Watch Sailing & Boating Adventures Around the World – Page 2 of 2

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 25-38 of 38 results
A DREAMY SAIL to MARVELLOUS MILOS | Sailing Across Greece Leg 2  • S4 EP2
Sailing Holly Blue

A DREAMY SAIL to MARVELLOUS MILOS | Sailing Across Greece Leg 2 • S4 EP2

In this DREAMY SAILING EPISODE, we continue the 2nd leg of our sailing passage across Greece...dropping the hook at MARVELLOUS MILOS Island. There's crystal waters, Paddle-boarding, Sea caves and other incredible geological sights. We even play chicken with a local ferry and tell you the story...
The ULTIMATE way to SAIL ACROSS GREECE! • S4:Ep1
Sailing Holly Blue

The ULTIMATE way to SAIL ACROSS GREECE! • S4:Ep1

After all the trials and travels of seasons before, we thought it would be nice to get back to some good old simple sailing. In this episode we show you the best way to sail across Greece (East to West) and also share info and advice on some useful sailing upgrades including our new HOLLYLAND C1 HE...
When BOAT LIFE meets REAL LIFE – what we haven’t told you • S3:Ep7
Sailing Holly Blue

When BOAT LIFE meets REAL LIFE – what we haven’t told you • S3:Ep7

This episode marks not only the end of Season , but also fills you all in on a period of time that shook our world and left us reeling. As a channel we always want to remain transparent about the reality of living on the ocean and also the fact that even though we might appear to be 'living th...
4 YEARS LIVING ON A BOAT IN GREECE! • S3:Ep6
Sailing Holly Blue

4 YEARS LIVING ON A BOAT IN GREECE! • S3:Ep6

In this Sailing Episode, we finally leave Kos after a fantastic visit and things go from high to low to high to low when the Meltemi bangs at the door once again and sends everyone in nearby anchorages and ports literally sideways on the islands of Tilos and Chalki! Laura also has a couple of '...
LIVING ON A BOAT IS EPIC…does it get any better than this? • S3:Ep5
Sailing Holly Blue

LIVING ON A BOAT IS EPIC…does it get any better than this? • S3:Ep5

More BOAT LIFE and SAILING in this episode as we set sail to another stunning anchorage on the Greek Islands. We’re all high on Boat Life in this sailing episode but remember what goes up must come down! Be sure to SUBSCRIBE and smash the BELL so you don’t miss out on what’s coming… Leave us a comm...
BOATLIFE: When Ya Feel Like Bailing Out S3Ep3
Sailing Holly Blue

BOATLIFE: When Ya Feel Like Bailing Out S3Ep3

In this Boat Life Reality episode, we sail from Kalymnos to Pserimos to Kos and back again! Along the way, we reveal the truth about Boat Life in the greek islands during the Meltemi season and why we may want a break from this part of Greece. We show some hardships and how we overcome them as a fa...
BOAT LIFE vs LAND LIFE • which one would you choose? • S3:Ep2
Sailing Holly Blue

BOAT LIFE vs LAND LIFE • which one would you choose? • S3:Ep2

🌎 Get 4 months for free on a 2-year plan here⇢ It’s risk-free with Nord’s 30-day money-back guarantee! ✌️ In this episode we sail from the Greek island of Leros to Kalymnos - the infamous 'Climbers Island' - where sky-high cliffs tower over the sailing port. Once docked the crew of Holl...
STUCK ON ANCHOR!…..Catch Up & Cook With Us • S3:Ep1
Sailing Holly Blue

STUCK ON ANCHOR!…..Catch Up & Cook With Us • S3:Ep1

Get 70% OFF on your next Huusk knife! Hey guys and WELCOME to Season 3! of our sailing adventures aboard our sailing yacht HOLLY BLUE! Today we reminisce a little - taking you on a flashback through our winter Boat Life....fast forward to our first sail of the season when the worst happened and w...
TOP TEN GREEK SAILING BEACH: Koufonisi, Cyclades S2:Ep31
Sailing Holly Blue

TOP TEN GREEK SAILING BEACH: Koufonisi, Cyclades S2:Ep31

Sometimes in Boat Life it’s down to the captain to make the final call. Ross goes with his gut and changes our plan again! But where do we end up? In a little piece of paradise! AKA Koufonisi which is a beautiful greek island with incredible crystal clear turquoise waters, clean white sandy beaches...
THE HARDEST THING ABOUT SAILING LIFE (Saying Goodbye) • S2:Ep30
Sailing Holly Blue

THE HARDEST THING ABOUT SAILING LIFE (Saying Goodbye) • S2:Ep30

In this BOAT LIFE episode , we share some home truths about the reality of living & working onboard before wrapping up our visit at ios island - we then sail for south Naxos where a little miracle happens! Leave us a comment & If your new here please LIKE, SUBSCRIBE and SMASH that BELL for ...
Living Our Best Life & Skinny Dips at Sunset.  Ios Island, Greece • S2Ep28
Sailing Holly Blue

Living Our Best Life & Skinny Dips at Sunset. Ios Island, Greece • S2Ep28

Hello Everyone and Welcome Join us on our sailing adventure to magical Ios island - famed for nudist beaches, crystal clear waters, beachside pool bars and rock jumping. Boat life isn’t always a dream though so watch out for the cliffhanger ending! If your new here please like, subscribe and smash...
BOAT LIFE: POOR SEAMANSHIP?  Tell us what you think!  Sailing Schoinousa Island, Greece • S2:Ep27
Sailing Holly Blue

BOAT LIFE: POOR SEAMANSHIP? Tell us what you think! Sailing Schoinousa Island, Greece • S2:Ep27

In this Sailing/Boat Life episode there’s dramas, spearfishing & sailing in a dose of real-life at sea. After some questionable poor seamanship our faith in humanity is restored by a random act of kindness on the beautiful island of Schoinousa. Another must visit Greek island if you want to get...
GLASSY SAILING IN THE GREEK ISLANDS & Diving a WW2 Plane Wreck! • S2:Ep26
Sailing Holly Blue

GLASSY SAILING IN THE GREEK ISLANDS & Diving a WW2 Plane Wreck! • S2:Ep26

In this Sailing episode, we take a "sexy" sail for the remote island of Iraklia, Greece….it really was one of our most special & amazing sailing experiences…hence why we always call them ‘sexy sails’! We then arrive at the secluded island (Iraklia) and tie up to rocks in the heavenly ...
S2:Ep7 A SEXY SAIL to TINY Archangelos Island – Laura talks NUDITY, BOAT LIFE & conquering FEAR!
Sailing Holly Blue

S2:Ep7 A SEXY SAIL to TINY Archangelos Island – Laura talks NUDITY, BOAT LIFE & conquering FEAR!

Hi guys! In this episode we talk sailing and nudity, the benefits of anchor life over marinas and how conquering your fears is the way to grow in this challenging lifestyle! Laura takes the helm and we have an awesome sail as we fly over some beastie waves to the tiny remote near-uninhabited Greek...
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