Top Portland Sightseeing Tours

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.

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.

Explore Oregon’s rocky northern coastline, dotted with beaches and sea cliffs, on a scenic full-day trip from Portland. Travel the picturesque US Highway 101 through quaint beach towns, stopping in Cannon Beach, Ecola State Park, and Oswald West State Park. Enjoy panoramic coastal views, geological wonders, and wind-swept beaches without the hassle of self-driving, and learn more from your guide than you would going alone.

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!

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.

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.

See Portland like a local—by bicycle—with this guided tour. Your guide will take you on an eight- to 11-mile ride through town, past beautiful neighborhoods filled with flowers and across the river via the pedestrian- and bicycle-only Tilikum Bridge towards downtown, with a stop at a local donut shop for some sugary fuel along the way.

Discover Mount Saint Helens from a unique vantage point on a private flight tour from Troutdale. Once airborne, soar over the Colombia River Gorge and Portland. Have your camera ready as the plane flies above and around Mt. Saint Helens' crater and see the destruction from its 1980 eruption. Note: The flight route is dependent on weather and may change last minute.

Visit the top attractions in the Columbia River Gorge National Scenic Area and Mt. Hood National Forest on this day trip from Portland. After spending the morning chasing waterfalls and marveling at 500-pound fish at Bonneville Fish Hatchery, enjoy free time for lunch in historic downtown Hood River. After lunch, we will visit a vineyard in the region for a wine tasting and drive more than halfway up the side of Mt. Hood to explore Timberline Lodge

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.

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.

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

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.

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.

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.

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.

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.

Get an insider's view of the Columbia River Gorge on this private tour from Portland. You'll take in fantastic views, visit the historic Vista House, and see Latourell Falls and the most famous waterfall of them all: Multnomah Falls. Your driver will pick you up at your hotel so that you can avoid the hassle of renting a car or obtaining vehicle permits.

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.

Discover lava tube caves, old-growth forests, waterfalls, and more on a guided tour of Mt. St. Helens. The park’s vastness and variety of attractions can be overwhelming on your own, but by visiting with a guide you don’t miss any of the highlights. Plus, you can learn about the area’s geology, ecology, and history—much of which you might miss if visiting the park on your own.

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 enjoy strolling in the World Forestry Center - Discovery Museum.

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 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.