Watch Sailing & Boating Adventures Around the World – Page 158 of 171

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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SABA, WTF is this Place!?— Sailing Uma [Step 82]
Sailing Uma

SABA, WTF is this Place!?— Sailing Uma [Step 82]

Spending some time in Saba made us realize just how magical this island is. Everyone is so friendly and everything has an interesting story (from the road, to the sulphur mine, to its crazy airport) We had an amazing couple of days exploring its wonders and without a doubt, Saba has officially becom...
The End
Finding Simon

The End

Music by Lion, Meets Lizard ( Changing directions, new travels, new adventures, and new videos coming very soon. Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Ca...
SECRET DIVE SITE in the BVIs — Sailing Uma [Step 81]
Sailing Uma

SECRET DIVE SITE in the BVIs — Sailing Uma [Step 81]

This week as we continue sailing the BVI's, we check out a super secret, very new and amazing dive spot off the North West coast of Virgin Gorda BVI. We also get our main sail repaired before sailing to Saba with a South African stowaway. If you enjoyed this episode, please give it thumbs up,...
Wild Nights and Deserted Islands~Sailing DRENCHED Ep.24~
Expedition Drenched

Wild Nights and Deserted Islands~Sailing DRENCHED Ep.24~

Goat stampedes, crabs, hot springs, and diving our very own private deserted island! This was probably one of the best 24 hours of our lives! After we meet a new friend Gonzi on the island of Nevis, we go on a whirlwind adventure of Pinney's (PENIS) beach, sunshine's beach bar, meet some ...
53 – In the Land of Hobbits (NZ Road Trip #6)
Out Chasing Stars

53 – In the Land of Hobbits (NZ Road Trip #6)

This is it. The final part of our New Zealand road trip. Fortunately, we end things with a bang, visiting the Weta Workshop in Wellington and then continuing up north to have a romantic Valentine's Day dinner (Amy's choice!) with all our hobbit friends at Hobbiton. Visiting Hobbiton was...
Falling Off a Cliff – Pushing North 113
Finding Simon

Falling Off a Cliff – Pushing North 113

Music by Julian Mae ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make travel ...
Struggling to Live Minimally – Pushing North 112
Finding Simon

Struggling to Live Minimally – Pushing North 112

Music by Dixxy ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make travel vlogs...
SHAKEDOWN SAILING TRIP Connecticut to Boston Harbor
Wicked Salty

SHAKEDOWN SAILING TRIP Connecticut to Boston Harbor

Our first time time using our new sailboat, taking her back home. Still figuring out how things work on the boat and what we will need for moving her down south to warmer latitudes for the winter. Prepping to be living on the boat full time coming up! Music by Oli McCracken Vlog #99! Help supp...
Sailing Off Anchor To Ten Bay Beach | Sailboat Story 54
Sailboat Story

Sailing Off Anchor To Ten Bay Beach | Sailboat Story 54

In this vlog, we sail off anchor from Rock Sound as we travel to Ten Bay Beach in Eleuthera. One thing I've noticed, is that Bahamians know how to cook good food. Wow. Case-in-point, take this day when we went to a local's house and enjoyed an amazing home-cooked meal of chicken, ribs, pe...
Naked Night Dive + Exploring the Baths — Sailing Uma [Step 80]
Sailing Uma

Naked Night Dive + Exploring the Baths — Sailing Uma [Step 80]

After seeing a group of night scuba divers show up, we decided to go along for the ride and free dive around them... We had no idea they would have actually spotted the fact that we were very much naked. After a good time at Great Dog island, we sailed over to the Baths and had some fun monkeying ar...
Sailing Around the World – Will This Man Save the Turtles? Ep. 34
Sailing Malou

Sailing Around the World – Will This Man Save the Turtles? Ep. 34

The discovering of our little paradise island Bequia continues. We make it to the far south point to watch some cool cave houses and play in a desserted playground… The next day we hike to the Turtle Sanctuary and meet its founder Orton King. And then we keep sailing south… Support us by becoming a...
Hot Motorbike Date – Pushing North 111
Finding Simon

Hot Motorbike Date – Pushing North 111

Music by Clueless Kit ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make trave...
Goodbye Friends – Pushing North 110
Finding Simon

Goodbye Friends – Pushing North 110

Music by Jacob Riggs ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make travel...
Champ the Floating Dog – Pushing North 109
Finding Simon

Champ the Floating Dog – Pushing North 109

Music by DIxxy ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make travel vlogs...
52 – Of Course We Stopped in Wine Country! (NZ Road Trip #5)
Out Chasing Stars

52 – Of Course We Stopped in Wine Country! (NZ Road Trip #5)

The weather was getting a bit too cold for our liking, so rather than continuing south, we cut over to the east side of the South Island. First stop was in Christchurch where we got to see an awesome museum exhibit on the 75 year history of Air New Zealand, complete with a virtual reality look at t...
The Beginning of the End of Vanlife – Pushing North 108
Finding Simon

The Beginning of the End of Vanlife – Pushing North 108

Music by Keith Beard ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make travel...
Van-Made Burger and Fries – Pushing North 107
Finding Simon

Van-Made Burger and Fries – Pushing North 107

Music by Julian Mae ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make travel ...
Beautiful Yoho National Park – Pushing North 106
Finding Simon

Beautiful Yoho National Park – Pushing North 106

Music by Andrew Rothschild ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make ...
Our Thoughts on Going Bare (MJ Sailing – EP 24)
MJ Sailing

Our Thoughts on Going Bare (MJ Sailing – EP 24)

'Why aren't you going to paint your hull?' 'If you're going to leave it bare, you should at least shine it up'. 'You're in for a ton of corrosion if you leave your hull bare'. These are just a sample of the questions and comments we've been gettin...
Big Furry Neighbours – Pushing North 105
Finding Simon

Big Furry Neighbours – Pushing North 105

Music by HHSweater ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make travel v...
Ancient Forest – Pushing North 104
Finding Simon

Ancient Forest – Pushing North 104

Music by Clueless Kit ( Really appreciate the support, check out the Patreon for more access and perks: If Patreon isn't your thing, I also have a Paypal.me link: paypal.me/ShelbyandSimon I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I make trave...
7] THAT’S NOT ALLOWED ON A BOAT! | Abandon Comfort – Sailboat Restoration
Abandon Comfort

7] THAT’S NOT ALLOWED ON A BOAT! | Abandon Comfort – Sailboat Restoration

I get asked all the time – Ryan, how do I get my [wife, gf, partner] on board? Compromise. Do you think I needed a queen mattress on board? No, I didn’t but the better-looking half of the dream did. Try to transition the conversation from “my” dream to “our” dream - my .02. Stay tuned for next Thurs...
Scuba Diving At Booby Island! ~Sailing Drenched Ep. 23~
Expedition Drenched

Scuba Diving At Booby Island! ~Sailing Drenched Ep. 23~

Join us as we sail from Statia to St. Kitts, where we check out the local scene, enjoy fiesta friday, ride the most beautiful train in the world, then cruise over to Nevis for some diving at Booby Island. Life is good onboard Sophisticated Lady! Help keep the dream afloat, support us on Patreon!...
51 – The West Side of the South Island (NZ Road Trip #4)
Out Chasing Stars

51 – The West Side of the South Island (NZ Road Trip #4)

Our New Zealand road trip continues as we take the ferry down to the South Island and explore along the north and west coasts. We do a bit of beginner level fishing (hoping our fishing mojo increases!), see some delicious looking pancake rocks, hike in the beautiful NZ countryside and even get out ...
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