback - so go add it to your cart if you don't already have it and y...
HD QUALITY: Prepping the Boat to Sail Off the Grid – Story 46
Chase the Story

HD QUALITY: Prepping the Boat to Sail Off the Grid – Story 46

Hey Everyone! Your eyes are not playing tricks on you, no -- this is the same video we uploaded yesterday...ONLY BETTER QUALITY. So sorry about the mix-up (that was me, Tasha, that effed up there), but somehow the video we uploaded was exported at the wrong size - arg! So rather than take down the ...
Prepping the Boat to Sail Off the Grid – Chase the Story 46
Chase the Story

Prepping the Boat to Sail Off the Grid – Chase the Story 46

Episode 46 - Prepping the Boat to Sail Off the Grid Our crew have all left and Cheeky Monkey is back to a crew of two: Tasha and Ryan. They're making plans to sail off the grid in French Polynesia so they can explore some remote islands and they need to do some work before the boat is ready to...
Moving to Tonga – Ep.1 Living the Island Life (Underwater Ally Adventures)
Sailing Popao - Underwater Ally Productions

Moving to Tonga – Ep.1 Living the Island Life (Underwater Ally Adventures)

Chasing an endless summer: Join us as we embark on an adventure of a lifetime chasing the sun to our new home in the Kingdom of Tonga. In this episode we show you our new island home and backyard dive site. We go out spearfishing and cook one of our favourite dishes. *** TONGA VOLCANIC ERUPTION** ...
In search of Tikis in the South Pacific – Chase the Story 45
Chase the Story

In search of Tikis in the South Pacific – Chase the Story 45

To see where the MEET UPS are happening, follow this link: In this video, Ryan and Tasha go on an epic roadtrip across the remote Marquesas island of Hiva Oa in search of the largest tiki statues in the world. It turned out we barely got out of first gear the entire way - the 42km from one corner ...
EXOTIC DANCING & SAD GOOD-BYES: THE MARQUESAS — Chase the Story 44
Chase the Story

EXOTIC DANCING & SAD GOOD-BYES: THE MARQUESAS — Chase the Story 44

Exploring remote Fatu Hiva on foot is not for the faint-of-heart but it does reward the crew of Cheeky Monkey with some of the most spectacular views we’ve ever seen. We attend a local village competition in Hanavave where Polynesians of all ages show off their spectacular singing and dancing talent...
It doesn’t get better than this!! Sailing the Pacific – Chase the Story 43
Chase the Story

It doesn’t get better than this!! Sailing the Pacific – Chase the Story 43

If you’ve ever wondered what it’s like to see land after three weeks at sea – this is the video for you. And it isn’t just any old land, this is Fatu Hiva, one of the most remote, untouched and breathtaking islands in the world! We rush to fill the freezer full of fish before arrival, while tackli...
OCEAN SAILING – Could you do this? Chase the Story 42
Chase the Story

OCEAN SAILING – Could you do this? Chase the Story 42

Ocean Sailing - Could you do this? Chase the Story 42 We get asked a lot by viewers about what it’s like to sail across an ocean. You ask, we deliver! :) So this is our video to answer that million-dollar question. We follow Liam around for a single day, recording what he gets up to, from his morni...
WHAT ARE WE AFRAID OF? Sailing Across the Pacific  – Chase The Story 41
Chase the Story

WHAT ARE WE AFRAID OF? Sailing Across the Pacific – Chase The Story 41

Sailing Across the Pacific: This is the moment we have all been excited about - but it turns out we're also a little afraid of also!! In our sail around the world, this voyage is probably going to be our furthest distance covered and longest time at sea. As we prepare to sail across the Pacific...
WHY SAILING IS THE BEST WAY TO TRAVEL THE WORLD! You must watch this!!
Chase the Story

WHY SAILING IS THE BEST WAY TO TRAVEL THE WORLD! You must watch this!!

Sailing: Why SAILING is the BEST way to TRAVEL the WORLD!! This video isn't one of our scheduled "stories" per se, but Kristi put together this short video focused on Tasha and her sailing and travel experiences and we just had to share it! It's short, it's sweet, and it gi...
GALAPAGOS ISLANDS – ARE THEY WORTH IT? – Chase the Story 40
Chase the Story

GALAPAGOS ISLANDS – ARE THEY WORTH IT? – Chase the Story 40

With our amazing sailing trip to the Galapagos Islands coming to an end, we go in search of the elusive penguins (yes - apparently there are penguins at the Equator - who knew??) Along the way, we come across swimming iguanas, a No Swimming Sign (which we thankfully listened to, as it was Shark Cent...
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