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
The Ragged Islands Are Pure Paradise! | Day 4-5
Leading the Escapade

The Ragged Islands Are Pure Paradise! | Day 4-5

We finally get a moment to breathe… After a wild crossing from Miami and getting hit with way more wind than expected, we wake up in the remote Ragged Islands in the Bahamas — and honestly, it feels like paradise. With the next weather window not quite ready for our push down to Colombia, we slow ...
Survival Mode at Sea + Monster Fish Caught | Day 2-3
Leading the Escapade

Survival Mode at Sea + Monster Fish Caught | Day 2-3

Day 2 & 3 of our sail from the United States to Colombia did not go to plan. What was meant to be a comfortable beam reach in 18–22 knots quickly turns into something very different. Instead of cruising south, we find ourselves stuck in gale-force winds, beating upwind for nearly two straight d...
It could have ALL ENDED HERE on CROOKED ISLAND! – Ep 26
Sailing Jibsea

It could have ALL ENDED HERE on CROOKED ISLAND! – Ep 26

Hey everyone, We sail from the Jumentos Cays, down to the Ragged Islands and an overnight sail to Crooked Island. We explore Bird Rock Lighthouse, mangroves, Turtle Sound and more. We spearfish, visit some flamingos and Travis encounters a little scare but overall, a great time. Crooked Island is ...
Sailing North: It’s All the RAGE, (Calico Skies Sailing, Ep. 62)
Calico Skies Sailing

Sailing North: It’s All the RAGE, (Calico Skies Sailing, Ep. 62)

This episode marks the beginning of a new chapter, as the Covid Crew begins to disband and go separate ways. We experience some fantastic sailing as we start our long trek north towards the States. Being a particularly windy year we almost always had enough to get Calico speeding along, and usually ...
Our Covid Experience, like something out of Gilligan’s Island! (Calico Skies Sailing, Ep. 60)
Calico Skies Sailing

Our Covid Experience, like something out of Gilligan’s Island! (Calico Skies Sailing, Ep. 60)

Our experience during covid sounds like something out of Gilligan's Island; twelve strangers find themselves isolated on a deserted tropical island for months on end learning to survive and forging life long friendships in the process. Before the pandemic erupted we had planned to be in the re...
The Founding of the Two Titty Yacht Club (Calico Skies Sailing, Ep. 59)
Calico Skies Sailing

The Founding of the Two Titty Yacht Club (Calico Skies Sailing, Ep. 59)

This episode depicts the birth of the TTYC or Two Titty Yacht Club, a sweet little spot on the beach at Double Breasted Cay that we end up spending a LOT of time at - Beginning in the early days of the Pandemic right on through the end of our Bahamas season. This sweet spot, built mostly from thing...
How to Get Groceries on a Deserted Island during a Pandemic (Calico Skies Sailing, Ep. 58)
Calico Skies Sailing

How to Get Groceries on a Deserted Island during a Pandemic (Calico Skies Sailing, Ep. 58)

In this episode we work out one of the more pressing issues we faced while we were 'stuck' in the Ragged Islands during the pandemic late Spring - How to get food. At the time, the Bahamas had banned inter-island travel which meant that we either had to head home to the U.S where the virus...
Ragged Island Regatta, (Calico Skies Sailing, Ep. 57)
Calico Skies Sailing

Ragged Island Regatta, (Calico Skies Sailing, Ep. 57)

In this episode we sail up the Ragged Island chain to Double Breasted Cay, a spot we will soon call home for the remainder of our time in the Bahamas (spoiler alert it's a LONG time). We decide to race our friends Ryan and Jerra on our sistership Zinzi and are lucky to have Conor and Steph film...
With a Little Help from My Friends (Calico Skies Sailing, Ep. 56)
Calico Skies Sailing

With a Little Help from My Friends (Calico Skies Sailing, Ep. 56)

Behind the scenes of cruising life there is a huge heaping pile of kind-hearted souls providing support and helping us through rough patches. These people are always ready to lend a hand with a project or boat fix, give advice, share knowledge and resources, and be a listening ear when the challenge...
Isolated in Paradise (Calico Skies Sailing, Ep. 55)
Calico Skies Sailing

Isolated in Paradise (Calico Skies Sailing, Ep. 55)

In this episode we experience all the best of what we consider to be ideal Bahamas cruising: Buddy boats to socialize with, friends supporting each other, and all in an incredibly beautiful and largely untouched paradise, abundant with sea life and filled with endless miles of pristine, white sand b...
Coming Together During Covid (Calico Skies Sailing, Ep. 54)
Calico Skies Sailing

Coming Together During Covid (Calico Skies Sailing, Ep. 54)

This episode depicts the early stages of our 'covid experience'. In it, we begin to make our way back up the Ragged Island chain enjoying a beautiful sail with our Code Zero or Gennaker. Upon arriving to our new spot we enjoy a bonfire on a gorgeous white sand beach and watch the sun set. ...
The Big Blow (Calico Skies Sailing, Ep. 52)
Calico Skies Sailing

The Big Blow (Calico Skies Sailing, Ep. 52)

In this episode, we travel to the Southern most island in the Ragged Island chain in search of protection from an impending storm. The Ragged's are known for having few islands that offer wind protection from every angle but thankfully, we were able to make it all the way to the bottom of the c...
Bahamas: It’s ALIVE (Calico Skies Sailing, Ep. 51)
Calico Skies Sailing

Bahamas: It’s ALIVE (Calico Skies Sailing, Ep. 51)

In this episode, we travel to the Southern most island in the Ragged Island chain in search of protection from an impending storm. The Ragged's are known for having few islands that offer wind protection from every angle but thankfully, we were able to make it all the way to the bottom of the c...
Sailing Off The Beaten Path: Ragged Islands (Calico Skies Sailing, Ep.50)
Calico Skies Sailing

Sailing Off The Beaten Path: Ragged Islands (Calico Skies Sailing, Ep.50)

In this episode, we sail from Long Island to Water Cay, north of the Ragged Island chain and enjoy perfect conditions with light breeze and the clearest, bluest water we’ve ever seen. We are visited by a dolphin and manage to catch a fish for dinner. The following day we do it all over again as we m...
WeBoating
Logo
Shopping cart