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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After the Storm and Stuck on a Reef 😔 (Calico Skies Sailing, Ep. 261)
Calico Skies Sailing

After the Storm and Stuck on a Reef 😔 (Calico Skies Sailing, Ep. 261)

Enjoying our channel? Consider joining the Calico Skies Patreon Crew to get lots of extra goodies :) 0:00 Intro 0:10 Recap 1:39 Setting a Kedge 11:57 Confusion, What Just Happened 13:58 Lessons Learned The marine environment is tough on our camera gear, help keep us filming! 5% off TotalBoa...
Sailors Helping Sailors – Head Injury After Dangerous Crash Jibe! (Calico Skies Sailing, Ep 256)
Calico Skies Sailing

Sailors Helping Sailors – Head Injury After Dangerous Crash Jibe! (Calico Skies Sailing, Ep 256)

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 Helping @Sailing_Songbird after dangerous crash jibe 2:53 Getting Out of Town and Exploring Tonga 4:50 Checking Out the Caves 7:47 Private Island 9:...
Tackling one of the trickiest passes in the South Pacific (Calico Skies Sailing, Ep 253)
Calico Skies Sailing

Tackling one of the trickiest passes in the South Pacific (Calico Skies Sailing, Ep 253)

Download Airalo today! Use code CALICOS3 for $3 off your first eSIM. 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 Overnight Sail to Maupiti 3:52 Entering the Pass 7:20 Dinghy Explore 12:02 Bonfi...
We Have a Problem 😣  (Calico Skies Sailing, Ep. 250)
Calico Skies Sailing

We Have a Problem 😣 (Calico Skies Sailing, Ep. 250)

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 Leaving Tahiti 3:55 Arriving to Mo'orea 4:59 Windless Issues 6:05 Beautiful Anchorage 8:34 Windless Troubleshooting 12:13 Exploring Mo'orea 17...
Made it to the Promised Land🤩 (We DID it!!) But … Was it worth it?? (Calico Skies Sailing, Ep 236)
Calico Skies Sailing

Made it to the Promised Land🤩 (We DID it!!) But … Was it worth it?? (Calico Skies Sailing, Ep 236)

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 Dodging Bommies 0:54 Deploying our Tender 1:45 Wrangling our Sail Bag Back Onboard 2:40 Cheers to the Tuamotus 5:10 Passage Reflection/Repair List 10:07...
Crossing the Pacific Ocean, Inter-Tropical Convergence Zone (Calico Skies Sailing, Ep 228)
Calico Skies Sailing

Crossing the Pacific Ocean, Inter-Tropical Convergence Zone (Calico Skies Sailing, Ep 228)

Join us on an unforgettable journey as we cross the vast Pacific Ocean, facing the perils of the Inter-Tropical Convergence Zone. From enduring strong squalls and navigating unpredictable winds, to catching a colossal wahoo fish, Calico Skies Sailing shares their exciting sailing experiences and exp...
The Realities of Crossing the Pacific Ocean, Part 1 (Calico Skies Sailing Ep. 225)
Calico Skies Sailing

The Realities of Crossing the Pacific Ocean, Part 1 (Calico Skies Sailing Ep. 225)

Calico Skies Sailing dives into the realities of crossing the Pacific Ocean, discussing their preparations, experiences, and dreams. Get a glimpse into their inspiring journey as they prepare to set sail.
Tomorrow we’ll say goodbye – Today, we celebrate 💕 😫 (Calico Skies Sailing Ep. 224)
Calico Skies Sailing

Tomorrow we’ll say goodbye – Today, we celebrate 💕 😫 (Calico Skies Sailing Ep. 224)

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 Early Morning Beer Delivery 3:31 Bingo Night at Lusty's 5:15 The Stowing Continues 6:04 Dock Renaming Ceremony 7:45 Saying Goodbye to Grace'...
3+ Months of FOOD .. but HOW will it fit on our 36ft Sailboat?! 😳 Send Help Please!!🙏🏻 (CSS, Ep 223)
Calico Skies Sailing

3+ Months of FOOD .. but HOW will it fit on our 36ft Sailboat?! 😳 Send Help Please!!🙏🏻 (CSS, Ep 223)

In this episode, Calico Skies Sailing tackles the extensive process of provisioning their 36ft sailboat with enough food for their 3+ month voyage through the Pacific Ocean. They break down the process of stocking up on supplies, dealing with limited space, and organizing the galley. With every item...
It Takes a Village!! Wrapping up our last projects pre-Pacific Crossing (Calico Skies Sailing 222)
Calico Skies Sailing

It Takes a Village!! Wrapping up our last projects pre-Pacific Crossing (Calico Skies Sailing 222)

Calico Skies Sailing shares the process of installing a stackpack, demonstrating the 'village' approach they take during an upcoming Pacific Crossing. The video showcases Grace, Bill, Ruth, Garrett and special guests as they work together to complete the final stages of this sailboat proje...
Back to Regular Life Again! (For a bit) 🙃 (Calico Skies Sailing, Ep 211)
Calico Skies Sailing

Back to Regular Life Again! (For a bit) 🙃 (Calico Skies Sailing, Ep 211)

Start speaking a new language within three weeks with Babble 🎉! Get up to 60% off your subscription here ⬇ 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 Final Push Towards the Mainland 2:00 This ...
Does Size Matter? 50ft vs 36ft Sailboat! (Calico Skies Sailing, Ep 200)
Calico Skies Sailing

Does Size Matter? 50ft vs 36ft Sailboat! (Calico Skies Sailing, Ep 200)

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 Racing Against Alegria - GulfStar 50 9:51 And the winner is ...? 10:50 Upwind Sailing 16:40 Raft Up Shenanigans! ~-~~-~~~-~~- For business inquiries...
Honey the Outboard must be TORN Apart to Try & Save our Season 🥹  (Calico Skies Sailing, Ep 199)
Calico Skies Sailing

Honey the Outboard must be TORN Apart to Try & Save our Season 🥹 (Calico Skies Sailing, Ep 199)

Help us win the "Inspirational Cruiser of the Year Award"! Make sure to confirm your vote in your email or it won't count! 🙌 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 Anchor L...
Whale Sharks at our Bow!  (Calico Skies Sailing, Ep 198)
Calico Skies Sailing

Whale Sharks at our Bow! (Calico Skies Sailing, Ep 198)

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 Pizza Night!!! 3:26 SouthBound Again 7:42 It's a Scorcher 10:01 Trying Out Our New Kite 15:51 On the Hunt for Whale Sharks 23:50 Fuel Mission ~-~~...
How We Live 100% Off Grid on Our Sail Boat  (Calico Skies Sailing, Ep 197)
Calico Skies Sailing

How We Live 100% Off Grid on Our Sail Boat (Calico Skies Sailing, Ep 197)

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 Beautiful Morning Aboard Calico Skies 1:32 Watermaking, Key to Off Grid Living 2:06 WaterMaker Maintenance 8:12 Diving & SpearFishing 10:59 Bread...
Too Hot for Clothes!! How to Survive the Desert in Summer on a Boat, Calico Skies Sailing Ep. 196
Calico Skies Sailing

Too Hot for Clothes!! How to Survive the Desert in Summer on a Boat, Calico Skies Sailing Ep. 196

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 The Heat Wave is Here! 3:24 Weather Models Don't Work Here 5:00 To Keep Cool Get in the Water 6:59 Running the Air Con on the Hook 8:35 Let's...
Nature is Healing…REAL LIFE Aboard Anchored Sailboat (raw and unfiltered) (CSS Ep 195)
Calico Skies Sailing

Nature is Healing…REAL LIFE Aboard Anchored Sailboat (raw and unfiltered) (CSS Ep 195)

Go to to get a FREE 1-year supply of Vitamin D3+K2 and 5 AG1 travel packs with your first purchase. Thanks to AG1 for sponsoring today's video! 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 ...
Engine STALLS After All Our Work … Why??! 😥 (Calico Skies Sailing, Ep 194)
Calico Skies Sailing

Engine STALLS After All Our Work … Why??! 😥 (Calico Skies Sailing, Ep 194)

Bouge RV CODE: CALICO20 FOR 20% OFF valid until 30th August BougeRV is celebrating Happy 6th Anniversary, please check it here: 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 Back Underway 2:13 ...
Harder Than We Remembered: Our FIRST Sail in 9 months😳(Calico Skies Sailing, Ep.193)
Calico Skies Sailing

Harder Than We Remembered: Our FIRST Sail in 9 months😳(Calico Skies Sailing, Ep.193)

👟 Check out Vessi styles at Use code CALICO for 15% off your order. Free shipping for CA, US, AU, JP, TW, KR, SGP. 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 Valve Cover Gasket Change 5:24 Fare...
We Are Saying FAREWELL to our Jerry Cans! 👋🏼 (Calico Skies Sailing, Ep. 191)
Calico Skies Sailing

We Are Saying FAREWELL to our Jerry Cans! 👋🏼 (Calico Skies Sailing, Ep. 191)

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 Installing New Fuel Tanks?! 2:18 Removal of Old Holding Tank 5:40 Prep Work to Measure for a New Tank 7:48 Templating for new Tanks 9:53 Installing the...
FIRST LOOK at our Brand NEW Jib ….& Logo!! 😲😲 (Calico Skies Sailing, Ep. 189)
Calico Skies Sailing

FIRST LOOK at our Brand NEW Jib ….& Logo!! 😲😲 (Calico Skies Sailing, Ep. 189)

Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) Thanks to @PrecisionSailLoftVictoria working with us on our new sails! 0:00 Intro 0:10 New Headsail 1:23 Replacing a Chafed Furling Line 4:18 Fixing Interior Cabine...
Failure to Launch ..We’re Taking on Water! (Calico Skies Sailing, Ep 188)
Calico Skies Sailing

Failure to Launch ..We’re Taking on Water! (Calico Skies Sailing, Ep 188)

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 Moving Calico into the Slings 2:22 Painting the Centerboard 3:41 The BIG Day is here, splash day! 6:37 Getting the Engine Going, Where the Water?!! 8:45...
The Road Forward (Calico Skies Sailing, Ep 187)
Calico Skies Sailing

The Road Forward (Calico Skies Sailing, Ep 187)

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 Return to Normalcy? 1:10 Launch Date Scheduled! 3:00 Packing Our Ditch Bag 3:58 Testing Our Diesel Motor 8:34 Scrub a Dub Dub 10:20 Patching the Ding...
Is Life as We Know It, Over? (Calico Skies Sailing, Ep 186)
Calico Skies Sailing

Is Life as We Know It, Over? (Calico Skies Sailing, Ep 186)

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 Unexpected Bad News 1:52 Surgery Recovery 11:35 Tour of the Hyperbaric Treatment Facility 16:26 Oncology Appt 20:21 Bill's Back at the Boat Closi...
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