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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How We Explored Annapolis for Little or No Money  Ep80
Sailing Roam

How We Explored Annapolis for Little or No Money Ep80

One of our favorite things about cruising is exploring the places we visit without spending a fortune. So while we’re in Annapolis, we set out to see how much of this historic city we could experience for little or no money. First up was a self-guided walking tour of the U.S. Naval Academy. Seeing ...
We Needed To Reconnect… | Sailing Greece’s Hidden Paradise
Sailing Holly Blue

We Needed To Reconnect… | Sailing Greece’s Hidden Paradise

After months of challenges, we escaped to one of the most beautiful corners of Greece in search of something we'd been missing... Taking advantage of some rare childcare from friends, we escaped for a few days to explore the beautiful islands of Kalamos, Kastos and Mytikas together. With hidde...
SHIPWRECKS, SABOTAGE, BOAT WORK & LIFE LESSONS IN TRINIDAD BOATYARD
The Cruising Kiwis

SHIPWRECKS, SABOTAGE, BOAT WORK & LIFE LESSONS IN TRINIDAD BOATYARD

SHIPWRECKS, SABOTAGE, BOAT WORK & LIFE LESSONS IN TRINIDAD BOATYARD This week we're experiencing the reality of boatyard life in Trinidad while finishing our haul-out, repairing systems, and discovering the unexpected kindness that makes the sailing community so special. While working agai...
WHY WE WENT SAILING – the answer may surprise you!
The Cruising Kiwis

WHY WE WENT SAILING – the answer may surprise you!

WHY WE WENT SAILING Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] This week's sailing vlog we're bac...
Choosing the Window | Leaving San Blas & Sailing to Shelter Bay
Sailing Big Lost

Choosing the Window | Leaving San Blas & Sailing to Shelter Bay

After weeks anchored in the San Blas islands, it was time to move again. In this episode, we leave the Swimming Pool anchorage and begin our passage toward Shelter Bay. The weather window wasn’t perfect — the seas were rolly — but with lighter winds and tougher conditions building ahead, it was the ...
Benefits of NUDE swimming + We Explore, Dive & Sail the Greek Islands of Meganisi – Kalamos • S5Ep4
Sailing Holly Blue

Benefits of NUDE swimming + We Explore, Dive & Sail the Greek Islands of Meganisi – Kalamos • S5Ep4

Discover the Hidden Magic of Meganisi & Kalamos 🌊 | The Real Benefits of NUDE Swimming! Join us on this unforgettable sailing adventure through the Greek Islands! 🇬🇷 We kick things off in Spartochori, Meganisi, exploring its breathtaking beauty before setting sail for Kalamos. Things get a litt...
Hurricane Season is Here! Sailing South to Trinidad
Travel Sketch

Hurricane Season is Here! Sailing South to Trinidad

The first time we arrived in Trinidad we thought it would be for 3 months... 21 months and more warranty repairs and mistakes than we ever could have imagined, our Leopard 45 relaunched. Now, it's time to go back! Starting in the live aboard cruisers hub of Le Marin and Sainte Anne in Martiniq...
NO SECRETS, NO FILTER: Answering all your questions during a DAY IN THE LIFE! – Ep 232
Sailing Jibsea

NO SECRETS, NO FILTER: Answering all your questions during a DAY IN THE LIFE! – Ep 232

Thank you to everyone who sent in their questions. This was so much fun :) Join us for a full day in the life as full-time world travellers, sailors, and liveaboard cruisers! We're answering your biggest questions about what it’s really like to live off the grid, travel the world by sailboat, ...
WE GOT HIT! Sailing Lefkada • S4Ep17
Sailing Holly Blue

WE GOT HIT! Sailing Lefkada • S4Ep17

Hi Guys in this we sailing episode, we start off in Lefkas Town where we are waiting for a vital engine part to finally let us set sail again...we took this chance to explore Ayia Mavra castle and enjoy the beautiful quaint Lefkas old town...Ross finally fixes up the engine and it's time to tes...
Swinging between STUNNING bays & Laura reaches TERRIFYING new heights! Sailing Lefkada • S4Ep16
Sailing Holly Blue

Swinging between STUNNING bays & Laura reaches TERRIFYING new heights! Sailing Lefkada • S4Ep16

In this SAILING episode, we enjoy boat life swinging between the bays on the east side of Lefkada ("The Mecca of Boating and sailing in Greece) before pointing the compass north and sailing up to Lefkas town. During this extended sailing video, we share with you some of the epic scenery that Le...
CARNAGE IN KEFALONIA: Sailing calamities, Jelly fish attacks & cowboy charter boats! • S4Ep15
Sailing Holly Blue

CARNAGE IN KEFALONIA: Sailing calamities, Jelly fish attacks & cowboy charter boats! • S4Ep15

Hi Guys - In this sailing episode, we drop anchor at Foki, which is close to Fiskardo on Kefalonia Island. We encounter all manner of mayhem with wasps, jellyfish stings and charter boat carnage! It’s not all doom and gloom though as we also had some amazing underwater sea-scooter swims & enjoy...
WE DO ZAKYNTHOS – 007 STYLE!  with plenty of sexy sailing amongst the superyachts!
Sailing Holly Blue

WE DO ZAKYNTHOS – 007 STYLE! with plenty of sexy sailing amongst the superyachts!

In this sailing episode, we dart about to many super sailing destinations on the island of Zakynthos and Kefalonia. We spend a lot of our time underwater, exploring the crystal clear waters, reefs and sea caves using Ross's "new toy" the Sublue Vapor aka the Ferrari of the ocean! La...
Giant Catamaran Catch & Cook in Trinidad
Travel Sketch

Giant Catamaran Catch & Cook in Trinidad

SPONSOR INDEPENDENT STORY TELLING 😎 ⛵ Gain access to our member only area: 👉 Tip jar: After 16 months on the hardstand completing warranty repairs on our Leopard Catamaran we broke free and spent a few days out on the water aboard the charter yacht HQ2! It's a 75ft Two Oceans catamaran ...
BOATLIFE GREECE – 5 years of FAILS & LESSONS LEARNT (our advice – don’t make the these mistakes!)
Sailing Holly Blue

BOATLIFE GREECE – 5 years of FAILS & LESSONS LEARNT (our advice – don’t make the these mistakes!)

Sailing enthusiasts Holly Blue share their 5 years worth of anchoring fails and lessons learnt in the stunning Greek Island waters of the Ionian. Join them as they recount close calls, near misses, and valuable life-saving techniques that every sailor must know when it comes to anchor handling in th...
No Clothes Required…Greece is on FIRE! (literally).  Sailing The Ionian.
Sailing Holly Blue

No Clothes Required…Greece is on FIRE! (literally). Sailing The Ionian.

Join Ross, Laura, Joshua, and Noah on a thrilling sail through Greece's picturesque Ionian Islands. They share their experiences with hospital stays, language barriers, and navigating the pristine waters of an untouched island. Alongside practical tips for maintaining life on board during off-g...
‘LESS IS MORE’…Sailing Kefalonia, Greece and Embracing Nature • S4:Ep13
Sailing Holly Blue

‘LESS IS MORE’…Sailing Kefalonia, Greece and Embracing Nature • S4:Ep13

Join Sailing Holly Blue on their captivating journey through the crystal-clear waters surrounding Kefalonia, Greece. Witness breathtaking sights, venture into awe-inspiring caves, and experience a truly remarkable sailing adventure as they embrace nature's wonders.
Trouble & Strife in Paradise…Sailing Zakynthos • S4Ep8 (re-upload)
Sailing Holly Blue

Trouble & Strife in Paradise…Sailing Zakynthos • S4Ep8 (re-upload)

Join Sailing Holly Blue in their season 4 episode 8 journey through Zakynthos where they experience the thrill of beautiful waters and stunning views but also face unforeseen problems that threaten their expedition. Witness their resilience as they overcome challenges to continue their voyage. Watch...
Sailing to the MOST FAMOUS shipwreck in the Med – NAVAGIO! • S4:EP10 (RE-UPLOADED)
Sailing Holly Blue

Sailing to the MOST FAMOUS shipwreck in the Med – NAVAGIO! • S4:EP10 (RE-UPLOADED)

Sail to the legendary Navagio shipwreck in Greece, explore stunning beaches, and soak in unforgettable views on this must-visit boating excursion.
“It’s a new dawn, a new day, a NUDE life for me…& I’m feelin’ good!” • S4:Ep12 (YouTube Edit)
Sailing Holly Blue

“It’s a new dawn, a new day, a NUDE life for me…& I’m feelin’ good!” • S4:Ep12 (YouTube Edit)

In this episode of Sailing Holly Blue, join Ross, Laura, Joshua, and Noah as they sail to the Ionian Islands in Greece. Learn about their experiences exploring these stunning locations, including Skala and Sami. Get practical tips for your own sailing adventures!
When a Gybe goes wrong ep45   4K
Motherload sailing

When a Gybe goes wrong ep45 4K

Join the adventurous journey of a family of seven as they embark on a practice run for the upcoming sailing regatta in Bocas Del Toro, Panama, aboard their 50' monohull. Follow along as they encounter challenges, including an oversteering incident and a sloppy gybe, resulting in Mom getting som...
Sailing to the MOST FAMOUS shipwreck in the Med – NAVAGIO! • S4:EP10
Sailing Holly Blue

Sailing to the MOST FAMOUS shipwreck in the Med – NAVAGIO! • S4:EP10

In this sailing episode we take you on a sunrise sail to the stunning and WORLD FAMOUS Shipwreck Beach - AKA Navagio! It's a tight squeeze manoeuvring out of our mooring spot at the beautiful anchorage in Agios Nikolaos Harbour but we work well together as a couple and get it done. Following ...
Is He Really Leaving Me…..?  Sailing Zakynthos, Greece • S4:Ep8
Sailing Holly Blue

Is He Really Leaving Me…..?  Sailing Zakynthos, Greece • S4:Ep8

Join us in this nail-biter of a sailing episode where tensions rise for us on the island of Zakynthos, where Murphy's law "Anything that can go wrong will go wrong." hits us in full swing!! Thanks for watching, please be sure to like, subscribe, share this episode with friends and hi...
Sailing Zakynthos: NUDE SULPHUR SWIMMING! We Explore This Beautiful Island S4:Ep6
Sailing Holly Blue

Sailing Zakynthos: NUDE SULPHUR SWIMMING! We Explore This Beautiful Island S4:Ep6

Apparently swimming in your birthday suit in the sulphur springs of Xigia beach has many health benefits so of course Laura was keen to take a skinny dip into the fountain of youth! haha!....There's a lot of fun in this cracker of a sailing episode. We finally explore our first Ionian Island: Z...
Watching out for Orcas on the sail to Gibraltar  |  Ep96
Sailing Fair Isle

Watching out for Orcas on the sail to Gibraltar | Ep96

Lots of sailing in this episode as we battle our way through the Balearics and over to the Spanish mainland towards Gibraltar. We get a real mix of conditions, some interesting sea life and battle broken boat bits... so just normal sailing then! ------------------------------------------------------...
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