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79 Oregon Luxury & Special Occasions

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You can reserve your spot today and pay when you're ready.Learn more

Columbia Gorge Waterfalls & Wineries from Portland: All-Inclusive Afternoon TourDay Trips

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Columbia Gorge Waterfalls & Wineries from Portland: All-Inclusive Afternoon Tour

star-5
Experiences both Portland’s rugged outdoors and renowned wine scene on this 6-hour small-group tour. Visit the Columbia Gorge National Scenic Area where you see waterfalls, admire the Cascade Mountain Range, and look out for Bald Eagles and Osprey. Then explore Hood River with its lush forests and stop at a variety of boutique wineries to sample locally produced wines including the much talked about Oregon Pinot Noirs. Leave the logistic and driving to your guide while you relax, taste fantastic wines, and learn about Oregon’s natural beauty.
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  • 6 hours 30 minutes
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  • Free Cancellation
From  
US$137 
US$155
US$19 savings
From  
US$137 
US$155
US$19 savings
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  • 6 hours 30 minutes
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  • Free Cancellation

Mount St. Helens & Ape Cave from Portland: All-Inclusive Small-Group TourDay Trips

Mount St. Helens & Ape Cave from Portland: All-Inclusive Small-Group Tour

star-5
Cross state lines into Washington on this full-day trip from Portland to Mount St. Helens, led by a professional naturalist guide with extensive knowledge about the local geology and ecosystem. Learn about the Pacific Northwest’s most famous active volcano through nature walks and exhibitions, and then make it back to Portland by evening.
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  • 10 hours 30 minutes
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  • Free Cancellation
From  
US$225 
From  
US$225 
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  • 10 hours 30 minutes
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  • Free Cancellation

Willamette Valley Character WineriesWine Tasting & Winery Tours

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Willamette Valley Character Wineries

star-5
We'll take you to 3-4 tasting rooms representing a variety of settings, wines, and personalities. Your wine industry-honed guide will introduce you to the Willamette Valley AVA while camaraderie develops among your small group. You will be wafted away to wine country while we provide you with background on the history, terroir, and character of Willamette Valley wine. Your guide will feel out the desires of your group in selecting among the 500 Willamette Valley wineries, and specific requests may be accommodated. We'll wander through the rolling hills of multiple Willamette Valley sub-AVAs, passing through charming little villages, while making stops at some of the most unique boutique wineries. You'll visit vineyards and tasting rooms that stand out, not only for the views and the character of their wine, but the intriguing personalities (both human and canine) involved. Lunch is included, tasting fees are not.
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  • 7 to 8 hours
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  • Free Cancellation
From  
US$116 
US$145
US$29 savings
From  
US$116 
US$145
US$29 savings
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  • 7 to 8 hours
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  • Free Cancellation

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Mt. Hood Waterfall & WineDay Trips

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Mt. Hood Waterfall & Wine

star-5
Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by local artisans during the Great Depression, and featuring the longest ski season in the US. To the north of Mt. Hood is the Hood River Valley and Columbia Gorge American Viticultural Area (AVA), the lovechild of the Columbia Valley and Willamette Valley AVAs. You will get intimate with this area through a visit to Timberline Lodge on Mt. Hood, wine tasting, and a stop at Multnomah Falls, the tallest waterfall in Oregon. Your expert guide, with formal background in ecology, natural resources, and wine, will teach you about the natural history, cultural history, and wine background of the area, as you drive the the Mt. Hood and Historic Columbia River Highway Scenic Byways. The guide will feel out the group’s tastes in choosing 2 wineries. We cover farm-to-table lunch, you cover tasting fees.
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  • 8 to 10 hours
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  • Free Cancellation
From  
US$130 
From  
US$130 
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  • 8 to 10 hours
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  • Free Cancellation

2.5-Hour Dinner Cruise Through Downtown PortlandDay Cruises

2.5-Hour Dinner Cruise Through Downtown Portland

star-4.5
Whether you want to relax after a long day of sightseeing or need to unwind at the end of your workweek, a sunset dinner cruise along the Willamette River is sure to do the trick. The journey offers spectacular views of the Portland skyline and city’s main landmarks. Listen to live music while you enjoy a freshly cooked Pacific Northwest meal.
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  • 2 hours 30 minutes
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  • Free Cancellation
From  
US$99 
From  
US$99 
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  • 2 hours 30 minutes
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  • Free Cancellation

Northern Oregon Coast Day TripDay Trips

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Northern Oregon Coast Day Trip

star-5
This day trip is a customized tour along a section of rugged coastline along Oregon's northern coast. There will be one or two town stops, and multiple stops at headlands and beaches. After your pickup in Portland, we'll discuss the interests of people in the group, and your guide will customize the itinerary to those interests. Regardless of interests, the trip will include driving the Pacific Coast Scenic Byway with a short hike through oldgrowth Sitka spruce forest, beach time, tide pools, sea stacks, viewpoint stops, and a lunch stop in a charming coastal town. If group interest allows, stops with a more technological history focus may be made, such as the Tillamook Air Museum, Tillamook Cheese Factory, or Camp 18. You'll be back in Portland early enough for dinner. - Please be prepared for whatever the weather may be when your tour runs (e.g. rain gear, sunglasses, hat, extra layers, sunscreen). - Wear shoes that you don't mind getting sandy and wet.
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  • 8 to 11 hours
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  • Free Cancellation
From  
US$110 
From  
US$110 
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  • 8 to 11 hours
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  • Free Cancellation

Explore Columbia River Gorge Half-Day Small-Group Tour Nature & Wildlife

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Explore Columbia River Gorge Half-Day Small-Group Tour

star-5
The 85-mile (137-km) long Columbia Gorge NSA would be a national park if it weren't a critical transportation corridor. It features waterfalls, mountains, monoliths, terraces, resort towns, vineyards, orchards, and The River, harboring a plethora of fish and birds, and unique plants and invertebrates. In the early 1900s, Portlanders would drive their Model T cars along the Columbia River Highway to gaze at waterfalls. It was the first scenic highway built in America. There is said to be over 4000 waterfalls; many are hidden away, but many are just a short hike off the Historic Highway. On this tour you'll explore the western, rainforested, southern side of the Gorge, dubbed "waterfall alley" where we'll have you getting wet under a waterfall, peering over cliffs, and learning stories of the area only the locals know. Your guide will return you to your departure location at the end of the tour. Book our Discover Portland Half-Day Small-Group City Tour as well, and receive $10 cash back.
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  • 3 to 4 hours
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  • Free Cancellation
From  
US$52 
US$65
US$13 savings
From  
US$52 
US$65
US$13 savings
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  • 3 to 4 hours
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  • Free Cancellation

2-Hour Champagne Brunch Cruise Through Downtown PortlandDay Cruises

2-Hour Champagne Brunch Cruise Through Downtown Portland

star-5
Start your day off right with a 2-hour brunch cruise along the Willamette River. Board the boat in the late morning and soak in the scenery of northern Oregon as your boat glides away from Portland. When you’re ready, help yourself to a buffet brunch accompanied by sparkling wine or apple cider. You can walk around the deck or sit near the cabin windows to view the stunning landscape.
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  • 2 hours
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  • Free Cancellation
From  
US$72 
From  
US$72 
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  • 2 hours
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  • Free Cancellation

Multnomah Falls: Hike the Columbia River Gorge waterfallsHiking & Camping

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Multnomah Falls: Hike the Columbia River Gorge waterfalls

star-5
The 80 miles of the Columbia River Gorge’s steep rocky sides offer some of the most spectacular scenery in the world: pounding waterfalls, eagles, century-old trees, ferns, flowers, ancient rocks. This half-day of exploring and meditating on wonders with very short hikes and visits to overlooks and vistas will have you gasping in awe. We'll visit waterfalls and overlooks, selected by our guides to include both the most iconic, like the unmissable Multnomah Falls, tallest in Oregon and one of the most photographed waterfalls in the world, and the special. Depending on weather conditions, this could include a few small hidden waterfalls and another spectacular plunge-style falls with columnar basalt. We'll also tell you stories, not just of the geology and botany and the oft-repeated tales of pioneers and road-builders, but also the old stories we've learned, of gods and animal spirits and the Beaver princess tragically turned into a waterfall.
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  • 4 hours
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  • Free Cancellation
From  
US$60 
From  
US$60 
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  • 4 hours
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  • Free Cancellation

2-Hour Columbia River Gorge Sightseeing CruiseDay Cruises

2-Hour Columbia River Gorge Sightseeing Cruise

star-4.5
Get an up-close look at the Columbia River Gorge on a sightseeing cruise that takes you under the Bridge of the Gods and past sights such as the Bonneville Dam, Native American fishing platforms, and locations where kite surfers and wind surfers show off their skills. Snacks and drinks are available for purchase on board the boat.
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  • 2 hours
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  • Free Cancellation
From  
US$44 
From  
US$44 
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  • 2 hours
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  • Free Cancellation

2-Hour Lunch Cruise Through Downtown PortlandLuxury Tours

2-Hour Lunch Cruise Through Downtown Portland

star-4
Enjoy lunch along the Willamette River on a 2-hour cruise in Portland. Great for newcomers and locals alike, the leisurely cruise presents an expansive vista of Portland from the water. In addition to exceptional views and food, the afternoon tour also includes commentary from your captain and live entertainment. Prepared with local ingredients, your meal can be upgraded to include an appetizer and dessert.
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  • 2 hours
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  • Free Cancellation
From  
US$63 
From  
US$63 
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  • 2 hours
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  • Free Cancellation

Tastes of Downtown Portland Walking Food TourHalf-day Tours

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Tastes of Downtown Portland Walking Food Tour

star-5
With its famous food carts in abundance of restaurants running the gamut from funky to chichi, Portland is a great place for foodies. This small walking tour takes you all around downtown Portland, with stops at a selection of great local eating spots. You can expect to taste all sorts of treats. Typical examples include local seafood, wine, and beer, delicious desserts, and seasonal farm-to-table delights!
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  • 3 hours
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  • Free Cancellation
From  
US$81 
US$89
US$9 savings
From  
US$81 
US$89
US$9 savings
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  • 3 hours
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  • Free Cancellation

Afternoon Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from PortlandNature & Wildlife

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Afternoon Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland

star-4.5
Escape the city for an afternoon exploring some of greater Portland's most scenic falls. Set out to see Multnomah Falls as well as other falls along the Columbia River Gorge, home to the largest concentration of waterfalls in the country. Take plenty of pics of the cascading waters or simply bask in their beauty. You'll enjoy incredible panoramic views from the Crown Point Vista House while an expert guide fills you and your group in on local flora, fauna and history.
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  • 3 hours 30 minutes
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  • Free Cancellation
From  
US$65 
From  
US$65 
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  • 3 hours 30 minutes
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  • Free Cancellation

2-Hour Columbia River Gorge Dinner CruiseDay Cruises

2-Hour Columbia River Gorge Dinner Cruise

star-4.5
Start your evening on the Columbia River on a dinner cruise that provides views of the Columbia River Gorge National Scenic Area from a historical sternwheeler. A seasonal menu features local ingredients for the 3-course dinner with bread, salad, main course, and dessert. Along the way, listen to stories and history about the river from the captain. Drinks are available for purchase.
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  • 2 hours
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  • Free Cancellation
From  
US$77 
From  
US$77 
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  • 2 hours
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  • Free Cancellation

Small Group: Columbia River Gorge Waterfalls and Mt Hood Day Tour from PortlandDay Trips

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Small Group: Columbia River Gorge Waterfalls and Mt Hood Day Tour from Portland

star-5
Explore the Columbia River Gorge and Mt Hood on a small-group tour from Portland with a guide who shows you the highlights of this vast nature destination. Stop at scenic viewpoints and a waterfall, have lunch in Hood River, and ascend Mt Hood to visit Timberline Lodge—a National Historic Landmark. Learn about the history and geography of Oregon, and get great photo ops as well.
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  • 9 hours
From  
US$174 
From  
US$174 
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  • 9 hours

Downtown Portland Food TourLuxury Tours

Downtown Portland Food Tour

star-5
Enjoy a savory spin through two Portland neighborhoods on this small-group walking tour through downtown Portland. Sample a wide variety of culinary delights, from both restaurants and the city's ubiquitous food carts alike. The menu may include bahn mi sandwiches, freshly made pasta ragu, and single-origin chocolates, all washed down with a local craft beer or wine. Learn about Portland's culinary history and culture from your expert guide. Group size is limited to 12 people.
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  • 2 hours 30 minutes
From  
US$92 
From  
US$92 
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  • 2 hours 30 minutes

Discover Portland Half-Day Small-Group City TourBus Tours

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Discover Portland Half-Day Small-Group City Tour

star-5
On this 3.5-hour tour, you'll get a broad overview of the Central City. We'll make stops at Pittock Mansion, the International Rose Test Gardens, and the Portland Aerial Tram. At Pittock Mansion, you'll get pictures of the best views of the city, and the five stratovolcanoes that are visible on a clear day. You'll have plenty of time to smell the roses at the Rose City's most famous garden. You'll get another great view of the city riding the Portland Aerial Tram, at no additional charge (not running on Sundays). Your expert guide will provide background on the sites and city history, while navigating through city traffic, so you don't have to. You'll meander through all of the major neighborhoods of inner Portland on both sides of the river while gaining views of 14 of Bridgetown's 22 notable bridges. Your guide will return you to your departure location at the end of the tour. Book our Explore Columbia River Gorge Half-Day Small-Group Tour as well, and receive $10 cash back.
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  • 3 to 4 hours
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  • Free Cancellation
From  
US$52 
US$65
US$13 savings
From  
US$52 
US$65
US$13 savings
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  • 3 to 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

40-minute Private Waterfall Air Tour for 3Luxury Tours

SPECIAL OFFER

40-minute Private Waterfall Air Tour for 3

star-5
See Oregon’s infamous waterfalls from above on a private airplane tour through the Columbia River Gorge. Get 360-degree views as you soar over the Vista House, Booneville Dam, the Bridge of the Gods near Cascade Locks, and more. This private experience allows you to customize your itinerary to fit your preferences. 
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  • 40 minutes
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  • Free Cancellation
From  
US$280 
per group
US$349
US$70 savings
From  
US$280 
per group
US$349
US$70 savings
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  • 40 minutes
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  • Free Cancellation

Ultimate Chocolate and Wine Lover's Walking TourWine Tasting & Winery Tours

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Ultimate Chocolate and Wine Lover's Walking Tour

star-5
Portland's chocolate scene is overwhelming; let us navigate you through its origins, passionate makers, and diversity with this walking tour that delves into what some call "decadence" but we call "delight." Chocolate is a virtue! And when paired with wine, another specialty of the Willamette Valley, we believe you'll find this tour unmatched in breadth and deliciousness. Our tour hits both the well-known highlights and some of the secrets of the chocolate scene, with a few surprises we don't want to give away. You'll taste chocolate in myriad forms and styles; think of it as a chocolate education. Trust that you will not leave the tour wanting! The tour in total is about 2.5 miles (4km), mostly flat walking, with several tastings of chocolate -- just the right amount so you'll have room for wine as well! We keep groups very small, so you'll have an intimate experience with your enthusiastic guides. (Contact us for larger groups or private experiences; we are happy to accommodate!)
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  • 3 hours 30 minutes
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  • Free Cancellation
From  
US$55 
From  
US$55 
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  • 3 hours 30 minutes
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  • Free Cancellation

A Chocolate City TourHalf-day Tours

SPECIAL OFFER

A Chocolate City Tour

star-5
Explore Portland’s chocolate scene, ride the streetcar between the East and West sides of the city, and learn how we've developed into a chocolate town. Enjoy views from the streetcar as you cross the Willamette river and hear about Portland’s urban planning and prioritization of art and small business. You will visit chocolate makers, learn about different varieties of chocolate and how to taste its intricate flavors, as one might wine.
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  • 3 hours
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  • Free Cancellation
From  
US$59 
US$69
US$11 savings
From  
US$59 
US$69
US$11 savings
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Willamette Valley Wine Tour from Portland with LunchWine Tasting & Winery Tours

Willamette Valley Wine Tour from Portland with Lunch

star-5
Immerse yourself in the beauty and bounty of Willamette Valley wine country on this full-day tour from Portland. Perfect for all level of wine enthusiast – from newcomers to connoisseurs – this 7.5-hour trip offers the insight of expertly trained guides and visits to 3-5 vineyards to sample unique varietals including renowned pinots, chardonnays and rieslings. Tasting fees are not included.
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  • 7 hours 30 minutes
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  • Free Cancellation
From  
US$175 
From  
US$175 
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  • 7 hours 30 minutes
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  • Free Cancellation

Willamette Valley Wineries & Waterfalls: All-Inclusive Day Tour from PortlandDay Trips

Willamette Valley Wineries & Waterfalls: All-Inclusive Day Tour from Portland

star-4.5
Oregon is known for its natural beauty and its burgeoning wine country; this small-group tour lets you experience both. See two towering waterfalls in Silver Falls State Park and then sip pinot noir and other varietals in three scenic, boutique, vineyards. Enjoy a fresh, seasonal lunch at Coelho Winery, and Avoid the hassles of driving and navigating. Learn about Oregon’s wildlife and insights on viticulture from your naturalist guide.
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  • 9 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$210 
From  
US$210 
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  • 9 hours
  • Reserve Now & Pay Later
  • Free Cancellation


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