Top Portland Sightseeing Tours in 2026

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.

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.

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.

Immerse yourself in immaculate Pacific Northwest scenery—and indulge in some special beverages along the way—on this private tour by e-bike. Meet your guide in Hood River, get acquainted with your bike, and then zip off. You’ll go for a 7-mile (11 -kilometer) ride along the Historic Columbia River Highway State Trail, will visit a local winery and brewery for tastings, and can opt to finish with a short hike.

Oregon's Willamette Valley is known for its Pinots and it's a fantastic place to go wine tasting, provided you leave the driving to someone else. This private tour will take you to three wineries, where you'll sample wine and learn about the ins and outs of Pinot production. You'll be able to sample safely, knowing that someone else will be doing the driving.

Create Your Perfect Oregon Adventure! Your tour, your way! Choose from the destinations and experiences listed in the itinerary, or let us create something entirely unique for your group. Whether you're interested in breathtaking scenery, local food and wine, fascinating history, or off-the-beaten-path discoveries, we'll help design a private tour around your interests. Choose from one of the options, or contact us for a private tour you don't see! We offer food tours as well!

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.

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.

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.

Visit the gorgeous waterfalls of the Columbia Gorge without renting a car or sorting permits with this package, which includes round-trip transportation to the Waterfall Trolley from Portland and all-day access to the trolley shuttle. Enjoy the freedom to visit different waterfalls and scenic areas with hop-on, hop-off access for added flexibility.

Get a bird's eye view of Portland, Oregon with this airplane tour over the city. In the span of about 40 minutes, you'll fly over iconic sights such as the Portland Sign and the Tilikum Crossing Bridge, sailing south over the Willamette River to Oregon City, where you'll soar over gigantic Willamette Falls.

See the highlights of Portland in just half a day on this private tour of Portland. You'll explore downtown Portland and the nearby NW 23rd shopping district, take in city views from the International Rose Test Garden and stroll through Lan Su Chinese Garden. If you come on a Saturday, you’ll visit the PSU Farmer’s Market.

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.

Columbia Gorge and Mount Hood Private Day Tour Experience the Columbia River Gorge and Mount Hood in just one day with this private tour from Portland. You'll meet your driver downtown and head out to the Gorge, stopping to take in the views at Vista House and Multnomah Falls before continuing toward Mount Hood National. Here you'll get to visit the historic Timberline Lodge, right on the mountain, before heading back to Portland.

This 140-mile driving loop explores the geologically violent and breathtaking Columbia River Gorge. Traveling from mossy rainforests to high-desert plateaus, you’ll trace pioneer history and dramatic landscapes carved by Ice Age floods. Highlights include: * Iconic Waterfalls: View the 620-foot Multnomah Falls and the elegant Latourell Falls. * Historical Marvels: Visit the "Crown Jewel" Vista House and a full-scale concrete Stonehenge. * Unique Legends: Discover the "Bigfoot Capital," where harming a Sasquatch is a felony. * Nature & Wildlife: Meet Herman, an 80-year-old sturgeon, and see "Silver Skeleton" forests recovering from fire. * Geological Giants: Marvel at the 848-foot Beacon Rock monolith.

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.

Mere minutes from the hustle of downtown Portland, a wooded wonderland awaits you. Forest Park boasts over 5,200 acres of lush greenery and 70 miles of pristine trails, making it one of the largest urban parks in the U.S. - and, in my humble opinion, our best! In this guided tour with a local expert, you'll hike beneath a grand canopy of majestic Douglas Fir, stunning Bigleaf Maple, whispering Western Hemlock, mighty Oregon White Oak and more. Hikers will enjoy jaw-dropping views of the Cascade mountain range, featuring Mount Hood - Oregon's highest peak at 11,250 feet. Other attractions on our tour include Portland's storied Witch’s Castle and the historic Pittock Mansion. We’ll stop outside the mansion for a small picnic of local goodies, restroom breaks, and Insta-worthy photo ops before trekking back down to the starting point.

Step aboard Portland's only tiki boat for a 1.5-hour river cruise blending laid-back island vibes, scenic city views, and playful onboard fun. Relax and take in downtown landmarks and iconic bridges, sip a drink, and enjoy the breeze as we cruise the Willamette. A lively host keeps the atmosphere fun with games like trivia and cornhole, plus chances to win prizes. Whether you're here to unwind, connect with family, meet new friends, or rediscover the city from the water, this cruise is designed to flow with the moment—a perfect mix of relaxation, socializing, and river adventure, all with unforgettable island style. This event is 2 hours in full with 1.5-hours guaranteed time underway, cruising along the Willamette. The first 30 minutes of the 2-hour event window is for check-in and boarding. Once all passengers are checked in, the boat departs. Please feel free to email directly with questions or to confirm your scheduled departure time.

Gone are the days of choosing between a drowsy shuttle bus driver or the self-proclaimed expert viticulturalist to guide your journey through Oregon wine country. Welcome to The Good Vibes Tour, we specialize in transporting you directly to the experts: the passionate artisans behind these exceptional Willamette Valley vintages. It all begins with The Vibe. Our drivers are adept at gauging the group and seamlessly adapting their interaction to enhance the collective; interacting as much or as little as adds to your experience. Then there’s our meticulously crafted luxury coaches. Far from your typical passenger van or conventional limousine, our transport evokes the ambiance of the Pacific NW; complete with an open and inviting floorplan, rustic wood accents, a simulated fireplace, and modern amenities like a coffee nook, Bluetooth music and optional karaoke. Take a photo/video tour of our fleet online and book your adventure!

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

If you’ve flown around one mountain, you know how incredible it is. Now imagine flying around three for the most up close aerial view you can have! Experience up close details of Mt. St. Helens, Mt. Hood, and Mt. Adams on this air tour that takes you around these three iconic Pacific Northwest mountain peaks. On this flight tour, you’ll see these mountains in incredible detail, including overflying vast forests filled with lakes, creeks, rivers, valleys, and trees. This will be an experience you’ll never forget.

There's no better way to explore Portland than on bicycle, and with this private electric bike tour, you'll get to see the best of what this city has to offer, like a local! This tour is led by a former city spokesperson who knows the city inside and out. There will be plenty of stops along the way for photos and snacks, and special requests can be made in advance.

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.

Solve a self-guided walking quest through Ladd's Addition, Portland's hidden architectural gem in the Southeast. Decode classic ciphers, hunt for landmarks, and explore a maze-like neighborhood with diagonal streets, five rose gardens, and over 100 historic homes. Use Questo app on your phone to follow 15 stops through Ladd's Addition: Seven Corners, Ladd Circle, the historic Hat Museum house, the East and West Rose Gardens, and hidden alleys. Solve riddles, decode A-to-Z ciphers, and find architectural details most visitors miss. Each chapter has its own puzzle and a real piece of Portland history, from the 1891 diagonal street plan to the bungalow and Craftsman homes that define Southeast Portland. Start anytime, pause whenever, and pick up where you left off. Bike-friendly: works on two wheels too. Perfect for architecture fans, repeat Portland visitors looking off the beaten path, families with curious kids, or anyone who wants to keep Portland weird.