Leading the Escapade: Who Are Jason and Janaye? (2023)

Everything You Always Wanted To Know

Joshua Smith

Founder and Editor at Cruising Freedom

This is the definitive guide on Leading the Escapade for 2023.

Over the last several years, I have spent many hours watching and researching everything I could about Leading the Escapade to learn more about their story.

(Yes, I really am super obsessed with fellow Australian sailors 😃)

If you wanted to know:

➜ How Leading the Escapade afforded their boat

➜ How they make their money today

➜ What boat do they have and its upgrades

➜ If Janaye offers uncut or nude footage

➜ How you can start crossing oceans

Then you’ve definitely come to the right place.

Before we start, a quick introduction from me…

The Cruising Freedom Author

Ahoy, Matey! I’m Joshua from Australia.

I’ve built the perfect business to sail the world.

A business model which can allow me to:

➜ Own a catamaran debt-free

➜ Go for weeks without WIFI

➜ Create semi-passive income

➜ Inspire others to dream big

But more on that later… 🙂

Leading the Escapade FAQs (April 2023)

Boat Name

S/V Escapade

Crew Members

Jason and Janaye MacDonald

They are both 28 years old from the Gold Coast Hinterland of Queensland, Australia.

The Boat

Leading the Escapade have a Jeanneau Sun Oddysey 40.


They have replaced their rigging and some of their electronics.


They are currently in Europe, or more specifically, Croatia:

Past Cruising

Apart from sailing Australia when they were younger, most of their cruising has been in the Mediterranean.

Affording It

Jason and Janaye just had ordinary jobs back home in Australia, but without any kids to look after, they were able to save up just enough to purchase their yacht for cash.

Net Worth

Leading the Escapade has a net worth of $350,000 Australian dollars. This is representative of their boat’s value and business income.

Making Loot

Yes, they do make money on YouTube through:

➜ Patreon and PayPal donations

➜ Affiliate links to Wise (online bank)

➜ Running their GoFundMe account

➜ Allowing ads on their YouTube channel

I estimate they’re making around $4,700/month which is enough to sustain them and their nomadic lifestyle.


As they are a younger channel, they haven’t had a chance to collaborate with other YouTubers. However, there are some similarities between them and Kristina’s Travels who are currently sailing up Australia’s east coast.

Big Moments

They have had a relatively stress-free experience while in the Med, apart from overstaying their Turkish Visa and getting into some serious trouble.

Future Plans

It’s likely that they’ll continue in the Mediterranean for this season, and eventually leave for the Caribbean. From there – I guess we’ll see them in the South Pacific, and eventually back home to Australia.

Key Takeaways

What can we learn from these young yet ambitious Australians?

➜ Create a purpose behind your travels

➜ Be willing to deal with some adversity

➜ Work hard to earn your freedom online

➜ Find someone who’ll support you today

And of course, make the most of every moment!


I’ve really enjoyed learning a ton from these guys. They know what they’re doing on YouTube by crafting killer content. They definitely deserve more subscribers!

Create Your Own Cruising Freedom

Hey! 😃 it’s Joshua again…

I’ve been very inspired by Leading the Escapade and their travels…

Some say I’m obsessed, but sailing the world is my childhood dream.

They’re living the dream, but that dream isn’t actually that far away.

I mentioned earlier about discovering the #1 cruising business model.

With this exciting opportunity, I’ll be able to:

➜ Generate a sustainable full-time income through learning basic skills

➜ Fund the purchase of my first sailing catamaran without any loans

➜ Do it without selling to friends and family (I found a better solution!)

➜ Share my lifetime passion for sailing, cruising and global adventures

Keen to discover more? Jump on the free training right now. 👨🏻‍💻

(I share more about it on the next page…🙂)