Watch Sailing & Boating Adventures Around the World – Page 3 of 4

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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Our World Sailing Adventure Just Keeps Getting Better [Ep.16] Sailing Greece Mainland  SV CUBA
Sailing SV CUBA

Our World Sailing Adventure Just Keeps Getting Better [Ep.16] Sailing Greece Mainland SV CUBA

Tag along as the temperatures rise and the crew decides to ditch SV CUBA for the day to escape the heat. We are on the hunt for a special place in Kalamaris, home to wetland creatures and amphibians. If you like to be part of our journey, please consider becoming a Patreon @ We are still sailing...
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 ...
OFF GRID SAILING HEAVEN. Moments living on a BOAT are all about • S2:Ep25
Sailing Holly Blue

OFF GRID SAILING HEAVEN. Moments living on a BOAT are all about • S2:Ep25

In this BOAT LIFE / SAILING episode, we set the Greek island scene from the sky, the land, under the water and on it. Starting with exploring Antiparos, Greece - we share with you all the ingredients that keep us connected in this amazing thing called life. A perfect mix of sailing, adventure and ...
Greek Boat Life: IT’S NOT ALWAYS SUNSHINE & SAILING! • S2:EP24
Sailing Holly Blue

Greek Boat Life: IT’S NOT ALWAYS SUNSHINE & SAILING! • S2:EP24

Hi Guys! In this Sailing Episode, we begin BOAT LIFE on Paros Island, where we explore the port of Parikia and our anchorage nearby. Laura enjoys a BoatFit Bikini Workout, Josh has a swimming challenge with spectators to dance/cheer him on and we shoot some incredible drone shots of Paros set under...
BOAT LIFE: SAILING Delos to…..???  S2:Ep23
Sailing Holly Blue

BOAT LIFE: SAILING Delos to…..??? S2:Ep23

Hi Guys! In this Sailing Episode, we begin BOAT LIFE in Rineia - Delos whilst sitting out the notorious & relentless Meltemi wind. We relax & enjoy this secluded island for a few days whilst deciding which Greek Island to set sail for next. Ross as captain of the boat has to decide whethe...
SAILING DELOS & MYKONOS, GREECE….gems of the Cyclades • S2:EP22
Sailing Holly Blue

SAILING DELOS & MYKONOS, GREECE….gems of the Cyclades • S2:EP22

Hi Guys! In this SAILING & BOATLIFE Episode, we SAIL past DELOS to an idilic anchorage on Rinia Island. We show some incredible drone shots of the view above....ALL but not before sharing with you the heavenly Monastery of Panagia Tourliani back in Mykonos. Be sure to watch to the end for mor...
BOAT LIFE: MYKONOS Island – we anchor at SUPER PARADISE BEACH! • S2:EP21
Sailing Holly Blue

BOAT LIFE: MYKONOS Island – we anchor at SUPER PARADISE BEACH! • S2:EP21

Hi Guys! In this Sailing Episode, we begin BOAT LIFE in MYKONOS and start to explore this famous island. All before the sexy bikini's come out to play and the beats begin at our anchorage - Super Paradise Beach! Be sure to watch to the end for more of the usual comical sailing family life abo...
SAILING TO MYKONOS – The leap of FAITH! • S2:EP20
Sailing Holly Blue

SAILING TO MYKONOS – The leap of FAITH! • S2:EP20

Hi Guys! In this SAILING episode we SAIL to MYKONOS via the stunning coastline of the Samos, Fournoi and Ikaria. The last leg Ikaria - Mykonos is across the middle of the Aegean sea which is notorious for its big swells and strong Meltemi winds. Ross has to plan and look at the weather very carefull...
Impactful TRUTH Learned while Sailing to Explore GREECE | BOAB 202
Bums on a Boat

Impactful TRUTH Learned while Sailing to Explore GREECE | BOAB 202

Did you know about this impactful TRUTH? On the 18th of Oct. 2021, I learned something from Judy @svfairisle that forever changed the way I communicate with others! If you've been holding back I hope this video give you the confidence to SPEAK UP and know your opinion is an important part of...
BOAT LIFE: WHERE DO WE GO FROM HERE?! S2•Ep19
Sailing Holly Blue

BOAT LIFE: WHERE DO WE GO FROM HERE?! S2•Ep19

Hi Guys! In this Sailing Episode we show you the last of SAMOS ISLAND! Noah caves and Ross gets ‘BUSTED’ all before Ross asks Laura "Where do we go from here?". It's not always easy keeping the family happy but in this part of the world, who could possibly complain?! We also reveal o...
WATCH THIS BEFORE YOU SAIL GREECE! Ep-10
Leading the Escapade

WATCH THIS BEFORE YOU SAIL GREECE! Ep-10

In this week's episode we take you back to the beginning of our time in Greece and cram our all the notable events into one episode to recap ​the up's & down's.
SAILING SAMOS! A heavenly MUST SEE anchorage – S2•Ep18
Sailing Holly Blue

SAILING SAMOS! A heavenly MUST SEE anchorage – S2•Ep18

Hi Guys! In this Sailing Episode, Laura changes our tack after doing some research - we set sail from Samos Port and head east to a unique anchorage called 'Posidonio'. This idilic spot could almost be heaven....just watch out for jellyfish! Be sure to watch to the end for more of the u...
OUR 5yr OLD LIVEABOARD SON SWIMS TO SHORE 😱😱 (proud parent moment) – S2•Ep16
Sailing Holly Blue

OUR 5yr OLD LIVEABOARD SON SWIMS TO SHORE 😱😱 (proud parent moment) – S2•Ep16

Hi Guys! In this sailing episode we continue Boat Life in Samos including more chats with the locals, boat schooling, visiting the infamous Blue street and Ross gives Noah the biggest challenge of his life! Will he overcome his fear? Be sure to watch to the end for more of the usual comical family l...
Finding Our LiveAboard Sailing Catamaran In Greece
Dutch Sailing Family

Finding Our LiveAboard Sailing Catamaran In Greece

We search for a liveaboard sailing catamaran in Greece in this episode! It has been our long time dream to live aboard a sailboat! Will we find what we're looking for? We have a look at a Lagoon 400, a Lagoon 410, and a Fountaine Pajot Lavezzi 40, and tell you about our experience with these sa...
Sailing Greece In October: Dodging Thunderstorms
Sailing Two Get Lost

Sailing Greece In October: Dodging Thunderstorms

We are on the beautiful Greek island of Patmos in the Dodecanese, enjoying calmer winds and beautiful sunrises, but also dodging thunderstorms and unsettled weather. This was our favourite month so far and we're so pleased we chose not to retreat to harbour for the Autumn months. If you enjoy...
KEEP CALM AND CARRY ON SAILING – Life On Board With A Chronic Illness • S2:EP12
Sailing Holly Blue

KEEP CALM AND CARRY ON SAILING – Life On Board With A Chronic Illness • S2:EP12

Hi Guys! In this sailing episode, Laura opens up about some personal struggles and how we manage as a sailing family.....we explore the beautiful scenery of Agathonisi and then set sail for Samos (two stunning greek islands)....but after the last little hell-ride (see Episode 11) in a force 6 - will...
CAUGHT IN A FORCE 6 IN THE AEGEAN!• S2:Ep11
Sailing Holly Blue

CAUGHT IN A FORCE 6 IN THE AEGEAN!• S2:Ep11

Sailing in Greece isn't always easy on our family and in this sailing episode, we show you to always be prepared for the weather to turn. Skipper Ross says "If you want to know what a force 6 feels like, this is it!" Join us for the ride in this awesome sail from Marathi to Agathonis...
Sailing out of Symi Island in Greece: Greek Island Hopping
Sailing Two Get Lost

Sailing out of Symi Island in Greece: Greek Island Hopping

After Medicane warnings, high winds and lots of work we set off sailing out of Symi island in Greece to continue our Greek island hopping adventure. If you enjoy the content and want to support us further then there are some suggestions below. Thank you, thank you, thank you! BUY US A BEER on PAY...
S2:Ep8 – BOAT LIFE REALITY & Sailing to Arkoi Island AKA “The Maldives of Greece”
Sailing Holly Blue

S2:Ep8 – BOAT LIFE REALITY & Sailing to Arkoi Island AKA “The Maldives of Greece”

Hi Guys! In this episode we walk you through our Boat Life, where family tensions run high and Laura goes skinny dipping to cool off... Also we explore Archangelos via 'Noah-cam' and sail Holly Blue to the remarkably beautiful Greek Island Arkoi - with a population of only 54 inhabitants...
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...
BOAT LIFE: Sailing to LIPSI ISLAND with seasick crew 🤢! S2:Ep5
Sailing Holly Blue

BOAT LIFE: Sailing to LIPSI ISLAND with seasick crew 🤢! S2:Ep5

Hey Everyone! Prepare yourselves for a bumpy ride as we finally head North on our Greek Island live aboard adventures...this time we sail towards the beautiful Greek gem - Lipsi Island! It's love at first sight after a turbulent trip and we celebrate Noah's 6th Birthday on the way...... ...
Join us for THE PERFECT SAIL! On The Greek Islands • S2:Ep4
Sailing Holly Blue

Join us for THE PERFECT SAIL! On The Greek Islands • S2:Ep4

Hello Everyone and welcome back! In this episode Ross experiences the stoke of a perfect sail, Laura celebrates a milestone and hits her ‘naughty forties’, we celebrate with a family day out and explore the gorgeous Greek town on Agia Marina... Finally we top the day off with a cold one at sunset....
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