Calico Skies Sailing: What Boat Do Bill and Grace Have? (2023)

Everything You Always Wanted To Know

Joshua Smith

Founder and Editor at Cruising Freedom

This is the definitive guide on Calico Skies Sailing for 2023.

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

(Yes, I really am *that* obsessed with Bill and Grace 😃)

If you wanted to know:

➜ How Calico Skies Sailing afforded their boat

➜ How they make their money today

➜ What boat do they have and its upgrades

➜ Who are they and their story

➜ 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… 🙂

Calico Skies Sailing FAQs (April 2023)

Boat Name

S/V Calico Skies

Crew Members

Bill Heaton (age 40)

Grace Heaton (age 39)

They are college sweethearts and met while studying at Manhattan College. They bought their sailboat 13 years ago and finally untied the lines about 3 years ago.

The Boat

Calico Skies Sailing owns a 1985 Sabre 36.


They have upgraded her with a water maker, 6x lithium batteries, 1100watts of solar, a wind generator, an inverter charger and even a generator just in case.


They are currently in Mexico.

Past Cruising

Most of their sailing has been in Central America, the Bahamas and the Caribbean.

Affording It

Like many YouTubers, Calico Skies Sailing simply worked hard to achieve their dreams. They were making huge money on Wall Street and were able to save most of their income.

Net Worth

YouTubers typically increase their wealth once they begin publishing videos consistently.

As of 2023, Calico Skies Sailing has a net worth of $770,000.

Despite their large net worth, they have opted for a cheaper boat and are proponents of the F.I.R.E. movement. That is – retiring early through mindful budgets and saving early.

Making Loot

Calico Skies Sailing makes $3,100/month on YouTube through:

➜ Monthly Patreon subscription

➜ Selling their own merchandise

➜ Allowing ads on their channel

➜ Accepting PayPal donations

This is *just* enough to keep them cruising. In addition, as experienced hedge fund managers, they do have some personal investments which keep them going.

They only spend around $2,000/month onboard together, making their cruising more affordable than living in a normal house.


Calico Skies Sailing is definitely an outgoing couple and has hung out with:

Sailing Into Freedom (Plukky, the legend!)

S/V Delos

Sailing Parlay Revival

They recently did a boat race against these guys. They have also hung out with David Shih at the Annapolis Boat Show.

Big Moments

Sailing has been relatively stress-free, although:

➜ They received some criticism about not being prepared before an ocean crossing as they had to ask for diesel fuel from a cargo ship

➜ They came across crocodiles in the San Blas Islands

Through these experiences, they have definitely learned some lessons along the way.

Future Plans

Where to next? It’s most likely that they’ll head west towards the South Pacific and eventually head to Australia. Plukky has probably inspired them. 🙂

Key Takeaways

This couple reminds us that we don’t need an expensive boat to have a ton of fun out there on the water! Despite having many friends who are millionaires, they decided to retire early and live simply, without all the stress from the corporate world.


I have really enjoyed watching their channel and can’t wait to see what more will come!

Create Your Own Cruising Freedom

Hey! 😃 it’s Joshua again…

I’ve been very inspired by Calico Skies Sailing 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…🙂)