A full Portland experience can be had in three days with an itinerary that combines the sights, culture, and adventures of Oregon’s largest city. Here are our top ideas for how to spend your time in Portland and its Pacific Northwest surroundings, including day trips to the mountains or wine country.
Day 1: See the City Sights
Explore Portland at your own pace on a hop-on hop-off trolley tour that allows you to visit the attractions that most interest you, such as Powell’s Books or Pioneer Courthouse Square. Allow time to discover Portland’s food scene: perhaps by taking a coffee and doughnuts tour, food cart tour, or a food tour of Mississippi Avenue. Beer and wine lovers can visit breweries or urban wineries on a bike tour, or skip food in favor of filming locations from the TV show Portlandia. More brews can be enjoyed in the evening on a haunted pub tour of the once-seedy Old Town district.
Day 2: Explore Portland Outdoors
Visit one of the largest urban forests in the country on a guided hike of Forest Park in northwest Portland, and then take to two wheels to explore Portland like a local with a bike tour along the Willamette River waterfront, through the green spaces of the Park Blocks, and into the popular Pearl District. For a more adventurous pursuit, head to the White Salmon River in Washington, a little over an hour north of Portland, for whitewater rafting. When evening rolls around, hop on a dinner cruise to admire the city from the waters of the Willamette, or perhaps ride through downtown on an evening Segway tour.
Day 3: Go Beyond the City Limits
Tucked among mountains, rivers, vineyards, and the Pacific Ocean, Portland is brimming with day trip options. Head west to visit the coastal towns of Cannon Beach and Manzanita, go south to enjoy pinot noir and other varietals in the Willamette Valley wine region, or travel north into Washington to see Mount St. Helens, an active volcano. The most popular day trip, however, is east of Portland along the Historic Columbia River Highway. Tours typically take you to several natural attractions including Multnomah Falls, the tallest waterfall in Oregon; the Columbia River Gorge, a popular windsurfing and kitesurfing destination; and Mt. Hood, the highest mountain in Oregon.