Sailing On A Whim: What Happened To Them? (2023)

Everything You Always Wanted To Know

Joshua Smith

Founder and Editor at Cruising Freedom

This is the definitive guide on Sailing On A Whim for 2023.

Over the last 2 years, I have spent 57 hours watching and researching everything I could about Sailing On A Whim to learn more about their story.

(Yes, I really am *that* obsessed with Sailing On A Whim 😃)

If you wanted to know:

➜ How Sailing On A Whim afforded their boat

➜ How they make their money today

➜ What boat do they have and its upgrades

➜ Where did they go? Are they coming back to YouTube?

➜ 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 On A Whim FAQs (April 2023)

Boat Name

S/V On A Whim

Crew Members

Dan (age 41)

Krista (age 34) is Dan’s friend, not his girlfriend.


The Boat

Sailing On A Whim has a 39′ yacht


They have upgraded their yacht with a water maker, solar panels and battery bank. The previous owner took great care of the boat so there wasn’t much to be done.


Their last video from Marsh Harbour was posted on the 25th of November, 2021:

No one really knows what happened to Sailing On A Whim. Perhaps they sold the boat, got divorced and left YouTube behind? If you do have more information, please let me know.

Past Cruising

While they were active on YouTube, they sailed to the Bahamas and back to the United States.

Affording It

Dan worked hard over several years to buy their dreamboat.

Net Worth

Sailing On A Whim are worth $260,000.

Making Loot

How can they afford to keep sailing?

➜ They run their own Patreon membership (3 paying subscribers only…)

➜ They put Amazon links in their video descriptions

➜ They run ads on their videos

That said – they haven’t uploaded for a while, but when they were, it’s estimated their income was around $2,500/month.


I haven’t seen them sailing on any other boats or featured on any other channels.

Big Moments

What happened during their journey?

➜ They ran aground (making them true sailors!)

➜ Touring the aftermath of Hurricane Dorian

Future Plans

Where to next? Are they still sailing? Did they sell the boat and return to land-life? So many questions left unanswered.

Key Takeaways

What can we learn?

➜ Buy an affordable boat

➜ Go small and go now


While small, I really did enjoy their channel. It felt simple yet knowledgeable unlike the ‘chicks for clicks’ YouTubers that dominate YouTube.

I can’t wait to see them return to the platform in the very near future.

Create Your Own Cruising Freedom

Hey! 😃 it’s Joshua again…

I’ve been very inspired by Sailing On A Whim 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…🙂)