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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Our worst nightmare happened and we weren’t as prepared as we thought.
Holly and Ray

Our worst nightmare happened and we weren’t as prepared as we thought.

Between the two of us, we’ve been sailing for a long time. We know the theory. We know where every piece of distress equipment on this boat is. We don’t skimp on insurance policies. But when an emergency actually happened, none of that seemed to matter. What we had was a pounding heart, a serious ...
The Emergency We Weren’t Ready For
Holly and Ray

The Emergency We Weren’t Ready For

Between the two of us, we’ve been sailing for a long time. We know the theory. We know what a MAYDAY call sounds like. We know where every piece of distress equipment on this boat lives. But when an emergency actually happened, none of that seemed to matter. What we had was a pounding heart, a seri...
We Never Expected to Find Family Here
Sailing Big Lost

We Never Expected to Find Family Here

When we left home to sail around the world, we thought the hardest part would be leaving our family behind. What we never expected was finding another family halfway around the world. After arriving in Moorea, we finally slow down enough to enjoy everything this incredible island has to offer—from...
What was your first serious boating-related injury, and did you struggle mentally afterward?🤕
Holly and Ray

What was your first serious boating-related injury, and did you struggle mentally afterward?🤕

I’m surprised by how difficult the emotional part of my recovery has been. Even though I’m back on the boat, one month later, I can’t seem to shake the bad dreams and catch myself hesitating over movements that used to feel completely natural. I’m determined to rebuild my confidence and get back to...
How We Get Paid to Sail in Paradise (Full-Time Boat Life)
Untide

How We Get Paid to Sail in Paradise (Full-Time Boat Life)

Take my sailor type quiz! - Hey Friends, It feels amazing to have finally arrived in Fiji! There are a countless number of islands to explore, and the Fijians have to be the friendliest and most welcoming people we have met on this voyage. Hope you enjoy! Join the Patreon here, for sailing opp...
I Should Be With Her: A Medical Emergency Sailing Fiji
Holly and Ray

I Should Be With Her: A Medical Emergency Sailing Fiji

What starts as a perfect day in paradise quickly turns into every cruiser's worst nightmare. We make a short hop to a beautiful mooring in Fiji, explore the local fresh market, and settle in to enjoy the sunset. Then Holly suffers a medical emergency that changes everything. With the local ho...
We Came for the Sailing… We Stayed for the Friendships
Sailing Big Lost

We Came for the Sailing… We Stayed for the Friendships

We thought sailing around the world would be all about the destinations. The turquoise lagoons. The remote islands. The adventure. But somewhere along the way, we realized the places weren't what changed us the most. It was the people. In this episode, we spend our final days in beautiful T...
We Thought Success Looked Like This    We Were Wrong
Sailing Big Lost

We Thought Success Looked Like This We Were Wrong

We crossed an ocean dreaming about places like Fakarava. World-famous dives, crystal-clear lagoons, black pearls, and remote islands were everything we had imagined. But somewhere along the way, we realized this journey was changing more than our location. It was quietly changing the way we measured...
This Is Why We Crossed The Pacific
Sailing Big Lost

This Is Why We Crossed The Pacific

After crossing the Pacific Ocean and spending weeks in the Marquesas, we finally arrived at one of the places we've dreamed about for years: the Tuamotus. In this episode, we leave Nuku Hiva behind and make the 500 nautical mile passage to Raroia Atoll. After carefully timing our arrival throu...
We Weren’t Ready to Leave Yet | Life in the Marquesas
Sailing Big Lost

We Weren’t Ready to Leave Yet | Life in the Marquesas

After returning to Taiohae Bay on Nuku Hiva, we thought we'd only be staying a few more days before continuing west toward the Tuamotus Islands. The route was planned. The boat was nearly ready. All we needed was the right weather window. What started as an unexpected delay quickly turned into ...
We Sailed to a FORBIDDEN ISLAND | Sailing Truth Show
Sailing Zingaro

We Sailed to a FORBIDDEN ISLAND | Sailing Truth Show

Most boats never make it to Mai'O. You can't just sail in... the island decides who comes ashore. Years ago, my girlfriend and I were anchored in Moorea when we met a man whose friend was from Mai'O. He asked if we could bring his friend home. We said yes — and what happened next was...
1500 Miles to Fiji through the ITCZ – Sailing Sweet Ruca [Ep. 192]
Sailing Sweet Ruca

1500 Miles to Fiji through the ITCZ – Sailing Sweet Ruca [Ep. 192]

Battling through the ITCZ (Inter Tropical Convergence Zone), we sail 1500+ miles from the Marshall Islands to beautiful Fiji. This is part one of our 12 day bluewater sailing voyage through some of the most remote parts of the pacific ocean. #sailing #storm #vlog #yachtlife #reallife
Sailing 1,300 Nautical Miles to TONGA⛵️
Holly and Ray

Sailing 1,300 Nautical Miles to TONGA⛵️

Join us as we complete a 10-day, 1,300 nautical mile voyage from French Polynesia to Tonga! We carefully navigate a reef pass into a peaceful anchorage, where we check into the country with ease—no dodgy docks, just smiles. After a brief rest, we lift anchor for a bumpy overnight sail to Vava’u, eag...
10 DAYS AT SEA⛵️Next Stop: Tonga!
Holly and Ray

10 DAYS AT SEA⛵️Next Stop: Tonga!

Let’s get the heck out of here‼️ Join us for a 10 day sail from French Polynesia to Tonga— a passage we’ve been looking forward to for quite some time… 😍 The journey begins with a beautiful overnight trip from Tahiti to Bora Bora, where we tackle some chores in preparation for our departure and soak...
Sailing SOLO Tonga to Fiji, Navigational Nightmare Even Pros Get Wrong! (CSS, Ep 257)
Calico Skies Sailing

Sailing SOLO Tonga to Fiji, Navigational Nightmare Even Pros Get Wrong! (CSS, Ep 257)

Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) 0:00 Intro 0:10 Passage Planning to Fiji 2:42 Cleared out of Tonga 5:37 Day 2 - Setting Boat up for Wing on Wing 9:47 Day 3 - Time for a Jibe 16:50 Day 4 - Course Chan...
Ocean to Table: Sailing New Zealand for Seafood – Episode 146
Sailing One Life

Ocean to Table: Sailing New Zealand for Seafood – Episode 146

Want to help support our video productions and get real time updates? 🌍➡️Join our One Life Crew here: In New Zealand? Check out our mate's fishing charter for the ultimate fishing experience: 💦Grab a Sailing One Life Epic Water Filters Bottle! Use discount code EPICONELIFE here: To watc...
Sailing Back to Tahiti: Preparing for Our Next Adventure
Holly and Ray

Sailing Back to Tahiti: Preparing for Our Next Adventure

We’re on the move! ⛵️ After an overnight sail from Tahuata to Nuku Hiva, we said goodbye to our family and restocked the boat with food and fuel before the World ARC arrived. Then, it was off on a six-day offshore passage back to Tahiti, the first leg of our journey toward New Zealand. Along the way...
LIGHTNING STRIKE over the boat! [Ep171 RED SEAS]
Sailing Red Seas

LIGHTNING STRIKE over the boat! [Ep171 RED SEAS]

A Massive Storm Caught Us Off Guard ⚡️🌊 We set out to visit Makatea Island, but huge waves forced us to change course, sailing an extra day to the nearest safe anchorage. Just as we started to relax, a terrifying lightning storm rolled in, passing directly over us! The thunder was deafening, the sk...
FINAL SAILING ATTEMPT: Will we ever reach this LOST WORLD? [Ep170 RED SEAS]
Sailing Red Seas

FINAL SAILING ATTEMPT: Will we ever reach this LOST WORLD? [Ep170 RED SEAS]

🌊 EPIC Night Sailing Adventure to a Hidden Paradise! 🏝️⛵ After nearly two years exploring French Polynesia, we’re taking on one of our biggest challenges yet—a treacherous night passage through the remote Tuamotus! 😱 With zero moonlight, strong currents, and an anchor stuck on coral, we navigate bl...
Sail Smarter: Orca Display & Core for Modern Navigation
Holly and Ray

Sail Smarter: Orca Display & Core for Modern Navigation

In this video, we review the Orca Core and Display navigation system—a modern take on the classic chartplotter. We highlight its key features, such as exceptional screen readability, radar capabilities, and remote autopilot control. We also share our honest assessment of whether it’s a valuable addi...
This has NEVER happened! [Ep169 RED SEAS]
Sailing Red Seas

This has NEVER happened! [Ep169 RED SEAS]

🌊 We Had This World-Class Dive Site ALL TO OURSELVES! 🦈 | Sailing French Polynesia After nearly 2 years of exploring the remote atolls of French Polynesia, we never expected to have one of the most famous dive sites in the South Pacific completely to ourselves! 🤯 No dive boats, no crowds—just us, o...
BOAT FAIL: we ran out of FUEL! (after sailing 1000 miles) [Ep168 RED SEAS]
Sailing Red Seas

BOAT FAIL: we ran out of FUEL! (after sailing 1000 miles) [Ep168 RED SEAS]

We are sailing 1000 miles from one end of French Polynesia to the other, and we don't have long to do it. We have loved our time exploring the remote islands of the Gambiers in the south but now it's time to get moving again and we need to be in Tikehau in the far north of the country in j...
Sailing the Marquesas Islands: 1 Year Living Aboard Our Sailboat in French Polynesia
Holly and Ray

Sailing the Marquesas Islands: 1 Year Living Aboard Our Sailboat in French Polynesia

All aboard! ⛵️ Join us for an overnight sail from Nuku Hiva to Hiva Oa, where we welcome family aboard for a memorable visit. We put our new Orca system to the test, cruise alongside a pod of dolphins, and take our guests to Tahuata to enjoy its crystal-clear waters and sandy beaches. Ray tackles a ...
ALL ALONE…why nobody sails here?! [Ep167 RED SEAS]
Sailing Red Seas

ALL ALONE…why nobody sails here?! [Ep167 RED SEAS]

We have sailed for seven weeks to reach the most southerly islands in French Polynesia - the truly remote archipelago of the Gambiers. But it's not all easy - shallow anchorages, shifting winds, and we're really far away from civilisation if anything goes wrong. But when all goes well, th...
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