Watch Sailing & Boating Adventures Around the World – Page 7 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 145-168 of 336 results
TRESPASSING – Our LOST Island Paradise | SailAway 189
SailAway World Sailing

TRESPASSING – Our LOST Island Paradise | SailAway 189

Our BEST memories DESTROYED. We're NOT ALLOWED on this island, but it means TOO MUCH to us not to GO ANYWAY. It's been 8 LONG YEARS since we last saw this place, the place our cruising history truly began. And in that time IRMA also happened. Not much is left of our cherished island pa...
Winter Sucks? WATCH THIS VIDEO | SailAway 188
SailAway World Sailing

Winter Sucks? WATCH THIS VIDEO | SailAway 188

Are you SICK of the COLD and SNOW? Or just having no access to a BOAT? We're here to help. :-). You see, we're in the BRITISH VIRGIN ISLANDS with no plans for anything but SUN, SAND, SEA, BIKINIS, RUM, REPEAT. If you've never been, you'll soon understand why we worked so hard ...
OFF-LIMITS NO MORE – The ONE Destination We’d Given Up On | SailAway 187
SailAway World Sailing

OFF-LIMITS NO MORE – The ONE Destination We’d Given Up On | SailAway 187

No place we've sailed has had such SPECIAL MEANING as the one were about to sail to. It's where we we MARRIED 8 years ago and for over 2 years we've been dreaming of returning aboard our own boat. But due to some pretty extreme (and many would say unreasonable) entry restrictions an...
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 ...
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...
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...
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...
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...
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...
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...
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...
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...
TIME’S UP! – Have We GOTTEN SOFT? | SailAway 176
SailAway World Sailing

TIME’S UP! – Have We GOTTEN SOFT? | SailAway 176

After THREE MONTHS of marina life, travels home, and the ANNAPOLIS BOAT SHOW, it's finally time for us to leave the CUSHY COMFORTS of marina life. But after so much time, have we gone a bit soft? We've had a lot of time to contemplate the difficulties of life at sea and while we're ...
TWO YEARS is TOO LONG – TWO Kinds Of HOMESICKNESS | SailAway 175
SailAway World Sailing

TWO YEARS is TOO LONG – TWO Kinds Of HOMESICKNESS | SailAway 175

Not being able to go HOME for 2 YEARS has TAKEN a TOLL. Now it's time for a whirlwind visit to the states including OLD FRIENDS, FAMILY, and all our favorite things from the old LAND LIFE. But as we travel to ANNAPOLIS to take part in the new YOUTUBE BOOTH, we find ourselves contemplating what...
Why We REALLY Do This | SailAway 174
SailAway World Sailing

Why We REALLY Do This | SailAway 174

Creative people have a NEED to SHARE. When we set off to SAIL the WORLD, we wanted to "bring along" our friends and families. Thus, YOUTUBE. This is an ARTISTIC venture for us, one in many we've both pursued in our lives. And as artistic types, the sharing of what we're passi...
DON’T Get TOO Comfortable – Hitting the RESET Button | SailAway 173
SailAway World Sailing

DON’T Get TOO Comfortable – Hitting the RESET Button | SailAway 173

It's been a LONG TWO YEARS at times, and we're finding ourselves WORN DOWN and a little weary of the demands of this crazy life. Can a couple months in a marina help us to hit the RESET button and get us mentally prepared for the next leg of our journey? Lots of luxuries are now at our d...
Are We GOOD? Or JUST LUCKY – a WEEK of CLOSE CALLS | SailAway 172
SailAway World Sailing

Are We GOOD? Or JUST LUCKY – a WEEK of CLOSE CALLS | SailAway 172

As a BATTERY threatens to EXPLODE and TWO TROPICAL STORMS approach our marina in PUERTO RICO, we start to ponder the LUCKY vs. GOOD proposition. We try our best to be "good" - to make good decisions, prepare, sail conservatively, etc., knowing we don't always get it right. But so fa...
How NOT To Travel – Breaking RULE NUMBER ONE | SailAway 171
SailAway World Sailing

How NOT To Travel – Breaking RULE NUMBER ONE | SailAway 171

We're usually about LESS RULES in this lifestyle, but there's ONE we really try to stick to. But as we RUSH around the NORTHERN COAST of Puerto Rico, in and out of AMAZING anchorages and towns to make it to our HURRICANE SEASON safe haven, we find ourselves breaking it to bits. But some ...
WORTH The RISK? | Sailing OFF The BEATEN PATH | SailAway 170
SailAway World Sailing

WORTH The RISK? | Sailing OFF The BEATEN PATH | SailAway 170

Sailing the UNBEATEN Path AND the WRONG WAY during hurricane season means we're truly ALONE out here much of the time. And some of our destinations have little to no information for us to go on. But we strike just the same and make as good of decisions as possible...hoping luck stays with us....
Back ON The Grid – Can We HANDLE THIS? | SailAway 169
SailAway World Sailing

Back ON The Grid – Can We HANDLE THIS? | SailAway 169

REVERSE CULTURE SHOCK. After 2 1/2 years OFF the GRID, we find ourselves immersed in CROWDS and CITY LIFE for the first time since the onset of THE GLOBAL CRISIS whose NAME SHALL NOT BE SPOKEN. And while enjoying all the amenities that SAN JUAN has to offer, we're feeling truly overwhelmed by...
SAILORS PLAN While The GODS LAUGH | SailAway 168
SailAway World Sailing

SAILORS PLAN While The GODS LAUGH | SailAway 168

Sailing the daunting NORTH COAST of PUERTO RICO en route to SAN JUAN (our favorite Caribbean city as it turns out) we think back to our ORIGINAL plans for our sailing life. We intended to move to the east coast of PR and sail our former boat, LAYLA, here, rent a house, and make this our center of e...
WILL SING for RUM – LIVE Set From The Captain! SUNDAY, 9/26 @ 2PM EST | SailAway
SailAway World Sailing

WILL SING for RUM – LIVE Set From The Captain! SUNDAY, 9/26 @ 2PM EST | SailAway

He used To SING for a LIVING...now it's for our FRIENDS! THIS MEANS YOU! This is our 2ND ANNUAL (though not limited to) DECK CONCERT, with Captain ERIC DOVE. LIVE from the serene waters and crystal blue skies of PUERTO REAL, PUERTO RICO. Join us for an hour of tunes from numerous genres - r...
WILL SING for RUM – LIVE Set From The Captain! Recorded SUNDAY, 9/26 @ 2PM EST | SailAway
SailAway World Sailing

WILL SING for RUM – LIVE Set From The Captain! Recorded SUNDAY, 9/26 @ 2PM EST | SailAway

He used To SING for a LIVING...now it's for our FRIENDS! THIS MEANS YOU! This is our 2ND ANNUAL (though not limited to) DECK CONCERT, with Captain ERIC DOVE. LIVE from the serene waters and crystal blue skies of PUERTO REAL, PUERTO RICO. Join us for an hour of tunes from numerous genres - r...
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