Sailing Olivia

01/01/2026

This past year has had setbacks, long days, and quiet wins.
This year reminded us that dreams don't always move fast, but they do move forward. Olivia continues to teach us patience, gratitude, and faith in the process.
As we head into the new year, we're thankful—for the journey, the lessons, and for each of you who've walked this path with us.
Here's to whatever the next chapter brings.

12/25/2025

🎄⚓️ Merry Christmas ⚓️🎄

From our home to wherever you may be, we wish you a Christmas filled with warmth, laughter, and a little salt in the air. Today we’re slowing the pace, soaking in the season, and feeling incredibly grateful—for family, old traditions, new dreams, and this wonderful community that follows along on Olivia’s journey.

Thank you for cheering us on, encouraging us through the messy middle, and celebrating the wins with us.
May your coffee be hot, your hearts be full, and your seas be calm.

Fair winds and following seas ❤️🎅🏼⚓️

With love,

~ Shawn and Jena ~

12/24/2025

🎄 Christmas Eve wishes from S/V Olivia 🎄

As the year winds down, we’re taking a short pause from sawdust, tools, and to-do lists to enjoy this Christmas season together.

This photo from Yellowstone reminds us why we’re doing all of this in the first place — the journey, the moments, and the people we get to share them with. Olivia will still be waiting when the holidays pass, and the work will continue… but today is for gratitude, rest, and time together.

Wishing you and yours a peaceful Christmas Eve filled with warmth, love, and simple joys. Thank you for being part of our journey. ❤️

— Shawn & Jena

12/23/2025

A lot of the work never really gets seen.

It’s Jeep struts in the driveway, rebuilding a battery bank, and bringing an old compass back to life. It’s organizing the shop and Olivia so the work can keep moving forward. It’s even building a shed so equipment could be moved safely outside, making room for big projects like the main and mizzen booms.

And in the middle of all that, when a friend needs help or a ride to the doctor, Shawn just shows up. No hesitation.

He works incredibly hard and rarely stops — which is exactly why Sundays are mandatory break days around here. (Jena’s orders. 😉)

These are the parts people don’t always see. The quiet work. The care. The old-fashioned way of doing what needs to be done and doing it right. And it all matters. 🛠️⚓❤️

12/23/2025

IKEA sells Christmas trees in a box…
We rebuild ours one cabinet, one template, and about a thousand test fits at a time. 🎄⚓️
Olivia doesn’t do “some assembly required.”

12/22/2025

New video is live 🎥

We’re starting the V-berth cabinetry—templates, cutting, and fitting everything onboard where final adjustments always happen. Still more to come on this space, but it’s a good start.

Also grateful to welcome 3 new subscribers overnight. Thank you for being part of Olivia’s journey.

We always enjoy reading your thoughts—comments are welcome.

In this video, we’re working on the V-berth cabinetry for Olivia - starting in the shop with templates and cutting, then moving back onboard for fitting and ...

12/22/2025

Shawn brought this old compass back to life, and we couldn’t be happier with how it turned out. It started as a compass that had fiberglass over the cover and was honestly headed for the dump. He removed the fiberglass, gave it a thorough sanding and cleanup, repainted it, brought the bronze back to life, replaced a few parts, and refilled it with fresh oil. It’s now as good as new.

Best we can tell, this is a Danforth Constellation Express compass. It appears to be pre-1980, likely from the late 1960s or early 1970s. Danforth didn’t date-mark these, and the design stayed largely unchanged for many years, so there’s no way to know the exact year for certain — but it’s a true classic.

This compass will go on Olivia’s helm and serve as our primary reference, especially if we ever lose electronic navigation. Tried and true, simple, and reliable — exactly how things were done for generations. Once headed for the dump, it’ll once again be navigating. 🧭⚓️

We love taking old things and making them new again — Olivia is the perfect example of that.

11/29/2025

After hours of edits and a whole lot of heart, our final Yellowstone video is finally live. I watched it tonight and it brought tears. Shawn simply said, “Well done you.” ❤️❤️
Here’s to chasing what matters. Hope you enjoy it. ⛵❤️

From geysers at dawn to the shadows of the Grand Tetons, this final chapter of our Yellowstone journey is one we’ll never forget. We left no stone unturned ...

11/28/2025

Happy Thanksgiving from Sailing Olivia!
As this picture reminds us… without sailing, we wouldn’t even have Thanksgiving 😄
Grateful for calm waters, big dreams, tired hands—and for all of you coming along on this journey with us

Fair winds and full plates today! 🦃🌊
~ Shawn & Jena ~

11/19/2025

The American Dream is often pictured as a house, a nice car, a fat retirement account, and mowing the same patch of grass year after year.

But honestly? Too many people work themselves to death trying to save for retirement…
and never live long enough to enjoy it.

We chose a different kind of dream.

Sometimes you don’t trade money for dreams… you trade comfort.

We traded comfort now for freedom later.
We poured time and sweat into a dream instead of savings.
We’re building a life we actually want, not the one we were handed.

Yes—we’re letting go of our “house.”
But we’re building our home on the water.

We didn’t wreck our future.
We re-wrote it.

We’re not without a home…
We’re creating one that moves with the tides. ⛵💙

Maybe the dream isn’t about what you own… but how deeply you live.

11/16/2025

After months of dreaming about this trip, we finally made it — from South Carolina to the wide-open skies of Wyoming. Our first video covers arriving in the park, settling into Mammoth Hot Springs, and spending two full days exploring the northern side of Yellowstone, including the beautiful Lamar Valley.

From bison crossings to sunset elk, quiet walks, long roads, and moments that felt straight out of a painting… this first chapter holds so much of what makes Yellowstone magical.

We’d love for you to come along with us as we begin this journey.

Thank you for supporting our little adventure. 💛

Welcome to Part 1 of our Yellowstone Adventure!We began our journey leaving home in South Carolina, connecting through Charlotte, and taking the long flight ...

11/15/2025

What a day aboard Olivia!
We went in this morning thinking we’d knock out some cleaning and then start on a list of projects… but mercy, what we did get done took us all day and kicked our tail in the process. 😅⛵️

We pressure washed her from bow to stern — cockpit, cushions, everything. She’s sparkling clean now and smells like fresh water and sunshine. The bimini went back on, too! We had to take it down for some much-needed repairs, and bless its heart, it’s seen better days. The sun has dry-rotted it pretty good. But we cleaned it up, patched it as best we could, and it’s back on again giving us shade until Shawn builds the new hard top out of beautiful oak. 💛

Then came the big jobs. We pulled both the main boom and the mizzen boom — the paint was chipping, the welding was rough, and the internal mechanisms all need to be updated. And because we like a good challenge, we hauled that 20-foot main boom home in our 6-foot truck bed. That was a sight to see. 😂

But the most exciting part? A gentleman from the sail shop came out and did a full digital model of our cockpit and boom positions. This is going to take a ton off Shawn’s plate when it comes to designing the new hard top and figuring out clearances. Seeing the lasers and measurements made it feel real — like another step closer to bringing Olivia back to life.

We’re tired, sore, and smiling tonight. These long days are part of the dream, and every little bit gets us closer to sailing her the way she deserves. 💙⚓️✨