Willamette Valley with Jonathan Ross + Twelve Thirty Club

Join the Twelve Thirty community as we explore the pinnacle of craft in Oregon wine country alongside Master Sommelier, Jonathan Ross.

Best of Oregon Wine Country

Sweeping vistas, stunning wines and true immersion with Jonathan Ross

July 2 - 6, 2023

One exclusive departure — limited to just 12 guests

5 Days, 4 Nights

McMinnville, Willamette & Chehalem Valleys

Price from


per person based on double occupancy

Questions? Call or text us

+1 (855) 219-8018

You’re standing in vineyards sipping the best Pinot noir you’ve ever tasted, surrounded by the very vines from where it was sourced. The bustling city and ocean are both just a stone’s throw away but you’re in a different world. This isn’t France, Germany, Argentina, even Napa. This is wine country the Oregon way. The people who planted these grapes 50 years ago were considered crazy. They were laughed at for the idea that quality wines could be produced here. How wrong those naysayers were. You raise a glass and toast the true pioneers of Oregon.

Joining us on this incredible five-day journey is one of Nashville’s most celebrated names in wine. With a buzzy new wine book on the horizon, Master Sommelier Jonathan Ross is a force to be reckoned with. He’s a favorite on the TV docuseries “Uncorked,” and his esteemed portfolio includes a five-year tenure as Head Sommelier at three Michelin-starred Eleven Madison Park. Ross is the perfect guide to Oregon’s award-winning vineyards, and we can’t wait to tour, taste, and blend alongside him this July.

If you love celebrating heritage, craftsmanship and the art of fine wine, this trip is for you. If you dream of valleys overflowing with vineyards and farm-to-fork dinners like none you’ve experienced before, join us. Come to the Pacific Wonderland and appreciate it as only a true Oregonian could.

Our Oregon is Unforgettable

Go Deeper

Meet the people behind Oregon’s top wineries and savor intimate exclusive meals prepared by some of the region’s top chefs.


With Master Sommelier Jonathan Ross and experience Oregon alongside a group of passionate foodies and wine-lovers.

Get Inspired

Marvel at some of the world's most scenic wine country — by e-bike, balloon, and foot — then rejuvenate in perfectly situated boutique accommodations.

Welcome to Oregon—a literal land of enchantment teeming with world-class Pinots and Chardonnays.

Willamette Valley Highlights


VIP Access

Join Jonathan for exclusive private tours and tastings, private champagne brunches and unmatched sunrises, meeting the winemakers and artisans who bring Oregon's wine country to life


Cascadian Cuisine

Savor the freshest produce, the most delicious Pinot noirs, designer olive oils, and Michelin-star meals by the best chefs in the Pacific Northwest


The Best Company

Sit down with pioneering vintners and winemakers, local chefs and Jonathan Ross, plus other passionate, curious Twelve Thirty Club members like you

Day by Day

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 1 Highlights

  • Private transfers from Portland airport
  • Arrival to wine country
  • Welcome dinner at Penner-Ash Wine Cellars
  • Stay at The Allison Inn & Spa

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 2 Highlights

  • Banks Vernonia bike tour
  • Winery lunch at Rex Hill
  • Blending blind masterclass
  • Stay at The Allison Inn & Spa

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 3 Highlights

  • Hot air balloon ride
  • Champagne brunch 
  • On-farm cooking class & dinner
  • Stay at The Allison Inn & Spa

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 4 Highlights

  • Olive oil and wine tastings
  • Wine blending class
  • Lunch at Argyle
  • Stay at The Allison Inn & Spa

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. 

Day 5 Highlights

  • Farewell brunch at Sokol Blosser winery
  • Transfers to PDX Airport

Where We Sleep

The heart and soul of wine country: our boutique hotels reflect the beauty and spirit of Oregon.

The Allison Inn & Spa


Nestled at the doorstep of wine country, this full service resort and spa is Oregon at its finest. The immaculate grounds boast a sprawling sculpture garden stocked with over 500 original works by local artists, while produce is harvested on site for stylish farm-to-fork offerings and designer cocktails at the bar.

Flawless attention to detail. Wonderful mix of elements to showcase Oregon's wine and cuisine.
Nikki C.
Your passion for travel and forging new relationships is infectious. I need more!!
Adrian C.
I loved how the little things were always taken care of.
Greg A.

Book Willamette Valley with Jonathan Ross + Twelve Thirty Club

Number of Travelers


Reserve your spot today with a $1,500 per-person deposit plus room supplements (if relevant). Full payment is due 180 days prior to your trip departure date. We’ll email you a reminder. If your trip departs in less than 180 days, we’ll collect full payment either 30 days from when we receive your deposit, or 60 days prior to your trip departure date, whichever is sooner. See our Terms of Service below for full details.


per person based on double occupancy

Can't travel on these dates?
Call us at

+1 (855) 219-8018


Read our FAQs below. Or text or call us at +1 (855) 219-8018 to speak with a Modern Adventure Trip Specialist.

  1. What does the price include?

    Four nights at unique, boutique accommodations; private transfers to / from the Portland airport to our hotel; private travel for all day trips and excursions; departure airport transfer; private tours with local guides and cultural experts; exclusive VIP access and tastings; guided activities, adventures and expeditions; entrance fees; daily breakfasts, most lunches and dinners; local beverages with meals.

  2. What does the price not include?

    Roundtrip airfare to / from Oregon; travel insurance; activities not included in the trip itinerary; hotel incidentals including room service, laundry service and hotel bar tabs; food and beverages not included in itinerary; gratuity for tour leader.

  3. Where does the trip start and end?

    Our adventure begins and ends at the Portland Airport (PDX). We've organized private transfers for all guests to travel to our hotel, The Allison Inn & Spa in Newberg, Oregon. If you're flying home, your flight from Portland's PDX airport should be scheduled to depart at 2pm or later.

  4. What travel documents are needed?

    US citizens and residents should check the TSA’s website for requirements and acceptable ID for domestic air travel. Some State issued IDs may no longer meet TSA standards. If you are a non-US Citizen traveling to Oregon, visit the US Consulate or Embassy for requirements and information about passports and visas.

  5. Do I need to pay a solo traveler supplement?

    For this departure, all rooms are reserved for two people. No single accommodations are available.

  6. Who is going on this trip?

    This adventure is limited to no more than 12 guests, plus Jonathan Ross and our Modern Adventure team. Our experiences are fun and inclusive and you can expect to be joined by a diverse group in terms of age, background and interests—including solo travelers, couples and friends traveling together. This adventure is for travelers age 21 and above.

  7. Who is leading this trip?

    This trip is led by an expert Modern Adventure trip leader. They're an experienced travel guide, a representative of Modern Adventure and your go-to person for questions or concerns on the trip. We’ll be joined throughout our adventure by local, expert guides who are deeply knowledgeable with respect to local cultures, customs and history and are passionate about sharing that with us.

  8. Do I need travel insurance?

    We highly recommend purchasing travel insurance. Travel insurance allows you to seek reimbursement for your trip costs; if your trip plans change for unforeseeable reasons, or if you need to get medical help, emergency transport, and for theft, loss or damage of items while traveling. For best coverage, always insure the full trip cost within two weeks of your initial trip deposit and note that most ‘Cancel For Any Reason’ policies must be purchased on the date of your initial deposit.

  9. What is the cancellation policy?

    You may cancel on or before March 4, 2023 and receive a full refund minus a $500 per-person service fee. If you cancel on or after March 5, 2023, there is a 50% cancellation fee; on or after May 3, 2023, there is a 100% cancellation fee. We highly recommend purchasing travel insurance as we are not able to make exceptions to this policy in cases of family/medical emergency or cases of the trip being canceled (see our Terms and Conditions for full details).