Watch Sailing & Boating Adventures Around the World

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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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...
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...
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 ...
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 ...
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...
Oh, HEY…I Guess We’re In THE US?! | SailAway 167
SailAway World Sailing

Oh, HEY…I Guess We’re In THE US?! | SailAway 167

Well, we're in AMAZING PUERTO RICO. We haven't been to the US in OVER 2 YEARS, but now it's starting to feel like WE'RE BACK! Puerto Rico has a hugely diverse landscape and culture, so it's easy to forget sometimes that it's part of the United States. As we finally m...
YEAH…Sometimes We FIGHT – The GOOD and BAD of SIMPLE LIFE | SailAway 166
SailAway World Sailing

YEAH…Sometimes We FIGHT – The GOOD and BAD of SIMPLE LIFE | SailAway 166

Even though sometimes SIMPLE THINGS are NOT SO SIMPLE, we do our best to EMBRACE the simple life....and USUALLY succeed. This week we celebrate the Captain's birthday in perfect simple sailing life style - lots of wing foil time in a perfect anchorage, a cake and some good food, and time toget...
GAMETIME Decision In HURRICANE ALLEY | SailAway 165
SailAway World Sailing

GAMETIME Decision In HURRICANE ALLEY | SailAway 165

So we're IN the HURRICANE ZONE this season and after ONE DAY in CULEBRA, our decision is already being tested with TROPICAL STORM ELSA. We think we have a plan in order, but Elsa causes us to scramble, eventually running and hiding in the tropical paradise of Culebrita. Completely alone at th...
Sailing the WRONG WAY for HURRICANE SEASON | SailAway 164
SailAway World Sailing

Sailing the WRONG WAY for HURRICANE SEASON | SailAway 164

This year we're NOT heading to GRENADA. Instead we're pointed to PUERTO RICO, which is of course very much in the HURRICANE BELT. WHY? you may ask? Well, we know IT'S A RISK. but it's a calculated one and we definitely have our reasons. This week we explain why as we wrap up ...
Departure Update!! (S2 E8)
Barefoot Travels

Departure Update!! (S2 E8)

Today we have decided to post an extra little video with our departure update! The time has come to leave Puerto Rico. We have decided to go with Plan B and head towards the Dominican Republic! Wish us luck on our maiden voyage on our new boat! Cheers guys! Thank you to everyone who has subscribed...
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