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 1-9 of 9 results
TRAINING TO AVOID DANGER ON A PERFORMANCE CATAMARAN
The O'Kelly's

TRAINING TO AVOID DANGER ON A PERFORMANCE CATAMARAN

This video could change how you sail! Olympians, World Champions, Hall of Famers! We have got some VERY cool friends. When we met out at a deserted island years ago, little did we know that Annie Gardner and Eric Witte on the Catana 472, El Gato were such accomplished sailors. This week, we soak up ...
Birth of The Dream
The O'Kelly's

Birth of The Dream

Part 2 of The Cruising Dream vs. The Cruising Reality, we hear how and why couples decide to set off for an epic trip
Before Cruising  – Dream vs Reality Video Series Part 1
The O'Kelly's

Before Cruising – Dream vs Reality Video Series Part 1

Part 1 of The Dream vs. Reality series of cruising videos. We introduce four couples who made The Cruising Dream a reality. In this segment, we give you a short background on: Rick and Corbie Von Stein, Ben and Lisa Newton, Pat and Ali Schulte, and Janna and Graeme Cawrse-Esarey.
Preparing to Sail Away – Dream v. Reality Part 4
The O'Kelly's

Preparing to Sail Away – Dream v. Reality Part 4

For most of us, getting ready to sail away is more than buying a boat.
Taking Off – DvR Video Series – Part 5
The O'Kelly's

Taking Off – DvR Video Series – Part 5

Leaving for the trip of a lifetime can stir some powerful emotions.
On Passage – DvR Video Series – Part 8
The O'Kelly's

On Passage – DvR Video Series – Part 8

Storms? Breakdowns? Pirates? Rationing food and water? We uncover the truth about the challenges of the longest passages.
Roles Change – DvR Series Part 7
The O'Kelly's

Roles Change – DvR Series Part 7

Pink vs. Blue jobs? It's more complicated than that for most couples setting off on a grand sailing adventure.
Relationships Change While Cruising – DvR Video Series Part 6
The O'Kelly's

Relationships Change While Cruising – DvR Video Series Part 6

Cruising together on a small boat will make or break any relationship.
PreDeparture Fears -Dream vs. Reality Video Series Part 3
The O'Kelly's

PreDeparture Fears -Dream vs. Reality Video Series Part 3

What fears do yo have about cruising? Storms, pirates, and sinking? The most paralyzing fears will be of a completely different nature. In the end, you just have to go.
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