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Gothic style arches of St Johns bridge in Portland, USA

Itineraries for Your Trip to Portland

Portland locals share their perfect days.
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2 Days in Portland for First Timers

Curated by Leah Still Jolla freelancer with a specialty in travel writing.

Two days in Portland gives you enough time to see multiple sides of the city, from its food culture to its interesting neighborhoods, lush natural beauty, and active lifestyle. Here are a few ways to create an itinerary that suits your interests.


Day 1: Morning

Book a hop-on hop-off trolley tour to see Portland at your own pace, which allows you to visit the attractions that most interest you such as Powell’s Books or Pioneer Courthouse Square. If you prefer to explore with a guide, opt for a morning city tour or a coffee and doughnuts tour.

Day 1: Afternoon

Enjoy Portland’s culinary delights on a food carts tour, a breweries or urban wineries bike tour, or a food tour of a specific neighborhood such as downtown or Mississippi Avenue. Alternatively, see places from the cult hit Portlandia on a tour of the show’s film locations.

Day 1: Night

Head to the once-seedy Old Town district on a haunted pub tour that includes beer samples, or learn how to take photos at the trickiest time of day on a nighttime photography tour, where a photographer guide gives you tips on capturing shots at dusk and dark.

Day 2: Morning

Discover the natural wonders just outside Portland on a morning tour to Latourell Falls, Bridal Veil Falls, and Multnomah Falls, the tallest waterfall in Oregon. Or stay in the city to take a guided hike of Forest Park, one of the largest urban forests in the country.

Day 2: Afternoon

Do as the locals do with a bike tour of Portland that takes you along the Willamette River waterfront, through the green spaces of the Park Blocks, and into the popular Pearl District. Or, for something more adventurous, head to the White Salmon River in Washington for whitewater rafting.

Day 2: Night

Admire the city lights of Portland from the water on a dinner cruise along the Willamette River that includes Pacific Northwest-inspired cuisine and live entertainment with a full bar on board. Or book an evening Segway tour of downtown to zip through this district without the daytime crowds.

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