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.
Showing 1-14 of 14 results
Sailing During Covid: Low Fuel.. Can we Divert?! (Calico Skies Sailing Ep.107)
We knew the route from Mexico to Panama would require a lot of motoring and that there was always a possibility we would have to divert course to get more fuel. Traveling during COVID makes these passage decisions even more difficult. Our route to Panama has three potential pit stops for Calico Skie...
Dry Tortugas, Isolated Gem of the Florida Keys (Calico Skies Sailing Ep 95)
It's time to escape the hustle and bustle of Miami and get back into what we regard as "real cruising" or sailing the boat to remote, less main stream locations. In this episode we complete an overnight sail from Key Biscayne to the Dry Tortugas. It was cool to watch the majestic Fort...
Off Season Cruising down the Chesapeake (Calico Skies Sailing, Ep 83)
Annapolis seems to have some sort of magnetic pull on us in the late fall 😂, this years challenge is to escape before the first snow falls..can we do it?! This town is a great stopover for us as we make our way up and down the east coast. We have lots of friends that live here and you can basicall...
Can We Escape Maine? Time to Sail South!! (Calico Skies Sailing, Ep 80)
We seem to make a habit of overstaying our season in each spot we travel to 🙃. Whether it is the sweltering heat of the Bahamas this past June (almost July) or the freezing cold air in Maine at the end of October, we just seem to stay too late LOL. Well the time has come for us to start our long tre...
Injury at Sea (Calico Skies Sailing, Ep. 79)
When it rains, it pours! This episode opens with us disconnecting our tow from S/V Delos and getting Calico Skies anchored under power from our dinghy. We being the process of flushing the transmission fluid several times after getting the dipstick caught in the gears. With the transmission issue r...
No wind, no transmission, no problem! S/V Delos to the rescue! (Calico Skies Sailing, Ep 78)
We are at the point in our season where we are starting to make our way back south and west after getting within ten miles of the Canadian border. Our first stop is Mud Hole. This sweet anchorage is only accessible at high tide. This entrance to this harbor is very tight, Brian (S/V Delos) jumps in ...
Off the Beaten Path, Sailing Down East Maine in the Fall (Calico Skies Sailing, Ep 77)
In this episode we decide to throw caution to the wind and sail to the very north eastern tip of Maine, right at the Canadian border. Its late September and we should be heading south but adventure calls! Exploring Cross Island is a real treat. The island shows the rugged side of Maine and also it...
Sailing in Maine, holy lobster pots!!! (Calico Skies Sailing, Ep 72)
In this episode we explore the Isle of Shoals, a beautiful island located right on the border of New Hampshire and Maine. The next day we continue our journey further North, rising at 4:30 am in anticipation of a long passage. The early beginnings of our little Maine adventure shows promise with on...
Land Ho! Our Beautiful Sail to Maine (Calico Skies Sailing, Ep 71)
After almost a month of boat work, the mast has been re-stepped and we’re finally headed back to cruising life. We head out with the wind, as we make our way towards Maine, our ultimate destination. In total about 500 nautical miles away, we tackle the passage in pieces stopping first in Cape May NJ...
Ditching Delos: My Hubby is Back! (Calico Skies Sailing, Ep.68)
When the rod head on our forward lower shroud broke on the fifth day of Bill's solo passage headed North from the Bahamas he had to divert course near Beaufort, North Carolina and head inshore. Grace is crewing on our friends boat s/v Delos and we’re ahead of Calico Skies, having begun our pass...
Rigging Failure Sailing Solo While My Wife is Crewing on Delos! (Calico Skies Sailing, Ep. 67)
It’s day four of our offshore passage north from the Bahamas headed up along the east coast of the US. Bill is about 30 miles offshore from North Carolina when the rod head on the forward lower shroud exploded. He’s sailing Calico Skies solo and Grace is crewing on our friends boat, s/v Delos. We’ve...
A Tale of Two Passages….Ripped Sails on Delos and Rig Failure on Calico Skies (Ep. 66)
This episode opens on night two of our passage from the northern part of the Bahamas to the east coast of the US. For this passage, Grace has joined our friends on Delos as crew and Bill has set sail solo. Together, we’re buddy boating on a northward trajectory, aiming for the Chesapeake Bay, still ...
I’m Leaving My Husband……to Join Delos, (Calico Skies Sailing, Ep. 65)
Well this is a first for us, Calico Skies is setting out to sea for an eight hundred mile passage without Grace onboard. What?! Ya! In this episode, Grace joins the S/V Delos crew to help sail her back to the US and play with little Miss Nugget. Always up for an adventure, Bill has volunteered to s...