Watch Sailing & Boating Adventures Around the World – Page 2 of 5

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 25-48 of 98 results
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...
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...
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...
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:
Testing our Relationship in New Smyrna | Sailing 42
Roaming Rupps

Testing our Relationship in New Smyrna | Sailing 42

In this week's video, we test our relationship with a broken shifter cable during anchoring and make our way to Cape Canaveral. Read more about today's vlog and our #sailing adventure on our site! ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @...
Cumberland Island to St Augustine | Sailing 41
Roaming Rupps

Cumberland Island to St Augustine | Sailing 41

In today's vlog we #sail our way south and stop at some great locations. We also get a little bit of help from before we jump into #Flordia. #sailing Read more about today's vlog and our #sailing adventure on our site! ▬ Support Us! ▬ We just started a Patreon to get our journey s...
Quick Trip to Cannes to See Some Yachts and Excess Catamarans
Roaming Rupps

Quick Trip to Cannes to See Some Yachts and Excess Catamarans

Come with me as Colin takes a quick trip to Cannes to see the boats how and visit the #Excess Catamaran factory. $50 hotel - ▬ 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!...
Sailing South and Knocking Out Nautical Miles | Sailing 40
Roaming Rupps

Sailing South and Knocking Out Nautical Miles | Sailing 40

In today's vlog, we knock out a few miles offshore in our never-ending love to get to the Bahamas. Things got a bit spooky offshore with near-zero visibility!!! Read more about today's vlog and our #sailing adventure on our site! ▬ Support Us! ▬ We just started a Patreon to get our jo...
Entering the port of Jacksonville
Roaming Rupps

Entering the port of Jacksonville

Read more about today's vlog and our #sailing adventure on our site! ▬ 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: ▬ Song credits ▬
New Fridge / Freezers and Composting Toilet | Sailing 40
Roaming Rupps

New Fridge / Freezers and Composting Toilet | Sailing 40

Roaming Rupps transform their sailboat's living space with new fridge, freezer, and composting toilet upgrades, improving functionality while preparing for an offshore journey.
Unlimited Drinking Water with our SeaWater Pro Watermaker | Sailing 39
Roaming Rupps

Unlimited Drinking Water with our SeaWater Pro Watermaker | Sailing 39

Watch this episode as we install a 40GPH SeaWater Pro Watermaker on our sailboat. We're getting ready to head off grid and make unlimited drinking water on our sailing adventures! 🌊
The Kitchen is DONE! So Close to Cruising | Sailing 36
Roaming Rupps

The Kitchen is DONE! So Close to Cruising | Sailing 36

Roaming Rupps embark on a sailing adventure to upgrade their boat's outdated kitchen while traveling. The family tackles a challenging renovation with limited space but is rewarded with a functional, stylish oasis perfect for their voyages.
Our biggest project to date. Creating an owners version
Roaming Rupps

Our biggest project to date. Creating an owners version

In today's video, we take on the biggest and most rewarding project yet. We create an owner's version by removing a beauty wall between two cabins to create one massive owner's cabin. Follow along as we show you step, by step how we added value and practicality to our #Beneteau Oceani...
Sailboat Refit Continues (Floorboard Restoration) | Sailing 33
Roaming Rupps

Sailboat Refit Continues (Floorboard Restoration) | Sailing 33

In today's video we give the floors a new lease on life and sew up some new stantons, I mean, shroud covers for the old girl! Bye Bye pacific blue, and good riddances! ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ We share more of our daily lives...
On the Hard Again, Bottom Paint Failure | Sailing 32
Roaming Rupps

On the Hard Again, Bottom Paint Failure | Sailing 32

In today's vlog, we have to #HaulOut again due to the keel paint failing. We see if they honor it under warranty and add a few cosmetic upgrades while she's out of the water. #sailing ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ We share mor...
New Anchor Day and Shifting Woes | Sailing 31
Roaming Rupps

New Anchor Day and Shifting Woes | Sailing 31

In today's vlog, we get our new #Rocna 73lb anchor, and Colin works on the shifter as she's sticky and makes close-quarters maneuvering interesting. 0:30 - Intro 2:30 - Rocna #anchor 8:18 - Shifter Woes 17:50 - Conclusion Read more about today's vlog and our #sailing adventure on...
Deck Maintenance (Adding KiwiGrip and Shine!) | Sailing 30
Roaming Rupps

Deck Maintenance (Adding KiwiGrip and Shine!) | Sailing 30

In today's vlog, we check out to see if SV Maniac makes it through the hurricane unscathed. Then Ashley gets hard to work polishing the hull with @meguiars and re-gripping the decks with #KiwiGrip. All while Colin is nowhere to be found, probably endlessly "cleaning the garage" Read ...
Sailing to Charleston and our Naming Ceremony | Sailing 24
Roaming Rupps

Sailing to Charleston and our Naming Ceremony | Sailing 24

Join us for our last #sailing video before we start our refit in #CharlestonSC ! After some unfortunate events, we also perform the #nameingceremony and introduce you to Sailing Vassel Maniac. Read more about today's vlog and our #sailing adventure on our site! ▬ Support Us! ▬ We just sta...
Sailing to find Kindred Spirits | Sailing 22
Roaming Rupps

Sailing to find Kindred Spirits | Sailing 22

Today's #sail takes us from Wrightsville Beach to Bird Island, NC. While sailing through #FryingPan Soals, we come across 4 feet under our keel. Could you imagine doing this sail without charts? Read more about today's vlog and our #sailing adventure on our site! ▬ Support Us! ▬ We ...
Finally Sailing to Bluer Waters | Sailing 21
Roaming Rupps

Finally Sailing to Bluer Waters | Sailing 21

Read more about today's vlog and our #sailing adventure on our site! ▬ 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: ▬ Song credits ▬
Smooth Sailing Inside the Outer Banks | Sailing 20
Roaming Rupps

Smooth Sailing Inside the Outer Banks | Sailing 20

Today we sailed the entirety of the #PamlicoSound. It was super chill and just what to doctor ordered after having a few white knuckle days in the #ICW. Read more about today's vlog and our #sailing adventure on our site! ▬ Support Us! ▬ We just started a Patreon to get our journey starte...
Nearly Running Aground in the Outer Banks | Sailing 19
Roaming Rupps

Nearly Running Aground in the Outer Banks | Sailing 19

We leave the safety of the #ICW to head toward the #Pamlico Sound. Along we way, we come incredibly close to running aground and seek shelter in our first marina in 2 weeks. Read more about today's vlog and our #sailing adventure on our site! ▬ Support Us! ▬ We just started a Patreon to ...
Was Not Expecting This | #sailing 15
Roaming Rupps

Was Not Expecting This | #sailing 15

The weather changed our plans, so we decided to head up the #DelawareBay. There might be a reason we saw no other boats the whole video... Read more about today's vlog and our #sailing adventure on our site! #Beneteau #BoatLife #Monohull #TravelVlog #sailboats #icw #Sailingusa ▬ Support U...
Dragging anchor to shore! | Sailing 14
Roaming Rupps

Dragging anchor to shore! | Sailing 14

Join us for this week's stressful #vlog! After just getting settled into Lewes, DE we get hit with an unpredicted strong storm. Once the winds picked up to 30kts, we realized we were dragging anchor...right towards shore!! After all efforts failed to reset the anchor, we try to start the motor....
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