Best Oregon Wines

Experienced Driver

Educational Experience

Choose which AVA you'd like to visit, and we take care of the rest!

Explore one of the nine AVA regions of your choice that we service, including Chehalem Mountains, Dundee Hills, Eola-Amity Hills, McMinnville, Ribbon Ridge, Yamhill-Carlton, Van Duzer Corridor, Laurelwood District, and the Tualatin Hills. This exclusive tour includes round-trip transportation from your hotel or Airbnb, tastings at four premier vineyards, lunch or snacks at the third vineyard, and plenty of refreshing water to cleanse your palate. Please note, tasting room fees and any additional expenses are not included.

Why Choose Us?

Be at ease on your ride, knowing your professional and experienced driver has more than two decades of professional driving experience

Enjoy a relaxed atmosphere from your driver as you are taken from each winery to the next

Sip on some of Oregon’s best wines while admiring the breathtaking views of the Willamette Valley

Let us take care of the reliable and safe roundtrip transportation so you can enjoy your wine experience to the fullest

Click the tabs below for more information

Trip Details

The Nitty Gritty


1-2 people: $90.00/hr

3-4 people: $100.00/hr

5-6 people: $110.00/hr

Minimum booking is for 6 hours.

A 2.6% Tourism Tax applies to all bookings.

An optional $100.00 concierge fee also applies if May Your Glass Be Filled sets up the tour.

Note: 1 hour drive time will be added to the total cost of the tour if May Your Glass Be Filled Tours has to travel more than 30 mins for pick up and drop off. Hourly price is specific to the type of tour you choose.

American Viticultural Areas

Choose one AVA (American Viticultural Area) from the following list when you make your booking, and we will take care of the rest:

  1. Chehalem Mountains
  2. Dundee Hills
  3. Eola-Amity Hills
  4. McMinnville
  5. Ribbon Ridge
  6. Yamhill-Carlton
  7. Van Duzer Corridor
  8. Laurelwood District
  9. Tualatin Hills

To learn more about the different AVAs in the Willamette Valley, explore the interactive AVA map here, or check out the static map below:

AVA map of Willamette Valley

Departure time

9:30 am*  – To insure a punctual arrival time for the first tasting. This is based on an itinerary including 3 stops with lunch/snacks at the final winery, or 4 stops without lunch.

*Example departure time for sample itinerary, the exact departure time of your tour is customizable.

Meeting point

Pick up at AirBnB or hotel


March to mid-December


6 hour minimum

Expect to spend 1.5 – 2 hours at each winery.

Group size

6 person maximum. Vehicle is a 2018 Chevrolet Suburban LS


With Concierge Service:

  • Experienced guide/driver
  • Winery reservations
  • Plenty of cold bottled water

Without Concierge Service:

  • Experienced guide/driver
  • Plenty of cold bottled water

Not included

  • Wine tasting fees
  • Lunch
  • Tips

What to bring

Comfortable clothes for the day’s weather

Participation requirements

Must be 21 years or older

Sample Itinerary

A server serving a glass of white wine.

The sample itinerary below is based on a 7-hour day with stops at 4 locations.

Your day begins at around 10:30 am. We will pick you up from your hotel to head towards your first tasting of the day at Winderlea, a boutique Oregon winery, and vineyard specializing in producing small lots of Pinot Noir and Chardonnay. You will savor each drop of wine that puts Oregon wine on the map!

After you’ve worked up a healthy appetite, you will have the option to choose between two local eateries for lunch. One option is Trellis, which features local, fresh, and in-season ingredients to create a delightful meal. The other option is Red Hills Market, a farm-to-table eatery known for its delicious cuisine. Additionally, customers will have the opportunity to visit Trisaetum, a family-owned winery that produces sustainable, high-quality wines. Following our tasty lunch, we’ll continue to a 2:00 pm tasting at Domaine Divio, another charming winery known for its Pinot Noir, in Ribbon Ridge. Lastly, at 3:30 pm, we’ll close the day with a tasting at Saffron Fields Vineyard, a lovely winery & vineyard with an estate and gardens. Afterward, we will drop you off at your hotel with a new appreciation for this innovative wine region.

Important: This is just a sample itinerary so you can get a feel for what you can do! With that said, the sky’s the limit and we are fully able to customize your experience to your needs. Check out Willamette Wines for more information on the wineries & vineyards in the Willamette Valley. Wine tastings and meals are not included in the tour price.

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