Day 1

Welcome to Portland! We’ll organize private transfers for you from Portland Airport, out across Oregon’s trademark tapestry of deep green forests and rolling vineyards to our hotel, where we’ll have time to get settled before our first event of the trip: a welcome feast at Penner-Ash Wine Cellars. Nestled between the Cascade Mountains and Chehalem Valley, the gravity-fed winery stretches across 15 acres of biodynamic gardens and ancient oak trees.

We’ll taste the bounty of this vibrant terroir over a five-course spread of seasonal morels, foraged porcini, fresh albacore tuna, local lamb, and an enviable wine selection crafted by seasoned sommelier (and our guide!), Jonathan Ross. It’s farm-to-fork dining at its best, and the perfect opportunity to raise our glasses in toast to Jonathan and the adventures to come. 

Day 2

We’re starting the day with a scenic ride through the Banks-Vernonia State Trail, a rolling, traffic-free route that cuts through rustic farms and thickly forested foothills. Bathed in the song of chatty chickadees, we’ll cruise our e-bikes along the path of an abandoned railroad bed to catch unrivaled glimpses of local wildflowers, leafy maples, and old trestle bridges. Our appetites pleasantly peaked, it’s time for lunch. On the menu? Seasonal bites at a stylish local winery, expertly paired with the estate’s most celebrated vintages.  

Once we’ve had time to digest, we’re off to a masterclass in blind blending at Antica Terra, an award-winning vineyard perched atop the Eola-Amity Hills. Blind blending is winemaking at its most creative, and we’ll harness our tasting prowess as we sample the full spectrum of Antica Terra’s esteemed portfolio. Alongside Antica’s award-winning winemakers, Jonathan will guide us through the art of layering our favorite vintages to craft a blend that’s harmonious and inspired. 

Day 3

We’re starting the day off in elevated luxury—literally. As the sun rises over the Valley, we’re floating high above the patchwork quilt of Willamette’s vineyards, farms, and forests in vibrant hot air balloons. It’s a pinch-yourself moment, but the brunch that follows is an equally extravagant affair, dominated by artisanal champagne and a symphony of decadent flavors.

After our jaunt in the sky, the afternoon is ours to explore the Valley’s offering of charming boutiques and mom-and-pop bistros. We’ll meet up again in the evening for an immersive dining experience at a local farm: there, we’re rolling up our sleeves to prepare a multi-course feast showcasing the season’s freshest produce. As we tuck into our spread, Jonathan will lead us through the evening’s wine pairings—elegant favorites he’s selected to draw out the flavors of our hyperlocal menu. 

Day 4

After breakfast at the hotel, we’re off to Durant at Red Ridge Farms, a sprawling countryside retreat brimming with lavender gardens and soaring views of Mt. Hood. There, we’ll sample the estate’s impressive portfolio of Pinots, Chardonnay, and Sauvignon Blanc before embarking on a tour of Durant’s stately Olive Mill. After we learn the ins-and-outs of extra-virgin olive oil production, we’ll put our newfound oil knowledge to the test during Durant’s signature “Blue Glass EVOO Tasting.”

Lunch today is a real treat. Jonathan’s eager to introduce us to his longtime friends at Argyle, a stylish Dundee winery with one of the most extensive wine libraries in the region. Each small plate we savor will be expertly paired with one of the estate’s best, exclusively blended to enrich the flavors of our food. As we sip, Jonathan and his team of Argyle ambassadors will guide us through their best wine pairing tips, building upon our knowledge from the previous day’s blending class. 

Day 5

All good things must come to an end, and our adventure through Oregon’s wine country is no exception. Fortunately, we’re saying goodbye in style: After checking out of our hotel, we’re toasting to our adventures over a private brunch at Sokol Blosser. The winery’s onsite chef has crafted an artisanal menu of savory and sweet bites, expertly paired with a curated selection of sustainably-sourced bubbles. It’s the sparkling finale to a trip we’ll cherish for the years to come.