So, you’re headed to Portland.
Maybe it’s your first time and you’ve heard the legends—bearded men on bikes, coffee that requires a barista certification exam, and locals who compost more seriously than they pay taxes. Or maybe you’ve been before and still can’t figure out why the donuts are shaped like voodoo dolls.
Either way, you want a solid, not-too-touristy, not-too-boring, and ideally “not-trying-to-bankrupt-me” way to spend 2 days in Portland.
Well, lucky you. I’ve put together a pretty darn good itinerary for your weekend (or any two days) in this beautifully bizarre city.
If this itinerary doesn’t quite float your boat, check out my Trip Planning Services. I specialize in custom itineraries based on stuff that will scream “all you.”
Portland Travel Itinerary Day 1
Breakfast at Besaws
Portland is known as one of the foodie capitals of the world, and a brunch capital, in particular – Besaws serves up its fantastic brunch seven days a week folks, from 8 am – 3 pm. So come on down! Besaws goes from down-home to fancy at the turn of a fork. What do I mean by that? Well, you can choose from a chicken fried steak stack to a duck confit cassoulet. And who doesn’t want duck confit for breakfast?!?
Do a Segway Tour (yes, seriously)
You’re not too cool for a Segway. I did it. I lived. I only mildly embarrassed myself. And guess what? I learned stuff—actual history—while rolling through downtown like a futuristic mall cop.
Why it rocks:
- You cover way more ground than on foot.
- You get to feel superior to pedestrians for 90 glorious minutes.
- You’ll see some of Portland’s best architecture and hidden gems (like the weirdly aggressive art installations and that one building that smells like sourdough).
Book browse at Powells
The world’s largest and most famous independent bookstore needs to NOT be missed. I don’t care if you call yourself a bookworm or not, you need to come here. Buy your book, SELL your book, Browse for a book (or a dozen). Genres are laid out quite nicely and color-coded throughout the three stories of their flagship store. Grab a map on your way in! Their periodical section (read: magazine) is to die for. You could easily spend the whole 2 days here just taking in everything. You can even have lunch at their café. But I recommend…
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Lunch at Laurelhurst Market
Just east of the bridge about 2.5 miles from Powells is the Laurelhurst Market. Not only is this a full-service butcher shop, but it is also a tasty lunch spot and neighborhood bar, serving spectacular sandwiches from 11 am – about 4 pm. Then for dinner, they switch to a full-service steakhouse, complete with a craft cocktail bar. Definitely one of the more versatile eateries in town and a local spot I don’t get to often enough.
Afternoon at OMSI
I love science (heck, I have a Biochemistry degree, for crying out loud), so the Oregon Museum of Science and Industry is a great, hands-on place to bring the kids, and the adults have plenty of fun, too. They are always hosting some new exhibit. And with a planetarium and a 3-D movie theatre, what’s not to like?
Not into science? No problem. Instead, wander the Pearl District and pretend to be interested in overpriced ceramics and artisan pickles. (I actually bought the pickles. No regrets.)
Do a Brewvana Brewery Tour
You could wander around aimlessly trying to find the best brewery. Or… you could let the pros handle it while you ride around on a literal beer bus (or beer bike, if you’re feeling cardio-inclined).
Yes, you’ll drink. You may even become besties with a stranger named Chad. But you should definitely eat something before. Book this tour here.
If you hate fun, skip this and go have a cocktail at Teardrop Lounge—classy, moody, and your best bet if you want to impress a date or at least feel like your blazer wasn’t a mistake.
Portland Itinerary Day 2
Breakfast at Pine State Biscuits
This Portland breakfast institution usually has a line out the door for a reason. I recommend the Reggie Deluxe. What is that, you say? It’s HEAVEN. A buttery flaky biscuit that sandwiches a hand-battered breast of chicken, complete with bacon, a fried egg, and cheese. Wow! Don’t worry too much about working this off, save your jog around the block for tomorrow. This mega-meal needs to digest properly. In order to do that, walk around Alberta Street and take in all of the eclectic shopping. (There’s another location on NW 23rd St. – which has great shopping.)
The International Rose Test Garden at Washington Park
Marvel at 550 species of over 7,000 rose varieties at this world-renowned rose garden. Having just celebrated their centennial in 2017, the garden hosts free public tours Memorial Day through Labor Day, daily at 1 pm. Washington Park itself is a wooded oasis in the heart of Portland. This is the home of the Portland Zoo, Hoyt Arboretum and an extensive network of hiking trails. It’s a great place to wear out the kiddos. This should be a part of any Portland outdoor itinerary!
Lunch at the Midtown Beer Garden (or any other food card pod you choose; they’re all good and I’m not your boss) There are tacos. There are dumplings. There’s probably a guy selling organic yak milk. (No, not really.) Portland’s food carts are where your lunch dreams go to live—or at least where your indecisiveness will be tested to the limit.
Nature Walk or Boozy Crawl — Your Call
Option A: Forest Park Hike
If your soul is craving trees and your thighs are ready for mild exertion, head to Forest Park. It’s basically a magical forest in the city, and there are trails for every mood—hangover included.
Option B: More Booze, Less Effort
If you’re morally opposed to sweating, head to Distillery Row instead. Try some gin. Pretend you know what botanical notes are. Buy a bottle you’ll never open again. It’s all part of the experience.
Dinner at Lardo
For the sandwich lover in ALL of us. Hallelujah! Vegetarian? The Griddled Mortadella will have your eyes rolling toward the back of your head. The Pork Banh Mi is out of this world. You’ll come out of there feeling like a, well…lardo. There are two locations in the Portland metro area, so your gluttonous desire for tasty food is covered.
That’s a solid two days in Portland, my friend.
Sure, there’s more you could do. But if you managed to hit even half this list, you’re already winning at travel—and you’ve got better stories than someone who just took a photo of a donut and called it a day.
You’re at the end! If you’ve stuck around, check out my post on Free Things to Do in Portland — because saving money means more budget for weird souvenirs and local whiskey.