Watch Sailing & Boating Adventures Around the World – Page 37 of 300

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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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...
First Look at Our New 40ft Sailboat! Full Boat Tour & Walkaround
Chesca & Ben

First Look at Our New 40ft Sailboat! Full Boat Tour & Walkaround

Here she is! – we bought a sailboat! Meet Flying Freedom ⛵️, our new floating home and the start of our biggest adventure yet. In this video, we’ll give you a full first look and tour of our 40ft Freedom 40/40 sailboat, showing you around every corner before we start the work to get her ready for li...
Sailing Into Trouble: The Day Our Anchorage Was a Crime Scene | Sailing Sitka Ep 179
Sailing Sitka

Sailing Into Trouble: The Day Our Anchorage Was a Crime Scene | Sailing Sitka Ep 179

Jay and Kenna lift the hook and set sail from Green Island toward the stunning Holadaze Cayes, one of the most picture-perfect anchorages in all of the San Blas Islands. But just when we thought we’d found paradise, we suddenly found ourselves—and Sitka—in the middle of an active criminal investigat...
Sailing 400 Miles with No Rules? | Bahamas to USA Adventure
Sailing Doodles

Sailing 400 Miles with No Rules? | Bahamas to USA Adventure

We sail more than 400 nautical miles across open ocean, leaving the Bahamas behind and heading back to the U.S. coast — destination: Charleston, South Carolina. The weather throws us some surprises, the seas don’t make it easy, and morale is tested. But the crew pulls through — especially Jennifer, ...
We sailed 280 miles to THIS paradise 🇧🇷 — Sailing Yabá
Sailing Yabá

We sailed 280 miles to THIS paradise 🇧🇷 — Sailing Yabá

Episode 277 | Sailing and exploring Ilhabela. Watching a regatta, chasing waterfalls, scuba diving and more! 💌 I’ve created a newsletter to share the moments the camera missed, the untold stories, behind-the-scenes moments, and little things that don’t make it into the videos. Sign up here: (it�...
Nippers: The Beach Bar with a Naughty Reputation (We Had to Investigate) VLOG 292
Sailing Sunday

Nippers: The Beach Bar with a Naughty Reputation (We Had to Investigate) VLOG 292

This week’s episode is a fun one — we officially move into our new rental here in the Bahamas, take a day trip to the (in)famous Nippers Beach Bar with friends, and head out for a relaxed sail with the crew from SV Escapade. No big drama, just a little slice of what life’s looking like right now — ...
The Snake Saga – It Kept Coming Back! | S4 E24
Sailing with six

The Snake Saga – It Kept Coming Back! | S4 E24

What was meant to be a quiet stop for small waves and simple boat life turned into an unforgettable showdown. When an unexpected intruder slithered aboard—not once, not twice, but three times—we had no choice but to face it head-on. From surf sessions to one very determined snake, this episode has ...
WE DID IT! BOAT TOUR AFTER 6 MONTHS REFIT OF OUR ALUMINUM EXPEDITION CATAMARAN
Sailing Dawn Hunters

WE DID IT! BOAT TOUR AFTER 6 MONTHS REFIT OF OUR ALUMINUM EXPEDITION CATAMARAN

Living Off-Grid Dawn Hunters Style on sailing catamaran! 📺 THIS IS DAWN HUNTERS SEASON #4 EPISODE 15 ➡️ S4E15 ⛵WANT TO KEEP VIDEOS COMING? SUPPORT OUR PRODUCTION HERE: If you’d like to help with this production please consider supporting us on Patreon. (SUPPORT TIERS GO AS LOW AS $5 PER MONTHS)...
Sailboat Projects: FINALLY the Help Warren Needed! | Episode 307
WE|Sail

Sailboat Projects: FINALLY the Help Warren Needed! | Episode 307

Welcome back to WE|Sail! The finish line is finally in sight! After what feels like endless boat projects, we're so close to getting Va back out on the open water where she truly belongs. But just when we thought we'd have to tackle the final stretch alone, something incredible happened.....
Our Last Bahamas Beach Day Was WILD! Jennifer is BACK!
Sailing Doodles

Our Last Bahamas Beach Day Was WILD! Jennifer is BACK!

Beautiful Jennifer rejoins the crew just in time for one last unforgettable beach day in the Bahamas! We sail up to stunning Spanish Cay, soaking in the final days of sunshine, clear blue water, and tropical vibes before setting our course back to the USA. It's peaceful, a little bittersweet, a...
I Ran Aground Sailing to Kāneʻohe Bay Sandbar – Hard Lessons Learned
Sailing With Phoenix | Oliver

I Ran Aground Sailing to Kāneʻohe Bay Sandbar – Hard Lessons Learned

Hello hello! Sailing adventures resume as my brother joins me in Hawai’i. We set sail from Waikiki Yacht Club into 30+ knot headwinds, bound for the stunning sandbar in Kāne‘ohe Bay, Oʻahu. What should have been a scenic day sail quickly turned stressful: wind advisories, towing mistakes, and hitti...
S3, Ep31 We Prepare for our Longest Sailing Trip Yet
Sailing Into the Mystic

S3, Ep31 We Prepare for our Longest Sailing Trip Yet

Sailing really slows down time and time is not a commodity you have when you are still working in the rat race. But we all found a week where we can go pretend like time doesn't matter to explore what we can. But first we must tackle the to-do list and get some of the stuff done on the boat s...
Having Diesel Engine Trouble up a River In Borneo – Small Boat Sailing Adventures in Wild Places
Sailing Triteia

Having Diesel Engine Trouble up a River In Borneo – Small Boat Sailing Adventures in Wild Places

Episode 432 : Hello Friends, On this episode I wake anchored 2.5 miles off shore in remote Borneo after a 435NM passage from Lombok. I have a very wet passage of unforecasted weather to anchor in a peaceful anchorage just inside the mouth of the Kumai River. After a few days rest, I nervously mad...
The STRUGGLE is REAL! Not all Journey’s are Easy… Ep 410
Sailing Nandji – Frothlyfe

The STRUGGLE is REAL! Not all Journey’s are Easy… Ep 410

For your special LELO discount, use the code word: Nandji10 at the check out - We have been on a difficult journey for years now. It is a subject a bit different from our usual sailing adventures, but sharing the highs and the lows is all part of telling our true story. Life at sea isn’t always sm...
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...
Dropping Anchor in a Lightening Storm⚡️ | Sailing Sunday VLOG 291
Sailing Sunday

Dropping Anchor in a Lightening Storm⚡️ | Sailing Sunday VLOG 291

This week’s video is a raw, unfiltered look at what sailing really looks like when a storm rolls in out of nowhere — and you’re trying to make it to safe harbour with a baby onboard. It's the kind of moment that reminds us why preparation matters… and also why sailing with a baby adds a whole ...
Why We Slowed Down, Patience is Pleasure. Sailing Vlog 36
The Foster Journey

Why We Slowed Down, Patience is Pleasure. Sailing Vlog 36

Sailing Long Island to Port Jefferson, we decided to have a little chat about our new view on sailboat travel. *Sorry it's been a while since we posted - life happens, responsibilities and all, but we're glad to share this one with you!! Thanks for watching.
We haven’t stepped foot on land in a week! (and heres why) | Sailing Sitka Ep 178
Sailing Sitka

We haven’t stepped foot on land in a week! (and heres why) | Sailing Sitka Ep 178

Jay and Kenna have been off the grid, not setting foot on land for over a week while sailing through the San Blas Islands. While anchored at Green Island, they took it slow to ride out some intense winds. With no working outboard and a less-than-reliable paddleboard, getting to shore has felt more l...
What Did I Find Inside This Abandoned Ship?
Sailing Doodles

What Did I Find Inside This Abandoned Ship?

Sailing solo through the stunning Abacos, I make my way from Great Guana Cay up to Green Turtle Cay in the Bahamas. But along the way, I spot something totally unexpected — a yacht, wrecked and abandoned on the beach with no one in sight. Curiosity gets the best of me, so I anchor Nauti Dogs nearby...
Our boat build is finished: LET’S SAIL THE WORLD! — Sailing Yabá 276
Sailing Yabá

Our boat build is finished: LET’S SAIL THE WORLD! — Sailing Yabá 276

Episode 276 | Sailing 250 nautical miles north to Ilhabela in rough seas 📡 *Starlink* made a huge difference for us doing our trip. We could check the forecast in real-time, video-call our families, talk to our friends, share our location live with patrons and even stay entertained. If you would li...
From Fee Debacle to Daily Rhythm | S4 E23
Sailing with six

From Fee Debacle to Daily Rhythm | S4 E23

What started with confusion over anchoring fees quickly turned into something more familiar — finding our family rhythm in a brand new spot. After dealing with paddling locals, unclear payments, and a bit of drama, we finally settled into daily life: school, work, afternoon surfs, and chats about sc...
WE are in Two VERY Different Places! | Episode 306
WE|Sail

WE are in Two VERY Different Places! | Episode 306

Welcome back to WE|Sail... This sail free week we again dive into boat projects, with the fiberglass barbecue and cooler once again taking the lion share of attention. Also we check in with Erica and her surgery from tearing her achilles tendon. WE are starting to feel the pressure and struggle wi...
Boat Yard Hustle! Inside Our DIY Haul Out Projects
Travel Sketch

Boat Yard Hustle! Inside Our DIY Haul Out Projects

With our catamaran safe and secure on the hardstand there's boat work happening every day! This episode we're replacing a critical part of the anchor windlass, upgrading the interior with DIY boat curtains, and getting some things done on our tender, an unusual dinghy which is designed to ...
Ep 176 Kevin & Wendy | Stellar Sailing from Guadeloupe to Antigua
Sailing Talisman

Ep 176 Kevin & Wendy | Stellar Sailing from Guadeloupe to Antigua

We complete our loop; Antigua, Sint Maarten, British Virgin Islands, USVI, St Croix, and Guadeloupe. This trip is always bittersweet, given that it marks our return home to Antigua. We love Antigua, and it’s our home base, but it means the adventure sailing is coming to an end. Soon it’ll be summe...
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