Crossing the Gulf Stream on a boat is an endeavor that must be taken seriously. Part of the preparation for a successful passage simply involves waiting for ...

Embark on a thrilling journey with us as we navigate through the treacherous waters of the infamous Whale Cay Cut aboard our sailboat. Witness the breathtaking ...

TROUBLE OFFSHORE. We're going to need to channel McGyver to get out of this one... Crossing from Galapagos - Easter Island - ripped sail, lost parts, ...

This bad news changes everything. On this episode of sailing sitka, we are stuck in a rough anchorage and if that wasn't bad enough, we figure out some ...

Embark on an unforgettable sailboat voyage with us as we set sail for the Bahamas, meticulously planning our route around weather windows to ensure a smooth ...

After a very tedious check in process we were cleared to explore the rest of Mexico, so we untied from the dock and sailed south on our longest passage yet! ...

Our very first offshore sail on Ruby Rose 2 takes us 200 miles from Koh Samui to Pattaya in Thailand. This is the first overnight passage and while we love ...

We finish our adventure in a spectacular way, with a sail in big breeze surfing to over 11 knots, navigating at night through heavy traffic, and dodging ...

Ahoy, beautiful Patrons! Join us for a Patron-only livestream where we'll share a bit of the islands with you, talk about everything that's been going on, ...

After months of planning, delays, and other misadventures we FINALLY sailed over the border from California to Mexico! Our first stop was Ensenada where we ...

First offshore passage of the season! In this episode of sailing sitka, we take our newly refitted sailboat on a sail across the Sea of Cortez after weeks of ...

During the Newport Boat Show we met up with one of our viewers, John, who made us an offer we couldn’t refuse. He had the missing part to our boat that a LOT ...

Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) ...

Join us as we finally leave Spain and sail east to the Italian island of Sardinia. We'll show you what we get up to on passage, and that while it might sound ...

sending out another commentary of our thoughts of how it is REALLY like to be out on the sea in our tiny little sailboat, for over 1000 nautical miles in the ...

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We sail across a stretch of water which may be more feared than Cape Horn! Even huge ships don't venture here in bad weather. We find out why as we deal with ...

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Last week we left you as we had to make an emergency entrance into Ocean City at midnight because our forestay started to unravel. This week we tackle fixing ...

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As Saoirse glides gracefully through the open waters of the Atlantic Ocean, we are now 400 nautical miles into our journey from Florida to Rhode Island. All ...

Part 2 of this sail: https://youtu.be/Bk2PUv7Fi8g 💙 GET THE EXTRAS 💙 For exclusive content, behind the scenes & live chats! ...