Watch Sailing & Boating Adventures Around the World – Page 2 of 14

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 322 results
[Ep 51] All Alone & Waiting for a Weather Window | Las Cocinas, Mexico
SmoCo Sailing

[Ep 51] All Alone & Waiting for a Weather Window | Las Cocinas, Mexico

After a lightning-filled change of plans, we sailed 40 miles north and dropped anchor in Las Cocinas, a quiet and remote anchorage in the Sea of Cortez. With no cell service, no town, and no amenities, life slowed down quickly. We settled into our off-grid routine and celebrated Armand’s birthday wi...
200 Episodes Later…Still Leaking (But Dancing) Ep200
Sailing Intermission

200 Episodes Later…Still Leaking (But Dancing) Ep200

🎶 **Sailing Intermission – Dancing, Exhaust, and a Bomb Cyclone?!** 🌊 This episode kicks off with Karen dancing to some surf music before we dive into boat projects and everyday life aboard. We finally get our riser prepped for reinstallation—this time for good and leak-free! That meant cutting awa...
Everything Changed This Year
Roaming Rupps

Everything Changed This Year

A lot has changed lately — some planned, some not. We made a few big decisions, welcomed another tiny human, and found ourselves rethinking what the next chapter looks like for our family. For now, we’re trading slip fees for open roads, slowing things down, and giving the kids time to grow while w...
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 vinyl click lock flooring that lays on top with carpet...
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. Packed sand sometimes looking like another wor...
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 shifting plans. Come along for our final Bahamas...
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 #sailing adventure on our site! ...
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 cart—only to find the grocery store had closed i...
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 more about today's vlog and our #sailing a...
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: it was absolutely worth it. After the nerve-wra...
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 give you all a fun fib...
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 @ We share more of our daily lives on our Instagram stories, so give u...
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 hard for years and the hustle has now tu...
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 ...
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...
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...
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!...
WeBoating
Logo
Shopping cart