PORTLAND · OREGON
Portland’s best days out.
The 15 most popular willamette valley wine tours in Portland. The ones worth your time, with what each costs, how long it runs and who to book through.
Small-group Willamette Valley wine tour from Portland with door-to-door pickup, lunch at a winery, and guided tastings at 3 wineries.
Most Popular“Great trip, Camille gave great base info about the valley and vineyards, good selection of wineries, fun but chilled group”
Willamette Valley wine tour from Portland with hotel pickup, a Mercedes Sprinter van, and three winery tastings in a small group of 8.
“The wine tastings were very good. Our guide was very knowledgeable and helpful. We enjoyed each of the vineyards we visited. Great tour!”
Small-group Willamette Valley wine tasting from Portland with safe driver-led transport, three winery stops, and expert commentary.
“My mom and I wanted to spend some time together and play tourist for a day. We are from the area and have been wine tasting before. But going with Wildwood Adventures and our guide, Will, made it more relaxing and fun. We didn’t have to worry about driving, or planning anything. We experienced new…”
Portland day trip to Multnomah Falls, Mt. Hood, and a Gorge winery. Small-group van ride, easy hotel pickup, great photo stops.
“Jay our tour guide was excellent. He went out of his way to make us comfortable. His knowledge of the area was extensive. We learned so much about the Hood River and its beautiful waterfalls. Our lunch stop in Mt. Hood was fantastic thanks to Jay’s recommendation. We were a party of 3 mature women…”
Small group Willamette Valley wine tour from Portland with tastings included at 3 wineries, guided stops, and comfortable 4x4 Mercedes transport.
“Our guide was extremely personable and knowledgeable. He is obviously well connected as he knew employees personally at the wineries. I love that the tasting fees were included. We tried 20 wines across 3 gorgeous locations! I can’t speak highly enough about our experience and it was the best part of our vacation!”
Private Willamette Valley winery tour with Carmine, lunch included, pickup, estate tastings, and stress-free transportation from Portland.
“Carmine was a fabulous guide! His knowledge and insight for grape viticulture and wine making in general and his extensive knowledge of Oregon wine making in particular made for an awesome educational and fun day!! I totally recommend him - from the experienced wine connoisseur to the beginner!! Definitely one of the best experiences my…”
A full-day Willamette Valley wine tour with door-to-door pickup, reserved tastings, and 3–4 wineries in top AVAs plus a lunch stop.
“I have been on wine tours before and this was on point. Our guide was great and the wineries were amazing. I would definitely recommend this to any wine lover.”
Private Willamette Valley wine day with Portland pickup, four stops, picnic lunch, and optional tastings for a budget-friendly Oregon getaway.
“The title says it all, Good Vibes all around! They were so easy to work with, made great recommendations for wineries to visit and just so much fun. Every detail is taken care of for you and so well thought through. We had the best day, learned new places to visit and I can't recommend…”
Full-day Portland tour to Mount Hood, wine tasting, Columbia Gorge cliffs, and Multnomah Falls. Small group, hotel pickup, lunch included.
“If you are debating to take this tour versus any other tour in Oregon , I hope you take My advice and book this specific tour with Terran Travels.”
Enjoy a small-group Willamette Valley wine tour from Portland with 3 tastings, hotel pickup in a Mercedes Sprinter, and Pinot-focused stops.
“Our tour guide - Gunner, was on time, very polite and knowledgeable. He keep us all well entertained as we traveled to the Willamette Valley. The day was very cold, but clear blue skies, with snow across the vineyards and surrounds and amazing views of the distant mountains. The wine tasting was very enlightening and…”
Gorge waterfalls, scenic viewpoints, and two Oregon wineries with pickup from Portland. Great guide pacing, plus Hood River time.
“Our tour guide Jeri was great. She was so knowledgeable about the area and the wineries. The weather was as beautiful scenery couldn’t have asked for more. Great tour!!”
Driver-led Willamette Valley wine and whisky day trip from Portland with lunch, snacks, and small-group tastings.
“The driver was kind and kept the conversation flowing but I will say he was more of a designated driver than a wine lover. One of the "wineries" that we visited was a tasting room and the lunch was a skimpy charcuterie board. Ken Wright (tasting room) tasting tour was awful the lady basically handed…”
Portland to Willamette Valley in one full day: 3 winery stops with a lunch pairing option, pickup, bottled water, and a small-group pace.
“Alex was absolutely fantastic and completely made this trip among the most memorable we've had! We love Pinot Noir from the Willamette Valley, and this was a culmination of some of the labels we chase back at home. Benza and Dusty Goose were the highlights. Definitely recommend Alex!”
Small-group Willamette Valley wine tour from Portland with 3 wineries, guided history, picnic lunch, and door-to-door transport.
“We booked a private 7-hour wine tour ($420, not including tasting fees) expecting a polished, curated experience. Our driver was friendly and knowledgeable, but the tour lacked consistency for the price. Winderlea Vineyard set the bar high with a professional host, structured tasting, clean setting, worth the $35 fee. However, tasting fees were actually $45–$90,…”
Taste Portland-area wines with pairings and neighborhood history on a small-group 3-hour tour starting in the Pearl District.
“This tasting tour was really fun and unique! It was great to try local wines without having to leave Portland. The guide was very personable and knowledgeable, and we had a wonderful time!”
Every corner of the region, and every way to see it.
