Oregon Wine Trail Private Journey

Wine Country to Glacier-Clad Mountains


Northern Oregon, one of America’s hidden scenic treasures, is also the country’s hottest winemaking region, responsible for a "record-breaking number of the Wine Spectator’s Top 100" and designated “Wine Region of the Year” by Wine Enthusiast magazine. It is blessed with a Mediterranean climate and a rural beauty equal to the valleys of the Loire, Rhine, and Douro—but has the added allure of the snow-capped volcanic peaks of the Cascades as a constant backdrop. This trip offers you a delightful variety of activities each day. In addition to beautiful vineyard walks and tastings of the region’s well known pinot noirs, you’ll hike majestic trails on iconic Mount Hood (11,240’), with its mantle of perpetual snow looming directly above, bike through private vineyards in the Hood River and Willamette valleys, and explore the vast Columbia Gorge, Oregon’s crown jewel, with the greatest concentration of breathtaking waterfalls in North America. Daily activities with your private guide are tailored just for you, with numerous fun add-on options that include a hot-air balloon ride, a cooking class, a horseback wine tour, and kayaking on the beautiful Columbia River. It’s easy to fall in love with Oregon—and this private journey will leave you smitten.

Itinerary at a Glance

Days 1-2
Portland / Willamette Valley / Dinner and Wine Tasting

From Portland, head to the green hills of the Willamette Valley for wine tasting, an olive-oil tasting tour, a winery dinner, and a full-day private tour with vineyard walks and a wine-pairing lunch. Overnights are in a luxury inn and spa with walking trails and valley views. Optional add-ons include a cooking class, a private vineyard cabana, a guided kayak trip, and a hot-air balloon ride.

Allison Inn and Spa
Willamette Valley, USA
Days 1 to 2 (2 nights)
Days 3-5
Mount Hood / Columbia Gorge / Wine Tasting By Bike

Take a panoramic hike on Oregon's highest peak, Mount Hood, travel through the picturesque Hood River Valley, with its farm stands amid orchards, vineyards, and lavender fields, hike the loop trail on Mosier Plateau for stunning views of the Columbia Gorge, enjoy a winery dinner, then head out for a guided wine tasting tour by bike, with exclusive access to private vineyards. Overnights are at a farm-style bed and breakfast in a pear and apple orchard. Return to Portland on Day 5 by way of a tour of the Columbia River Gorge National Scenic Area. Optional add-ons include a brunch cruise on the Columbia by sternwheeler, kayaking, hiking, biking, whitewater rafting, flightseeing tour of the Columbia Gorge, and a food cart tour of Portland.

Sakura Ridge
Hood River, USA
Days 3 to 4 (2 nights)

Optional Add-On's Include:

  • Hot Air Balloon Ride and Champagne Brunch
  • Cooking Class
  • River Kayaking
  • Mountain Biking
  • Columbia River Cruise or Sailing Tour
  • Horseback Riding
  • Private Vineyard Cabana
*Ask our Area Specialist for details about each of these options



Two exclusive winery dinners
Full-day private guided tour in the Willamette Valley
Winery tour by bike in the Hood River Valley, with exclusive private access to vineyards
Hikes with panoramic views of Mount Hood and the Columbia Gorge, olive oil tour and tasting
Delightful accommodations, from a luxury spa to a cozy farm-style bed and breakfast
Options for a hot-air balloon ride, a cooking class, a private vineyard cabana, and river kayaking


Length: 5 days
Cost From: $4595  
Arrive: Portland, Oregon
Depart: Portland, Oregon
Lodging: 4 nights boutique hotels and lodges
Meals: All meals except 2 dinners as indicated in the Detailed Itinerary (B=Breakfast, L=Lunch, D=Dinner)
Activity: Walking, Hiking / Trekking, Culinary
Trip Level:

Hiking and biking, tailored to be as relaxing or strenuous as you wish