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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We Live on a Lagoon 42 in Greece
Sailing Bluefish

We Live on a Lagoon 42 in Greece

A small glimpse of our life aboard Sailing Bluefish — sailing and living full-time on a Lagoon 42 in Greece and the Mediterranean.
SECRET to Safely Docking on a Rocky Ancient Quay
Dylan Magaster

SECRET to Safely Docking on a Rocky Ancient Quay

🌿 Upgrade your skin with Captain's Salve: Our latest sailing adventure led us to the infamously rough fishing quay at Agia Anna, presenting a unique docking a boat challenge. We meticulously navigated the vessel, taking every precaution to protect it from damage at this new location. This jour...
Unconventional Tour of the Largest Cyclades Island | Naxos, Greece
Dylan Magaster

Unconventional Tour of the Largest Cyclades Island | Naxos, Greece

We sailed to one of Greece’s most overlooked islands — Naxos — and uncovered ancient secrets hiding in plain sight. From the legendary Cave of Zeus to abandoned Jesuit monasteries, stone bridges in ghost villages, and timeless terraced hillsides, this island feels like stepping through a portal int...
The Most Important Jesuit Ruin You’ve Never Heard Of
Dylan Magaster

The Most Important Jesuit Ruin You’ve Never Heard Of

Upgrade your skin with Captain's Salve: Beneath layers of overgrowth and time lies an abandoned Jesuit monastery hidden on the Greek island of Naxos, untouched, undocumented, and almost erased from the historical record. But who were the Jesuits really? Missionaries? Master educators? Or a sec...
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 ...
Have we Devolved? Exploring Delos, Ancient Greece
Dylan Magaster

Have we Devolved? Exploring Delos, Ancient Greece

Step back in time to ancient Delos, a city that was once the financial hub and melting pot of various cultures and religions in Greece. Our detailed exploration delves into the rich history, magnificent architecture, and what life may have been like on this legendary island over 2,300 years ago.
We sailed to a Shipwreck on an Uninhabited Island | Peristera, Greece
Dylan Magaster

We sailed to a Shipwreck on an Uninhabited Island | Peristera, Greece

Dylan Magaster and Niki Sail SV Arianrhod from Steni Vala, Alonissos, Greece to the island and shipwreck of Peristera Support on Patreon: Support with Bitcoin: 1C2GuZPscVskvzScBJSQpdeXqGz2moJHaC Follow Dylan Magaster: Business inquires or music submissions: [email protected] Music: ...
Diving a WW2 PLANE WRECK after a glorious sunrise sail.  This is why we live on a sailboat!
Sailing Two Get Lost

Diving a WW2 PLANE WRECK after a glorious sunrise sail. This is why we live on a sailboat!

When sailing rocks! We dive on a WW2 plane wreck after a glorious sunrise sail to another beautiful Greek island! Thanks to everyone for your support - like and subscribe if you enjoyed :) and below are some more ways you can support the making of these sailing videos. BUY US A BEER on PAYPAL - tw...
An AWESOME SAIL: Greek Island Hopping In The Cyclades
Sailing Two Get Lost

An AWESOME SAIL: Greek Island Hopping In The Cyclades

An awesome sail in the Cyclades. We go Greek island hopping and find the perfect place to spend the night at anchor. Thanks to everyone for your support - like and subscribe if you enjoyed :) and below are some more ways you can support the making of these sailing videos. BUY US A BEER on PAYPAL ...
Boat Life – Installing our new LOFRANS WINDLASS and an awesome sail to Zante – Vlog #13
Sailing Two Get Lost

Boat Life – Installing our new LOFRANS WINDLASS and an awesome sail to Zante – Vlog #13

We fit our BRAND NEW LOFRANS WINDLASS and kiss goodbye to all our anchoring woes! After several months of hauling up the anchor by hand this is a really exciting moment for us! We finally leave Argostoli and have an awesome sail over to the Greek island of Zante. SUBSCRIBE to get notified when ou...
A BIRTHDAY SAIL on our Kadey Krogen 38 – Vlog #11
Sailing Two Get Lost

A BIRTHDAY SAIL on our Kadey Krogen 38 – Vlog #11

Warning: This video is mostly just us eating delicious food. You can tell we don't currently have any food on board! We anchor in our favourite anchorage of all time on the island of Atokos and celebrate Emily's birthday with multiple meals out and way too much alcohol! Support us by S...
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