The Ultimate Guide to Rick Moore

Here's Everything You Wanted To Know

Joshua Smith

Joshua Smith

Founder and Editor at Cruising Freedom

This is the definitive guide on Sailing Sophisticated Lady for 2023.

Over the last 6 years, I have spent 47 hours watching and researching everything I could about Rick and Sophisticated Lady as one of his most loyal fans. This is long before every other sailing channel blew up on YouTube!

(Yes, I really am *that* obsessed with his adventures 😃)

If you wanted to know:

➔ How Sophisticated Lady afforded their boat

➔ How they make their money today

➔ What boat they have and its upgrades

➔ 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…. 🙂

Sophisticated Lady FAQs (January 2023)

Boat Name

S/V Sophisticated Lady. This is not to be confused with the MV Sophisticated Lady based in the UK.

Crew Members

Rick Moore (age 54)

Maddalena Alessio (age 47)

Brenden Moore (age 25)

Captain Rick Moore is now married to Maddalena. They got married in early 2021.

They now have a baby boy together called Riccardo.

Sasha and Valentina were previous crew members.

The Boat

Sophisticated Lady is a 1995 36-foot yacht.


Rick has upgraded his boat with:

➔ New furling roller

➔ New solar panels

➔ New security system


Rick Moore and his boat Sophisticated Lady remain mostly in The Caribbean. His boat is used for charter purposes and provides him with much of his income.

However, he has sailed extensively throughout South America through some sketchy places.

Captain Rick Moore is also fluent in Spanish.

This is one of their most recent videos:

Past Cruising

Rick has previously sailed around the world, but today remains in paradise.

He has a beautiful boat, great lifelong friends and most importantly, a beautiful, supportive wife.

What more could one want? 😃

Affording It

Rick bought his loyal yacht after 10+ years of diligent saving and investing, with his past career in the marine industry.

Making Loot

Rick Moore from Sophisticated Lady earns $12,000/month with a networth of $592,000.

He makes his money through:

➔ YouTube ad-revenue from their videos

➔ Earnings from his daily charter business

➔ Various sailing brand sponsorships

➔ Print-on-demand products from their store

➔ Donations from their loyal Patreons


Rick has collaborated with:

SV Delos

Sailing Miss Lone Star

Sailing Into Freedom (the legendary Plukky!)

Plus various other smaller influencers.

Big Moments

Rick Moore probably has the biggest and best moments of any cruising YouTube in existence.

Some notable include:

➔ Covering the disappearance of Andreas Sipsakas

➔ Dealing with the British Virgin Islands hurricane

➔ Helping various credit card captains from crashes

➔ Visiting various nudist beaches with his women

Future Plans

It’s anticipated that Captain Rick Moore will continue sailing for many years to come, with his channel eventually reaching over 1,000 episodes.

His son will become the next generation of sailing icons no doubt!

Key Takeaways

Rick is a legend amongst the sailing community.

We can learn that:

➔ Life is short, so make the most of every day

➔ Cruising isn’t always sunshine and rainbows

➔ Don’t buy an expensive boat and crash it


Rick has earned a name for himself and his travels. He was one of the very first cruising YouTubers with his first video about 14 years ago with his parrot.

Today he may not have the audience that Sailing La Vagabonde has, but his keeps his content real, relevant and unscripted.

…And with a lack of women’s clothing thrown in!

Creating Your Own Cruising Freedom

Hey! 😃 It’s Joshua again….

Clearly I’ve been very inspired by Rick Moore and Sophisticated Lady.

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

His is living the dream, but that dream isn’t actually that far away.

Earlier I mentioned about finding the perfect cruising business model.

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

➔ Generate a sustainable $15,000/month with proof (yes, seriously!)

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

➔ Do it without selling to friends & family (’cause that’s icky, am I right?!)

➔ Share my lifetime passion of sailing, cruising and global adventures

Curious to learn more? Jump on the free training right now. 🔥