Watch Sailing & Boating Adventures Around the World

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Episode 15: The Problem That May Have Put me On The Reef (Calico Skies Sailing – New Horizons)
Calico Skies Sailing – New Horizons

Episode 15: The Problem That May Have Put me On The Reef (Calico Skies Sailing – New Horizons)

Get your Stainless Steel Chain Anchor from cromox! This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subsc...
Episode 10: Finding My Way Back to the Sailing Life & How to Rig a Code Zero (Calico Skies Sailing)
Calico Skies Sailing – New Horizons

Episode 10: Finding My Way Back to the Sailing Life & How to Rig a Code Zero (Calico Skies Sailing)

This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! Ov...
Episode 1: Get by With a Little Help from my Friends – Where has Calico Skies Sailing been??
Calico Skies Sailing – New Horizons

Episode 1: Get by With a Little Help from my Friends – Where has Calico Skies Sailing been??

This video was difficult to make. After nearly 23 years together Grace and I are separating. This is sad and a distinct end of a chapter. Maybe a chapter is inadequate, it's more like the end of a book. We have been together since we were 19 years old which is more than half our lifetime. Grace...
How Bad Is The Damage After Our Crash on a Reef?  (Calico Skies Sailing, Ep 262)
Calico Skies Sailing

How Bad Is The Damage After Our Crash on a Reef? (Calico Skies Sailing, Ep 262)

Get an exclusive 15% discount on Saily data plans! Use code calicoskies at checkout. Download Saily app or go to Enjoying our channel? Consider joining the Calico Skies Patreon Crew to get lots of extra goodies :) 0:00 Intro 0:10 Emergency Repairs to get the Rudder moving 2:21 Damage Assessmen...
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...
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...
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:...
40 Knot Gale off Tonga, Big Waves Big Wind, The Real Story (Calico Skies Sailing, Ep 255)
Calico Skies Sailing

40 Knot Gale off Tonga, Big Waves Big Wind, The Real Story (Calico Skies Sailing, Ep 255)

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 Day 8 of our Passage to Tonga 1:43 The Wind Starts to Build 3:25 Good Old Fashioned Gale has Built 9:51 What are the odd's? Literally Almost Runni...
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...
The Realities of Crossing the Pacific Ocean, Part 3 Champagne Sailing (Calico Skies Sailing, Ep 227)
Calico Skies Sailing

The Realities of Crossing the Pacific Ocean, Part 3 Champagne Sailing (Calico Skies Sailing, Ep 227)

Join Calico Skies Sailing as they share their journey across the Pacific Ocean, overcoming technical difficulties while experiencing "champagne sailing" conditions. Learn about their solar power setup and more.
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...
Life Update, What It Really Takes To Cross an Ocean (Calico Skies Sailing, Ep 220)
Calico Skies Sailing

Life Update, What It Really Takes To Cross an Ocean (Calico Skies Sailing, Ep 220)

Get 20% off Magic Mind using code SAILING20 Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) For business inquiries contact [email protected] The marine environment is tough on our camera gear, hel...
Pirates of La Cruz?! (Calico Skies Sailing, Ep 219)
Calico Skies Sailing

Pirates of La Cruz?! (Calico Skies Sailing, Ep 219)

Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) It always a blast when we can get together with other channels, special shout out to: @SaltandTar @CruisersAcademy @BreakingWavesSailing 0:00 Intro 0:10 Continuing...
A VERY bad passage – One that even made Bills radar 🫣🥺 (Calico Skies Sailing, Ep. 218)
Calico Skies Sailing

A VERY bad passage – One that even made Bills radar 🫣🥺 (Calico Skies Sailing, Ep. 218)

Get your own Bottlebottle, 15% Off code: 15CalicoYT Bottlebottle Amazon Shop: Bottlebottle Official Web: 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 Barre de Navidad 4:40 Commissionin...
Its Getting Dirty Over Here 😝 – I’m taking over boat work!!! (Calico Skies Sailing, Ep 217)
Calico Skies Sailing

Its Getting Dirty Over Here 😝 – I’m taking over boat work!!! (Calico Skies Sailing, Ep 217)

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 0:12 The Ladies Service the Winches 0:50 Recap ...
We waited a long time for this! (Calico Skies Sailing, Ep 213)
Calico Skies Sailing

We waited a long time for this! (Calico Skies Sailing, Ep 213)

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 Chamela Anchorage 5:38 Hair Cut Time! 7:50 Bill's Flying Solo Again 8:34 New Crew Aboard Continuing South 11:47 Doctor Calls with Good News! 13:...
It had to happen eventually …. every Sailors WORST nightmare 🥺 (Calico Skies Sailing, Ep 212)
Calico Skies Sailing

It had to happen eventually …. every Sailors WORST nightmare 🥺 (Calico Skies Sailing, Ep 212)

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 Recap 1:04 Isla Isabel 3:56 Gorgeous Stop but Time to Sail On 8:41 Did We Just Sail OVER a Whale?! 14:08 Arrival to Chacala, Setting the Stern Hook Fo...
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 ...
HORRIBLE Sail- Everything’s broken!! 😥(Calico Skies Sailing, Ep 208)
Calico Skies Sailing

HORRIBLE Sail- Everything’s broken!! 😥(Calico Skies Sailing, Ep 208)

Get 10% off your own Superior Life Saving Life Raft using the Coupon Code CALICOSKIESSAIL 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 After Over a Year Finally Departing Puerto Penasco! 4:42 Bac...
Last Push: The Boats (Almost) Ready to Go But What About Me?! 🫣 (Calico Skies Sailing, Ep 207)
Calico Skies Sailing

Last Push: The Boats (Almost) Ready to Go But What About Me?! 🫣 (Calico Skies Sailing, Ep 207)

Start speaking a new language in three weeks with Babble 🎉! Get 60% off your subscription during their Black Friday sale 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 Time to Install a New ...
Escaping the Sea of Cortez (Calico Skies Sailing, Ep 201)
Calico Skies Sailing

Escaping the Sea of Cortez (Calico Skies Sailing, Ep 201)

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 Dolphins in the Anchorage 2:35 Diving/Spearfishing 6:07 Potluck Dinner with Friends 8:20 We Gotta Go! 14:11 Passage North 18:18 Back in Penasco 19:27 Po...
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