Watch Sailing & Boating Adventures Around the World tagged “Sailinglife”

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.

Showing 1-24 of 401 results
How To Get To The RIO DULCE, Guatemala From FLORIDA! Checking On Our CUSTOM Sailboat S4:E13
Sailing The Far Side

How To Get To The RIO DULCE, Guatemala From FLORIDA! Checking On Our CUSTOM Sailboat S4:E13

Hey Everyone! It's finally time to head to Guatemala!! The Far Side has gone through a lot these past few years and the end is drawing near! So getting to the RAM Marina from Guatemala City is quite the hike! 4.5-9 hrs depending on traffic and road condit...
Ep 50 | The GLOW UP our boat needed!
Sailing Rum Punch

Ep 50 | The GLOW UP our boat needed!

It's so nice to finally be back together on the boat, as we catch you up to speed on what we achieved this summer! We tackle a big project this week, taking full advantage of the days we can squeeze in together and boy does it make the boat look pretty dar...
Planning an Epic Sailing Adventure California to Spain!
Sailing Life on Jupiter

Planning an Epic Sailing Adventure California to Spain!

Our plan to sail from California to Spain: four passages, one dream, and a huge adventure ahead. In this video, we share our full passage plan to relaunch Jupiter² and sail from Mexico all the way across the North Atlantic to Spain within a year. It’s ...
Ep 49 | BIG tools, BIG problems!
Sailing Rum Punch

Ep 49 | BIG tools, BIG problems!

After quite the achievement with the scraping of the hull in last week's episode, we've moved back inside to carry on with the fourth section of our living area. Follow along as we look at building our 'single bedroom' along with of course the next thing o...
California to Spain: Our Epic Sailing Passage Plan
Sailing Life on Jupiter

California to Spain: Our Epic Sailing Passage Plan

We’re finally revealing our most ambitious journey yet: sailing Jupiter² from California all the way to Spain. After three years on the hard and countless hours of work, we’re preparing our performance aluminum sailing catamaran for a true ocean epic....
Breakfast of champions #windedvoyage #sailinglifestyle #boatlife #africa
Winded Voyage Sailing

Breakfast of champions #windedvoyage #sailinglifestyle #boatlife #africa

Breakfast is essential for sailors to have healthy eating habits while sailing sailing, sailinglifestyle, travel, adventure, Africa, #windedvoyage #sailing #sailinglifestyle #travel
ATTACKED AT ANCHOR IN REMOTE BRAZIL –  Sailing Ilha dos Lençois
The Cruising Kiwis

ATTACKED AT ANCHOR IN REMOTE BRAZIL – Sailing Ilha dos Lençois

ATTACKED AT ANCHOR IN REMOTE BRAZIL - Sailing Ilha dos Lençois Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon https://www.patreon....
Ep 48 | We’re Seeing DOUBLE!
Sailing Rum Punch

Ep 48 | We’re Seeing DOUBLE!

Feels good to be coming back to you every two weeks with a new episode, catching you up on everything we've been up to so far in 2025! We hope you enjoy this next ep :) E & B xx -- SUBSCRIBE & FOLLOW OUR REFIT FROM THE BEGINNING: https://www.yo...
Ep 47 | Back in Business!
Sailing Rum Punch

Ep 47 | Back in Business!

Welcome back from our little haitus! Cannot believe it's been SO long since we put an episode out, life just became a little hectic. We've missed you all and are so happy to be back on here! This week, we go back to where we left off and combat a week of b...
Thailand Pit Stop: Mini Boat Refit Sprint | S4 E31
Sailing with six

Thailand Pit Stop: Mini Boat Refit Sprint | S4 E31

After months sailing through remote Indonesia with no access to parts or services, we finally reached Thailand — and dove headfirst into a jam-packed week of boat projects. In this episode, we tackle a mini refit sprint: • Fresh dinghy chaps to prote...
Day 3:  Lightning, Longevity & Leaving Wahine Behind #LongevityJourney #boatlife  #BlueZone
Pacific Solo

Day 3: Lightning, Longevity & Leaving Wahine Behind #LongevityJourney #boatlife #BlueZone

Day 3 of my 30-day journey through Japan’s longevity hotspots took a surprising turn. While bailing out my tender in heavy rain, lightning struck close enough to shake the boat and leave me wondering if Wahine herself had been hit. Thankfully, everything...
Day 1: Celebrating Respect for the Aged Day in a Remote Japanese Village
Pacific Solo

Day 1: Celebrating Respect for the Aged Day in a Remote Japanese Village

It’s Respect for the Aged Day here in Japan 🇯🇵—a national holiday that began back in 1947 as “Old Folks Day” before being renamed in the ’60s. I just learned that you officially qualify as “aged” here at 70… which makes me a newbie to...
Somewhere in Japan: Secret Beaches and Charming Harbors #SailingJapan #SecretBeaches #liveaboard
Pacific Solo

Somewhere in Japan: Secret Beaches and Charming Harbors #SailingJapan #SecretBeaches #liveaboard

Blue skies. A sparkling coastline. A secret beach for a midday dip. This is sailing in Japan — beautiful, empty, almost untouched. In the Med or Caribbean, this would be crowded with yachts. Here, I counted just two others in the harbor. That’s what ma...
Sailing to the Isle of Harris | VHF Failure, Windlass Breakdown & Fresh Scallops
Living With The Tide

Sailing to the Isle of Harris | VHF Failure, Windlass Breakdown & Fresh Scallops

This episode takes us from Carbost to Ardmore Bay, enjoying a beautiful sail until our VHF suddenly stops working. With safety in mind, we run tests to track down the fault before heading off again. The next day we enjoy a sunny, perfect sail north to th...
Mold Check, Sea View, and Sailing Lessons Ahead #SailingLife #Liveaboard #NeverTooLate
Pacific Solo

Mold Check, Sea View, and Sailing Lessons Ahead #SailingLife #Liveaboard #NeverTooLate

Back on board Wahine after six weeks away. No mold (a sailor’s small victory!) and Buren Bay is as beautiful as ever. In this short, I share a quick check-in and a teaser for my upcoming video: the five things I wish I had done before buying a boat. Whet...
The Island of Dreams – Where My Sailing Journey Began #sailinglife #tokyobay #itsnevertoolate
Pacific Solo

The Island of Dreams – Where My Sailing Journey Began #sailinglife #tokyobay #itsnevertoolate

Wahine’s home when I found her was at Yumenoshima Marina — Tokyo’s “Island of Dreams.” Built on landfill, transformed into a marina and park, it was here that my journey with Wahine truly began. On this day off from writing, meetings, and even b...
Family Aboard & Castles on the Coast | Sailing Scotland’s West with a Live Cannon Show!
Living With The Tide

Family Aboard & Castles on the Coast | Sailing Scotland’s West with a Live Cannon Show!

In this episode, we welcome Matt’s brother aboard in Oban and set sail for a trip filled with Scottish castles, family time, and stunning coastal views. Along the way, we visit several iconic spots — including a front-row seat to a live firing demonstr...
We disappeared for 6 months… Here’s why…
Sailing Rum Punch

We disappeared for 6 months… Here’s why…

We're back!!!! Well....almost....after a 6 month hiatus, we are finally able to be back on our boat! This is just a small update to fill you all in on what you've missed and what's to come! We can't wait to bring back more episodes regularly and look forwa...
Adrift in the Doldrums: Storms & Bucket Showers (Days 12-18 Pacific Crossing)
Slim & Soph - Sailing Nakama

Adrift in the Doldrums: Storms & Bucket Showers (Days 12-18 Pacific Crossing)

AD Thanks to June's Journey for sponsoring this video. Download June's Journey for free here: https://cherrypick.gg/SlimAndSoph The lack of wind in an ocean of endless calm is met with both celebration and despair. On one hand, it means we’ve entered t...
Sailing to the Isles of Scilly | A Feathered Stowaway, Tangled Lines & Island Wonders
Living With The Tide

Sailing to the Isles of Scilly | A Feathered Stowaway, Tangled Lines & Island Wonders

In this episode, we set our course for the stunning Isles of Scilly—but not without a few surprises along the way! Mid-voyage, a curious pigeon joins us on deck, much to Lancer’s disapproval. Things take a turn when we accidentally run over our tender ...
Unexpected Ocean Passenger 🐦⛵ #Shorts
Captain German Exploring

Unexpected Ocean Passenger 🐦⛵ #Shorts

In the middle of the open ocean, this little bird landed on our yacht out of nowhere. A surprising visit from the sky — far from land! 👉 Subscribe for more sailing adventures and unexpected moments at sea. #sailinglife #birdonboard #oceanwildlife #yac...
Taking Out the Trash: BoatLife in Japan #boatlife #sailingjapan japan #cruisinglife
Pacific Solo

Taking Out the Trash: BoatLife in Japan #boatlife #sailingjapan japan #cruisinglife

Taking out the trash isn’t always straightforward—especially when you live on a sailboat, anchored off a remote Japanese hamlet. In this short glimpse, I row ashore to meet the garbage man and navigate the very local—and very specific—rules of Jap...
The Island Called Me Back  #japan  #boatlife  #bluezone  #sailingjapan
Pacific Solo

The Island Called Me Back #japan #boatlife #bluezone #sailingjapan

Welcome to Pacific Solo, where I, Lowell Sheppard, share my sailing adventures and discoveries around Japan. Initially, my goal was to sail across the Pacific solo before turning 70, but that journey is on permanent hold due to unforeseen circumstances. No...
Battling HEAVY SWELLS on our way to Niece //FRENCH RIVIERA S3 Ep.12
Good Deeds Sailing

Battling HEAVY SWELLS on our way to Niece //FRENCH RIVIERA S3 Ep.12

What was supposed to be a straightforward sail to Nice quickly changed into a challenging ride. Join us aboard Good Deeds as we navigate heavy swells, unpredictable conditions, and plenty of sea spray on our way to one of France's most iconic coastal citie...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart