Top Oregon Private and Luxury - page 7

Escape Portland for full-day of hiking and exploring stunning waterfalls in the Columbia River Gorge! Admire spectacular viewpoints from the Portland Women’s Forum State and Crown Point Vista House, and then visit the Gorge’s signature falls including Bridal Veil, Horsetail and, of course, Multnomah Falls.

Ever wonder what animals and plants you're seeing when you hike and what makes each one special? Wish you could have a naturalist along to help you learn more about the places you're exploring? Then this tour is for you! Not only is your guide, Rebecca Lexa, a certified Master Naturalist, but she literally wrote the book on nature identification--The Everyday Naturalist: How to Identify Animals, Plants, and Fungi Wherever You Go (Ten Speed Press, 2025). Questions are welcome and encouraged, so bring your curiosity no matter your age!

Bend, Oregon is one of the most well known craft beer towns in this country. With over 35 craft breweries, the beer scene is a way of life around here. We will visit three of our favorite breweries in town, each with their own unique and fun vibe as well as styles of beer. You will also enjoy several flight tastings, providing you plenty of beer to compare tasting notes from the different breweries. Join us for a great afternoon of touring, lots of tasting and hopefully making some new friends while enjoying the Bend beer scene like a local.

From fiery deaths to watery graves: In this 1.5 mile cemetery walking tour, we weave what we know of the peoples who lived here for millennia with verifiable stories of recent centuries. We can only guess, based on our psychics’ readings and eerie coincidences we have observed, where people here before us feared to walk and canoe at night. As a wise person wrote, every story ends as a ghost story. Our ghosts are legion. We now call it Oregon; “ourigan” was ancestral home to hundreds of thousands. They have left a darkness here, expressed with stories from the earliest days of our written history to modern times. Starting with early disasters, we will tell ghost stories we have collected, from fiery deaths to those in the waters of nearby river; from self-inflicted to deaths brought by the state or a rich man’s guilt. Our route takes us through the inner eastside, where more of Portland’s disasters have happened than any other part of the city & where many early settlers are buried.

Explore Portland's hipster-friendly Buckman neighborhood on foot and try out some fantastic local fare along the way with this small-group walking tour. While dining options vary depending on availability, you're likely to visit some of Portland's top international restaurants, try out treats from a food pod, and spend time at a local distillery, all with a guide to provide context and narration.

Intimidated by Portland’s surfeit of food trucks, restaurants, and must-try eateries? Leave all the planning to your guide—and sample some of the best bites that Portland has to offer—on this small-group foodie walking tour. Meet your guide in the morning, and come with an appetite: you’ll be visiting numerous businesses in the Mississippi District for brunch bites, ranging from pastries and sandwiches to drinks and beyond.

Raft, swim, and enjoy a day in the sun on this full-day white-water rafting trip on the Deschutes River. Admire gorgeous canyon scenery as you glide through gentle and challenging rapids alike—your guide leads you the whole time, ensuring a fun and safe ride for you and your group.

Venture outside of Portland—and discover the magnificent Pacific Northwest scenery that lies beyond city limits—on this full-day, small-group tour. Depart in the morning from Pioneer Courthouse Square, drive along the Columbia River Gorge, and stop to view the picture-perfect Multnomah Falls. After lunch (own expense) in Hood River, continue to Mt. Hood: one of the best-known peaks in the Cascade Range.

Get off the beaten path to explore Portland's Kerns neighborhood with this guided food tour. You'll head up to the stretch of NE 28th Avenue known as "Restaurant Row," for a 1.2-mile-long walk with a guide, with stops at six different eateries along the way to sample local flavors.

Enjoy superb views of the Portland riverfront on a 90-minute sailing cruise along the Willamette. Set out from Portland on a small-group tour up the river, stopping to view Portland's floating homes as well as uninhabited Ross Island. Savor the surrounding scenery―including placid Holgate Channel and the Oaks Bottom Wildlife Refuge―as you go. Bring your own snacks, refreshments and spirits to satisfy both hunger and thirst throughout.

Whether it's the stories of human trafficking described as the Shanghai Tunnels, the origin of the vampire tales in Twilight, or the crafty madam with the floating brothel, from fiery deaths to watery graves, we explore it all. The city of Portland Oregon was built on an ancient crossroads; known as a place to step into alternate worlds. What visit to the city would be complete without lifting the veil, for at least a minute, between the living and the spirit worlds? Weaving in historical tales with what fiction authors and filmmakers (including Twilight author Stephenie Meyer) with local ties have written about this place, we tell the stories of darkness, death and the liminal space that comes beyond. Our 1.5 mile (2.5 km) walking tour along the waterfront will include luminous views of the city lights along the river, encounters with our local corporeal spirits (the crows!), and plenty of recommendations to extend your gothic experience to restaurants, cafes and bars nearby.

Go bar hopping with a local resident with this casual, friendly walking tour of Portland's local bars. Your enthusiastic local guide will take you and your group to some of his favorite local haunts, with a heavy focus on interacting with locals and checking out the city's neighborhood vibes.

Discover the rugged beauty of the Mt Rainier National Park on this full-day trip. Travel aboard a comfortable van through historic Gold Rush towns to reach the park, where you’ll be amazed by supersized natural wonders.Take a hike among ancient sequoia trees, and enjoy several hours to explore the park’s wonders on your own as well as with the guide. This tour will have a maximum of 14 travelers per van We can also ensure that all travelers are from only one group/party if needed.

Visit Mount Hood and Oregon's most celebrated waterfall on this private experience from Portland. Let an expert plan all the logistics and start with a drive out to Multnomah Falls in the Columbia River Gorge, before heading to Hood River for lunch, shopping, and a drive through the “Fruit Loop” agricultural region. Before heading back to Portland, get the chance to stop at Timberline Lodge at Mount Hood.

Are you staying at THE ALLISON INN & SPA? This high-end tour offering was custom designed to take guests from the Allison to small family owned boutique wineries, which reflect the best of Willamette Valley. This private tour takes you deep into the heart of Willamette Valley to explore the cult wines, best quality for value wines, and legendary vineyards of Willamette Valley! We love building unique tours according to your preferences and ensuring you leave Oregon wine country with lasting memories and plenty of good wine to remember us by. Our tours will take you to 3 or 4 wineries (depending on your desire for a slower pace or more experiences) and will include elevated tours if you choose. Your guide will also take you to and join you for lunch at one of the valley's celebrated lunch spots. Our ALLISON private tour isn't simply about providing a driver, but creating a unique educational and immersive experience specifically with ALLISON INN & SPA clients in mind.

The Columbia Gorge NSA 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. 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 afternoon half-day tour you'll make new friends while exploring "waterfall alley", including views of the Vista House and a stop at Multnomah Falls, the tallest waterfall in Oregon and most visited site in the Pacific Northwest. Your expert guide will teach you about the natural history, cultural history, and wine background of the area, as you drive the Historic Columbia River Highway Scenic Byway. You'll continue on to stop at a vineyard in the Columbia Gorge American Viticultural Area (AVA). Tasting fees included.

Enjoy an immersive way to explore the beauty of the Oregon Coast—and check off many scenic highlights in just one day—on this small-group hiking tour. Departing in the morning from Portland, travel to Cannon Beach, and learn insider facts about its history from your guide. Have time to hike and explore at multiple coastal highlights, including Haystack Rock, Tillamook State Forest, and more, before returning to the city.

Get taken to three (3) wineries in the Willamette Valley, with some fun local guides who are there to make this day all about you, who will also be your drivers. They will take you to the best wineries in the area, some they know well, in a casual, laid back and fun atmosphere. Their safety and your enjoyment are their biggest priorities. We will be visiting 3 wineries from the list depending on availability. Parrett Mountain Cellars, Potter's Vineyard, Blakeslee Estate, Meraviglioso, Laurel Ridge and Hawks View Cellars. You’ll also get tours of the vineyards, and a boxed lunch included.

Spending a full day on the river independently can be a lot to handle on your own, no matter where you are. A guide leads this full-day Rouge River and Hellgate Canyon rafting tour in Oregon, so you can feel safe as you raft. Choose from a total of three different raft and kayak options, and get a thorough orientation before you go. A riverside lunch is included.

Fly over Portland and the nearby Columbia River Gorge with this private flight experience. You’ll see the Portland Sign, fly over ancient rock formations, and soar past multiple waterfalls (including Multnomah Falls) all the way to the Bridge of the Gods in the Cascade Locks before heading back into Portland.

Experience the best of Oregon's nature in a small-group tour. The adventure begins with hotel pickup from your Portland accommodation to Silver Falls State Park. Here, you’ll follow your guide on a moderate 5.7-mile (9.2-kilometer) hike along the Trail of Ten Falls. Then, enjoy tastings and a freshly prepared picnic lunch.

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.

Choose between a half-day/full-day experience exploring the Willamette Valley wine region, world famous for its Pinot Noir, rolling hills and fresh local ingredients. Our itinerary is carefully curated and we will feast on gourmet wood fired pizzas at a vineyard setting for lunch. Our tour guides are local experts in Oregon, and you will gain an insider's perspective into the landscape, the wine regions history and growing practices as we visit 2-4 select vineyards surrounded by stunning views, unique architecture as you sip and taste exceptional wines. Expect to be pampered, entertained, and truly have a memorable trip in Oregon's Wine Country. We will carefully plan out your day including making all necessary reservations. Our goal is for your group to bring home lasting memories and we strive to achieve that by curating the best possible day for your private group, prices are based on group size so proceed to checkout to see final price.

This is Portland’s elevated sushi night out: a small-group, omakase-style progressive dinner across three top sushi spots downtown. Instead of tiny samples, you’ll sit down at each stop for chef-selected dishes—crafted to highlight different styles, cuts, and techniques—so you leave genuinely full and seriously impressed. Over 2–3 hours, you’ll enjoy a curated progression that can include nigiri, sashimi, specialty rolls, and seasonal plates (selection varies by night). Your guide keeps it fun and approachable while explaining what you’re eating, how to spot quality, and how to order with confidence the next time you’re at a sushi bar. All food is included, and group size is capped so the experience stays personal and high-touch. —and if you have dietary needs (gluten-free or vegan), message us after booking so we can plan your best possible menu. Why this is worth it: you’re getting a guided, chef-curated sushi progression at three restaurants in one night—without the guesswork.