We’ve spent years driving the back roads of the Willamette Valley for our stories, and our private wine-country tours are built from that legwork. You tell us what you like to drink and how you like to travel; we design a day around it, handle the appointments and send a licensed, insured chauffeur to your door in Portland. All you have to do is taste, linger over lunch and watch the hills roll by from the back seat. Whether it’s your first Pinot Noir pilgrimage or your fifteenth, we aim to show you a side of Oregon wine country that feels personal rather than packaged.
At a glance
- Duration: Half-day (about 5 hours) or full-day (about 8 hours), door to door
- Group size: Private groups of 2–12 guests
- Starting price: From $195 per person; every quote is customized to your route, group size and vehicle
- Availability: Year-round, seven days a week, subject to winery appointment availability
- What’s included: Custom route planning, chauffeured transportation, 3–4 winery visits with reserved tastings, picnic or winery lunch, bottled water and a printed tasting map
What’s included
Every tour is private. You won’t share a van with strangers or follow a fixed loop that every other group runs that weekend. A typical booking includes:
- A custom route. We build your day around a single sub-region or a thoughtful mix — the Dundee Hills for its red volcanic Jory soils, the Eola-Amity Hills for wind-cooled, energetic wines, the Chehalem Mountains for a range of elevations and soil types, or quieter corners of the valley that rarely make the guidebooks.
- Door-to-door transportation. Pickup and drop-off at your Portland home, hotel or rental, in a vehicle sized to your group and driven by one of our licensed, insured chauffeur partners.
- Three to four winery visits. Half-day tours usually include three stops; full days include up to four. We reserve seated tastings where they’re offered, so you aren’t jostling at a crowded bar.
- Lunch. Choose a picnic assembled with local bread, cheese and charcuterie to enjoy at a winery that welcomes it, or a reserved lunch at a winery that serves food.
- Planning notes. A printed map of the day with a few words on each stop and space for your own tasting notes.
Winery tasting fees are often folded into your quote; when a winery charges at the door or waives fees with purchase, we’ll tell you in advance so nothing is a surprise.
How it works
- Get in touch. Send us your preferred dates, group size and a few words about the wines you enjoy (or want to discover).
- Short planning call. We talk through pace, budget, dietary needs, accessibility and anything you’re celebrating.
- Proposal and quote. Within a few business days you’ll receive a draft route and a customized quote.
- Confirm and book. Once you approve the plan and pay the deposit, we lock in tasting appointments, lunch and your chauffeur.
- Final details. A few days before the tour you’ll receive your pickup time, the day’s itinerary and suggestions on what to wear and bring.
- Tour day. Your driver arrives at your door; we handle the logistics so you can simply enjoy the day.
Who it’s for
Our tours suit couples planning a weekend away, friends marking a birthday or anniversary, visitors who want to see the valley without renting a car, and companies hosting clients or rewarding a team. Newcomers get a gentle, story-rich introduction to Oregon wine; seasoned collectors can ask us to focus on single-vineyard bottlings, older vintages or small producers that open by appointment only. If you’re pairing a tour with a longer trip, our custom culinary itineraries can fill in the rest of your stay.
Sample full-day itinerary
This is one example of how a Dundee Hills and Chehalem Mountains day might unfold. Your route will be built from scratch.
| Time | Stop | What to expect |
|---|---|---|
| 9:30 a.m. | Portland pickup | Your chauffeur meets you at your door; roughly an hour’s drive southwest into the valley. |
| 10:45 a.m. | Winery one — Dundee Hills | A seated tasting focused on estate Pinot Noir grown in red volcanic soil, with views across the valley. |
| 12:15 p.m. | Winery two — Dundee Hills | A smaller family producer; a chance to taste Chardonnay and compare vineyard sites side by side. |
| 1:30 p.m. | Lunch | A picnic on a winery lawn or a reserved lunch at a winery kitchen. |
| 3:00 p.m. | Winery three — Chehalem Mountains | Higher-elevation wines and a different soil story; sparkling wine if it’s on the list that day. |
| 4:15 p.m. | Winery four (optional) | A short, relaxed final stop or a walk through the vines, depending on your energy. |
| 5:30 p.m. | Return to Portland | Drop-off at your door with your purchases safely stowed. |
Add-ons & options
- Hosted tour. A member of our team rides along to lead tastings, add context and answer questions throughout the day.
- Celebration touches. A sparkling wine toast, a birthday dessert at lunch or a surprise stop arranged ahead of time.
- Multi-day trips. Two or three days in the valley with lodging suggestions and a different sub-region each day.
- Corporate tours. Larger vehicles, client gifting and a branded tasting map for company groups.
- Wine shipping guidance. We’ll help you arrange shipping of purchases home where wineries offer it and your state allows it.
- Pair with a class. Start the week with one of our wine education sessions so you arrive in the valley ready to taste with confidence.
Good to know
- Pricing. The $195 per person figure is a starting point for a half-day tour with a full group. Final quotes depend on group size, vehicle, tour length, lunch choice and winery fees.
- Deposits and cancellations. A deposit secures your date. Please review our terms of use for cancellation and rescheduling policies before booking.
- Age requirement. All guests who taste must be 21 or older and may be asked for valid ID at each winery. Non-drinking guests are welcome to ride along; please let us know in advance.
- Never drink and drive. That’s the whole point of a chauffeur. Please don’t plan to drive yourself after the tour, and pace your tastings — spit buckets are there for a reason.
- Seasons and weather. Harvest season and summer weekends book quickly; winter tours are quieter and often more intimate. Some wineries keep seasonal hours, so we confirm every appointment before your date.
- Accessibility and diets. Tell us about mobility needs, allergies or dietary preferences and we’ll plan around them.
Want to read up before you go? Our Willamette Valley Pinot Noir guide is a good place to start.
Ready to plan your day in wine country? Tell us about your group and preferred dates, and we’ll send a custom route and quote.
Frequently asked questions
How much does a private wine country tour cost?
Tours start from $195 per person. Every quote is customized based on group size, tour length, vehicle, lunch choice and winery tasting fees.
Which parts of the Willamette Valley do you visit?
We build custom routes through sub-regions such as the Dundee Hills, Eola-Amity Hills and Chehalem Mountains, tailored to the wines and pace you prefer.
Who drives on the tour?
Transportation is provided by licensed, insured chauffeur partners, with door-to-door pickup and drop-off in Portland, so no one in your group needs to drive after tasting.
Is there an age requirement?
Guests who taste must be 21 or older and may be asked for ID at each winery. Non-drinking guests are welcome to join; just let us know in advance.
