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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Peloponnese Sailing | Monemvasia, Wildfire Planes & Tight Harbor Maneuvers 🇬🇷
Sailing Okaliptüs

Peloponnese Sailing | Monemvasia, Wildfire Planes & Tight Harbor Maneuvers 🇬🇷

Ep. 207 ~ After finally escaping Milos, we change sail plans and return to mainland Greece and sail to the Peloponnese. We are thoroughly entertained by a few dolphins and arrive to one of the most incredible places we’ve visited in Greece... the medieval fortress town of Monemvasia. This sail had...
Ionian Sailing 🇬🇷 Lefkada to Ithaca | Regatta + Unexpected Raft-Up
Sailing Okaliptüs

Ionian Sailing 🇬🇷 Lefkada to Ithaca | Regatta + Unexpected Raft-Up

Ep. 203 ~ We sail the stunning Ionian Islands of Greece, departing Lefkada and heading south to Ithaca—home of Odysseus and one of the most beautiful sailing destinations in the Mediterranean. What starts as a peaceful anchorage in Desimi Bay quickly turns into an adventure, with shifting winds, an ...
We Didn’t Expect THESE in the Ionian 🇬🇷 | Life in a Greek Winter Marina
Sailing Okaliptüs

We Didn’t Expect THESE in the Ionian 🇬🇷 | Life in a Greek Winter Marina

Ep. 199 ~ After a winter of land travel through Central Europe, we’re back aboard our catamaran in Preveza, Greece getting ready for another sailing season in the Mediterranean. But life in a winter marina isn’t just boat work… In this episode, we experience Greek Carnival festivities, celebrate S...
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...
What Happens If You Drop Anchor in the Wrong Spot?
Dylan Magaster

What Happens If You Drop Anchor in the Wrong Spot?

Get Captain's Salve: A routine sailing trip quickly became a challenge when swim bouys were laid directly in front of the boat, tangling the anchor rope. This video captures the intricate process of trying to retrieve the anchor while ensuring the boat remains stationary and the tow float unha...
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 ...
Sailing to Andros: Ancient Bridges, Caves, and Crystal Seas | Greece
Dylan Magaster

Sailing to Andros: Ancient Bridges, Caves, and Crystal Seas | Greece

Try Captain's Salve — handcrafted skin balm for the wild life: Sailing to Andros, Greece, we expected wild winds — but instead we motored across glassy seas through one of the windiest passages in the Aegean. Along the way, we explore abandoned villages, ancient stone bridges, crystal clear be...
Upgrading My Sailboat for Summer: Solar, Teak & Adventures in Greece
Dylan Magaster

Upgrading My Sailboat for Summer: Solar, Teak & Adventures in Greece

Support on Patreon: After months of lockdown on the Greek island of Evia, I finally upgraded my sailboat’s solar power, repaired the teak, fixed the outboard, and patched up the dinghy — all to get ready for the next big adventure. In this video, I take you behind the scenes as I prepare for summer...
SAILBOAT ENGINE FAILURE: They say bad luck comes in threes!
Sailing Two Get Lost

SAILBOAT ENGINE FAILURE: They say bad luck comes in threes!

SAILBOAT ENGINE FAILURE: They say bad luck comes in threes! In this week's episode, Emily's worst nightmare happens and we lose our engine! After nearly sinking, losing the dinghy and then this we're starting to feel this season is a little cursed! But what doesn't kill you ma...
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