Calico Skies Sailing

Two dreamers traveling the world on our 36ft sailboat
We don’t always know where we’re going but we’re always going!
30,000+ miles in 2 years, 0 plans to stop!

Here’s to enjoying the ride & a life uncommon!

Calico Skies Sailing Journey and Videos Locations

Calico Skies Sailing Latest Episode

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Calico Skies Sailing Latest videos

Showing 1-6 of 301 results
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 https://saily.com/calicoskies Enjoying our channel? Consider joining the Calico Skies Patreon Crew to get lots of extra goodies :) https://ww...
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 :) https://www.patreon.com/CalicoSkiesSailing 0:00 Intro 0:10 Recap 1:39 Setting a Kedge 11:57 Confusion, What Just Happened 13:58 Lessons Learned The m...
We Crashed on a REEF: Can We Save Our Sailboat?! #shorts  #sailing
Calico Skies Sailing
We Crashed on a REEF: Can We Save Our Sailboat?! #shorts #sailing
Check out the full video here: https://youtu.be/coNQC-Sa8NE
We Crashed on a REEF: Can We Save Our Sailboat?! (Calico Skies Sailing, Ep 260)
Calico Skies Sailing
We Crashed on a REEF: Can We Save Our Sailboat?! (Calico Skies Sailing, Ep 260)
Enjoying our channel? Consider joining the Calico Skies Patreon Crew to get lots of extra goodies :) https://www.patreon.com/CalicoSkiesSailing 0:00 Intro 0:10 We've washed up on a REEF 1:58 Flashback of events leading up to the reefing 6:12 The Fight to...
Code Zero: Our Engine Saver is back! (Calico Skies Sailing, Ep 259)
Calico Skies Sailing
Code Zero: Our Engine Saver is back! (Calico Skies Sailing, Ep 259)
Enjoying our channel? Consider joining the Calico Skies Patreon Crew to get lots of extra goodies :) https://www.patreon.com/CalicoSkiesSailing 0:00 Intro 0:10 Leaving Vuda Point 2:11 Calibrating the Autopilot 4:09 Flying Our New Code Zero 6:55 Reef Navi...
Violent Squall! (Calico Skies Sailing, Ep 258)
Calico Skies Sailing
Violent Squall! (Calico Skies Sailing, Ep 258)
If interested in AIRLOCK for you Boat/RV use Code“CALICOSKIES” for a $30 discount; https://www.airlockusa.com/ Enjoying our channel? Consider joining the Calico Skies Patreon Crew to get lots of extra goodies :) https://www.patreon.com/CalicoSkiesSai...

Watch Calico Skies Sailing from the Beginning!

Showing 1-12 of 301 results
Place your bets! (Calico Skies Sailing Ep. 1)
Calico Skies Sailing
Place your bets! (Calico Skies Sailing Ep. 1)
As temperatures drop in Gibralter this fall we decide to make a beeline back to the Caribbean and have big money riding on our plan to complete the 3400 mile trip in just 25 days - no crew - just us, our 36 foot sailboat, and a whole lot of ocean. -~-~~-~...
Trans-Atlantic Crossroads (Calico Skies Sailing Ep. 2)
Calico Skies Sailing
Trans-Atlantic Crossroads (Calico Skies Sailing Ep. 2)
It's around the 5 or 6 day mark of our Trans-Atlantic and we're just starting to get into the groove when we're forced to make a choice which becomes a defining moment in our passage. We're facing the first big challenge on this journey but its all just pa...
Trans-Atlantic: In for the Long Haul (Calico Skies Sailing Ep. 3)
Calico Skies Sailing
Trans-Atlantic: In for the Long Haul (Calico Skies Sailing Ep. 3)
After being at sea for a week we are in the groove of our passage. We decide to skip a stop in the Canary Islands and take our chances continuing non-stop to the Caribbean! -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying our channel? Consider joining th...
Trans-Atlantic: Tough Stuff (Calico Skies Sailing Ep. 4)
Calico Skies Sailing
Trans-Atlantic: Tough Stuff (Calico Skies Sailing Ep. 4)
We're at the mercy of Mother Nature when rough weather brings breakages, leaks, and a whole lot of discomfort. -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying our channel? Consider joining the Calico Skies Patreon family for as little as $2 a month to g...
Trans-Atlantic Arrival: Land Ho!! (Calico Skies Sailing Ep. 5)
Calico Skies Sailing
Trans-Atlantic Arrival: Land Ho!! (Calico Skies Sailing Ep. 5)
We're on the home stretch of this mammoth journey and time seems to stand still until all at once and in an instant we experience what it feels to see land after nearly a month at sea. -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying our channel? Conside...
Anchors down! Welcome to the Caribbean (Calico Skies Sailing Ep. 6)
Calico Skies Sailing
Anchors down! Welcome to the Caribbean (Calico Skies Sailing Ep. 6)
A celebration is in order after arriving to the Caribbean after almost 27 days at sea! In this episode excitement is at an all time high and it takes us some time to ease back into the good ole regular cruiser life. -~-~~-~~~-~~-~- Thanks to our Patrons! ...
Minisode 1: Island Hopping: Sailing the Caribbean Sea
Calico Skies Sailing
Minisode 1: Island Hopping: Sailing the Caribbean Sea
We had a beautiful 300 mile, 45 hour sail from Guadeloupe to Puerto Rico in ideal Caribbean sea conditions. Check out the highlights in this 'Mini-sode' and get a glimpse of our sailing journey as a crew of two in this real time clip. More to come when we ...
The Cruising Life: Fixing the Boat in Exotic Places (Calico Skies Sailing Ep. 7)
Calico Skies Sailing
The Cruising Life: Fixing the Boat in Exotic Places (Calico Skies Sailing Ep. 7)
It's time to get moving on boat repairs after our big transatlantic passage. But like anything in life, its all about balance. In this episode we tackle sail repairs and a solar panel installation but also make our way deep into Grenada's lush, tropical ju...
Chocolate, Rum and Our Golden Ticket (Calico Skies Sailing Ep. 8)
Calico Skies Sailing
Chocolate, Rum and Our Golden Ticket (Calico Skies Sailing Ep. 8)
This week we learn how rum is made, tour a chocolate factory and find our very own golden ticket when our Amazon order arrives and it's everything we've ever dreamed of and more! We also continue repairing breakages from the transatlantic and move one step...
When Opportunity Knocks we Top Up the Cruising Kitty (Calico Skies Sailing Ep. 9)
Calico Skies Sailing
When Opportunity Knocks we Top Up the Cruising Kitty (Calico Skies Sailing Ep. 9)
This week we take on a couple of odd jobs to help offset the cost of transatlantic boat repairs. We also make time to explore Grenada's north shore and make a trip to a stunning deserted island off the coast. As per usual, there's also more boat repairs m...
We are a Sailboat Again! (Calico Skies Sailing Ep. 10)
Calico Skies Sailing
We are a Sailboat Again! (Calico Skies Sailing Ep. 10)
This week we FINALLY finish boat repairs: Calico Skies has never been in better shape, and we've never been more excited! We still need to prepare for departure though, which means provisioning (aka buying lots of chocolate), cleaning the boats anchor chai...
Welcome to the Jungle (Calico Skies Sailing Ep. 11)
Calico Skies Sailing
Welcome to the Jungle (Calico Skies Sailing Ep. 11)
It's all fun and games in the exotic Caribbean island of Dominica. In this episode we make the 36 hour sail from Grenada and arrive into a mountainous island covered in rain forest and dense, tropical jungle. The first thing we do is take a trip via rowboa...

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