3 Days in Portland: Suggested Itineraries

By Viator, May 2015

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Day 1: Explore Southwest and Northwest

Start your day with an organic breakfast at Wildwood, where everything's sourced in the Pacific Northwest.

Head up to the green hills of Washington Park and meander through the Japanese Garden, the International Rose Test Garden, the Hoyt Arboretum, the Oregon Zoo and more. You could spend the entire morning up here, taking in sweeping views of the city, the Cascade Range and learning about nature.

At lunchtime, swing over to upscale Nob Hill, which is also known as the Alphabet District; all the east-west streets here are in alphabetical order and named for a different person, place or thing in Portland history. Tuck into a hearty, artisanal sandwich at Besaw's, then take yourself boutique shopping along leafy NW 23rd Street. Catch your second wind with an Austrian pastry and coffee mit schlag at Papa Haydn.

If you feel like walking, hit the trails in Forest Park and luxuriate in a canopy of tall trees, rushing streams, mossy rocks and an aviary's worth of native birds. If you'd prefer a drive, wend your way over to the nearby Columbia Gorge and breathe in the forest through your car windows, making sure to stop at towering Multnomah Falls to feel its spray. If you're up for another attraction, visit the stately Pittock Mansion for a look back at Portland's beginnings and to gaze at the endless city view.

For dinner, tuck into dishes from all over Mexico and Portland's best margaritas at Por Que No?, or head to the Mississippi Marketplace to sample the wares of permanently-stationed food carts. Afterwards, try to catch a play at the Portland Center Stage, which makes its home in the former Portland Armory.

Day 2: Explore More of the Southeast and Northeast

Head to Mt Tabor Park for a morning hike, keeping an eye out for glimpses of Mt Hood, downtown Portland and wildlife.

Tuck into a Country Skillet breakfast at Dufour's in residential Irvington, then take a stroll to see some of the city's most elegant, historic homes. Visit Grant Park's Beverly Cleary Sculpture Garden, which features bronze statues of characters of children’s author (and Portland native) Beverly Cleary.

Go explore the corrugated steel charm of the Alberta Arts District, which is full of small galleries exhibiting the work of local artists, and stop into the colorful Tin Shed for a friendly lunch. Then take yourself over to the Buckman neighborhood for hipster boutique shopping and a crawl along the area's many micro-breweries.

For dinner, indulge in the farm-to-table delights of clarklewis, which sources almost all of its ingredients from local, sustainably-run farms. Nearby, catch an indie music act at the Doug Fir Lounge, or head to the 1920s vintage Alberta Rose Theatre to attend a raucous taping of Live Wire Radio!, a locally-produced variety show featuring comedy, musical acts and compelling interviews with writers.

Day 3: Explore Downtown

First thing in the morning, grab a local Stumptown Roasters coffee and go for a stroll beside the mighty Willamette River. At the Tom McColl Waterfront Park, you can check out "The Portland," a still-working steamboat often docked by the seawall, read occasional plaques that illustrate the city's history and watch fishing boats and rowing sculls sluice along the river.

Head to the north end of the park to explore the Saturday Market (Saturday, 10am-5pm and Sunday, 11am-4:30pm), a sprawling warren of tented stalls offering locally-made crafts, food and more. Nibble your way through the Market, or head to nearby Mother's Bistro for homemade biscuits in an airy, Victorian-era dining room hung with chandeliers.

Take an hour's meander through Asian and Native American artwork at the Portland Art Museum, then go lose yourself in the stacks at the enormous flagship Powell's City of Books. Take a few blocks' walk from there to the leafy North Park Blocks in the Pearl District, followed by a poke around the Museum of Contemporary Craft and the neighborhood's many art galleries and independent boutiques.

Indulge in some live jazz and afternoon tea at the historic Heathman Restaurant, or yet more coffee at Spella, which uses a hand-pumped, piston-driven espresso machine. If you're up for one more attraction, head through the ornate arches of Chinatown and visit the graceful water lilies at the Portland Chinese Garden.

Also in Chinatown, enjoy steamed Chinese pork buns and drinking-vinegar cocktails at Ping, or head to the nearby Via Tribulani for thin-crust Neopolitan-style pizza baked in a traditional tiled oven. Try to leave room for a quirky, jelly-oozing Voodoo Doughnut, then catch a movie and a glass of Oregon wine in a big leather armchair at the swanky Living Room Theaters.

Tours & Tickets

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Best of Portland Small-Group Sightseeing Tour

4.5 star rating: Recommended 70 Reviews

Experience one of the Pacific Northwest’s most dynamic cultural hubs on this small-group Portland sightseeing tour. As you travel by luxury vehicle with your ...  Read more

Location: Portland, Oregon
Duration: 3 hours 30 minutes (approx.)

From USD $75.00

Portland Sightseeing Tour Including Columbia Gorge Waterfalls

5 star rating: Highly Recommended 250 Reviews

On this full-day tour, you’ll see the best of the Portland area including downtown's Pioneer Square, the famous food carts, eclectic neighborhoods and the ...  Read more

Location: Portland, Oregon
Duration: 8 hours 30 minutes (approx.)

From USD $105.00

Downtown Bend Culinary Walking Tour

5 star rating: Highly Recommended 1 Reviews

While Portland is known across the country for its food trucks and farm-to-fork fare, the city of Bend is Oregon’s secret culinary gem that only locals are ...  Read more

Location: Bend, Oregon
Duration: 3 hours (approx.)

From USD $45.00

Bend Farm and Ranch Tour

Farming is the new cool. As much of the country becomes more and more interested in where food comes from, the spotlight is being put on the American farm. ...  Read more

Location: Bend, Oregon
Duration: 3.5 to 4 hours

From USD $65.00

Bend Fermentation Tour with Beer Tastings

Already known for its craft beer industry, Bend is also home to many other fermentation specialists that provide an interesting way to get to know the city. ...  Read more

Location: Bend, Oregon
Duration: 3 hours (approx.)

From USD $60.00

Bend Culinary Tour

For a medium-sized town, Bend offers an impressive level of quality and variety in its food scene. This 3-hour tour led by an insider food guide goes deep into ...  Read more

Location: Bend, Oregon
Duration: 3 hours (approx.)

From USD $50.00

Portland Segway Tour

5 star rating: Highly Recommended 33 Reviews

See the sights of downtown Portland by Segway, and learn about this hip yet historic city from an expert local guide! Choose a 1-hour riverfront sightseeing ...  Read more

Location: Portland, Oregon
Duration: 1-2 hours (approx.)

From USD $49.00

'Portlandia' Tour of Portland

5 star rating: Highly Recommended 10 Reviews

Whether you know what ‘put a bird on it’ means or not, this one-of-a-kind Portland tour is a great way to learn about ‘Portlandia,’ a popular TV show created ...  Read more

Location: Portland, Oregon
Duration: 3 hours (approx.)

From USD $75.00

Portland Combo: Hop-On Hop-Off Sightseeing Trolley and Columbia River Gorge Tour

5 star rating: Highly Recommended 22 Reviews

See Portland’s best sights and the spectacular natural beauty of the nearby Columbia River Gorge with this combo tour. Use your 2-day hop-on hop-off ...  Read more

Location: Portland, Oregon
Duration: 2 days (approx.)

From USD $86.00

Multnomah Falls and Columbia River Gorge Tour from Portland

5 star rating: Highly Recommended 58 Reviews

This scenic tour from Portland takes you into Oregon’s stunning wilderness to view Multnomah Falls and the Columbia River Gorge. Enjoy panoramic views from ...  Read more

Location: Portland, Oregon
Duration: 4 hours 15 minutes (approx.)

From USD $54.00

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