Top Oregon Private Sightseeing Tours - page 3

Experience the Willamette Valley, Oregon's largest wine region, on this wine-tasting tour from Portland. In a small group, head south of Portland to the Willamette Valley wine region, famed for its Pinot Noir. Spend the day tasting different wines (at your own expense) at three select wineries and learn about the region, and Oregon’s wine industry, from your guide.

We offer premium, curated wine experiences that are perfect for travelers, wine lovers, and private groups. Explore beautiful vineyard landscapes while enjoying expertly guided tastings at 2 -4 hand selected boutique and estate wineries. Our tours can be customized to fit your desires, whether you’re interested in gourmet food pairings, private luxury experiences, or special event packages. Enjoy our transparent pricing with no hidden fees and comfortable vehicle for a relaxing day in wine country. - Explore 3-5 boutique and estate wineries with expert guides - Tailored private luxury tours for couples and groups - Enjoy exclusive reserve tastings and artisan food pairings - Flexible half-day and full-day options available

Immerse yourself in the beauty and bounty of Willamette Valley's renowned wine country on this full-day, small-group tour from Portland. Perfect for all levels of wine enthusiasts—from newcomers to connoisseurs—this tour whisks you to three or four top-rated vineyards. Sample a range of varietals (tasting fees own expense), enjoy a picnic lunch, and benefit from door-to-door service.

Tours will include presentation by the owner and wine maker of vineyard maintenance, production of both white and red wines, fermentation activities, barrel issues, and final bottling and distribution.

Two park rangers — warm, quick-witted Quinn and old-soul storyteller Boone — trade off in your ear, playing automatically by GPS as you walk. You'll stroll completely behind four of the ten waterfalls while they unspool the canyon's real legends and lost history — no tapping, no signal needed, it plays fully offline. Buy once and keep it forever; both the full loop and the shorter loop are included.

Paddle through the calm, winding waterways of Scappoose Bay, one of the most serene and wildlife-rich kayaking areas in the region. This guided experience takes you into quiet tidal channels surrounded by wetlands and forest, where it’s common to spot birds, river otters, fish, and other native wildlife. The tour follows a relaxed pace, with time to float, observe nature, and take photos rather than rushing. With stable kayaks and attentive guidance, it’s well suited for both first-time paddlers and those seeking an easy, enjoyable outing on the water. What truly sets this experience apart is its private and unrushed format. The route and rhythm are adapted to the group and conditions, creating a more personal connection with the landscape. To keep things seamless, private transportation from a location chosen by the traveler is included, along with fresh snacks and water—so you can focus entirely on the experience.

Jeff Davies has 30+ years of guiding the Multnomah Falls / Mt. Hood "Loop" Tour with Columbia River Gorge Waterfalls. I have top reviews on TripAdvisor, Google and Yelp for Private Tours & Group Tours. My commentary will give guests insider knowledge. I can specialize the tour to suit your taste.

Willamette Valley is world-class wine country — but the best way to taste it is with someone who can tell you why it matters. On this private, fully customizable tour, your guide brings 10+ years of wine-industry experience, pairing standout Oregon Pinot with the stories of how wine has shaped Western culture. It's for people who love a great glass and a great story in equal measure. We keep it small and unhurried — no big buses, no rigid script. Just your group, a comfortable luxury vehicle, and a hand-picked route through the boutique, family-owned wineries at the heart of the valley: three at a relaxed pace, or four if you want to cover more ground. We'll even stop where the locals go for the kind of sandwich people plan road trips around. Round-trip pickup from your hotel or Airbnb is included. Lunch and winery tasting fees aren't, so you're free to choose what you eat and pour. Come tour the valley in style — relaxing, delicious, and quietly fascinating.

Crash through the rapids on a whitewater rafting trip with your friends or family. This Deschutes River tour is an exhilarating full day adventure. Enjoy exciting rapids, deep canyons, and placid pools. No prior experience is necessary; professional guides support you every step of the way.

Explore the Willamette Valley, the largest wine-producing region, on this private tour designed with large groups in mind. You'll get the chance to visit three or four wineries. During your full day wine tour experience there will be an opportunity to partake in food pairings at a vineyard or a separate lunch stopall with a guide/driver to help make your experience safe, fun, and informative.

Discover Oregon's world famous wine region known as Willamette Valley and experience the best pinot noir, chardonnay, rose and other varietals guided by local wine lovers on this 8 hour tour. An excellent trip for new and seasoned wine lovers, a romantic weekend, or last minute vacation with your friends. Gain an inside perspective about the growing region, the winemaking process and the history of this valley. Expect to be pampered, entertained, and truly have a memorable trip in Oregon's Wine Country. This is a joinable small group tour for 2 persons or more. We will explore 3 of the finest vineyards in the valley and do a sit down lunch at our favorite establishment or vineyard lunch pairing. Proceed to check availability to see your exact price for the group size, we will handle all route planning and reservations on your behalf and offer door to door pickup and dropoff.

Explore the eerie side of Old Town with this haunted pub tour in Portland. Learn about some of the city's scary history as you walk through 19th-century buildings. Sample local beers as you hear about Portland's era of kidnapping, gangs, prostitution and opium dens.

Take a scenic cruise along the Willamette River while you learn about Oregon's history. Your captain will take you on a 44-mile journey, showing you historic attractions such as the Wheatland Ferry Crossing, which first began operations back in 1845. This tour is totally private and up to six passengers can be accommodated.

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.

Jeff Davies has 30+ years of guiding Willamette Valley Wine Tours. I have top reviews on TripAdvisor, Google and Yelp for Private Tours & Group Tours. My commentary will give guests insider knowledge and our winery visits will give guests memorable encounters with winery staff. I can specialize the tour to suit your taste. I prefer wineries with amazing wine and beautiful views but, it's your choice. You can choose your wineries and can also pick them . Also, there are lunch choices to be made.

There’s nothing better than exploring the Oregon Coast at your own pace, with a flexible itinerary on this private full-day tour. Discover the stunning Northern Oregon Coast from Portland! Explore iconic beaches, dramatic cliffs, and scenic viewpoints, stroll through Cannon Beach and tide pools, snap photos at Neahkahnie Mountain and Cape Meares, and enjoy a delicious lunch and cheese tasting at Tillamook Creamery. Perfect for families, photographers, and nature lovers — book now for an unforgettable coastal adventure!

Explore the Oregon coast on your own terms, with this private, customizable tour led by a local guide. You'll have three hours of guide and driver service at your disposal. You’ll be able to either explore areas that you've researched ahead of time or simply get recommendations from your guide, depending on your interests.

Embark on an unforgettable journey with our exclusive vineyard, stable and historic Governor's farm house. Your tour begins with seamless pickup from the airport, your hotel, or anywhere along the Portland to Eugene, OR corridor. Dive into the charm of West Hills Vineyards, where your adventure begins at the stunning West Hills Stables—home to a state-of-the-art dressage facility and a remarkable collection of Classic Cars. Explore the scenic beauty of Holmes Gap Vineyard, and conclude your day with a delightful wine tasting and gourmet meal in the historic Oregon Governor's farmhouse, built in 1857. Don’t miss this chance to indulge in luxury, history, and world-class wines!

Are you looking for the romantic, quaint or cozy tastings rooms in Willamette Valley, but also want to experience some of the best boutique wineries Willamette Valley has to offer? Our *Winter Special* wine tour is designed to get you to the handful of tasting rooms who offer world-class wines, amazing hospitality and also have the cozy fireplace ambiance to make your getaway memorable, restful or simply magical. On this tour, we will go to three wineries at a relaxed pace; or, if desired, four wineries at a fast clip. We will stop for lunch at one of the celebrated sandwich spots in the valley and your guide will join you for lunch. If wine by the fire is what you are after, then look no further!

See the highlights of Portland in just one afternoon, without having to sort out transportation on this tour. Learn about local history, culture, and everyday life while exploring downtown and its surrounds. Peruse the revamped Pearl District and visit Pioneer Square. Experience what makes Portland and the surrounding area unique with stops at the International Rose Test Garden (seasonally), Pioneer Courthouse Square, NW 23rd Avenue, and more.

Experience the breathtaking beauty of southern Oregon on a scenic boat ride along the Rogue River. Glide through lush forests, dramatic canyons, and sparkling rapids while spotting wildlife like eagles, otters, and deer. Learn about the river’s rich history and enjoy peaceful stretches mixed with gentle thrills. Perfect for all ages, this unforgettable adventure offers a unique way to connect with nature and explore one of Oregon’s most iconic waterways.

Explore the northern stretches of the Oregon Coast with a local guide on this private, customizable tour from Portland. You'll get to ride along the Pacific Coast Scenic Byway, take a hike through old-growth forest, and stop at one or two local towns or attractions of your choosing along the way.

Explore Oregon's natural beauty on this McKenzie River tour, featuring riding in style with a Tesla. Enjoy a scenic 1.25 mile hike with stunning views of the McKenzie River. Marvel at the impressive Sahalie Falls and the tranquil Koosah Falls, each showcasing the region's breathtaking landscapes. Take a moment to appreciate a historic covered bridge before visiting the McKenzie General Store for local goods or a meal at the Obsidian Grill. - Stylish Tesla ride along the scenic McKenzie River Highway - 1.25 mile hike with stunning views and two majestic waterfalls - Visit a charming covered bridge and explore local history - Stop at the McKenzie General Store for provisions or a meal at Obsidian Grill

Escape the city for half a day—and explore the scenic highlights of the popular Columbia River Gorge—on this private tour. Pick between morning and afternoon start times, set off in a luxury Mercedes, and head into nature. You’ll discover stretches of the 74-mile (119-kilometer) highway, and immerse yourself in the Pacific Northwest scenery. Discover waterfalls like Latourell Falls and Multnomah Falls, admire Beacon Rock, stop at scenic viewpoints, and more.