Top Portland Multi-day Tours

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.

Immerse yourself in the beauty and bounty of Willamette Valley wine country on this full-day tour from Portland. Perfect for all level of wine enthusiast – from newcomers to connoisseurs – this 7.5-hour trip offers the insight of expertly trained guides and visits to 3-5 vineyards to sample unique varietals including renowned pinots, chardonnays and rieslings. Tasting fees are not included.

This tour is currently running on a modified itinerary due to a wildfire in the Columbia River Gorge. Visit the top attractions on the Washington side of the Columbia River Gorge and 2 amazing wineries on this guided, Gorge/Wine Tour. Visit the Columbia Gorge Interpretive Center Museum, viewpoints, Beacon Rock, and the Washington Shore Visitor Complex of Bonneville Dam. After lunch, we will visit 2 vineyards in the region for some amazing wine tasting and learn about the region history and culture as it has developed in the wine industry in the area. Discover the postcard-perfect scenery and great wines of the Columbia River Gorge during this flexible-length sightseeing trip from Portland. Gaze in wonder at the Gorge’s towering cascades including Multnomah Falls, enjoy the charming town of Hood River, and make stops at two local vineyards for included tastings. Round-trip hotel transport is also covered.

Start your day off right with a 2-hour brunch cruise along the Willamette River. Board the boat in the late morning and soak in the scenery of northern Oregon as your boat glides away from Portland. When you’re ready, help yourself to a buffet brunch accompanied by sparkling wine or apple cider. You can walk around the deck or sit near the cabin windows to view the stunning landscape.

Head out to the Columbia River Gorge for half a day of visiting cascading waterfalls and scenic overlooks with this tour from Portland. You'll visit Multnomah Falls, the highest waterfall in the state, as well as lesser-known falls throughout the region. You'll also have the chance to take mini-hikes in the area to get better views of waterfalls and the surrounding scenery.

Want to see a bit of Portland and get some exercise while you're at it? Try a walking tour in the center of the city. You can choose from three tours based on your interests: the first covers the city's architecture and parks, the second focuses on the arts scene, and the third is dedicated to what makes Portland weird.

Immerse yourself in the beauty and culture of central Portland as a local would—by bike. On this bike tour, ride through Portland’s historic west side, exploring art galleries, food carts, iconic breweries and 19th-century architecture. Then head to Waterfront Park for great river views and bridge spotting.

Donuts are big business in Portland, and with this bicycle tour, you’ll get to visit some of the city's most popular donut shops and sample their confections. Possible stops include NOLA Doughnuts, Coco Donuts, Fills Donuts, and Delicious Donuts. You'll also get to visit Portland's most famous donut makers, Voodoo, where you'll skip the oftentimes long lines and head straight in for a Bacon maple bar.

Experience the best of Willamette Valley wine country on a guided wine-tasting tour from Portland. With a small group of fellow wine lovers, spend half a day visiting three handpicked wineries such as Colene Clemens Vineyards and Montinore Estate. Meet local vintners and sample award-winning varietals while marveling at Oregon’s stunning countryside.

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.

Visit many of Portland's highlights in just half a day with this small-group tour of the city. You'll make stops along the way to see the thousands of flowers at the International Rose Test Gardens and take in the views from the elegant Pittock Mansion. You'll also pass plenty of the city's most interesting sights and neighborhoods, making this tour a great option for those who want to orient themselves.

Forest Park and Washington Park Small-Group Hike Hike from the city and up into massive Forest Park and the adjacent Washington Park with a guided hike. The morning tour will take you through Northwest Portland and up into the International Rose Test Garden, while the afternoon tour starts in the Goose Hollow neighborhood near downtown. Both will pass by some of the parks' prettiest spots, including the Japanese Garden and the Witch's Castle.

This will be your very own private tour to Columbia River Gorge and Mt. Hood and, will mean a worry-free opportunity to travel in luxury while enjoying the incredible beauty of these two Pacific Northwest destinations! The Columbia River is the largest and mightiest in western North America and the Gorge is considered one of Oregon’s Seven Wonders! A sought after tourist destination with visitors from around the globe, the region’s snow-capped mountains, lush forests, abundance of wildflowers and numerous and varied waterfalls are reminiscent of the Swiss Alps. Our guests always enjoy learning the history of the area from Swiss Tour Master, Erwin, as he makes numerous stops for photo ops and short hikes allowing guests to get the most out of their tour experience! Experience the tour in English or German! Enhancing the adventure - a rafting trip you won’t forget, to fully experience the Columbia! Be prepared for your private party of 2-6 to be thoroughly pampered and cared for! Enjoy!

The Columbia River Gorge is a magical place with mountain views, waterfalls, rivers, streams, mossy trees and beautiful smells and an electric bike and your feet will unlock them all, while also getting you off the beaten path. Megan has over 10 years of professional bike touring experience that leaves people with memories, happy stomachs and new friends. She will customize the tour to any age, ability level and dietary need.