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.

Go west and you hit the Oregon coastline – Cannon Beach
Go south and you are in wine region – Willamette Valley
Go east and you enter waterfall heaven – Columbia River Gorge
And then you have downtown Portland itself

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	Willamette Valley Wine Region	Tasty N Daughters
	Night		Salt and Straw
Thursday	Morning	Hiking Columbia River Gorge	Common Ground Coffeehouse
	Afternoon	Hiking Columbia River Gorge	Sugarpine Drive In
	Evening		Le Pigeon
	Night		Le Pigeon
Friday	Morning	Driving the Oregon Coast	Stumptown RoastersSleepy Monk
	Afternoon	Driving the Oregon Coast	Tillamook Creamery
	Evening	Return car by 5PM	VooDoo Doughnuts
	Night
Saturday	Morning	DowntownJapanese Gardens Powell’s Books	Blue Star DountCase Study Coffee
	Afternoon	DowntownJapanese Gardens Powell’s Books	Deschutes Brewery Portland Food Pods
	Evening		Harlow
	Night	Concert: Planet Booty
Sunday	Morning	Flight home