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 328 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...
We Traded the Ocean for the Mountains | Our Journey to Minca, Colombia
Sailing Big Lost

We Traded the Ocean for the Mountains | Our Journey to Minca, Colombia

We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. In this episode of Sailing Big Lost, we head inland for a change of scenery—trading the Caribbean coast for the lush mountains of Minca, Co...
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...
A Week That Didn’t Go to Plan | Rain & Marina Life in Grenada
Sailing Big Lost

A Week That Didn’t Go to Plan | Rain & Marina Life in Grenada

Not every week is turquoise water and perfect anchorages. This week in Grenada, heavy rain, canceled plans, and marina life kept us tied to the dock — and gave us a real dose of the cruising lifestyle. Between endless boat chores, a soggy anniversary outing, sewing a DIY bow shade, and watching our...
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...
BVI Bound! The Next Leg of Our Southbound Sailing Adventure
Sailing Big Lost

BVI Bound! The Next Leg of Our Southbound Sailing Adventure

After picking up long-awaited spare parts in the US Virgin Islands, we leave Honeymoon Bay behind and set sail for the British Virgin Islands—our next stop on the journey south to Grenada for hurricane season. Our first destination: Norman Island, where we blow off some steam at the infamous floati...
We Finally Made It! 1,051 Nautical Miles to Saint Thomas 🌊⛵
Sailing Big Lost

We Finally Made It! 1,051 Nautical Miles to Saint Thomas 🌊⛵

After 7 days and 2 hours at sea, we finally made landfall in Saint Thomas! This was our longest passage yet — and our first without extra hands on deck — so we’re incredibly proud to have safely navigated 1,051 nautical miles as a family. Along the way, we battled rough seas and squalls, replaced a ...
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.
Shipyard Setbacks & Small Wins | One Step Closer to Sailing Again
Sailing Big Lost

Shipyard Setbacks & Small Wins | One Step Closer to Sailing Again

We’ve made it through another challenging week in the shipyard — and let’s just say, it hasn’t been smooth sailing. Between two hit-and-runs, a broken sail drive, and a pile of unexpected invoices, it’s felt like for every few steps forward, we take one back. 😅 But finally... we’re seeing a light a...
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...
The Truth About Our Boat Buying & Selling Journey
Sailing Big Lost

The Truth About Our Boat Buying & Selling Journey

We bought a catamaran. Then we sold it. Now we’re living the landlubber life in Florida… while working our way through the contract contingencies on our next catamaran. ⛵️🌴 Yep, it’s been a journey — full of wild lessons, emotional decisions, and a whole lot of growth. In this video, we’re opening ...
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...
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