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5 Days Exploring Portland Oregon Itinerary

Last updated: 2024 Jun 14

Introduction to Portland

Morning

Start your day with a delightful breakfast at Mothers Bistro & Bar, known for its comfort food. Afterward, head to Pioneer Square, often referred to as Portland's living room. This bustling square is the perfect place to get a feel for the city's vibe.

Afternoon

Enjoy lunch at Tasty n Alder before visiting the Portland Art Museum. This museum houses an impressive collection of Native American artifacts and contemporary art. Then, take a leisurely stroll through the historic South Park Blocks, lined with trees and sculptures.

Evening

For dinner, dine at Andina, a highly-rated Peruvian restaurant in the Pearl District. End your evening exploring the vibrant Portland Pearl District, known for its nightlife and trendy shops.

Bedtime

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Pioneer Square

4.72

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Portland Art Museum

4.82

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South Park Blocks

4.79

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Portland Pearl District

4.72

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Nature and Gardens

Morning

Have breakfast at Voodoo Doughnut to try some unique doughnuts. Then visit the serene Portland Japanese Garden, considered one of the most authentic Japanese gardens outside of Japan.

Afternoon

Head over to Pok Pok for some delicious Thai cuisine. After lunch, explore the beautiful blooms at the International Rose Test Garden. Next, visit the nearby Hoyt Arboretum which offers miles of trails through various plant collections.

Evening

Dine at Le Pigeon, known for its innovative French cuisine. Conclude your day with a visit to the historic mansion and stunning views from Pittock Mansion.

Bedtime

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Portland Japanese Garden

4.87

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International Rose Test Garden

4.76

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Hoyt Arboretum

4.88

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Pittock Mansion

4.93

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Cultural Exploration

Morning

Start your day with coffee and pastries from Stumptown Coffee Roasters. Visit one of Portland's most iconic landmarks, Powell’s City of Books, where you can easily spend hours browsing through millions of books.

Afternoon

Have lunch at Lardo, famous for its sandwiches. Spend your afternoon exploring Chinatown by visiting the tranquil oasis that is the Lan Su Chinese Garden. Then take a walk around historic Old Town Chinatown.

Evening

Enjoy dinner at Ox Restaurant, an Argentine-inspired eatery. Afterward, take a stroll along the scenic riverfront near the iconic steel bridge: Portland Steel Bridge.

Bedtime

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Powell’s City of Books

4.60

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Lan Su Chinese Garden

4.57

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Portland Steel Bridge

4.46

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Adventure and Fun

Morning

Kick off your morning with breakfast from Blue Star Donuts before heading out on an adventurous hike in Forest Park, one of America's largest urban forests.

Afternoon

Grab lunch from one of Portland's famous food carts in downtown during Portland Food Carts Pods & Patios Tour. Afterward, spend some time learning about science and technology at Oregon Museum of Science and Industry (OMSI).

Evening

Dine at Nostrana, an Italian restaurant known for its wood-fired pizzas. End your day with an exhilarating experience: From Portland City Lights Nighttime Helicopter Tour.

Bedtime

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