Anniversary Weekend in Southern Oregon: Caves, Canvas & a Touch of Wine

For our anniversary this year, we wanted something a little different—something that combined a bit of nature, a little luxury, and a whole lot of quality time together. Southern Oregon delivered all of that and more with a weekend that took us underground, to the vineyard, into the spa, and finally to an intimate dinner we won’t soon forget.

Day 1: Oregon Caves & Watercolor Creativity

We kicked off our weekend with a visit to the Oregon Caves National Monument, and it was every bit as magical as we’d hoped. Tucked away in the Siskiyou Mountains, the drive alone was worth the trip—winding roads, dense forest, and that fresh mountain air. The cave tour itself was fascinating, weaving through marble passageways and intricate formations that felt like stepping into another world. It was cool, quiet, and full of natural wonder—an unforgettable way to start our celebration.

Later that afternoon, we switched gears and tapped into our creative sides with a watercolor class. It was relaxing, fun, and the perfect contrast to the morning’s adventure. With brushes in hand and inspiration from the scenery still fresh in our minds, we painted, laughed, and just enjoyed the process. No pressure to be perfect—just a chance to slow down, sip something warm, and connect in a different way.

Day 2: Ashland Adventures & Anniversary Indulgence

On day two, we took a leisurely day trip to Ashland, one of our favorite little towns with big personality. Our first stop was Irvine & Roberts Vineyards, just outside town, and honestly—it was a highlight. The views from the tasting room are incredible, with rolling vineyards and distant hills, and the wine? Smooth, balanced, and perfect for sipping slowly. We toasted to another year and soaked in the calm.

Next, we treated ourselves to a spa day at Waterstone Spa, right in downtown Ashland. After a deep tissue massage and time in the relaxation room, we both felt completely refreshed. It was the kind of anniversary gift we didn’t know we needed until we walked out feeling totally renewed.

We capped off the day with a romantic dinner at Osteria La Briccola, a cozy, tucked-away Italian spot in Ashland. From the house-made pasta to the perfectly paired wine, every bite was memorable. The intimate atmosphere, candlelight, and great service made it the perfect ending to a weekend that felt both restorative and celebratory.

Grateful for Time Together

This anniversary wasn’t about flashy plans or big destinations—it was about slowing down, exploring beautiful places, and making time for the little things that matter. From deep caves to spa vibes, and wine to watercolor, this weekend gave us everything we needed to reconnect and celebrate our story.

Here’s to more adventures like this one.

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