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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E239 – Kastellorizo – The Tiny Greek Island You’ve Probably Never Heard Of
Sailing No Regrets

E239 – Kastellorizo – The Tiny Greek Island You’ve Probably Never Heard Of

After seven years of creating sailing content, we take a well-earned break from filming and spend a month exploring Cyprus. We visit Larnaca, Nicosia and Paphos, dive the famous Zenobia shipwreck, and explore incredible sites including Kolossi Castle, Kykkos Monastery and the ancient ruins of Nea Pa...
Real Boat Life in Greece | Sailing Our Lagoon 42 Around Kefalonia
Sailing Bluefish

Real Boat Life in Greece | Sailing Our Lagoon 42 Around Kefalonia

We sail our Lagoon 42 around Kefalonia in Greece, moving from Ithaca to Argostoli and Xi Beach as we settle into the everyday rhythm of full-time boat life in the Ionian Islands — including a morning thunderstorm with lightning surrounding the anchorage. This week is less about big passages and mor...
This Is Why We Chose Boat Life | Sailing Our Lagoon 42 in Greece
Sailing Bluefish

This Is Why We Chose Boat Life | Sailing Our Lagoon 42 in Greece

After a few busy days in London, we are back aboard Bluefish, our Lagoon 42, and back to full-time boat life in Greece. We leave Lefkada and sail through the Ionian Islands towards Mytikas, Kastos and eventually Vathy on Ithaca — settling back into the simple rhythm that made us choose this life in ...
The BEST Ionian Anchorages We Keep Coming Back To | Sailing Greece 🇬🇷
Sailing Okaliptüs

The BEST Ionian Anchorages We Keep Coming Back To | Sailing Greece 🇬🇷

Ep. 217 ~ Looking for the best Ionian anchorages in Greece? Join us as we revisit some of our favorite places while sailing our catamaran through the beautiful Ionian Islands. In this episode, we leave Ithaca and head to the tiny island of Kastos, where we compare the peaceful Easter season to the ...
Sailing Greece on a Lagoon 42 | Greece’s Underrated Island
Sailing Bluefish

Sailing Greece on a Lagoon 42 | Greece’s Underrated Island

After a calm start from Poros, we head north towards Kea for a windy sail through the Greek islands. The wind builds during the passage, with gusts up to around 24 knots, and our Code Zero gives us a small reminder that sailing plans do not always unfold exactly as expected. Just one of those real ...
My BIGGEST Diving CHALLENGE
Dylan Magaster

My BIGGEST Diving CHALLENGE

I sail to a Greek island for my biggest Scuba dive challenge yet. Am I ready to be a Divemaster? If you're interested in group travel: Dive with Walter: Support on Patreon: Support with Bitcoin: 1C2GuZPscVskvzScBJSQpdeXqGz2moJHaC In this video we will embark on the PADI Divemaster course...
Cliff Monastery Built 1000 Years Ago | Amorgos
Dylan Magaster

Cliff Monastery Built 1000 Years Ago | Amorgos

Support on Patreon: Support with Bitcoin: 1C2GuZPscVskvzScBJSQpdeXqGz2moJHaC Follow Dylan Magaster: Business inquires or music submissions: [email protected] Music: Filmed by Dylan Magaster: Edited by Dylan Magaster:
This Greek island has everything – sailing, fishing, mystery
Dylan Magaster

This Greek island has everything – sailing, fishing, mystery

Welcome back to another beautiful day in the Aegean Sea, as we continue our travel vlog from the Greek islands. This sailing journey takes us from Kufanisia towards the large island of Amorgos, offering stunning ocean views along the way. We also get a chance to go freediving and catch and cook some...
Sailing and Spearfishing in the Aegean Sea | Koufonisia
Dylan Magaster

Sailing and Spearfishing in the Aegean Sea | Koufonisia

Join us on a sailing trip around the stunning Naxos and Koufounissia in the Cyclades, Greece, showcasing the beautiful "sailing cyclades" experience. We navigate past the large island of Naxos, anchoring in the protected bay of Panarmos, a perfect example of "sailing greece" and ...
Beginner vs. 25 Knot Wind: Can She Handle It?
Dylan Magaster

Beginner vs. 25 Knot Wind: Can She Handle It?

Timeless skin nourishment, Infused with ancient herbs: ➤ What if sailing could transport you through time? In this episode, we ride 25-knot winds across the Aegean Sea to reach one of Greece’s most legendary monuments: the Gate of Apollo on the island of Naxos. With only one sail, rough seas, and ...
This Greek Island Was Once the Center of the World! | Delos
Dylan Magaster

This Greek Island Was Once the Center of the World! | Delos

Upgrade your Skin with Captain's Salve: In the heart of the Aegean Sea lies Delos, Greece the mythical birthplace of Apollo and Artemis… and one of the most mysterious archaeological sites in the ancient world. Today it’s a ruin — but 2,000 years ago, it was a booming tax haven, religious cap...
Is This the Strangest Island in Greece? | Tinos
Dylan Magaster

Is This the Strangest Island in Greece? | Tinos

Support your skin with Captain's Salve: Join us as we go sailing through the Cyclades islands and explore this beautiful part of travel greece and the greek islands. Come with us to the Greek island of Tinos! Terraced landscape, strong winds, The biggest pilgrimage site in Greece and legendary...
Is this Hidden Gem of a Greek Island My Favorite? | Skyros
Dylan Magaster

Is this Hidden Gem of a Greek Island My Favorite? | Skyros

🔥 Support the journey and get the salve I use daily in the sun, sea, and wind: We set off to explore one of the most underrated Greek islands — Skyros. What started as a peaceful scooter ride quickly turned into a breakdown saga, hidden beaches, ancient ruins, mysterious cats, and wild island horse...
Sailing Into a Storm | Greek Island Adventure to Skyros
Dylan Magaster

Sailing Into a Storm | Greek Island Adventure to Skyros

🌊 Support the Journey: We set sail from a quiet bay on the island of Proso, heading toward Skyros — a place of tiny horses, lobsters, and ancient legend. What began as a calm journey quickly turned into a tense wait-out as a lightning-laden storm rolled in. On a sailboat, thunderstorms aren’t just...
Anchored in Paradise: Discovering Nissos Peristera and Prasso, Greece
Dylan Magaster

Anchored in Paradise: Discovering Nissos Peristera and Prasso, Greece

Support your skin and support the channel with the best skin salve: In today’s adventure, we set sail to the stunning, uninhabited island of Nissos Prasso, one of Greece’s most remote and beautiful locations. With no permanent residents, this hidden gem offers pristine beaches, crystal-clear waters...
We Found a Shipwreck in Greece and Explored It
Dylan Magaster

We Found a Shipwreck in Greece and Explored It

Grab a jar of Captain's Salve at: We left Steni Vala and found ourselves anchored next to a decaying shipwreck off the coast of Peristera, in the Northern Sporades in Greece. What happened to this mysterious vessel? Join us as we explore it by dinghy and FPV drone, and reflect on the eerie bea...
This Tiny Greek Island is Full of Surprises
Dylan Magaster

This Tiny Greek Island is Full of Surprises

► Captain Salve: --- Today we sail from Skopelos to Alonissos — an island full of hidden history, pirate tales, monk seals, and unexpected mishaps. We anchor in crystal bays, ride a scooter to remote villages, crash (literally), and cross paths with a wild endangered seal with a reputation. From...
Her First Sail to a Hidden Beach Only Boats Can Reach
Dylan Magaster

Her First Sail to a Hidden Beach Only Boats Can Reach

Nikki had never been sailing before—but today, we set out on her first real voyage across the Aegean. We’re sailing from Skopelos to the remote, unreachable-by-road beach of Lalaria, one of the most famous and mysterious beaches in Greece. The cliffs are steep, the water is cyan, and for a moment, w...
Anchor Stuck, Drone Launched, Sailing to Meet a Girl
Dylan Magaster

Anchor Stuck, Drone Launched, Sailing to Meet a Girl

A jammed anchor chain, a shifting wind, and the quiet truths that come with movement. What began as a simple sail to the other side of Skiathos, Greece became a meditation on change, stability, and impermanence. This episode unfolds through challenge and calm—revealing how the rhythm of boat life mi...
What Happens If You Never Clean Your Boat Propeller?
Dylan Magaster

What Happens If You Never Clean Your Boat Propeller?

Support on Patreon: After 6.5 months of not moving, my sailboat’s propeller was nearly useless—forcing me to dive in and clean it by breath-hold. In this video, I take you through the challenges of underwater maintenance, the unpredictable wind of Greece, and deeper thoughts on why most modern sail...
Solo Sailing After 6 Months Land Locked – First Voyage Back!
Dylan Magaster

Solo Sailing After 6 Months Land Locked – First Voyage Back!

Support on Patreon: After 6.5 months locked down in Oreoi, Greece, I finally set sail again — solo. This episode follows the nerves, the boat prep (rigging, anchor, propeller issues), the tough upwind beating to Skiathos, and the mindset lessons of overcoming challenges at sea. Watch as I shake off...
Sailing the Cyclades: Antiparos to Despotiko | Temple of Apollo
Sailing Okaliptüs

Sailing the Cyclades: Antiparos to Despotiko | Temple of Apollo

Ep. 140 ~ Join us as we set sail from Antiparos to the secluded island of Despotiko in the stunning Cyclades! 🌊⛵ In this episode, we navigate through the Aegean Sea, finding the perfect anchorage to wait out another strong mini Meltemi wind before continuing our Mediterranean sailing adventure to *...
Sailing To Paros: Our Catamaran Journey To Parikia And Naoussa
Sailing Okaliptüs

Sailing To Paros: Our Catamaran Journey To Parikia And Naoussa

Ep. 138 ~ Join us on an unforgettable sailing adventure to the stunning island of Paros in the heart of the Cyclades Islands in the Mediterranean. In this episode, we set sail aboard our floating home... a Fountaine Pajot catamaran... and explore the charming towns of Parikia and Naoussa. Discove...
Exploring Lesvos: Sailing The Greek Islands & Crossing The Aegean Sea On Our Catamaran
Sailing Okaliptüs

Exploring Lesvos: Sailing The Greek Islands & Crossing The Aegean Sea On Our Catamaran

Ep. 127 ~ Set sail with us on an unforgettable journey through the enchanting Greek Islands! In this episode, we explore the stunning island of Lesvos aboard our full-time home, a trusty catamaran. After saying farewell to Türkiye and clearing customs in the vibrant port city of Mytilene, we embark...
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