13 Fantastic Wine Tours In Oregon

Oregon’s wine country is a true gem for those who love exceptional Pinot Noir and Chardonnay, thanks to its cool climate and volcanic soils. The Willamette Valley alone boasts over 900 wineries, many small and family-owned, offering robust, nuanced wines you won’t find elsewhere in the U.S. This guide explores the best wine tours in Oregon, from high-flying helicopter trips to intimate private tastings, helping you choose the right experience based on price, duration, and what’s included. Whether you’re after a luxury adventure, a relaxed private day, or a history-rich journey, you’ll find options that highlight Oregon’s terroir and charm.

We’ve included tours with award-winning wineries, custom itineraries, and even fun-themed experiences like wine and classic cars. Each offers something unique—whether it’s a gourmet lunch in the vineyards, meeting winemakers behind the scenes, or scenic drives with breathtaking views. Planning ahead is key: some tours feature all-inclusive tasting fees, others are private and customizable, and a few combine educational stories with wine sampling. Read on to find the experience that best suits your taste and pace.

1. Tour DeVine by Heli – Helicopter Wine Tour

This heli-wine tour sets itself apart with an unforgettable perspective—flying over Oregon’s lush vineyards in a personal helicopter. For around six hours, you’ll visit three hand-picked wineries, sampling award-winning wines while enjoying panoramic views of the Pacific Northwest. The tour includes a gourmet lunch at Red Hills Market, snacks, and a safety briefing before takeoff. Each flight offers a stunning vantage point of the rolling hills and vineyards, making it a top choice for travelers craving a luxury adventure.

Rated a perfect 5.0/5 from 75 reviews, visitors praise the professionalism and safety of the crew, along with the intimate experience of visiting small wineries. The $2,357.50 per person price reflects its exclusivity, but for those seeking a once-in-a-lifetime vantage point and top-tier service, it’s well worth the splurge. The tour’s highlight is the personalized nature—flying in style and seeing the vineyards from above.

Bottom line: Perfect for those celebrating a special occasion or wanting a breathtaking view of Oregon’s wine country in style.

2. Willamette Wine Tour from Newberg (Tasting Fees Included)

This custom private tour takes you deep into the Willamette Valley’s best wineries, including Elevee in Dundee Hills and Winderlea Vineyard, both known for spectacular wines and stunning scenery. The tour typically includes visits to 3 or 4 wineries, with a flexible schedule based on your preferences. It’s ideal for couples or small groups looking for a personalized experience with tasting fees included.

Rated 5.0/5 from 15 reviews, travelers appreciate the thoughtful itinerary and knowledgeable guides who tailor the day to your interests. For around $339, you get a luxury experience with insider access, including visits to boutique wineries with beautiful gardens and biodynamically farmed vineyards. The tour is well-suited for those wanting quality wines and authentic stories behind the vineyards.

Bottom line: An excellent choice for small groups seeking a customizable, intimate day with top wineries and a professional guide.

3. Wine History Tours in Willamette Valley Oregon

If you love wine and history, this 5-hour tour combines educational storytelling with tastings at four premier wineries, including Beaux Freres and Domaine Divio. The tour provides behind-the-scenes access—walking through vineyards, visiting barrel rooms, and learning about Oregon’s winemaking evolution. It’s perfect for history buffs who want to deepen their understanding of the region’s cultivated reputation.

Rated 5.0/5 from 9 reviews, travelers mention the well-informed guides and the delicious wines they sample. Priced at $285, this tour offers a mix of culture and flavor, making it a thoughtful choice for those who enjoy a story behind their wine. The tour’s highlight is its focus on boutique wineries that showcase Oregon’s distinctive terroir.

Bottom line: Best suited for curious wine lovers who want a rich, educational experience with memorable tastings.

4. Willamette Valley Boutique Winery Tour with Lunch

This private tour focuses on 3 to 4 boutique wineries, each selected to highlight Oregon’s distinctive flavors. It includes a delicious boxed lunch and hotel pickup within 40 miles of McMinnville. The tour is ideal for relaxed afternoons with friends or family wanting a personalized experience without the crowds.

Rated 5.0/5 from 8 reviews, travelers value the personal attention, the local restaurant lunch, and the careful selection of wineries. At $250, it offers good value for a custom experience with all logistics handled, allowing you to focus on tasting and enjoying the scenery.

Bottom line: Great for those seeking a quiet, personalized wine day with excellent local food.

5. Willamette Wine Tour from McMinnville (Tasting Fees Included)

This private tour from McMinnville is designed for serious wine fans, visiting Elevee, Winderlea, and other top wineries. It caters to 4 or 5 wineries depending on pace, with tasting fees included. The guide, Ken, is known for his local knowledge and careful planning, ensuring a smooth, engaging experience.

Rated 5.0/5 from 5 reviews, visitors commend the spectacular wine choices and the friendly, informative guide. At $335, it’s a mid-range option delivering quality over quantity, perfect for those wanting in-depth tastings and beautiful vineyard sights.

Bottom line: Ideal for travelers wanting a flexible, well-curated private day with excellent wines.

6. Amy & Reba’s Day Drinking Wine Tours

This laid-back, fun tour features three wineries in the Willamette Valley, with guides who are also your drivers. It’s perfect for groups seeking a casual, social experience. The tour includes a boxed lunch and visits to favorites like Parrett Mountain Cellars and Blakeslee Estate.

Rated 4.5/5 from 22 reviews, patrons love the relaxed vibe, enthusiastic guides, and the affordable price of $225. The tour is best for those who prefer a fun, no-pressure environment and don’t mind paying extra for tasting fees.

Bottom line: Suitable for groups of friends wanting a casual, fun day with included food and plenty of good wine.

7. Private wine tour with local Sommelier

For the ultimate personalized experience, this private tour features a local sommelier guiding you through top vineyards, with walks through the vineyards and visits to barrel rooms. It includes a seasonal farm-to-table lunch and is tailored around your preferences.

Rated 5.0/5 from 3 reviews, travelers rave about the customized storytelling and inside access. For $2,250, it offers a luxury, behind-the-scenes experience, making it perfect for wine connoisseurs who want to connect deeply with Oregon’s winemakers.

Bottom line: Best suited for serious wine lovers and gourmets seeking a bespoke, immersive experience.

8. Best Wines Best Views | Full Day Private Willamette Valley Tours

This custom private tour combines top-rated wineries like Bergstrom and Winderlea with stunning views. The itinerary can be tailored, typically visiting 3 or 4 wineries, and includes excellent wines and beautiful scenery.

Rated 5.0/5 from 3 reviews, travelers mention the knowledgeable driver, awesome wine selection, and amazing vistas. At $269, it’s a balanced option for those wanting comfort, scenery, and quality wine in one day.

Bottom line: Perfect for groups wanting a flexible, scenic experience with premium wines.

9. From Portland: Willamette Valley Wine Tasting Tour

This day trip from Portland offers a comprehensive 7.5-hour exploration of three wineries in the Willamette Valley, with scenic drives and behind-the-scenes tastings. It’s ideal for visitors based in Portland wanting a full experience without the complication of planning.

Rated 4.9/5, travelers appreciate the organized itinerary and beautiful views. At $149, it provides excellent value, especially for those wanting a guided tour with educational insights.

Bottom line: Suitable for weekend visitors or those short on time who still want a rich tasting experience.

10. Heart of Willamette Winery Pass 2024: Wine Tastings and Discounts

This affordable pass at $45 gives access to over 150 USD in value across multiple wineries, including Airlie Winery and Benedetto Vineyards. The pass allows flexibility—you can visit as many wineries as you like during the validity period.

Ideal for independent travelers who enjoy self-guided exploration and sampling at multiple venues. The pass offers discounted tasting flights and the chance to explore multiple small wineries at your own pace.

Bottom line: Best suited for savvy budget travelers or those wanting flexibility in their wine tasting.

11. Private Willamette Valley Character Winery Tour

This private tour focuses on wineries with character—places with unique stories or personalities. It includes 3 to 4 wineries, with lunch included, and is tailored to your interests.

Rated 0/5 (yet to be reviewed), it’s appealing for travelers who want a personalized, story-rich experience. At $594, this is a luxury option for serious wine enthusiasts wanting deep dives into Oregon’s winemaking.

Bottom line: For those who want a bespoke, narrative-driven day with premium wineries.

12. Wine, Stables and Classic Cars Willamette Valley Tour Experience

Combine wine tasting with a visit to classic cars and a historic farmhouse, making this tour unique. Starting with a pickup from the airport or hotel, it includes stops at West Hills Vineyards, Holmes Gap Vineyard, and West Hills Stables.

Rated 0/5, but the itinerary suggests a fun, multi-interest day blending wine, history, and cars. The $297 price reflects its focus on a diverse experience rather than just tasting.

Bottom line: Great for adventure seekers who want an eclectic day of wine, history, and vintage cars.

13. Winter Focused Willamette Valley Wine Tour (Tastings Included)

This seasonal tour emphasizes cozy tasting rooms with fireplaces, visiting 3 wineries like Granville and Winderlea. It’s designed for winter travelers seeking a warm, intimate atmosphere with top boutique wineries.

Rated 0/5, but travelers will appreciate the relaxed pace and specific winery choices. At $339, it provides a specialized winter experience with delicious wines and fireside ambiance.

Bottom line: Perfect for cold-weather wine lovers craving comfort and quality.

How to Choose the Best Oregon Wine Tour for You

Selecting the right tour depends on your budget, time available, and what kind of experience you desire. If you’re after a luxury adventure with breathtaking views, the Tour DeVine by Heli offers an unparalleled perspective. For a more intimate, private experience, tours like the Willamette Valley Boutique Winery Tour with Lunch or Private Sommelier-led Tour excel. Budget-conscious travelers will find excellent value with self-guided passes like the Heart of Willamette Winery Pass or the From Portland guided tours.

Consider whether you prefer a guided narrative like the Wine History Tours, or a casual day with friends like Amy & Reba’s Day Drinking Tours. For those wanting scenic drives with multiple stops, the Best Wines Best Views tour is an ideal pick. Remember, booking early is wise during peak season (spring through fall), especially for private or high-end tours.

Final Thoughts

Oregon’s wine tours offer a range from luxury helicopter flights to custom private days exploring boutique wineries. For adventure seekers, the Tour DeVine by Heli is a jaw-dropping experience. If you want an educational yet relaxed day, the Wine History Tours are perfect. For those who prefer to drive themselves or have a flexible itinerary, the Winery Pass or self-guided tours provide excellent options.

Whatever your style, this list provides a solid starting point for planning a memorable wine trip in Oregon. Be sure to reserve early, especially for tours with limited availability or special dates. Cheers to discovering Oregon’s vibrant wine scene—your glass awaits.