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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My First ever Catch and Cook with a rusty Speargun
Dylan Magaster

My First ever Catch and Cook with a rusty Speargun

First-time spearfishing while living on a sailboat in Greece — freediving in the Aegean Sea near Naxos and Rineia to catch wild fish for food using a speargun, including white trevally and triggerfish, then cleaning, filleting, and cooking fresh seafood at anchor as part of an off-grid sailing lifes...
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...
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 ...
Sailing from the Cyclades to the Dodecanese Islands, Greece (Ep 6)
Sailing Wishful Thinking

Sailing from the Cyclades to the Dodecanese Islands, Greece (Ep 6)

We sail Wishful Thinking from the Cyclades to the Dodecanese Islands, making our way to eastern Greece ready to head to Turkiye. We stop at Naxos, Koufonisia, Astipalea, Kos, Tilos and Alimia along the way. We'd planned to check out of Greece in Kos, but decided to make our way to Rhodes instea...
Sailing the Cyclades, Greece: Naxos, Paros & run into by a super yacht (Ep 5)
Sailing Wishful Thinking

Sailing the Cyclades, Greece: Naxos, Paros & run into by a super yacht (Ep 5)

We explore Naxos and Paros in the Cyclades Islands, Greece. While in Paros a super yacht collides with us in the middle of the night when its stern line breaks. Luckily there was no damage to our boat!
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...
Sail from Naxos to Paros | Sailing Wisdom [S5 Ep16]
Rigging Doctor

Sail from Naxos to Paros | Sailing Wisdom [S5 Ep16]

▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PHOTOGRAPHY FROM OUR VOYAGE: We have a wonderful sail from #naxos to #paros with @JoshPostVlogs @Bumsonaboat @OceanCruisers , and @svfairisle where we have a beach party and then search for a late night dinner. Special #thanks to ...
Big Seas: Rough Sail to Naxos! | Sailing Wisdom [S5 Ep15]
Rigging Doctor

Big Seas: Rough Sail to Naxos! | Sailing Wisdom [S5 Ep15]

▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PHOTOGRAPHY FROM OUR VOYAGE: After an incredible #sail from #delos to #naxos with @JoshPostVlogs , @Bumsonaboat , and @OceanCruisers , we tour @svfairisle and really get to know them. This day is what #Greek Sailing is all about! Spe...
WATCH THIS BEFORE YOU SAIL GREECE! Ep-10
Leading the Escapade

WATCH THIS BEFORE YOU SAIL GREECE! Ep-10

In this week's episode we take you back to the beginning of our time in Greece and cram our all the notable events into one episode to recap ​the up's & down's.
Awen Does Naxos @SailingAWEN
Sailing AWEN

Awen Does Naxos @SailingAWEN

A little ditty about getting from our sailboat, anchored in the boonies on Naxos Island (because we are trying to shelter from an incoming Meltemi) and trying to get into downtown Naxos to rent a scooter and tour the island…and try to make it back. We had to swim to shore but our drybag had a hole a...
Episode 81 – We sail from Anti-Paros to Naxos then on to Schoinousa – Carl and Jenny
Carl and Jenny

Episode 81 – We sail from Anti-Paros to Naxos then on to Schoinousa – Carl and Jenny

In this episode we sail from Anti-Paros to Naxos, but on arrival we decide the anchorage isn't that comfortable so carry on to Schoinousa. 00:00 - Intro 00:47 - Map 01:33 - Narration 02:39 - Sailing 03:59 - Coming into Naxos 05:40 - Update in anchorage 08:17 - Update from Jen 10:58 - End of sai...
Why did I check the oil? [Ep60] Sailing Salacia Star
Sailing Salacia Star

Why did I check the oil? [Ep60] Sailing Salacia Star

As a good Captain, Rick was going through Salacia's check list & one thing was to check the oil on the generator. It has not worked since that day, this is nearly 2 months ago. We are going into a marina for one month when we get to Spain & will have it all check out then. Will be int...
Why did we leave Vulcano Island? [Ep 59] Sailing Salacia Star
Sailing Salacia Star

Why did we leave Vulcano Island? [Ep 59] Sailing Salacia Star

In this weeks episode we wondered if we could climb the volcano all the way to the top in the midday sun & show you how we passage plan as a team. SUBSCRIBE LIKE FOLLOW What happens to most of us when our kids have families, careers & children of their own? It can feel lonely,...
Can we out run the storm? [Ep 58] Sailing Salacia Star
Sailing Salacia Star

Can we out run the storm? [Ep 58] Sailing Salacia Star

You can't always rely on the weather man! But we are not telling sailors anything you don't already know. SUBSCRIBE LIKE FOLLOW What happens to most of us when our kids have families, careers & children of their own? It can feel lonely, left out & down right depressing...
PAROS Travel Guide | Top 10 things to do on the popular Greek getaway island   |   4K
Kristina's Travels

PAROS Travel Guide | Top 10 things to do on the popular Greek getaway island | 4K

Not sure what to do in Paros, Greece? Here are our 10 TOP places to see and do on the majestic getaway island, a short ferry ride away from Naxos and Mykonos!
Ep 93 A Whirlwind of Cruising – Saying Farewell to the Greek Aegean Sea
Sailing Talisman

Ep 93 A Whirlwind of Cruising – Saying Farewell to the Greek Aegean Sea

Wow! What to say. We sailed to so many cool places in a relatively short period of time that it all seemed to blend into one. The winds filled our sails and the sun shone. The water took on the light turquoise color you get when sun and sand bottoms come together. And the food! Such incredible memor...
17.  Exploring Taormina and We get trapped in a storm! | Life on a Sailboat | Sailing Sunday
Sailing Sunday

17. Exploring Taormina and We get trapped in a storm! | Life on a Sailboat | Sailing Sunday

We spent an entire day around Naxos and then made the trek up the mountain to Taormina, it was such a hot day and we took the LONG way up!!
Small Cyclades – Sailing Greatcircle (ep.64)
Cat Greatcircle

Small Cyclades – Sailing Greatcircle (ep.64)

Feels like summer out of the wind on the front deck going south from Naxos to the Small Cyclades. All alone in a small bay on Iraklea and the next day to the harbour of Koufonisi where we are taken by surprise by a sudden 50 knots
Cyclades – Naxos – Sailing Greatcircle (ep.63)
Cat Greatcircle

Cyclades – Naxos – Sailing Greatcircle (ep.63)

Sailing from Mykonos to Naxos to find shelter in Naxos Marina.
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