Watch Sailing & Boating Adventures Around the World tagged “Liveaboards”

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 1-24 of 306 results
Get Down on the Floor Ep189
Sailing Intermission

Get Down on the Floor Ep189

We’re going mad!!!! Squeak, squeak, squeak our sub-floor is squeaking and driving us crazy. When it was replaced five years ago apparently we didn’t install enough furring strips. That’s what we are doing in this episode along with replacing the viny...
I’ll Draw You Nude Ep186
Sailing Intermission

I’ll Draw You Nude Ep186

Karen is at the gym. Stretching and straining her body. Steve wants to be her artist and draw her nude. Back to the beach we continue talking about living on a sailboat. Steve has a suggestion about a new bikini bottom for her. Nice walking at low tide. Pa...
Saying Goodbye to the Bahamas ⛵ Storms & Surprises Ahead!
Roaming Rupps

Saying Goodbye to the Bahamas ⛵ Storms & Surprises Ahead!

We wrap up this season’s Bahamas adventures with a dramatic exit! Cold fronts are rolling through and the squalls just won’t stop, forcing us to change our course. Instead of making it all the way to Jacksonville, we’re faced with tough decisions and...
My wife and child left me | #Hurricane season in the #Bahamas
Roaming Rupps

My wife and child left me | #Hurricane season in the #Bahamas

In today's video, Ashley and Fleix make their way back to the States. Colin hunkers down for some serious squalls before a new crew arrives to sail the boat back to the States. #hurricane #bahamas #liveaboard #family Read more about today's vlog and our ...
They left me. #sailing #boating #bahamas #hurricane
Roaming Rupps

They left me. #sailing #boating #bahamas #hurricane

Read more about today's vlog and our #sailing adventure on our site! https://roamingrupps.com/ ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon.com/RoamingRupps We share more of our daily ...
Hope Town, Abacos: Cruisers Tips, Tricks & The Golf Cart We Didn’t Need
Roaming Rupps

Hope Town, Abacos: Cruisers Tips, Tricks & The Golf Cart We Didn’t Need

In today’s vlog, we sail into Hope Town, Abacos, to ride out a blow, stock up on provisions, and share our best tips for visiting this charming Bahamian town. But the day takes an unexpected turn when we’re manipulated into renting an unnecessary golf ...
Hope Town Tips & The Golf Cart We Didn’t Need 🚤🇧🇸 #hopetown #abacos #bahamas
Roaming Rupps

Hope Town Tips & The Golf Cart We Didn’t Need 🚤🇧🇸 #hopetown #abacos #bahamas

We sailed into Hope Town, Abacos, to ride out a blow, grab some provisions, and share our top tips for visiting. But instead… we got stuck renting a golf cart we didn’t need after finding the grocery store closed for good. Add in a last-minute visa run...
Egg Island to Hope Town: A Calm Start… Then It Got WILD!
Roaming Rupps

Egg Island to Hope Town: A Calm Start… Then It Got WILD!

We set sail from beautiful Egg Island with hopes of a peaceful anchorage—but Mother Nature had other plans. With rolling anchor conditions and dark skies closing in, we made a split‑second decision: head for the safety of Hope Town in the Abacos. Read...
Calm sail to the #Abacos!  #eleuthera #liveaboard
Roaming Rupps

Calm sail to the #Abacos! #eleuthera #liveaboard

Read more about today's vlog and our #sailing adventure on our site! https://roamingrupps.com/ ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon.com/RoamingRupps We share more of our daily ...
What its like to run aground in the #Bahamas #eleuthera #boatlife
Roaming Rupps

What its like to run aground in the #Bahamas #eleuthera #boatlife

In our recent vlog, we go through the process where you put a little too much trust in the locals. ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon.com/RoamingRupps We share more of our da...
Goodbye #Eleuthera: Devil’s Backbone, Shallow Water Drama, Gorgeous Anchorages
Roaming Rupps

Goodbye #Eleuthera: Devil’s Backbone, Shallow Water Drama, Gorgeous Anchorages

We finally said farewell to #Eleuthera—but not before taking on the legendary Devil’s Backbone. With a local pilot guiding us through the razor-thin shallows, we made our way off the island and into some of the trickiest water we’ve seen yet. Spoiler...
Episode 256 – Can we Manage the Fiberglassing on Our Catamaran After Major spinal Problems…
Sailing Pickle Family

Episode 256 – Can we Manage the Fiberglassing on Our Catamaran After Major spinal Problems…

Yes guys I'm still struggling with My spinal damage, I'm having all the tests necessary like MRI's an EMG's to workout the best course of action, but in the mean time we are still trying to progress with all the boatwork we had planned! This week we'll giv...
Sailing back to Paradise | Sailing Sitka Ep 172
Sailing Sitka

Sailing back to Paradise | Sailing Sitka Ep 172

Despite recent engine troubles, Jay and Kenna felt the pull to keep moving. With their sights set on the tropical paradise of San Blas, they set sail from Linton Bay—upwind and into the chop. Will they make it? Hit subscribe to follow the journey.
Off the Grid in Eleuthera: Caves, History, and Hidden Roads
Roaming Rupps

Off the Grid in Eleuthera: Caves, History, and Hidden Roads

In today’s vlog, we explore abandoned Navy bases, visit the stunning #CathedralCaves, and take a scenic drive across #Eleuthera. #bahamas ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon....
San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163
Sailing Sitka

San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163

Jay and Kenna depart from Shelter Bay marina after a week straight of boat work and diagnosing problems. Finally, after stopping in Linton bay for one night, they sail to the desolate and world renowned San Blas islands. A dream come true. They've worked h...
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 a...
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 #...
Sneak preview of our Devil’s Backbone Vlog!  #liveaboard #sailing  #bahamas
Roaming Rupps

Sneak preview of our Devil’s Backbone Vlog! #liveaboard #sailing #bahamas

See why why decided to hire a pilot to help us navigate the coralheads and reefs from Spanish Wells to Harbour Island via the Devils Backbone. ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patre...
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 cou...
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 hideaw...
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 e...
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 she...
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 @ https://www.patreon.com/RoamingRupps We share more of...
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! https://roamingrupps.com/ ▬ Support Us! ▬ We just s...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart