Sailing Kittiwake: Where Did They Go? Are They Missing?

Everything You Always Wanted To Know

Joshua Smith

Founder and Editor at Cruising Freedom

This is the definitive guide on Sailing Kittiwake for 2023.

Over the last 5 years, I have spent 17 hours watching and researching everything I could about Elana and Ryan to learn more about their story.

(Yes, I really was *that* obsessed with them 😃)

If you wanted to know:

➜ How Sailing Kittiwake afforded their boat

➜ How they made their money on YouTube

➜ What boats they had and its upgrades

➜ Are they missing? What happened to them?

➜ 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 Kittiwake FAQs (April 2023)

Boat Name

S/V Kittiwake

Crew Members

Elana Manighetti (age 29) from the United Kingdom, but she grew up in Italy.

Ryan Osborne (also 29) from the United Kingdom

The Boat

They owned two boats in their 5 years on YouTube.

The first was a 1977 Heavenly Twins 26ft catamaran

The second one was a 1976 Tayana 37


Of course, they had to do a ton of upgrades to each boat.

You’ll find an extensive refit history on their YouTube channel.


Neither Ryan or Elena have uploaded for more than 1 year. The Cruising Freedom team isn’t sure where they are. If you have any news, please write in and I can update this article.

Past Cruising

Sailing Kittiwake ventured to many places:

➜ The Mediterranean

➜ The Caribbean

➜ An Atlantic Crossing

Affording It

They didn’t have any kids or mortgages to look after. This allowed them to save as much as they could and were location-independent travelers for some time before purchasing their catamaran.

Surprisingly, that only cost $10,000 but required a lot of work to get seaworthy.

Net Worth

Sailing Kittiwake are definitely fans of the F.I.R.E. Movement and had a reasonably large net worth of $270,000 while enjoying high incomes and minimal expenses.

Making Loot

How did they make their money? Well, Ryan was a freelance designer while Elana was a content marketer (like me!) and worked with numerous startups.

Both earned a consistent income while sailing.

They also earned from:

➜ Their Patreon subscribers

➜ YouTube advertising revenue

Their sailing kitty was fueled through consulting, and their monthly expenses were only $500 ($250 each) which is surprisingly slow.


Sailing Kittiwake didn’t really collaborate with any other YouTubers. They preferred to keep to themselves despite sharing anchorages with other popular cruising YouTubers.

Big Moments

What epic experiences did Elana and Ryan share?

➜ Sailing in 57-knot storms

➜ Completing one Atlantic crossing

➜ Elena sailed by herself on occasions

➜ Missing a few hurricanes

Future Plans

It’s hard to know is the future for Elana and Ryan. They haven’t posted for over a year. Did they separate?

Key Takeaways

What can we learn from this power couple?

➜ You can definitely live quite cheaply and cruise

➜ Learn the hard skills of boat ownership today

➜ Work remotely if at all possible, starting now


Given that they haven’t posted any updates for a while, I’ll be the first to admit that I really miss their banter and educational videos. They were much more appealing than the ‘mainstream’ YouTubers and it was nice to support a smaller channel.

I do look forward to seeing them return in the near future.

*Watch this space*

Create Your Own Cruising Freedom

Hey! 😃 it’s Joshua again…

Clearly, I’ve been very inspired by Kittiwake 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…🙂)