Perfect 4 Day Itinerary for Portland, Oregon

Perfect 4 Day Itinerary for Portland, Oregon

July 2019

Perfect 4 Day Itinerary for Portland, Oregon

The Pacific Northwest had been a gaping hole in our US destinations and while we would have liked to have dedicated over a week to exploring the entire region, we only have four days to work with. After some consultations, we decided on Portland as the base for our introduction to the region.

Know before you go

There is a lot going on in and around Portland so I would recommend renting / having a car for some or all of your trip. We actually ended up using Portland more as a home base and spent most of the trip outside of the city. There is also public transportation you can use to get in and around the city.

Where to stay?

Make sure to do a safety check before booking places as there are not so great spots in Portland that you will want to avoid. Since we had a car, we needed somewhere with parking. Our Airbnb is located in the southeast corner of the city in between Hawthorne Blvd and Division St which is a great location with easy access to two downtown hubs. 

What is there to do?

There is honestly something for everyone! Weather you enjoy city life, beach life, or outdoor life you can focus or mix and match your trip. For us, the trip that planned itself! There is something completely different in every direction.

With each of these taking up a day it made for the perfect four day itinerary to visit Portland Oregon.

Where to eat?

Oh goodness, everything we ate was amazing!

  • Do not miss out of the coffee, donut, ice cream culture – we indulged in each daily
  • Go to Pok Pok for a casual night (get the wings) and Le Pigeon for a treat your self night (incredible!)
  • On your way back from Columbia River Gorge hit Sugarpine Drive In 
  • On your way back from Cannon Beach hit Tillamook Creamery

Here was our complete itinerary! 

Activity Food
Tuesday Night Flight to PDX Pok Pok

Salt and Straw

Wednesday Morning Pick up car rental Pine State Biscuits
Afternoon Willamette Valley Wine Region Red Hills Market for picnic
Evening Tasty N Daughters
Night Salt and Straw
Thursday Morning Hiking Columbia River Gorge Common Ground Coffeehouse
Afternoon Sugarpine Drive In 
Evening Le Pigeon
Friday Morning Driving the Oregon Coast Stumptown RoastersSleepy Monk
Afternoon Tillamook Creamery
Evening Return car by 5PM VooDoo Doughnuts
Saturday Morning DowntownJapanese Gardens

Powell’s Books

Blue Star DountCase Study Coffee
Afternoon Deschutes Brewery Portland Food Pods
Evening Harlow 
Night Concert: Planet Booty
Sunday Morning Flight home 

Read the full trip details here!

If you have been to Portland before, let me know what I missed and what your favorites are!

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