Watch Sailing & Boating Adventures Around the World – Page 2 of 5

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 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...
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...
ABANDONED MONASTERY on an Remote Greek Island | Skantzoura
Dylan Magaster

ABANDONED MONASTERY on an Remote Greek Island | Skantzoura

Support your skin and this channel get a jar of Captain's Salve: We anchored near a forgotten island in the Northern Sporades and discovered an abandoned monastery once inhabited by Byzantine monks… and later, political exiles. What we found inside shocked us — beds still made, shoes untouched...
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...
Is This Greece’s Most Beautiful Underrated Island?
Dylan Magaster

Is This Greece’s Most Beautiful Underrated Island?

Get Captain’s Salve - natural skin care that belongs in the wild: We sailed to the underrated Greek island of Skopelos—and what we found was unforgettable. From crystal-clear waters and ancient monasteries to scooter crashes and wild octopus encounters, this episode had it all. Join us as we sail f...
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...
30 Minutes of Underwater Cleaning Satisfaction | ASMR
Dylan Magaster

30 Minutes of Underwater Cleaning Satisfaction | ASMR

30 uninterrupted minutes of underwater cleaning—no voiceover, no music, just the raw sounds of the sea and the scraping of years of marine growth. This is the real work behind sailing: clearing off barnacles, algae, and buildup from the hull by hand. Whether you're here for the ASMR, the visua...
The Wind Was Wrong. I Sailed Anyway.
Dylan Magaster

The Wind Was Wrong. I Sailed Anyway.

This sail from the Greek mainland to Skiathos wasn't supposed to work. The wind was wrong. The forecasts were off. But with enough experience, intuition, and faith in the process — you learn how to dance with reality instead of fight it. In this episode, I single-hand through shifting winds, re...
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...
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...
The 1995 Card Game Predicted the Future
Dylan Magaster

The 1995 Card Game Predicted the Future

This card game was released in 1995. What’s inside is… unsettling. In this full unboxing and deep dive, I explore the "Illuminati: New World Order – One With Everything Factory Set" trading card game released in 1995 by Steve Jackson Games. Together let's go through hundreds of strang...
Support the Creator, Not the Algorithm
Dylan Magaster

Support the Creator, Not the Algorithm

After months of silence, I'm finally posting again. But this isn’t just an “update video.” This is a manifesto. If you want to support independent creators, this is how we survive: In this video, I talk openly about why I disappeared, what happened to over 30 deleted videos, and why I'm c...
I Thought FPV Was Just Flying.. Then This Happened
Dylan Magaster

I Thought FPV Was Just Flying.. Then This Happened

Learning FPV drones as a complete beginner was way harder than I expected. This is the first part of my FPV drone journey—from simulator crashes to soldering wires I didn’t even know existed. Inspired by Johnny FPV and the incredible cinematic drone shots he's known for, I decided to dive headf...
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.
Mythical Graveyard or the Island of Miracles? | Tinos, Greece
Dylan Magaster

Mythical Graveyard or the Island of Miracles? | Tinos, Greece

Tinos Island, located in Greece, is renowned not only for its breathtaking landscapes and fascinating history but also for being a paradise for sailing enthusiasts due to the unique winds found nowhere else in the country.
Sailing & Exploring the Greek Island of Andros | Greece
Dylan Magaster

Sailing & Exploring the Greek Island of Andros | Greece

Discover the captivating island of Andros, Greece as you sail its pristine waters, explore mysterious beaches and uncover historical legends on a voyage like no other. Join us for an unforgettable adventure!
Making a Hot Wire Foam Cutter for Shaping Foam/ Spray Foam Insulation
Dylan Magaster

Making a Hot Wire Foam Cutter for Shaping Foam/ Spray Foam Insulation

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:
Boating Gets Weird: My Folding Catamaran Adventure
Dylan Magaster

Boating Gets Weird: My Folding Catamaran Adventure

Get your Stellen Doer Toolshed: As a liveaboard sailor living on anchor on SV Arianrhod in Las Palmas de Gran Canaria in the Canary islands in Spain I decided to take 2 foldable portable kayaks and convert them into a sailing foldable catamaran. What do you think could you design and build a better...
Octopus Defends itself against Hungry Triggerfish
Dylan Magaster

Octopus Defends itself against Hungry Triggerfish

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:
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