Top Oregon Sightseeing Tours in 2026

See the snowy peaks of Mount Hood and the surrounding dense forests and waterfalls from unparalleled views on this small-group flight. After boarding your flight, your pilot soars over the Columbia River, past Multnomah Falls and Latourell Falls, and right up to Mount Hood, the highest point in the state. These are views you can't find anywhere else.

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.

See the highlights of the Columbia River Gorge with a local guide by your side on this private of the region. You'll get the chance to take in the views from numerous viewpoints, visit both Multnomah Falls and Latourell Falls, and spend time learning about hydropower and fish hatching at Bonneville Dam, all in just half a day.

A full-day private tour of Oregon wine country offers a personalized travel and tasting experience. Visit four small-production wineries and learn about the wine-making process—sometimes from the winemakers themselves. Your guide gives you palette notes during each tasting and drives you and your group of up to four people safely between vineyards.

See the Columbia River Gorge in a way that few people ever will by taking this thrilling flight over the region. Fly over the tallest waterfall in Oregon—Multnomah Falls—for a bird's-eye view of this famous landmark. Have plenty of time to take pictures of the wonder, without worrying about crowds or traffic queues, before flying back to Portland.

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.

Experience highlights of the Portland area on this full-day sightseeing tour, including the blossoming food cart culture, diverse neighborhoods, Pioneer Courthouse Square, and the unspoiled beauty of the Columbia River Gorge. Immerse yourself in a guided tour of Portland’s fascinating history and quirky contemporary culture. Explore with a small group or upgrade for a private tour.

Go wine tasting in Oregon's largest wine region, the Willamette Valley, with this tour. Your guide will take you and your group to three or four tasting rooms where you'll get to try some stand-out wines that really represent the region. You'll also learn about wine-making in the Willamette Valley, with a stop for an included lunch along the way.

One of Portland's many nicknames is Bridgetown, not much of a surprise given that the city is split by a river crossed by 10 bridges. With this tour, you'll hop aboard a pontoon and head from the southernmost of the city's bridges, the Sellwood Bridge, making your way north. You'll pass through downtown, eventually coming to the last bridge within the inner city: the towering Freemont Bridge, before heading back south.

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.

Explore Portland from a unique vantage point on the water, cruising beneath its iconic bridges while spotting bald eagles, ospreys, sea lions, and other Pacific Northwest wildlife. Led by a US Coast Guard–licensed captain and a Oregon-certified professional guide, each tour blends natural beauty with Portland’s rich 200-year maritime history. Guests may reserve a premium private charter for up to six people for an intimate luxury experience, or join a shared cruise with up to 18 passengers—available daily—for a lively and accessible way to discover the city’s scenic waterways.

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. There is said to be over 4000 waterfalls; many of which you have to hike to see. On this tour you'll hike the western, rainforested, southern side of the Gorge, dubbed "waterfall alley" where we'll have you getting misted by waterfalls, peering over cliffs, and learning stories of the area only the locals know.

You don't need to set aside a whole day to experience the thrill of whitewater rafting on this half-day adventure through Oregon's Rogue River. Conveniently located near the freeway, this efficient trip lets you see the area's natural beauty up close. Build your confidence rafting as the route gradually increases from smaller whitewater to larger class IV rapids by the end.

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.

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.

There’s nothing better than exploring Astoria at your own pace, with a flexible itinerary tailored to your preferences. Step back in time and immerse yourself in the rich history of Astoria, Oregon's oldest American settlement. From its roots as a vital port city to its iconic landmarks, Astoria offers a perfect blend of history, natural beauty, and coastal charm. Discover its significant role in American exploration and maritime history, and enjoy breathtaking views of the Columbia River and the Pacific Ocean. This full-day tour takes you through the highlights of Astoria, offering a memorable journey through Oregon’s coastal heritage.

There’s no better way to experience the magic of Silver Falls State Park, a true gem of Oregon, than on a private tour. From its enchanting waterfalls to its scenic trails, this is your chance to immerse yourself in the awe-inspiring cascades and lush beauty of the park. Choose the tour that best suits your desire: - Short: 2.5 miles / 403 feet elevation gain / 1:30 hrs - Long: 4.8 miles / 915 feet elevation gain / 2:30 hrs Book your tour today and let the mesmerizing waterfalls and breathtaking landscapes leave you in awe!

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.

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.

This tour goes above and beyond your average city tour. Accompanied by an expert local guide who has deep insight into the history and culture of each district, this tour of Portland allows guests to stop at iconic Portland destinations and venture off the beaten path to discover exciting hidden gems of the city.

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

Explore Astoria, Warrenton, Seaside, and Cannon Beach on an approximately 7-hour small-group tour with a local guide. Enjoy coastal scenery, movie locations, local legends, and history while we handle the driving. Highlights may include Haystack Rock, Ecola State Park, Fort Stevens, Battery Russell, the Peter Iredale Shipwreck, and Astoria’s historic neighborhoods. Paint a rock for Seaside’s Painted Rock Beach, explore magnetic black sand and collect a magnetite keepsake, and visit the Astoria Column with the option to climb its 164 steps and launch a wooden glider plane. Enjoy an included seasonal charcuterie lunch at Ecola State Park, plus snacks and water. Transportation, guiding, and activity supplies are included. Please tell us about dietary needs when booking. Saturday: Astoria pickup at 9:30 AM. Sunday: Seaside pickup at 10:30 AM. Pickup and drop-off are within each town’s city limits on its designated day. Stops and activities vary with weather, tides, and park access.

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.

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!