Watch Sailing & Boating Adventures Around the World – Page 19 of 43

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.

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Before you launch that boat! Old Sailboat – Ep 173 – Lady K Sailing
Lady K Sailing
25 Years Sailing – How Did We Screw THIS Up?! | SailAway 186
SailAway World Sailing

25 Years Sailing – How Did We Screw THIS Up?! | SailAway 186

Cruising the CARIBBEAN has lots of UPS and DOWNS, sometimes ALL AT ONCE! As we make headway with some recent BOAT ISSUES, we maybe get a little cocky. What better time to get KNOCKED DOWN A PEG by a seemingly simple maneuver. But it's all about learning so we don't screw it up the next ...
Mirage – What is the fastest cruising sailboat? Lady K Sailing – Ep 172 – Lady K Sailing
Lady K Sailing

Mirage – What is the fastest cruising sailboat? Lady K Sailing – Ep 172 – Lady K Sailing

Support Lady K - Or Photo Credit: htttp://cdn.cnn.com/cnnnext/dam/assets/120625085007-brest-sailing-regatta.jpg
Our $3,000+ MISTAKE – How Do We Make This WORK? | SailAway 185
SailAway World Sailing

Our $3,000+ MISTAKE – How Do We Make This WORK? | SailAway 185

Over a YEAR ago, our GENERATOR became a $15,000 PAPERWEIGHT. Now, tons of STRESS and WAY too many $$$ later, the saga finally concludes. The difficult decision has ALWAYS been - how much do we need this? And how much money is it worth to try and resurrect it? We've obviously made due over t...
Hans Christian – Is This The Best Cruising Boat – Ep 171 – Lady K Sailing
Lady K Sailing

Hans Christian – Is This The Best Cruising Boat – Ep 171 – Lady K Sailing

Support Lady K - Or Hey all, is this the best cruising boat ever made? The Hans Christian line of boats! Photo Credit:
BAD Luck, EXPENSES, and DIFFICULTIES – When It RAINS It POURS | SailAway 184
SailAway World Sailing

BAD Luck, EXPENSES, and DIFFICULTIES – When It RAINS It POURS | SailAway 184

We've had WEEKS of random DIFFICULTIES followed by some BAD LUCK, all of which have ADDED to already growing EXPENSES. These things happen to everyone, and out here they seem to come in waves. And when getting things done and just GETTING things is already difficult, we find ourselves frustra...
CAL Yachts vs Ranger – Ep 170 – Lady K Sailing
Lady K Sailing

CAL Yachts vs Ranger – Ep 170 – Lady K Sailing

Support Lady K - Or Join us as we explore east coast vs west coast, the mighty Ranger vs Cal Yachts! Photo Credit:
TOP 5 22 FOOT SAILBOATS & SEE YOU IN BAHAMAS? Ep 169 – Lady K Sailing
Lady K Sailing

TOP 5 22 FOOT SAILBOATS & SEE YOU IN BAHAMAS? Ep 169 – Lady K Sailing

Support Lady K - Or The top 5 22 foot sailboats or the best boats to buy for your first sailboat! Photo Credit:
CLOSE Encounters With GIANT BOATS – City Anchoring in the CARIBBEAN | SailAway 183
SailAway World Sailing

CLOSE Encounters With GIANT BOATS – City Anchoring in the CARIBBEAN | SailAway 183

Things can get DICEY when anchoring next to MEGA YACHTS and CRUISE SHIPS. But it's NOT always PRISTINE anchorages and remote, desolate BEACHES that define the SAILING LIFE. For us, a good dose of METRO ANCHORING works wonders at times. When you're out here for YEARS, sometimes dropping t...
THE BEST 30′ SAILBOAT EVER??? C&C 30 Why and Why Not, EP 168 – Lady K Sailing
Lady K Sailing

THE BEST 30′ SAILBOAT EVER??? C&C 30 Why and Why Not, EP 168 – Lady K Sailing

Support Lady K - Or C&C 30, 30 foot sailboat, Caribbean Cruiser, Sailboat Racing Photo Credit:
Balancing The TWO Cruising Life ESSENTIALS | SailAway 182
SailAway World Sailing

Balancing The TWO Cruising Life ESSENTIALS | SailAway 182

2 PRIMARY ASPECTS make this life enjoyable. And BOTH things FEED each other to keep this crazy life working. Without ONE, the other suffers and vice versa. This week we take you on an INCREDIBLY DICEY anchoring, along with one of the best bio-bays in the world. Then it's off to ST. THOMAS t...
Are You a SAILOR or a CRUISER? – The 4 Main Differences | SailAway 181
SailAway World Sailing

Are You a SAILOR or a CRUISER? – The 4 Main Differences | SailAway 181

SAILING PURISTS often look at CRUISING with a slight air of DISDAIN, especially when that cruising involves MOTORING. How much motoring is too much? When do you STOP being a sailor at all? And does it matter? We began as pure sailors and soon discovered the definition of what we are now is quite...
Top 5 Sailboats 30 feet – Episode 167 – Lady K Sailing
Lady K Sailing

Top 5 Sailboats 30 feet – Episode 167 – Lady K Sailing

Support Lady K - Or 30 foot sailboats, best 30 foot sailboats Photo Credit:
BIGGEST SAILBOAT MISTAKES, TOP 5 – Ep 166 – Lady K Sailing
Lady K Sailing

BIGGEST SAILBOAT MISTAKES, TOP 5 – Ep 166 – Lady K Sailing

Support Lady K - Or Sailboat mistakes Photo Credit:
Herby Breaks Down in Tears | Sailing Wisdom [S4 Ep14]
Rigging Doctor

Herby Breaks Down in Tears | Sailing Wisdom [S4 Ep14]

▸ PAINTING COMMISIONS: [email protected] ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: The most beautiful snorkeling in Puerto Rico con...
Celebrating LIFE at the BOX of the DEAD | SailAway 180
SailAway World Sailing

Celebrating LIFE at the BOX of the DEAD | SailAway 180

As humans we're often GUILTY of TAKING LIFE FOR GRANTED. Even though we live this life to escape that cycle, it still gets its grips on us sometimes. But sometimes it just takes a holiday and a few fortunate events to snap us out of it, and we're back to celebrating every day we get on t...
Swimming Naked in the Bio Bay | Sailing Wisdom [S4 Ep13]
Rigging Doctor

Swimming Naked in the Bio Bay | Sailing Wisdom [S4 Ep13]

▸ PAINTING COMMISIONS: [email protected] ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: For generations, Herby's family would play ...
What You DIDN’T See – Memories From The CUTTING ROOM FLOOR | SailAway 179
SailAway World Sailing

What You DIDN’T See – Memories From The CUTTING ROOM FLOOR | SailAway 179

After our CIRCUMNAVIGATION of PUERTO RICO, we realized a LOT of our favorite memories never made the cut. But WE still thought you might want a look at them. So here is a compilation of fun footage you've NEVER seen and our reasons why some great footage just doesn't make a video sometim...
Girls Like to Walk Around NAKED on Boats | Sailing Wisdom [S4 Ep12]
Rigging Doctor

Girls Like to Walk Around NAKED on Boats | Sailing Wisdom [S4 Ep12]

▸ PAINTING COMMISIONS: [email protected] ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ↓BINGE WATCH↓ CROSSING THE ATLANTIC THE 1ST TIME: CROSSING THE ATLANTIC THE 2ND TIME: SAILING AROUND EUROPE: VAN TRIP THROUGH EUROPE: We meet up with @Bumsonaboat in Guanica, PR near...
Would you buy this? – EP 165 – Lady K Sailing
Lady K Sailing

Would you buy this? – EP 165 – Lady K Sailing

Support Lady K - Or Beneteau Oceanis 45 Phot Credit:
Our #1 OBSESSION – Why It RULES OUR LIFE | SailAway 178
SailAway World Sailing

Our #1 OBSESSION – Why It RULES OUR LIFE | SailAway 178

Cruising FULL TIME entails lots of factors and TONS of DECISIONS that dictate our DAILY MOVES. But there's one VERY complicated factor that is and OBSESSION with all cruising sailors. And that's weather. Not just the big stuff...sure we fret about hurricanes and big storms...but somethi...
The BEST Sailboat EVER?? Episode 164 – Shannon Sailboats – Lady K Sailing
Lady K Sailing

The BEST Sailboat EVER?? Episode 164 – Shannon Sailboats – Lady K Sailing

Support Lady K - Or In Episode 164 we explore the legendary Shannon Sailboats and the builder who set out to build the best sailboat ever made! Best cruising boat. Best blue water sailboat. Photo Credit:
SAILBOAT FAMILY – What’s it Like CRUISING FULL TIME? | SailAway 177
SailAway World Sailing

SAILBOAT FAMILY – What’s it Like CRUISING FULL TIME? | SailAway 177

Our SMALL FAMILY has been sailing FULL TIME in the CARIBBEAN for 2 YEARS now. After hurricane season in PUERTO RICO, it's time to move EAST for ROUND TWO! We show you what it's like to sail the islands as a FAMILY aboard a SMALL BOAT as we make our way through the eastern Caribbean and o...
Deck Saloon Sailboats – Oyster – Episode 163 – Lady K Sailing
Lady K Sailing

Deck Saloon Sailboats – Oyster – Episode 163 – Lady K Sailing

Support Lady K - Or Oyster sailboats, deck saloon sailboats, deck salon sailboats, cruising sailboats Photo Credit:
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