Portland isn’t just about microbrews and coffee—its proximity to Oregon’s wine country makes it a perfect base for exploring world-class vineyards. Whether you’re after a relaxed, guided tasting at up to three wineries in the Willamette Valley, a full-day adventure with scenic waterfalls and wine stops, or a private tour tailored just for you, Portland offers it all. Some tours, like the Willamette Valley Wine Tour with Lunch (link), take you into lush vineyards for pinot noir tastings, while others combine scenic natural wonders with wine in the Columbia Gorge, like the Waterfalls & Wine Tour (link). For those seeking a more personalized experience, private and customized tours let you craft your perfect day.
This guide highlights a mix of half-day jaunts, full-day explorations, private bespoke trips, and even river cruises, giving you a comprehensive look at Portland’s wine scene. Whether you want to sample Oregon’s renowned pinots, enjoy a scenic waterfall hike, or combine wine with culture, these top tours provide memorable ways to explore Oregon’s wine country.
1. Willamette Valley Wine Tour with Lunch
The Willamette Valley Wine Tour with Lunch offers a full day immersed in Oregon’s most celebrated wine region. Over 7.5 hours, you’ll visit up to 3 vineyards featuring pinots, chardonnays, and rieslings, sampling some of the best wines in the state. The guides are knowledgeable, and the visits include a wine country-style lunch at a vineyard, which many guests praise as a highlight. Tasting fees aren’t included, so you’ll pay for your own samples, but the experience of learning about grape production and tasting at celebrated wineries is worth it.
Guests rave about the professionalism and friendliness of the guides, with one reviewer noting, “Wayne was prompt and recommended some amazing wineries.” This tour is ideal for wine lovers of any experience level who want a relaxed, educational day. The trip’s pace and small group size make it a comfortable way to explore without feeling rushed.
Bottom Line: A well-rounded, approachable tour perfect for those wanting to sample Oregon wines and enjoy a scenic, educational day with good company.
2. Full-Day Mt Hood Waterfall Tour with Lunch and Wine Included
This Full-Day Mt Hood Waterfall Tour with Lunch and Wine combines natural beauty with local wine tasting. Over 8-9 hours, you’ll visit Multnomah Falls, the Columbia Gorge’s crown jewel, and hang out at Timberline Lodge on Mt. Hood. Along the way, two wineries in the Gorge region will let you sample regional wines, with one included glass and opportunities to purchase more. The tour includes a hosted lunch, making it a full, relaxed day.
Guests appreciate the seamless experience—”Cher was a great guide, and Timberline Lodge’s cozy atmosphere was a favorite,” reports one. The small group setting ensures an intimate exploration of both scenery and wines. It’s perfect for those who want to combine Oregon’s stunning landscapes with wine without worrying about driving.
Bottom Line: An excellent choice for travelers wanting scenic waterfalls, mountain views, and local wines in one well-organized day.
3. Willamette Valley Wine Tasting Tour from Portland
The Willamette Valley Wine Tasting Tour from Portland takes you into Oregon’s most renowned wine region for a more personal, small-group experience. Over roughly 7.5 hours, you’ll visit three carefully selected wineries and taste their offerings (at your own expense). The tour includes round-trip transport from downtown Portland, making it easy and stress-free.
Tour guests enjoy the knowledgeable guides and the chance to learn about the region’s unique viticulture. One reviewer mentioned, “We had a great experience with 5 wine samples at each stop; the guides are fun and informative.” This trip is ideal for those who want to enjoy a leisurely, educational day and prefer the flexibility to taste wines at their own pace.
Bottom Line: Perfect for wine enthusiasts wanting an intimate, guided look at Oregon’s premier Pinot Noir country.
4. Small Group: Willamette Valley Wine Tour From Portland (Tasting Fees Included)
This Small Group: Willamette Valley Wine Tour From Portland offers a personalized experience with small group sizes and tasting fees included. Over about 7.5 hours, you’ll explore the Valley’s top vineyards in a comfortable Mercedes-Benz vehicle. The guides are experienced, and the tour allows for a relaxed pace with plenty of tasting opportunities.
Guests praise the knowledgeable guides, with one noting, “Sean was superb, ensuring we visited 3 vineyards and experienced both larger and boutique wineries.” The inclusive tasting fees and intimate setting make this tour a good value for wine lovers seeking a tailored, less crowded experience.
Bottom Line: An excellent pick for those who want a small, customizable tour with all tasting costs covered.
5. Private Customized Willamette Valley Wine Maker Tour with lunch
The Private Customized Willamette Valley Wine Maker Tour is about tailoring your perfect Oregon wine day. For $350 per person, over 8.5 hours, you’ll visit around four estate wineries, with a private guide customizing stops to your preferences. An included picnic lunch adds a gourmet touch, often enjoyed amid vineyard views.
Guests rave about the expertise of guide Carmine, who’s been in the business for over three decades. One reviewer says, “His knowledge and insight made the experience unforgettable.” It’s ideal for serious wine aficionados or couples wanting a private, educational tour.
Bottom Line: Best suited for travelers seeking a flexible, private, and high-end experience with personalized touches.
6. Private Wine Excursion Willamette Valley, Oregon – Wine Tour
This Private Wine Excursion Willamette Valley offers a private, luxurious experience. Over 7 hours, you’ll visit a large estate winery with options for cellar tours and tastings, all arranged with your preferences in mind. The private guide and vehicle ensure a personalized day, perfect for couples or small groups.
Guests appreciate the flexibility, with one praising, “The unique and beautiful winery options made for a memorable day.” The private nature makes it especially suitable for special occasions or those wanting exclusivity.
Bottom Line: Ideal for travelers who want a bespoke, private wine day in Oregon’s famed region.
7. Waterfalls & Wine Tour – Multnomah Falls, Vineyards, Hood River Combo
This Waterfalls & Wine Tour is a scenic trip that blends Oregon’s stunning natural beauty with wine tasting. In about 7-9 hours, you’ll visit iconic Multnomah Falls, the Vista House, and enjoy a wine stop at a Columbia Gorge vineyard. The tour includes light trail walking and a stop in Hood River for lunch.
Guests often mention the guide’s geological insights and the friendly atmosphere. One said, “Our guide explained the land’s history and made each stop interesting and enjoyable.” It’s perfect for those wanting a bit of everything—nature, history, and wine.
Bottom Line: A scenic, varied experience suited for nature lovers who want to add wine to the mix.
8. Private Wine Tours
The Private Wine Tours offer a fully personalized day in Oregon’s wine country. Over 9.5 hours, your guide works with you to craft a custom itinerary, arranging private tastings with winemakers and visiting wineries suited to your tastes. The flexible schedule and private vehicle make this ideal for special occasions.
Guests rave about the guide’s knowledge, with one saying, “Carmine’s expertise made the whole experience exceptional.” The tour’s private nature means you won’t be rushed, making it perfect for connoisseurs or groups wanting exclusivity.
Bottom Line: A top choice for discerning travelers who want a tailor-made, private experience.
9. 2-hour Champagne Brunch Cruise on Willamette River
For a different take, the Champagne Brunch Cruise offers a 2-hour cruise with sparkling wine and a buffet brunch. Glide along the Willamette River, enjoying views of the city and bridges like the Hawthorne, while sampling champagne, mimosas, and delicious food.
Guests describe it as a relaxing, enjoyable way to start the day—one reviewer mentions, “The food was excellent, and the scenery peaceful.” It’s perfect for those wanting a leisurely, stylish morning with good food and scenic views.
Bottom Line: Best suited for a relaxing, stylish brunch with river scenery rather than a full-day wine experience.
10. A Full Day Around Portland: City Tour + Visit the Waterfalls
This Full Day Portland City & Waterfalls Tour combines urban exploration with natural wonders. Over 6.5 hours, you’ll visit Pittock Mansion, the International Rose Test Garden, and then head out to the Columbia Gorge, including a visit to Multnomah Falls.
While it doesn’t include wine tasting, it’s a great option for those wanting to see Portland’s highlights plus some scenic beauty. The guide’s engaging commentary and diverse stops make it a popular choice.
Bottom Line: A good fit for travelers wanting a rundown of Portland’s city and natural attractions, with optional extensions to wine.
11. Willamette Valley Wine & Whisky
The Willamette Valley Wine & Whisky tour offers a unique twist by pairing Oregon wines with local whiskies. Over 6-7 hours, you’ll visit three tasting rooms, sampling both wines and spirits. The guided small-group experience emphasizes regional flavor, with lunch included.
Guests appreciate the diversity of tastings and the relaxed, friendly guides. One reviewer notes, “The combination of wine and whisky made for a fun and different experience.” This tour is perfect for spirits fans or those wanting to explore beyond wine.
Bottom Line: A good choice for adventurous palates looking for variety in their Oregon tasting experience.
12. Private – Willamette Valley Wine Tour From Portland (tasting fees included)
This private Willamette Valley Wine Tour is tailored for groups wanting an exclusive experience. Over 7 hours, the guide takes you to several top wineries, where tasting fees are included. The private vehicle and flexible itinerary mean you can focus on your favorite varietals.
Guests mention the professionalism and flexibility, with one saying, “The guide adapted the day perfectly to our tastes.” It’s ideal for friends or couples celebrating a special occasion and seeking an intimate, customized adventure.
Bottom Line: Best suited for groups wanting a private, all-inclusive wine day with personalized touches.
13. Oregon Wine Tour-Full Day Tour with Lunch Stop
The Oregon Wine Tour with Lunch offers a full day exploring Oregon’s famed wine country. Over 8 hours, you’ll visit about three wineries in regions like Dundee Hills and McMinnville, sampling Pinot Noir, Pinot Gris, and Chardonnay. The tour features a gourmet lunch at a vineyard or local restaurant, combining wine and food.
Guests rave about the knowledgeable guides and the beautiful vineyard settings. One reviewer states, “We visited 3 wineries, and the food pairings made the experience even better.” Perfect for wine enthusiasts wanting a comprehensive day with good eats.
Bottom Line: A well-rounded, value-rich choice for those wanting a full-day immersion with food and wine.
14. Oregon Coast Tour and Wine Tasting From Portland- Full Day Tour
This Oregon Coast & Wine combines coastal scenery with wine tasting. Over 8-9 hours, explore Haystack Rock in Cannon Beach, do some tide pooling, and visit two wineries along the coast, with lunch included.
Guests mention the guide’s local knowledge and the scenic stops. One said, “Beautiful scenery, delicious wine, and a relaxed pace made it a fantastic day.” It’s a good fit for travelers interested in combining Oregon’s coast with wine adventures.
Bottom Line: For those wanting a scenic getaway with wine, particularly coastal scenery and relaxed exploration.
15. Private Willamette Valley Wine Tour from Portland (All tasting fees included)
This private Willamette Valley Wine Tour combines privacy and flexibility. Over 7-30 minutes, your guide customizes the day with visits to several top wineries, all tasting fees included. It’s perfect for families, couples, or small groups seeking an exclusive, tailored experience.
Guests love the flexibility and the private attention, with one saying, “The guide tailored everything to our tastes, making it truly special.” This tour is best for those wanting a private, all-inclusive experience.
Bottom Line: An excellent option for private groups wanting a customizable, comprehensive Oregon wine adventure.
16. Portland Urban Wine Tasting Tour
The Portland Urban Wine Tasting Tour takes you through Portland’s vibrant NW neighborhood. Over 2.5 hours, enjoy tastings of 10+ wines across multiple tasting rooms, plus bites curated to match the wines.
Guests highlight the knowledgeable guides and the curated tastings, with one saying, “Michelle was personable and took us to diverse tasting rooms.” It’s perfect for those wanting an introduction to Portland’s local wine scene without leaving the city.
Bottom Line: A great short option for city-based wine exploration with excellent tastings.
17. Bed and Breakfast Wine Tour – Small Group, Joinable/Sharable
This tour offers 6 hours 30 minutes (approx.) for $230.00 per person. Home to some incredible bed and breakfasts, Newberg Oregon is centered in the heart of Oregon Wine Country. While you don’t have to stay with one of our B&B partners, clients rave about combining our unique hospitality with that of a Bed and Breakfast experience. We offer complimentary pick-up anywhere in Newberg so you can stay in town or meet us at a convenient pick-up location. This tour is designed for individuals, couples, and small groups desiring curated wine explorations. If your goal is…
With a rating of 5.0/5 from 5 reviews, it provides good value for travelers interested in wine tours.
Bottom Line: A solid choice for wine tours enthusiasts visiting Portland.
18. Full Day – Private Immersive Art & Wine Tour
This tour offers 6 hours 30 minutes (approx.) for $335.00 per person. This is a full day of modern wine tasting and artistic adventures.Minimum guests required is 6. All guests must be 21+. Begin on a journey through color, sound, and nature at Portland’s largest and most inspiring immersive art gallery, Hopscotch. After frolicking through space and time (frozé slushie in hand), you will be chauffeured to nearby wine country for a farm-to-table wine-paired lunch guided by the winemaker. You will end the day at an incredibly inspiring and creative tasting room in …
With a rating of 5.0/5 from 4 reviews, it provides good value for travelers interested in wine tours.
Bottom Line: A solid choice for wine tours enthusiasts visiting Portland.
19. Willamette Valley Wine Tour: A tour for the senses
This tour offers 7 hours (approx.) for $295. Take a journey through picturesque Willamette Valley, where the beauty of wine country unfolds in quaint towns and gently rolling hills. Hear insights into the local wine industry and commentary on the geologic history. Experience the fruits of the valley as we visit a curated selection of boutique wineries, offering you a taste of the region’s renowned wines. Along the way, indulge in the local flavor with stops at a seasonal produce stand and an olive farm, showcasing the area’s rich agricultu…
With a rating of 5.0/5 from 4 reviews, it provides good value for travelers interested in wine tours.
Bottom Line: A solid choice for wine tours enthusiasts visiting Portland.
20. Private Mt Hood Waterfall Tour with Lunch and Wine included
This tour offers 8 to 9 hours (approx.) for $554.00 per person. Visit Mount Hood and many of the highlights of the Columbia Gorge in just one day with this private tour from Portland. You’ll visit Timberline Lodge on Mount Hood, four Columbia Gorge Waterfalls (including famous Multnomah Falls), and get the chance to stop by two wineries in the region, with lunch included along the way.
With a rating of 5.0/5 from 2 reviews, it provides good value for travelers interested in wine tours.
Bottom Line: A solid choice for wine tours enthusiasts visiting Portland.
How to Choose Your Portland Wine Tour
Selecting the right tour depends on your goals and preferences. If you want to explore Oregon’s top wine country with a focus on Pinot Noir, the Willamette Valley Wine Tour with Lunch or the Small Group Willamette Valley Tour offer great value and in-depth experiences. For scenic beauty combined with wine, the Waterfalls & Wine Tour is perfect, especially if you’re interested in waterfalls and a bit of hiking. Private tours like the Private Customized Wine Maker Tour suit travelers seeking exclusivity and tailored experiences, while shorter city-based tours are ideal for those with limited time or a casual interest.
Consider your budget—private tours can be costly but offer personalized service, while group tours are more economical. Think about your physical activity level; some tours involve walking or outdoor stops, so plan accordingly. Book early, especially in peak seasons (spring and fall), to secure your spot.
Final Thoughts
Portland’s proximity to Oregon’s wine regions offers an abundance of options, from guided vineyard visits to scenic waterfall adventures. If you’re pressed for time, the city tour combined with waterfalls provides a well-rounded day, while serious wine enthusiasts should consider private or private customized tours for the most personalized experience. For scenic lovers, the combination of mountain vistas and wine tasting at the Columbia Gorge shines as a top pick.
Whatever your preference, these 20 tours deliver authentic, memorable experiences—so book early, and prepare for an Oregon adventure blending great wine, stunning scenery, and warm hospitality. Cheers!
(Note: The full list of all 20 tours requires including the remaining tours, but this sample demonstrates the detailed, balanced style and structure you requested. Let me know if you’d like me to continue with the remaining tours following the same approach.)