Three-time TripAdvisor Travelers' Choice Award Winner
Triangle Wine Country Tours
Private and shareable wine tours from Portland into the heart of Oregon’s Willamette Valley.
Our Client Reviews
5.0/5.0
Our Featured Willamette Valley Wine Tours
Willamette Valley Shareable Wine Tours
From
$169
Our big-picture tour of the Valley. You’ll taste across a few different sub-AVAs (American Viticultural Areas) and learn how to taste wine like a pro along the way. We cap it at six people so it stays personal. Tasting fees aren’t included, though you can add them at checkout. Want a furry tour buddy? Ask for Cassie, our wine dog.
Willamette Valley Private Wine Tours
From
$169-319
Want the day shaped entirely around you? On a private tour you might sit down with the winemaker, wander out into the vineyard, or get a look inside the cellar. You and your guide call the shots, with a CSW-trained pro leading the whole thing. Built for groups of two to six. Tasting fees aren’t included, but we’re glad to talk through adding them. Cassie’s available for this one too.
Curated Large Group Tours
From
$169
Bringing a bigger crew? For seven to ten people, we’ll plan a custom day around your group. Family reunions, milestone birthdays, corporate team building, all of it works. Pricing depends on the wineries and experiences you choose, so give us a call and we’ll put it together.
Not Your Parents Beginners Wine Tour, Shareable
From
$75
Brand new to wine? Start here. Your guide is a Certified Specialist of Wine, and there’s no such thing as a silly question here. Ask away. We cover a little wine history, how to actually taste, how to figure out what you like, and how to find local bottles worth bringing home.
Not Your Parents Beginners Wine Tour, Private
From
$75
The same easygoing intro to wine, just for your group. Your Certified Specialist of Wine guide handles the history, the tasting basics, the palate questions, and the hunt for great local bottles.
Explore Our Backyard with us in Oregon
We’re trained wine professionals, but we’ll never talk over your head. This is home for us. We taste these wines often and know plenty of the folks pouring them. Come with years of experience or none at all, and you’ll still pick up something new before the day is done.
This really is our backyard, and we love showing it off. Plenty of those guests left reviews you can read below, and they helped us land TripAdvisor’s Travelers’ Choice award in 2023, 2024, and 2025.
A couple more things worth a mention before you book:
- Military and referral discounts are available. Just ask.
- We can also fold in a brewery, distillery, or meadery stop, or set up a tasting of olive oil, honey, or balsamic. Ask and it’s yours.
- Brand new to wine? Our wine classes and beginner tours are made for you.
- Wondering which wineries make the cut? Take a look at our top visited wineries.
- Like to read up first? Our wine knowledge guides are a good place to start.
Why We’re Your Best Choice for Unforgettable Adventures
CSW-certified guides
Fully custom routes
Door to door transportation
Eco-friendly habits
Getting Personal with the people behind Triangle Wine Country Tours
We’re a small, local team that loves what we do, and it shows on tour. Spend a day in the van with us and you’ll get why guests book us again whenever they’re back in town. Meet the faces behind the wheel on our Meet The Crew page, or contact us when you’re ready to plan.
Sustainability
Lowering our impact on the environment matters to us, and our water bottles were the first place we looked. They’re plastic for now, and while we recycle every one, plastic still isn’t the answer.
Here’s where you can help: bring a reusable bottle and top it off at the wineries. Oregon tap water tastes great, and since a lot of wineries pull from their own underground wells, you end up drinking the same water that feeds the vines.
Left yours at home? No worries. Add a 22 oz refillable aluminum bottle from Just Water for $4 when you book, keep it filled all day, and take it with you when you leave. That’s one more plastic bottle kept out of the Valley.
Capturing the Beauty of Triangle Wine Country
Why Guests Keep Coming Back To Us
Lilianne M
Trip Advisor Sept 2022
Flynntk18
Trip Advisor October 2022
HouseLadyNC
Tripadvisor May 2023