Buying a Sailboat With No Experience | Our Journey With Roaming Wild: What We Got Right (and What We Definitely Didn’t)

Written By Ash Howard

We bought Roaming Wild (formerly JibSea) with no sailing experience while working full-time and raising kids. The real lessons, mistakes, and why we don’t regret starting early.

If you’re searching for buying a sailboat with no experience, first-time sailboat ownership, or how families start sailing full time, welcome, you are very much in the right place. Because that’s exactly what we did. We bought a sailboat that many people already knew as JibSea.  Yes, that boat from the YouTube channel Sailing JibSea, and gave her a new name: Roaming Wild. Same boat. New chapter. Very real learning curve.

From JibSea to Roaming Wild

When we tell people which boat we bought, the reactions are usually immediate:

“Wait… that JibSea?”, “Do you already know how everything works?”, and “That’s a big boat to learn on…”

Fair questions. Honest answers: Yes, that boat. No, we didn’t and still don’t know everything. And yes, it’s been humbling in the best possible way. Renaming her Roaming Wild wasn’t just cosmetic. It marked the start of our story with this boat, one rooted in family, growth, adventure, and learning as we go.

Let’s be clear: we still work full-time jobs

One thing we want to say upfront, because social media can make things look very different than they are; Josh and I both still have full-time jobs. We are not sailing off into the sunset yet. We are not living on the hook full-time. We are in the build and prepare season. Most days look like:

  • Working regular jobs

  • Managing life with two kids and two dogs

  • Heading to the boat whenever we can

  • Fixing, learning, researching, and fixing some more

This phase isn’t glamorous, but it’s intentional.

Buying a used sailboat with no experience

Buying a used sailboat is exciting… and eye-opening. Boats are very good at hiding things. Especially things that only show up once you start actually using the systems. We learned quickly that:

  • “Minor fixes” often aren’t minor

  • One project almost always leads to another

  • And YouTube becomes your best friend around 10:30 PM

There have been plenty of moments where one of us said, “I told you we should’ve checked that,” and the other replied, “Okay, but neither of us knew to check that.” Marriage, but nautical.

Preparing Roaming Wild for full-time sailing with kids and dogs

Our goal isn’t casual weekend sailing forever. We are actively working toward full-time sailing with two kids and two dogs, which changes everything. That means:

  • Systems need to be reliable, not just “working for now”

  • Space needs to function for real life

  • Safety isn’t negotiable

  • And comfort matters more than aesthetics

We’re not fixing Roaming Wild to make her perfect, we’re fixing her to make her livable. This stage of the journey is about learning how the boat truly works, understanding what needs attention now vs. later and building confidence before we untie the dock lines for good.

The mistakes we made (and why they mattered)

If you’re researching how to buy your first sailboat, here’s the honest truth, we underestimated:

  • How interconnected boat systems are

  • How long repairs actually take

  • How much confidence comes from hands-on learning

We also believed we needed to know more before we started. What we actually needed was curiosity, patience, a sense of humor, and the willingness to be wrong and learn fast. Every fix taught us something new. Every mistake made us more capable. Every “I told you so” moment turned into knowledge we’ll never lose.

Following our journey (on and off the boat)

For those who prefer video over long reads, yes, we also share this journey on our YouTube channel and TikTok, Sailing Roaming Wild. We have an IG and Facebook under the same name. Right now, this season of life looks like working full-time jobs, raising two kids, managing two dogs, and slowly, intentionally refitting Roaming Wild.

Video content takes time, especially when real life comes first but we’re actively filming, learning, and building toward more consistent uploads as we prepare for full-time sailing. The blog is where we share the details, lessons, and “behind-the-scenes” moments that don’t always make it into a video and where everything we’re building long-term comes together. If you’re early in your own sailing journey (or just dreaming), you’re right on time.

Why we don’t regret buying Roaming Wild when we did

Even on the hard days, we don’t regret buying Roaming Wild early in our journey. We’re learning faster than we ever would have otherwise, we’re gaining real, earned confidence, and we’re preparing while living life, not waiting for the perfect moment. Sailing isn’t about knowing everything before you start. It’s about starting and figuring it out along the way. If you’re dreaming of sailing but waiting until you feel “ready,” this is your sign. You don’t need to know everything to begin, you just need to begin!

 

Ash Howard