Sailing Fair Isle: How Old is Judy? What Is Their Boat? (2023)

Everything You Always Wanted To Know

Joshua Smith

Founder and Editor at Cruising Freedom

This is the definitive guide on Sailing Fair Isle for 2023.

Over the last 2 years, I have spent 22 hours watching and researching everything I could about Sailing Fair Isle to learn more about their story.

(Yes, I really am *that* obsessed with these energetic old timers 😃)

If you wanted to know:

➜ How Sailing Fair Isle afforded their boat

➜ How they make their money today

➜ What boat do they have and its upgrades

➜ Who is Judy and what is her age

➜ 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… 🙂

Sailing Fair Isle FAQs (January 2023)

Boat Name

S/V Fair Isle

Crew Members

Steve (age 59)

Judy (age 55)

The Boat

Sailing Fair Isle has a Hans Christian 48.


They have upgraded their yacht with modern technology, including radar, AIS, GPS and UHF.


They are currently in Montenegro. They have been here for a while actually.

Past Cruising

They have sailed around the world already, so they now get to choose where they want to discover without any agenda.

Affording It

Both have worked in the travel industry.

Net Worth

Sailing Fair Isle has a net worth of $450,000.

Making Loot

How do they sustain themselves?

➜ Allowing ads on their channel

➜ Affiliate links to Surf Shark

➜ Their loyal Patreon subscribers

Sailing Fair Isle aren’t trying to make money on YouTube, but they do make around $2,000/month through creating simple videos. The rest comes from their retirement accounts.


They have hung out with some smaller creators on YouTube here:

Most notable is Bums On A Boat which also produce some awesome cruising content!

If you’re looking for a similar channel on YouTube, then check out Sailing Emerald Steel who has been sailing on the same old boat for 30 years.

Big Moments

Despite having a large and old boat, they haven’t had anything disastrous happen. Most things have been easily fixable with basic tools.

They also haven’t created controversy or drawn criticism. Many admire them for simply producing simple content while sailing on an older vessel.

Future Plans

Where to next? I’m not totally sure but they won’t stop cruising anytime soon. 🙂

Key Takeaways

What can we learn from this wonderful couple?

➜ Start working hard for your dreams

➜ Be prepared to put in the hard yards

➜ People in old boats are highly respected

➜ Find a traveling partner who supports you

And of course, be willing to deal with some challenges.


Sailing Fair Isle was one of my earliest inspirations into the world of sailing, and I highly recommend checking out their Patreon membership.

They are truly sailors, not influencers, and can handle a boat with pride. Certainly I’m subscribed and can’t wait to see more!

Create Your Own Cruising Freedom

Hey! 😃 it’s Joshua again…

I’ve been very inspired by Sailing Fair Isle 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…🙂)