Drake Paragon: What Sailboat Do They Have? (2023)

Everything You Always Wanted To Know

Joshua Smith

Founder and Editor at Cruising Freedom

This is the definitive guide on Drake Paragon for 2023.

Over the last 10 years, I have spent so many hours watching and researching everything I could about Drake Paragon to learn more about their story.

(Yes, I really am *that* obsessed with Drake and Monique 😃 the originals on YouTube)

If you wanted to know:

➜ How Drake Paragon afforded their boat

➜ How they make their money today

➜ What boat do they have and its upgrades

➜ More details about their boat and Eanna

➜ 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… 🙂

Drake Paragon FAQs (April 2023)

Boat Name

S/V Paragon

Crew Members

Drake Roberts (age 52)

Monique Davis (age 49)

Éanna did spend some time onboard but has since left.

The Boat

Drake Paragon owns a Westsail 42.


They have upgraded their boat with:

➜ Woodstove

➜ Singer sewing machine

➜ Replaced rigging

➜ New electronics

➜ A wind generator

Drake goes into deeper details within his videos.


Drake Paragon is currently in the Faroe Islands.

They haven’t uploaded for around 2 weeks:

Past Cruising

They have effectively sailed most of the world, predominantly in colder climates.

Affording It

They worked hard and saved diligently to buy their yacht, for which they have lived on for the last 10 years, aside from some short travels abroad.

Net Worth

Drake Paragon has a net worth of $270,000 based on their boat value and business valuation.

Making Loot

They command a lot of respect on YouTube for producing videos for 10+ years now.

With that, many people are OK with them making a bit of coin here and there.

They do this by:

➜ Allowing YouTube to put ads on their channel

➜ Accepting donations via Patreon and PayPal

➜ Doing some freelance work (writing/consulting)

I estimate they’re making around $3,200/month which is enough to sustain themselves and their journey.


Their best collaboration was this video:

They have avoided hanging out with all the rich and famous cruising couples, instead choosing to connect with those who are more realistic.

Big Moments

They have experienced a ton in their journey, most notably going through multiple storms.

Future Plans

They’re going to continue cruising and I don’t see any reason for them to stop.

Key Takeaways

What can we learn? I really think it boils down to their unique content designed for SAILORS, not the general public.

They have avoided the ‘chicks for clicks’ type of content (you know, bikinis and more bikinis) and instead, focused on real-life boat work and cruising.

This goes to show how you CAN be genuine on YouTube and build an audience. As they say “The Real Cruising Life”


Drake Paragon follows the well-known philosophy…

Go Small. Go Simple. Go Now.

And I totally agree!

It’s been working for them for 10 years, and I can’t wait to see what’s next.

Create Your Own Cruising Freedom

Hey! 😃 it’s Joshua again…

I’ve been very inspired by Drake Paragon 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…🙂)