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Happy Holidays from Calico Skies Sailing!
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Real time update coming at ya!! We're getting Calico Skies decorated for Christmas and because we're underway it's gotta be done sailboat style (aka can ...

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Lake Livin’: Sailing Lake Bras d’Or (Calico Skies Sailing Ep. 33)
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In this episode, we get busy living our best life on Lake Bras d'Or, Nova Scotia. We pass the time paddling, hiking, making bon fires, and occasionally moving ...

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Sailing Nova Scotia: A Cruiser’s Playground (Calico Skies Sailing Ep. 32)
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This episode sets the theme for our first Canadian Cruising Experience: A little thing we like to call Adult Summer Camp! First, we set sail and head into Lake ...

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This is Bliss: Offshore Sailing at it’s Finest (Calico Skies Sailing Ep. 31)
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Sailing is about the journey, not the destination and this episode is evidence of that. It begins on the fifth day of our 1,000 mile passage from North ...

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Offshore Sailing & The Gulf Stream: Riding the Magic Carpet North (Calico Skies Sailing Ep. 30)
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In this episode we set out on our 1000 mile sailing passage to Canada. Initially we encounter steep waves and choppy seas off Beaufort NC but offshore ...

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The Great Escape: Hello Sailing, Goodbye East Coast! (Calico Skies Sailing Ep. 29)
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Temperatures are soaring here in Beaufort, North Carolina, but that does little to slow us down. In this Episode, we do some more provisioning, and Bill ...

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There are Two Types of Sailors: Those who Run Aground & Those who LIE about it  (Ep. 28)
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This is an old saying so we can't take any credit for it, but since we run aground in this Episode it seemed to fit! In it, we get to work on fixing our ...

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Offshore Sailing: Our Boat’s Taking on Water!! PART II, (Calico Skies Sailing Ep. 27)
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This episode chronicles our passage from the Bahamas to Canada, and begins on a relative high note when a new lead results in an improvement to the autopilot’s ...

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Autopilot Failure at Sea PART 1 (Calico Skies Sailing Ep. 26)
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In this episode we take you with us on our planned 12 day offshore sailing passage from the Bahamas, headed north. We begin by sailing off anchor and face calm ...

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Offshore Passage Planning for our Sailboat (Calico Skies Sailing Ep. 25)
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When you take big jumps offshore as opposed to a couple of nights here and there, overall travel time is reduced but preparing for the passage takes longer. To ...

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Bahamas Sailing; crossing from Eleuthera to the Abaco’s (Calico Skies Sailing Ep. 24)
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With temperature's rising, mother nature is giving us all the signs that it's time to head north! We enjoy a lovely sail across the North East Providence ...

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Exploring Eleuthera’s Caves  (Calico Skies Sailing Ep. 23)
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We've got one last thing to do before saying Goodbye to Eleuthera and beginning the journey North as hurricane season approaches. And that's to hit the road ...

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Bahamas Sailing: An Episode about Nothing (Calico Skies Sailing Ep. 22)
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How do you name an episode when there is no central theme, we are the main characters, and the story is just about a typical day in our lives? If you are a ...

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Bahamas Sailing; Water, water everywhere, Nor any drop to drink (Calico Skies Sailing Ep. 20)
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It may seems like cruising the Bahamas is all about sunsets and rum cocktails but it wouldn't be boat life without dealing with mechanical breakdowns. This ...

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Bahamas Sailing; Navigating through Devil’s Backbone (Calico Skies Sailing Ep. 19)
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After much planning we finally complete the passage through the notoriously tricky Devil's Backbone reef and arrive at a beautiful secluded beach north of ...

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Buddy Boats Reunite to Sail the Bahamas!!! (Calico Skies Sailing Ep. 18)
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Sailing the Bahamas is better with friends! We left NYC in the fall of 2017 with our friends Chris and Michele of S/V Andromeda, making the trip down to the ...

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The Good Life: Cruising our Sailboat in the Bahamas (Calico Skies Sailing Ep. 17)
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After dreaming, scheming, and sailing for the past four months we are finally back in Bahamas and ready to settle into the cruiser life! It feels like the ...

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Sailing to the Bahamas without a Gulf Stream crossing!! (Calico Skies Sailing Ep. 16)
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In previous episodes we provisioned and prepared our sailboat for a long blue water crossing, well my friends the time to embark has finally come! Join us as ...

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Bienvenido a Culebra! (Calico Skies Sailing Ep. 13)
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The tiny island of Culebra packs a big punch - From the incredibly clear and beautiful greeny-blue water full of sea life to the numerous chill bars with easy ...

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Neighbor Island’s: Same Caribbean, Different Worlds (Calico Skies Sailing Ep. 12)
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It's hard to top the enchanting Indian River we explored in last week's episode but our discovery of an incredible waterfall just inland from our anchorage ...

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Welcome to the Jungle (Calico Skies Sailing Ep. 11)
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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 ...

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We are a Sailboat Again! (Calico Skies Sailing Ep. 10)
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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 ...

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When Opportunity Knocks we Top Up the Cruising Kitty (Calico Skies Sailing Ep. 9)
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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 ...

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Chocolate, Rum and Our Golden Ticket (Calico Skies Sailing Ep. 8)
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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 ...

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