Watch Sailing & Boating Adventures Around the World – Page 3 of 42

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.

Showing 49-72 of 996 results
Locked Out by Disney: What Happened to This Bahamian Beach?
Roaming Rupps

Locked Out by Disney: What Happened to This Bahamian Beach?

Today, we finally stepped off the boat to explore one of our favorite spots in the Bahamas—only to find out we couldn't get there. What used to be a peaceful, easy-to-reach beach has now been taken over by Disney. We were shocked to discover restricted access, fences, and signs that redirected ...
WANAKA’S Hidden Gem Rob Roy Glacier Is A MUST SEE! | Ep 97
Sailing Paradise Falls

WANAKA’S Hidden Gem Rob Roy Glacier Is A MUST SEE! | Ep 97

This week of van life we discover Wanaka's hidden gem, Rob Roy Glacier, in this must-see episode! Explore the beauty of Mt. Aspiring and other South Island, New Zealand attractions like Lake Tekapo and Wanaka lavender farm. We stop to smell the lavender at Wanaka Lavender Farm, hike the most A...
WE|Sail’s Epic Van Life: White Water Rafting & Stunning Hikes in Rotorua, NZ!| Episode 296
WE|Sail

WE|Sail’s Epic Van Life: White Water Rafting & Stunning Hikes in Rotorua, NZ!| Episode 296

Welcome back to WE|Sail! Our latest adventure as we explore the breathtaking landscapes of New Zealand's North Island! In this episode, we dive into exhilarating white water rafting and embark on stunning hikes around Rotorua. Discover the beauty of nature, thrill-seeking activities, and our va...
Devil’s Backbone: Spanish Wells to Harbour Island (Why You NEED a Pilot!)
Roaming Rupps

Devil’s Backbone: Spanish Wells to Harbour Island (Why You NEED a Pilot!)

The Devil's Backbone is no joke! Watch us navigate this challenging reef passage from Spanish Wells to Harbour Island. We hired a pilot for $100; it is cheap insurance and calmed our nerves. See the stunning but dangerous beauty of this route. #Caribbean #liveaboard #sailboat #TravelVlog #baham...
Van Life Gets EXTREME! Mountain Biking & Hot Springs in Rotorua  | Episode 295
WE|Sail

Van Life Gets EXTREME! Mountain Biking & Hot Springs in Rotorua | Episode 295

Welcome back to WE|Sail! We’re trading the ocean for the trails as we dive into the extreme side of van life! This week, we hit Rotorua—New Zealand’s adventure capital—for some epic mountain biking (one of our first loves before sailing! 🚵‍♂️), followed by a much-needed soak in the hot springs. Let...
Van Life:  Exploring Far North of New Zealand | Episode 294
WE|Sail

Van Life: Exploring Far North of New Zealand | Episode 294

Welcome back to WE|Sail! 🚐 Van Life in New Zealand is getting better and better! 🌿🏔️ We’re finally hitting our stride with van life and taking in the best of New Zealand’s Northland! From sandboarding (and Warren eating a face full of sand 🤣) to reaching the very top of NZ at Cape Reinga, this ro...
We Got CAUGHT Painting Our RV! 😳 | Roadtrip USA Vlog 276
Sailing Sunday

We Got CAUGHT Painting Our RV! 😳 | Roadtrip USA Vlog 276

We just wanted to paint our renovated RV, but it all went WRONG! 😱 Pulling into an industrial lot in Los Angeles seemed perfect until we got caught after the first coat and kicked out... 🚨 Should we sneak back in at night to finish the job? Subscribe to find out and follow our journey across the US...
Sailing to Meeks Patch: Bonfires, Beach Bliss & a Freezer Fail
Roaming Rupps

Sailing to Meeks Patch: Bonfires, Beach Bliss & a Freezer Fail

Join us as we set sail from Royal Island to the beautiful Meeks Patch! We have the entire beach to ourselves for a perfect beach day, let the dogs run free (while dodging the island’s famous wild pigs), and soak in the peaceful cruising life. But, of course, no adventure is complete without a little...
Van Life Tested Us… But We Never Gave Up! | Episode 293
WE|Sail

Van Life Tested Us… But We Never Gave Up! | Episode 293

Welcome back to WE|Sail! Our van life adventure got off to a bumpy start… literally. 😅 After a couple of unexpected breakdowns, we were starting to wonder if this whole van life thing was a mistake. But after some trial, error, and a little thinking, we finally cracked the case and fixed the proble...
Life on the Road: Why You Should NEVER Let Your Guard Down! | Vlog 275
Sailing Sunday

Life on the Road: Why You Should NEVER Let Your Guard Down! | Vlog 275

RV life is full of surprises, some funny, some frustrating and nn this road trip, we start the week off with Ryan stepping in dog poop, which we thought would be good luck!!! but we accidentally left the hood up while driving then almost got scammed at a truck stop!! Watch to see how we handled thes...
Sailing to Spanish Wells: Abandoned Getaway, Stormy Weather & Snake Trouble!
Roaming Rupps

Sailing to Spanish Wells: Abandoned Getaway, Stormy Weather & Snake Trouble!

In today’s adventure, we set sail from Rose Island to the charming Spanish Wells, navigating beautiful Bahamian waters with our little crew! We spend a few days catching up on boat life chores, riding out a storm, and exploring an abandoned island hideaway built by a wealthy Florida man—only to disc...
Boat Life to Van Life… Did We Make a Mistake? | Episode 292
WE|Sail

Boat Life to Van Life… Did We Make a Mistake? | Episode 292

Welcome back to WE|Sail! We’ve hit pause on boat life and jumped into our next big adventure—van life! But… was that a mistake? 😬 Our first "shakedown" trip in the van didn’t exactly go as planned. From unexpected breakdowns to questioning if this life on wheels is really for us, we’re wo...
Crossing a DEADLY Mountain Pass in Winter… With ZERO Experience ❄️😨| VLOG 274
Sailing Sunday

Crossing a DEADLY Mountain Pass in Winter… With ZERO Experience ❄️😨| VLOG 274

This week, we’re taking on one of the most dangerous mountain passes in America, The Siskiyou Pass, with our 35' 5th wheel .......in the middle of winter. ❄️🥶 With steep 6% grades, icy roads and the threat of black ice, this stretch of I-5 is no joke! We’re racing against an incoming massive s...
From Sailboat Celebrations to Van Life Adventures in New Zealand | Episode 291
WE|Sail

From Sailboat Celebrations to Van Life Adventures in New Zealand | Episode 291

Welcome back to WE|Sail! Join us for a magical Christmas on the water. In this episode, we set sail with our friends on their sailboat, giving us a little reminder of our love for the water while we are hauled out and boosting our Christmas spirit. As we wrap up our time on the water, we're p...
Berry Islands to Nassau Madness, a 15HP 2-Smoker… & Finally Relaxing!
Roaming Rupps

Berry Islands to Nassau Madness, a 15HP 2-Smoker… & Finally Relaxing!

Join us on another real-life Bahamas cruising adventure! We make the jump from the Berry Islands to Nassau, where things get a little crazy! From the hustle and chaos of Nassau to navigating busy waters, we also pick up a 15HP Yamaha 2-stroke to add some extra speed car. But after all the madness, w...
ESCAPING CANADA! But Canada Fights Back… | Vlog 273.
Sailing Sunday

ESCAPING CANADA! But Canada Fights Back… | Vlog 273.

🚐 We’re finally leaving Canada! After months of renovating our 5th wheel and Baby Oakley, we were ready to hit the road and chase the sunshine… but Mother Nature had other plans. ❄️ Instead of heading south straight away, we got VIP tickets to the NHL to watch the Vancouver Canucks hockey game, the...
Bahamas Cruising Gone Wrong? Bimini to Berry Islands & Riding Out a 40kt Blow!
Roaming Rupps

Bahamas Cruising Gone Wrong? Bimini to Berry Islands & Riding Out a 40kt Blow!

Join us on our real-life Bahamas cruising adventure! Everything isn’t always perfect as we hop from Bimini to the Berry Islands, facing the challenges of boat life along the way. From breathtaking island views to unexpected surprises, we finally find shelter in Great Harbour Cay as a 40-knot blow ro...
Boat’s Out, Work Begins, Sailing Crew Deserts Us | Episode 290
WE|Sail

Boat’s Out, Work Begins, Sailing Crew Deserts Us | Episode 290

Welcome back to the worlds greatest sailing channel!! Just kidding, wanted to see if you are really reading these descriptions!! But for real, this week finds us officially hauled out of the water and sitting pretty on the hard in our new yard, and our home for the next six months! Our sailing cre...
Leave Your Boat Behind and You Will Be Punished – Episode 145
Sailing One Life

Leave Your Boat Behind and You Will Be Punished – Episode 145

Get an exclusive 15% discount on Saily data plans! Use code SAILINGONELIFE at checkout. Download Saily app or go to Want to help support our video productions and get real time updates? 🌍➡️Join our One Life Crew here: 💦Grab a Sailing One Life Epic Water Filters Bottle! Use discount code EPICONE...
Can We Jump to Bimini before Disaster Strikes?
Roaming Rupps

Can We Jump to Bimini before Disaster Strikes?

In this weeks video we make the jump to #Bimini #Bahamas and hit a few road blocks along the way. #sailing ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ We share more of our daily lives on our Instagram stories, so give us a follow! Ashley: Colin:
Boat Work or Explore New New Zealand; Can WE Do Both?| Episode 289
WE|Sail

Boat Work or Explore New New Zealand; Can WE Do Both?| Episode 289

Last week we finished our big sail south to New Zealand and got checked into the country. On this week's episode we don't waste any time and get our butts up to the small port where we haul out. We go through the similar process where that we have experienced six time before, and safely ge...
Five Surprising Truths About Van Life in New Zealand – Episode 144
Sailing One Life

Five Surprising Truths About Van Life in New Zealand – Episode 144

Want to help support our video productions and get real time updates? 🌍➡️Join our One Life Crew here: 💦Grab a Sailing One Life Epic Water Filters Bottle! Use discount code EPICONELIFE here: Check out Whitiangler Fishing Trips in Coromandel: To watch our journey from the beginning, click on o...
New Zealand by Land & Sea – Episode 143
Sailing One Life

New Zealand by Land & Sea – Episode 143

Take your personal data back with Incogni! Use code SAILINGONELIFE at the link below and get 60% off an annual plan: Want to help support our video productions and get real time updates? 🌍➡️Join our One Life Crew here: 💦Grab a Sailing One Life Epic Water Filters Bottle! Use discount code EPICON...
Sailing Solo for the First Time: How to Single-hand Safely – Episode 142
Sailing One Life

Sailing Solo for the First Time: How to Single-hand Safely – Episode 142

Go to for 4 extra months of Surfshark at an unbeatable price! 🦈 Want to help support our video productions and get real time updates? 🌍➡️Join our One Life Crew here: 💦Grab a Sailing One Life Epic Water Filters Bottle! Use discount code EPICONELIFE here: To watch our journey from the beginnin...
WeBoating
Logo
Shopping cart