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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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 ...
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...
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 ...
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...
Sailing to an Abandoned Mine [Ep.21] 60 Years Untouched – URBEX Milos Greece – Sailing SV CUBA
Sailing SV CUBA

Sailing to an Abandoned Mine [Ep.21] 60 Years Untouched – URBEX Milos Greece – Sailing SV CUBA

Jump on board SV CUBA as we sail the Greek Islands on our journey around the world. Today when we encounter a strange object floating in the distance. So, the hunt to grab the mysterious object is on and after a few attempts we finally reel in an impressive catch on our boathook. But we are not out...
Birthday UNDER THE STARS in a SECLUDED ANCHORAGE:Sailing to the Greek island Serifos in the Cyclades
Sailing Two Get Lost

Birthday UNDER THE STARS in a SECLUDED ANCHORAGE:Sailing to the Greek island Serifos in the Cyclades

We celebrate Emily's birthday under a sky full of stars in a secluded anchorage on the Greek island of Serifos in the Cyclades. It was magical, and we hope we've managed to capture some of it for you! Thanks to everyone for your support - like and subscribe if you enjoyed :) and below ar...
Making a SAIL run for MYKONOS – SAILING Cyclades Islands – Boat life | Ep.17
see the little things

Making a SAIL run for MYKONOS – SAILING Cyclades Islands – Boat life | Ep.17

SUBSCRIBE and hit that BELL notification for weekly SAILING VIDEOS! Don't forget to give the video a thumbs up, it helps more than you think :) We planned to spend more time in the Cyclades and make a circle visiting about 10 islands, but the Meltemi will be blowing fiercely in a few days and...
Off to Kythnos, Cyclades Islands – BOAT LIFE of a sailing couple | Ep. 16
see the little things

Off to Kythnos, Cyclades Islands – BOAT LIFE of a sailing couple | Ep. 16

A DAY IN THE LIFE Another regular day on the boat. We get up really early and finally leave Poros. We are off to Kythnos, an island in the Cyclades and continue sailing in Greece. At least that is the plan, until we are 1 hour out and suddenly our batteries start burning up and draining like crazy.....
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