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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The Good, Bad & Ugly of Cruising Life + Why are all the Fish DEAD?? (Calico Skies Sailing Ep.145)
Calico Skies Sailing

The Good, Bad & Ugly of Cruising Life + Why are all the Fish DEAD?? (Calico Skies Sailing Ep.145)

In this life we always say the high are really high and the lows are super low. In this episode we get to experience the whole range. From beautiful Costa Rican anchorages, boat breakages, and an awful case of red tide destroying large population of fish 😳. There's never a dull moment in the sa...
Swimming in a Croc River?!!!!  (Calico Skies Sailing Ep144)
Calico Skies Sailing

Swimming in a Croc River?!!!! (Calico Skies Sailing Ep144)

Rosetta Stone Limited time offer: $179 from $299 for the Lifetime Subscription!! There's a lot of unknowns in our this lifestyle, most of them inconsequential but some potentially resulting in breakage or worse. The longer we cruise the more conservative we've become overall. But when we...
Dirty, Hot and Miserable 🙃.. sailing the MOST Biologically Diverse Place in the World (Ep143 )
Calico Skies Sailing

Dirty, Hot and Miserable 🙃.. sailing the MOST Biologically Diverse Place in the World (Ep143 )

Cruising Costa Rica epitomizes the old saying that cruising is full of high, highs and low, lows. Almost a bipolar existence. We are blown away by the beauty of the Osa Peninsula. Covering an area of just 700 square miles on the southern Pacific coast of Costa Rica, the Peninsula is estimated to hou...
Why this life may not be for you 🙃…blasting our car (dinghy) through a 6ft surf break (Ep. 142)
Calico Skies Sailing

Why this life may not be for you 🙃…blasting our car (dinghy) through a 6ft surf break (Ep. 142)

In this weeks episode we set off for our next stop in Costa Rica, the gorgeous Osa Peninsula. This region is known as one of the most bio diverse areas in the entire world. However our alternator has other ideas. We don't know for sure what the issue is but we open the engine compartment and se...
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