Watch Sailing & Boating Adventures Around the World – Page 164 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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Van Gets Smashed and Bleeds – Baja or Bust 65
Finding Simon

Van Gets Smashed and Bleeds – Baja or Bust 65

Music by Twisla ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 months....
Champ’s Birthday – Baja or Bust 63
Finding Simon

Champ’s Birthday – Baja or Bust 63

Music by Ambalance ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 mont...
The Pinnacle of Glamping – Baja or Bust 62
Finding Simon

The Pinnacle of Glamping – Baja or Bust 62

Go-Van ( ( Music by Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 mon...
Busses by the Bridge – Baja or Bust 61
Finding Simon

Busses by the Bridge – Baja or Bust 61

Go-Van ( ( Music by Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 mon...
We have the URGE to SUBmerge! ~DRENCHED Ep. 12~
Expedition Drenched

We have the URGE to SUBmerge! ~DRENCHED Ep. 12~

Want to win a dive package for 2 on the Big Island of Hawaii?! Check out our Patreon page: To see the episodes that feature the dives you can win: Manta Night Dive: Blackwater Dive: In this episode we go on one of the funnest, craziest dive missions we've ever attempted. We kayak out ...
Route 66 – Baja or Bust 60
Finding Simon

Route 66 – Baja or Bust 60

Go-Van ( ( Music by Drowned Sound ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North Am...
Megan Heads Home – S1:E16
Sailing Doodles

Megan Heads Home – S1:E16

In this Episode we explore the lower exumas, snorkel near David Copperfield's private island and dive the stainless steel piano he had placed underwater. Megan heads back to Kansas to witness the birth of her sister's first baby. This channel is funded by viewers like you. Visit our web...
Camping in Joshua Tree – Baja or Bust 59
Finding Simon

Camping in Joshua Tree – Baja or Bust 59

Rubbertramp YouTubers:: Brocton Films ( Psychic Sojourns ( Dave2D ( Wanderlustman ( GrungeLuggage Tours ( Caravan Carolyn ( Debra Joy ( RV Pandemonium ( Music by Ambalance ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ott...
Meet the Rubbertramps – Baja or Bust 58
Finding Simon

Meet the Rubbertramps – Baja or Bust 58

BoondockingLife ( Bex Cat-herder ( Dave2D ( Music by Random Temple ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van wit...
Broke My Damn Camera – Baja or Bust 57
Finding Simon

Broke My Damn Camera – Baja or Bust 57

Music by Stick/Slip Behaviour ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America...
The Grand Finale – Baja or Bust 56
Finding Simon

The Grand Finale – Baja or Bust 56

Music by Mons Vi ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 months...
Exploring Caves – Baja or Bust 55
Finding Simon

Exploring Caves – Baja or Bust 55

Music by Huxlay ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 months....
Insane ICW Bridges Of South Florida | Sailboat Story 30
Sailboat Story

Insane ICW Bridges Of South Florida | Sailboat Story 30

We go through many icw bridges as we sail South along the intracoastal waterway, getting closer and closer to the Bahamas everyday! Things change the further South that you get along the ICW. The water gets clearer, the people get crazier, and the bridges become MUCH more numerous. These changes o...
Meet the Maui MERMAID! ~DRENCHED Ep. 11~
Expedition Drenched

Meet the Maui MERMAID! ~DRENCHED Ep. 11~

Mermaids and Turtles! What a great first day in Maui! In this episode we leave Big Island (after a near death encounter with a centipede that has left me with nightmares) and head over to Maui. We take you along for a work day as we film a marketing video for Maui Spearfishing Academy and finish ...
Amazing Natural Hot Spring in the Mountains – Baja or Bust 54
Finding Simon

Amazing Natural Hot Spring in the Mountains – Baja or Bust 54

Music by Ambalance ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 mont...
Camping in the Clouds – Baja or Bust 53
Finding Simon

Camping in the Clouds – Baja or Bust 53

Music by Lion, Meet Lizard ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America fo...
SandBoganning – Baja or Bust 52
Finding Simon

SandBoganning – Baja or Bust 52

Music by Lion, Meet Lizard ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America fo...
Face Off with a 14ft Tiger Shark~DRENCHED Ep. 10~
Expedition Drenched

Face Off with a 14ft Tiger Shark~DRENCHED Ep. 10~

An erupting volcano creating new earth as lava flows into the sea, and the Tiger Shark mugging of a lifetime. Probably the best two days of our lives (except for the running out of gas part, but that was still kinda fun its own way) Support us on Patreon and become our dive buddy: If you liked o...
Gorgeous Foothills Free Camping – Baja or Bust 51
Finding Simon

Gorgeous Foothills Free Camping – Baja or Bust 51

Music by Knomad ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 months....
1] Goodbye $50,000 Debt, Hello Bluewater Sailboat | Abandon Comfort
Abandon Comfort

1] Goodbye $50,000 Debt, Hello Bluewater Sailboat | Abandon Comfort

We hope our series will serve as a place for actionable advice for those looking to pursue an alternative lifestyle. Whether it be sailing the world or just living smaller. We have never been happier than we are now. Living small on our bluewater sailboat has exceeded our every expectation and we wa...
Exploring a Space Base – Baja or Bust 50
Finding Simon

Exploring a Space Base – Baja or Bust 50

Music by Sentimentalist ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6...
Post Hurricane — Sailing Uma [Step 55]
Sailing Uma

Post Hurricane — Sailing Uma [Step 55]

After Matthew had passed through, it was time to put everything back together and sail back to Grand Goave and see how things looked on land. If you enjoyed this episode, please give this video a thumbs up :) WANT MORE? Visit and become a patron to get access to the vault, where we keep our most...
My Sister is HERE – Baja or Bust 49
Finding Simon

My Sister is HERE – Baja or Bust 49

Music by SpaceCrime ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America for 6 mon...
Day Off at Glamis Dunes – Baja or Bust 48
Finding Simon

Day Off at Glamis Dunes – Baja or Bust 48

Music by Lion, Meet Lizard ( Really appreciate the support, check out the Patreon for more access and perks: I'm a Canadian photographer from Ottawa who got rid of everything to travel to world. I moved from my tiny apartment to an even tinier van with Shelby and we traveled North America fo...
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