The Ultimate Guide to Gone With The Wynns
Here's Everything You Wanted To Know
Joshua Smith
Founder and Editor at Cruising Freedom
This is the definitive guide on Gone With The Wynns for 2023.
Over more than 3 years, I have now watched 91 hours of their YouTube channel learning everything I could about Jason and Nikki.
I guess you could call me obsessed with their sailing travels 
And yes, I’ve noticed Nikki’s hair length grow over time while she’s become more feminine!
If you wanted to know:
➔ How Gone With The Wynns afforded their boat
➔ How they make their money on YouTube today
➔ What boat they have and its many upgrades
➔ How you can start world cruising just like them
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…. 🙂
Gone With The Wynns FAQs (January 2023)
Boat Name
S/V Curiosity
Crew Members
Jason Wynn (age 37)
Nikki Wynn (age 36)
Their 2 cats, Cleo and Singa, sailed with Jason and Nikki as stowaways for 13,000 nautical miles.
Sadly, they could not continue and were left behind in the United States to an emotional farewell.
They left before the Wynns started their voyage across the Pacific towards Tonga and New Zealand.
Their reasoning was mainly due to biosecurity challenges in the countries they desired to visit.
The Boat
Sailing vessel Curiosity is a 2005 Leopard 43.
As it’s for sale, you can view the listing here.
The catamaran in a 3-cabin owner’s version, with the main cabin taking up the entire starboard hull.
Upgrades
The Wynns have done many upgrades to Curiosity.
Notable items include:
➔ 2 Airconditioners
➔ Washing machine and dryer
➔ Composting toilet (taken from their old RV)
➔ Portable freezer
You can find their list of boat upgrades here.
Location
Gone With The Wynns are in the South Pacific.
Past Cruising
The Wynns have done roughly the same amount of land miles when compared to sea miles.
To date, apart from some coastal cruising, they have done the popular route across the Pacific from the United States to New Zealand.
We look forward to seeing them in Australia in 2022!
Affording It
Jason and Nikki claim to have simply “saved up” to buy their catamaran, however, some of their audience disputes these claims.
Rumours on the internet reveal that at least one of the Wynns comes from a very wealthy family.
After all, they appear quite affluent on their channel.
Quite surprisingly, Jason was simply a photographer and Nikki a makeup artist, with Jason later opening his own studio which they later sold for a profit.
From there, they began to travel in their RV and blog/vlog full-time, building a loyal audience.
It’s best assumed that they bought their catamaran using personal savings earned from their previous RV travels, plus it’s cheaper to live on the road.
Curiosity cost approximately $400,000 US Dollars.
Net Worth
YouTubers typically downplay their wealth so they can appear more relatable to their audience.
As of 2023, Gone With The Wynns have a net worth of $2,700,000 USD. This is based on the value of their boat, online business and investment portfolio.
They did NOT come from rich parents.
Making Loot
Today in 2023, Jason and Nikki make most of their money through Amazon affiliate links both placed under their YouTube videos and on their blog.
In addition, they make an income through:
➔ Freelance writing for travel-related websites
➔ Running ads on both their videos and website
➔ Creating their own recommend gear store
➔ Earnings from their hundreds of Patreons
➔ A few dollars via their tip jar on their blog
Now they’re earning an estimated $19,000 per month, so they each make a 6-figure income from their boat.
Collaborations
Their two best collaborations are with Sailing Ruby Rose and Sailing Zatara.
Jason and Nikki aren’t afraid to hang out with other cruisers, and I look to seeing them meet other popular YouTube sailors.
They have had numerous guests on board including Dior, Nikki’s mom and Jason’s brother.
Big Moments
Some of the best moments by The Wynns include:
➔ Sailing with Mark who had only 6 months to live, creating one of the best fundraisers in YouTube cruising history
➔ Being approached by fishermen late at night, in what some viewers were describing as a potential pirate attack
➔ Experiencing a rough sail from Tonga to New Zealand where Jason became quite ill
➔ Getting a huge hole and losing their lifecraft in their boat on the same voyage
Future Plans
The Wynns are now in New Zealand and are looking to sail north to Australia and onwards into Asia.
They are currently selling their catamaran, Curiosity.
There are however no confirmed plans for the future, but they are looking to buy their next boat.
Key Takeaways
We can learn from The Wynns that:
➔ Living on a boat is more affordable than ever
➔ You can combine a blog and YouTube channel
➔ Working remotely attainable for most people
➔ The world cruising community is very generous
➔ Brand new modern sailboats are unnecessary
Conclussion
The Wynns clearly have an outgoing and adventurous spirit. Their generous style has become appealing to the cruising community, despite their young ages and low experience in ocean voyages.
They remind us that we only live once on this spinning marble, and in their own words: “We share in hopes of inspiring you to find your adventure.“
To that, we can simply say: Thank you. 😊
Creating Your Own Cruising Freedom
Hey! 😃 It’s Joshua again….
Clearly I’ve been very inspired by Gone With The Wynns and their travels…
Some say I’m obsessed, but sailing the South Pacific is my dream today.
They’re 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. 🔥