In the end, we only regret the chances we didn’t take.

Tucked In & Rolling Out

Our boat is all tucked in for the winter months. It’s always a little bittersweet when sailing season ends, but this year we’re trading sails for wheels. As much as we’ll miss life on the water, there’s also a spark of excitement (and yes, a bit of nervous energy) about this next chapter.

All tucked in and ready for winter—our floating home is officially on dry land until next season

We officially moved into the RV about three weeks ago. For now, we’ve been parked at my parents’ place, which has been such a gift as we’ve figured out our new rhythm. In just two days, it’s time to actually hit the road! The transition from boat to RV went pretty smoothly—there’s a little more elbow room here (not much, but every inch counts when you’re living small).

These first weeks have been about settling in—finding a flow between living, working, and homeschooling. It’s definitely taken some creativity (thank you, outdoor space and nice weather!), but little by little, we’re finding our groove.

A Day in the RV

A typical day looks something like this:
I get up early (though not quite as early as I’d like since it’s still dark when my alarm goes off) to get in a walk and workout. While I’m out, Trygg enjoys some reading time. When I return, he and I usually do yoga or a short “brain break” video together to get some movement in before his school day starts.

Derek sets up his workstation while I wrangle breakfast and coffee. Trygg starts school around 8:00–8:30, and depending on the day, he’s done somewhere between l1:30 and 1:00. Afternoons are a mix of library runs, outside play, and (let’s be honest) giving Derek some much-needed quiet for work. Evenings have been filled with little projects to get the RV road-ready.

It’s not glamorous, but it’s ours—and slowly starting to feel like home.

Wild Wind Homeschool

People often ask how homeschooling is going. The short answer? Some days are awesome, and some days are… well, not.

There are mornings when Trygg breezes through his work with focus and hardly a complaint. Then there are days when just getting started feels like climbing Everest.  Despite the ups and downs, I am so incredibly proud of him. We’ve turned his world upside down—selling our house, moving onto a boat, then into an RV. He’s navigating a small living space, missing school friends, and trying to adjust to a whole new lifestyle.

Yes, there are moments when I think, what on earth are we doing? But then I breathe and remember: more time together, more adventures, and more memories we wouldn’t trade for anything.

We’re also finding ways to keep him connected. If you know Trygg, you know he’s very social and loves making new friends. He’ll be sending postcards and letters to his friends back home, and we’re looking forward to finding new connections once we start traveling.

RV Lessons (So Far)

Three weeks in, and the RV has already taught us a few important lessons:

• Don’t use glass—if it falls, the counter will win.
• Don’t store heavy objects in overhead cabinets unless you want to dodge flying projectiles when you hit a bump.
• And most importantly: if the black tank says it’s full (even if it’s not), the toilet won’t flush. Enough said.

Gratitude & Goodbyes

As we prepare to leave in two days, I want to say a huge thank you to my parents for letting us live in their driveway these past weeks. This may end up being one of the hardest parts of our transition. Trygg has always been close to them—seeing them a few times each week, and now every day while we’ve been here. When he needs a break from school, he just runs over to Grandma’s house for some extra love.

Pulling away in two days will be tough, maybe tougher than I’ve let myself admit. Thankfully, we’ll see them again in October when they travel west to visit family. We’ll get to camp together for a few days before parting ways once more.

We are so grateful to have family who not only support our adventure but encourage us to live the life we dream of (even if they might be questioning that decision just a little right now).
Leaving won’t be easy, but we know this: every challenge brings growth, every adventure adds to our story, and in the end, we only regret the chances we didn’t take.

Life Aboard: 14 Weeks on Our Floating Home

It’s official—we’ve been living aboard our 32-foot catamaran for 14 weeks! What started as a big leap into something new has quickly become our “normal.” We’ve learned to adapt, laugh at the challenges, and soak in the moments that make this adventure so worth it.

Yes, there are times we feel a little cramped. But whenever the walls feel like they’re closing in, all we need to do is step outside. The horizon stretches out before us, and suddenly we remember: our home comes with unlimited waterfront property!

Favorite (and Not-So-Favorite) Things

One of the best parts about this adventure is hearing how each of us experiences life aboard a little differently.

Derek’s Highlights:
✅ Sleeps better than ever
✅ Loves how this lifestyle has brought us closer as a family
✅ Wherever we go, home comes with us

Derek’s Challenge:
🌬 Getting slammed into the dock on windy nights

Trygg’s Highlight:
✨ When our boat moves, our house moves because we live in it!

Trygg’s Challenge:
📦 There’s not much extra space!

Jillian’s Highlights:
💛 Growing closer as a family
🧹 Cleaning the boat takes way less time than a house
🏡 Feeling at home wherever we go

Jillian’s Challenge:
🍳 Not a lot of space for food prep

Sailing Adventures

In July we set out for Silver Bay with friends and family. The trip there was… let’s just say “character building.” Think rain, gray skies, and lightning right before we made it to the marina. We arrived safely, but I quickly confirmed what I already suspected: I am a fair-weather sailor!

Thankfully, the sail back was dreamy—calm winds, smooth water, and sunshine. Just the kind of day that makes you forget the stormy ones.

August brought our annual trip to Cornucopia, WI. We had hoped to sail, but with zero wind, we ended up motoring five hours instead. From Corny we continued on to Little Sand Bay, with a forecast that promised perfect sailing conditions. Reality? Not so much. We battled 3–4 foot waves at first, and I’ll admit, I had a moment (or ten) of questioning all our life choices. Halfway across, though, the wind shifted, the waves eased, and suddenly it was smooth sailing again. Just like that, I remembered why I love this life.

A Day in the Life

Life aboard may sound exotic, but most days have a simple rhythm:

• Morning: I sneak out early for a workout and a walk while Derek and Trygg ease into their day. By the time I return, Derek is already working, and Trygg is reading or watching a show. I brew the coffee, make breakfast, and get us moving.
• Midday: In June and July, Trygg attended an incredible outdoor camp four days a week, which freed up time for Derek to work without interruptions and for me to dive into projects—planning Vacation Bible School, organizing a silent auction fundraiser, and tackling boat and RV to-dos.
• Evenings: Swimming lessons, beach walks, board games, or just quiet family downtime before dinner.

Summer days well spent!

Looking Ahead

With summer winding down, our focus has shifted to prepping the boat for winter. That means:

• Building a frame to support our winter cover
• Clearing out anything that can’t stay aboard
• Winterizing the engine and water lines

As bittersweet as it is to wrap up this chapter, I have to admit—I’m beyond excited to move into our RV! We’ve already started mapping routes, planning stops, and dreaming about our trip out west.

Living aboard has been both challenging and rewarding, pushing us to grow in ways we never imagined. And while moments of doubt creep in, they’re quickly outweighed by the memories we’re making.

As we continue this journey—whether it’s out on the water or down the open road—we’re reminded that every challenge brings growth and every adventure adds to the story we’re writing together. In the end, we only regret the chances we didn’t take.

Hello from the Traveling Trio – Derek, Jillian & Trygg!

We’re about to embark on a grand adventure, and we couldn’t be more excited (or nervous… or exhausted… or all of the above!).

On June 27, we closed a chapter—maybe even an entire book—to begin writing a brand-new one.

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The Spark

This past February, while enjoying our annual family vacation down south, soaking up the sunshine and spending time with loved ones, we found ourselves wishing that this could  be our everyday life. While hiking in the desert, Derek and I began asking a question we couldn’t ignore: “Could this really be our life?”

We’ve always imagined ourselves traveling someday—someday when we were retired. But sometimes life delivers a wake-up call. A few months ago, Derek lost a relative unexpectedly, and we were reminded just how uncertain life can be. Retirement and growing old together aren’t guaranteed. Life is unpredictable—and incredibly precious.

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The Decision

After a lot of soul-searching, we decided it was time to stop waiting. It was finally time to start living the life we’d always dreamed of—one full of travel, adventure, sailing, and, most importantly, time spent together. That meant selling our house, moving aboard our 32-foot catamaran, and buying an RV that we could live, travel, work, and homeschool in.

Sounds simple, right?

Well… let’s just say, we had about 50 unfinished house projects standing in our way—not to mention the enormous task of downsizing our possessions and becoming RV experts overnight. Most people would give themselves at least a year for a transition like this. But if you know me (Jillian), you know once I set my mind to something, there’s no stopping me. So I told Derek, “Let’s have the house listed by June 1”—a goal we missed by just one day.

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The Journey So Far

March, April & May Recap

The spring was a whirlwind of change and preparation:

🛠️ Long days (and nights) tackling project after project
📦 Sorting, donating, and major downsizing
⛵ Outfitting our sailboat for full-time life on the water
🚐 And diving head-first into the wild world of RV research
  (I now know way too much about RVs!)

June & July Recap

The past two months have been full of adventure and big transitions:

⚓ Countless boat projects
🚐 Touring (so many) RVs
✅ Finally purchasing our RV!
🏡 Adjusting to life in 400 sq. ft. on the boat (goodbye, 1100 sq. ft. house)
⛵ Plenty of sailing
💛 Even more time spent together

It’s been exhausting. But as we stand on the edge of this new life, we know every sacrifice and sleepless night will be worth it.

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Thank You

We want to give a huge thank you to both our families for their unwavering support. We couldn’t have done this without you—and we’re so grateful.

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Follow Our Adventure

We’ll be updating this blog as often as we can to share the joys (and struggles!) of life on the road in our 35-foot Super C RV and on the water aboard our 32 foot catamaran. We hope you’ll join us for the ride, the lessons, the laughter—and everything in between.

In the end, we only regret the chances we didn’t take.

Let the adventure begin!

– Derek, Jillian & Trygg
Traveling Trio