I originally made this Portland Travel Guide in a Facebook message for a friend who was asking for another friend. This guide is one that I've since sent to clients, friends, family and extended friends and family.
You can absolutely see Portland in four days if you plan ahead! My suggestion is to stay in Portland for two days and the other two take day trips, one out to the Columbia River Gorge and one day spent on the Oregon Coast. These are not to be missed and I've included them at the end of this guide. You can use this guide to plan. You can do all of Downtown, Northwest and Southwest Portland in one day. Day two can be spent wandering through Southeast and Northeast Portland. Without further ado let's get to the good stuff!
This is a five neighborhood city. Many people come to Portland and only hangout in one or two of these areas. I highly suggest checking out at least three or four neighborhoods in some way, Portland is super easy to drive around so just go! The east side of Portland is considered more hipster but also has some of the best food and bars in the city. I've also left off North Portland, I love this area but I do find that in this amount of time it's just a bit further out than most want to go just to grab a drink.
Sprinkled throughout Portland are Food pods which is Portland's version of food trucks! These are serious fun and many are worth checking out. Here's a map of Pods around Portland: http://www.foodcartsportland.com/maps/
Shop: Portland Saturday Market (walk to Voodoo Donuts from there) and walk along the riverfront
Eats: Irving Street Kitchen
Culture: The Portland Art Museum is great!
Fun: Powell's Bookstore (huge, don't miss this!!)
Shop and Drinks: 21st, 22nd and 23rd Streets between Burnside and Thurman
Eats: Justa Pasta
Hike: Forest Park
Walk: International Rose Test Garden and Japanese Garden
Mississippi Street - start at Proust (grab a German beer) and walk down.
Drinks and Music: Bar Bar and Mississippi Studios
Alberta Street - begin around 15th Street and walk up to about 31st
Eats: The Bye and Bye - delicious vegan
Drinks: Kennedy School - don't forget your swimsuit, The Knock Back and Radio Room
Hawthorne Street - park near 34th (just look up and down the street, there's a ton to do) The people watching alone is worth it! So many vintage shops (clothing, shoes, furniture and more!) sprinkled all over this area!
Drinks: Baghdad Theater - burgers and a movie theater and cool historic spot
Hike: Mt Tabor Park
Drinks: Roadside Attraction
Culture and Fun: OMSI is the science museum and super cool
Rent a Car!
For a day or two and drive to the coast and through the Columbia River Gorge.
Hike Multanomah Falls or add on another waterfall and do the Wahkeena Falls Trail Loop. I highly suggest the Oneonta Gorge Hike but there are plenty of beautiful hikes in the Gorge. There's the Gorge Vista House for a snack and relax after a hike. I like to drive through the Gorge to Hood River and have lunch or dinner, it's a cool town. I also like to cross The Bridge of the Gods from I-84 in Oregon to Route 14 in Washington along the Columbia River. It's a beautiful drive back to Portland.
Eats and Drinks: Full Sail Brewing. Also use this map - Breweries in the Gorge to help you find other great breweries along the way!
My favorite spot is Cannon Beach! It was named as "One of the Worlds 100 Most Beautiful Places" by National Geographic. Cannon Beach hosts beautiful huge sea stacks in the water and endless beach. Haystack Rock also has Tufted Puffins! It's typically chilly and rainy but don't let that stop you, it's a must do.
Eats: Tom's Fish and Chips!
Drinks: Pelican Brewery
Pro Tip: Bring a raincoat and rain boots, leave your umbrella at home.
PS Don't forget to check out my new Portland City Map bracelets, these are perfect for navigating your way around the City of Roses!