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.

Showing 1-23 of 23 results
Stunning views in Patmos and then a visit to Lipsi! (Sailing Dakini – Leave to Roam Ep. 112)
Leave to Roam

Stunning views in Patmos and then a visit to Lipsi! (Sailing Dakini – Leave to Roam Ep. 112)

In this episode we spend our last few days in the water for 2025 visiting some popular anchorages around Leros. These include Alinda and Agia Marina where we weather the most amazing electrical storm which knocks power out to the whole island! We finish off in Blefouti, where Al visits the yard for...
‘My Nude Greek Life’ Part 2 • Season 4 (special extended cut!) • Sailing ALL of Greece (E-W)
Sailing Holly Blue

‘My Nude Greek Life’ Part 2 • Season 4 (special extended cut!) • Sailing ALL of Greece (E-W)

Welcome to this extended SPECIAL CUT of our Season 4 Sailing Adventures - reproduced for your enhanced viewing pleasure. Get an exclusive 15% discount on Saily data plans! Just use our code [hollyblue] at checkout. Simply Download Saily app or go to  Hey guys, and welcome to this extended speci...
Inside the Real “Below Deck”: The daily life of a British couple living and sailing aboard a yacht.
Carl and Jenny

Inside the Real “Below Deck”: The daily life of a British couple living and sailing aboard a yacht.

----------------------------------------------------------------------------------------------------- This has got to be our worst sail yet with regards to high seas. The plan was to sail from Koufonisi to Levithia where we had planned to stay overnight then continue on the following morning to Ler...
Sailing across the Cyclades in March – Cold, stormy & AMAZING! Winter / off season in Greece (Ep 14)
Sailing Wishful Thinking

Sailing across the Cyclades in March – Cold, stormy & AMAZING! Winter / off season in Greece (Ep 14)

We finally launch Wishful Thinking in Leros, Greece, ready for our second sailing season. We're nervous about our launch as we've done lots of work below the waterline and found a leak after launching last year. Our friends (along with their cat, Chicho) invite us over for a boat tour of t...
Anchor and chain upgrade & water maker refurb (Katadyn / PUR 40E) (Ep 13)
Sailing Wishful Thinking

Anchor and chain upgrade & water maker refurb (Katadyn / PUR 40E) (Ep 13)

We upgrade our anchor and chain, replacing our Chinese knock-off Bruce with a shiny new Spade. Ryan also refurbishes a Katadyn/PUR 40E water maker and installs a cockpit/deck shower. We finish off lots of other jobs ready for launch day, while Chicho the ginger tom keeps us company.
Spring refit and boat work on Leros island, Greece – New solar, bilge alarm and fridge (Ep 12)
Sailing Wishful Thinking

Spring refit and boat work on Leros island, Greece – New solar, bilge alarm and fridge (Ep 12)

We fly back to Leros island in Greece where we left Wishful Thinking for the European winter on the hard at Moor and Dock Boatyard. We get straight into boat work to prepare to launch her for our second sailing season. Below the waterline we remove rust on the keel, replace some thru hulls, fibregla...
Hauling out and winterising our sailboat on Leros island, Greece (Ep 11)
Sailing Wishful Thinking

Hauling out and winterising our sailboat on Leros island, Greece (Ep 11)

Wishful Thinking is hauled out on Leros island in eastern Greece for the European winter. We pack away the sails, service the engine and seacocks, fog our dinghy outboard and do lots of other jobs to prepare to leave her for the winter. We engage a technician from the boat yard to service and repack...
‘My Nude Greek Life’ – freedom, sailing, happiness & heartbreak…Season 3 (special extended cut!)
Sailing Holly Blue

‘My Nude Greek Life’ – freedom, sailing, happiness & heartbreak…Season 3 (special extended cut!)

In this season, we show you the kaleidoscope of experiences a sailing lifestyle offers - not only will you gain a true account of what relationships go through & boat life is really like here in Greece but you’ll also learn about many other factors (SEE TIMESTAMPS BELOW). You’ll catch our cultu...
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...
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...
CAUGHT IN A FREAK STORM!  The one where we almost beach the boat…. • S2:Ep34
Sailing Holly Blue

CAUGHT IN A FREAK STORM! The one where we almost beach the boat…. • S2:Ep34

This is the last Sailing episode of our Season 2 & we’re going out with a bang! BOAT LIFE in autumn is quite the contrast to summer here in the Aegean and our tenacity is once again tested as the weather becomes very unpredictable… Leave us a comment! and if your new here please LIKE, SUBSCRIB...
HAULING OUT BY TRACTOR for the first time!
Sailing Two Get Lost

HAULING OUT BY TRACTOR for the first time!

Hauling out our 38ft sailboat home by tractor for the first time ever, and removing our centreboard. Also, this was Tiny Cats first stay in a house. What do you think she prefers, land life or sailboat life!? Like and subscribe if you enjoyed :) Find out more.... We've spent months puttin...
Life On A TINY SAILBOAT HOME
Sailing Two Get Lost

Life On A TINY SAILBOAT HOME

Our life on a tiny sailboat home. We get stuck at anchor for three weeks during a lockdown in Greece, and this is what it was really like! Like and subscribe if you enjoyed :) Find out more.... We've spent months putting together EVERYTHING we've learnt about running away to sea. This...
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....
“SNAKES IN THE WATER!” – life living on a SAILING BOAT in Greece!• S2:Ep3
Sailing Holly Blue

“SNAKES IN THE WATER!” – life living on a SAILING BOAT in Greece!• S2:Ep3

Hi Guys! In this episode Laura has an encounter of the slithery-kind, Ross takes us on a trip up the coast after making a snap decision to up-anchor and we show that boat life isn't always the heavenly sunny situation it might appear to be on our sail boat! Thanks for watching! Join us on th...
THE BEST FEELING EVER! Sailing away from the madness🤘👊 S2:Ep1
Sailing Holly Blue

THE BEST FEELING EVER! Sailing away from the madness🤘👊 S2:Ep1

Welcome to SEASON TWO of Sailing The Greek Islands! In this first episode, after spending the winter in Leros Marina and 3 MONTHS in LOCKDOWN, we are finally set free to sail and get back to one of what is arguably one of THE BEST feelings ever....anchor life! Join us as we begin this EPIC season o...
We Buy Gifts For A WHOLE CAMP Of Refugees!
Sailing Holly Blue

We Buy Gifts For A WHOLE CAMP Of Refugees!

Hi guys! This episode is a little different from our usual sailing and Greek Island travels..... Over Christmas 2020 we decided that we wanted to do something special and create some extra cheer for those less fortunate. Our winter home of Leros Island in Greece is also a hot spot for refugee'...
THE END OF BOAT LIFE?! Leros Island, Greece 🇬🇷
Sailing Holly Blue

THE END OF BOAT LIFE?! Leros Island, Greece 🇬🇷

In this episode we reach our final (?) destination of the season - The gorgeous Greek Island of Leros - a quirky, unique and undiscovered gem with great anchorages and many marina/port options in Lakki Town - commonly known as ‘the weirdest town in Greece’. Leros is an incredibly interesting place...
Leros Marina – The safest natural harbour and Marina in Greece!
Sailing Holly Blue

Leros Marina – The safest natural harbour and Marina in Greece!

For Marina Enquiries please visit: www.lerosmarina.gr This is our review of Leros Marina, which became our 'safe haven' over the winter of 2019/20....and subsequently during the world pandemic and lockdown in Greece.....we wanted to make this review to personally thank the Marina and sta...
ROSS GOES INTO HERO MODE: Drama At Milos Port – Talk About ‘Crossing Swords’!• Ep5
Sailing Holly Blue

ROSS GOES INTO HERO MODE: Drama At Milos Port – Talk About ‘Crossing Swords’!• Ep5

In this episode we start by giving a quick update of our current Covid19 isolation situation, during our lockdown in Greece amidst the Coronavirus pandemic. We then pick up from where we left off in Sifnos (see ep 4) as we sail South West to the islands of Kimolos and then on to Milos.... We explor...
We sail to Kalimnos and explore Leros – Carl and Jenny – Ep.39
Carl and Jenny

We sail to Kalimnos and explore Leros – Carl and Jenny – Ep.39

In this episode we set sail for Kalimnos. We then head for Leros where we hire a scooter and go and explore the island. We see Mousolini's holiday home, the bay where the Italian sea planes were based during WW2 the and explore the tunnels of Leros. ---------------------------------------------...
WeBoating
Logo
Shopping cart