The Perfect Portland Itinerary You'll Want to Steal

Planning a Portland itinerary can be difficult because there is so much to see, eat, and do in this famous Oregon city. As a Seattle resident, I’ve been heading to Portland at least 1-2 times a year for the past decade. As a result, I’ve become a pro at planning the ultimate trip depending on if I have one or a few days.

Over the years, I realized my perfect itinerary is mostly made up of eating and drinking, with a few activities sprinkled in between meals. That’s because Portland is a serious food city, so doing anything else besides gorging is a waste of time (I kid! Sorta…).

So if you’re looking for unique things to do in Portland that mostly revolve around eating, drinking, and a few stops for views and shopping, here are my recommendations for the perfect Portland itinerary.

The Perfect Portland Itinerary

This itinerary assumes you have three days in PDX. However, if you only have one day I share how I’d spend my perfect day at the end of this post.

Not seeing what you’re looking for? Let me plan you a custom travel itinerary!

Day 1: Farmers market and shopping

If you’re traveling on a Saturday, start your getaway with a trip to my favorite farmers market, shops, and restaurants. You can always swap this day with another if your first day doesn’t fall on Saturday!

Get breakfast at HA & VL

HA & VL is a Vietnamese restaurant tucked in a strip mall in East Portland. You might be thinking, “Uh, what, soup for breakfast?” And I’m here to tell you yes.

These soups were nominated for a James Beard award they’re so good. They only serve two options each day, letting them focus on really developing the flavors. They’re so popular they often sell out, so get there for close to when they open at 8 AM!

Grab some locally-roasted coffee

PDX is a huge coffee town so not partaking in some java would be a sin. There are so many great PDX coffee shops to try, so if you see one, chances are they are serving excellent locally-roasted beans. Here are some of my favorites:

Don’t forget to bring some beans home so you can compare them to the best coffee roaster in Seattle!

Hit up the Saturday Farmers Market

Portland has some of the best farmers markets in the Pacific Northwest. My favorite is the year-round Saturday farmers market at Portland State University. Every Saturday until 2 pm, it’s and a fun way to spend a weekend in Portland.

You’ll find more than 100 vendors selling food goods, including some of the most beautiful produce I’ve ever seen. It’s a great place to pick up foodie souvenirs, produce for a picnic/hike, or food for your Airbnb.

Note, it’s easy to confuse this farmers market with the Portland Saturday Market. They’re near-ish each other, but the Saturday market has more kitsch and crafts. I prefer the farmers market filled with locals instead of packed full with tourists.

Get lunch at Kachka

Kachka is a Russian restaurant full of kitsch that makes you feel like you’re in a grandmother’s home. It might seem like an odd choice, but if I only have time for one sit-down lunch during my Portland itinerary, this is it.

Don’t miss their dumplings and salmon blini. The salmon blini is served cold with beet-cured salmon and a bright parsley pesto. It’s acidic and beautifully presented with flower garnishes on top.

There are options when you order dumplings. If you only have room for one dish, get the pan-fried sheep cheese and scallion dumplings. They have a complex cheesy flavor with a crunchy crust and soft pillowy interior. If you can stomach more than one dumpling dish, also get the meat dumplings served classic (boiled and topped with sour cream).

Explore Forest Park

I like to head to Forest Park for some easy hikes. There are 5,200 acres to explore, making it one of the largest urban parks in the US.

There are 80 different hikes to choose from. I haven’t found a favorite yet, but have thoroughly enjoyed every trail I’ve tried.

Get a snack at Blue Star Donuts

Most people head to Voodoo Donuts, but I don’t think they’re worth waiting in line for. Instead, head to nearby Blue Star for yummy yeasted doughnuts. If available, don’t miss the lemon and lime curd cream doughnut.

Go shopping

Portland is a shopping lover’s dream. It’s a city full of makers and people obsessed with supporting local, so you’ll find so many awesome boutiques.

Here are my must-visit gift shops and antique shops in PDX to add to your Portland itinerary:

Vintage Pink – Fabulous mid century furniture store (pictured above)
Monticello Antique Marketplace – Big vintage mall with multiple vendor
Beam & Anchor – Home goods shop worthy of a feature in Kinfolk Magazine
Wild Shaman – The most beautiful vintage rug store I’ve ever seen
Urbanite – Large warehouse with different vendors selling vintage and handmade goods
Canoe – Minimalist home and gift shop
Woonwinkel – Scandinavian-style home decor store

These are scattered across the city, so if you only have time to stay in one area, here are some of my favorite shopping areas:

Mississippi Ave. – Starting south of N. Skidmore Street, there are a lot of funky boutiques along this street.
Hawthorne Blvd. – Starting around SE 32nd Ave. and SE 48th Ave., this is another area with boutiques and a slightly younger, college-y crowd. But it’s where Vintage Pink is and a few other solid vintage spots.
Downtown and Pearl District – Downtown Portland has a lot of great shops congregated along multiple blocks. I find the blocks between SW Alder and Everett the best.
Buckman – This is a good area with a lot of vintage shops and great eats.

Get dinner at Tusk

Picking one dinner restaurant in Portland was so hard. However, if I could only ever eat dinner at one place in Portland, it would be Tusk. Heck, I think this is one of the restaurants worth the drive from Seattle.

This Middle Eastern-inspired restaurant gets crowded, so go during off times. They make consistently incredible, vegetable-forward plates meant for sharing within a beautifully-decorated space. Don’t miss the hummus…it’s one of the best I’ve ever had.

Get dessert at Cheese & Crack

Cheese & Crack pretty much combined some my favorite things — cheese, wine, and soft serve ice cream — and opened up a restaurant. My favorite of those three is their soft serve. It’s creamy and deeply flavored, which is difficult to accomplish with plain vanilla ice cream.

You can get it dusted with different flavors like espresso, strawberry, or macha. You can also get it topped with a chocolate cowboy hat, which would really up the sex appeal of this dessert for the ‘grams.

Day 2: Food carts and beers

I’d argue the main draw of Portland is it’s food and drink, so a full day of eating is a must during your Portland itinerary. Get on those stretchy pants!

Explore Portland’s food truck pods

Portland is known for their food trucks. There are pods scattered across the city, making for a hip stop when you need a quick bite to eat.

Here are my favorite pods for a crawl:

Hawthorne Asylum – This is my favorite food cart pod. It’s in SE Portland around the corner from Cartopia, so you can hit up a lot of places in one go.
Lil’ America – This is a great pod featuring BIPOC and LGBTQ+ vendors. Don’t miss Bake on the Run for Guyanese food. Get the salt cod bake!
Nob Hill Food Cart Pod – This is a great little pod in the cute Nob Hill neighborhood. Don’t miss BingMi.
Prost! Marketplace – This pod has 10 carts parked at the top of Mississippi Ave in North PDX. Don’t miss Fried Egg I’m in Love for breakfast sandwiches!
Piknik Park – This pod is in Sellwood just south of Portland. It has 8 carts, including the best Korean fried chicken from Jin Dak.

Go on a brewery crawl

Portland has a ton of breweries serving craft beer, some of them clustered together so you can do a crawl. One afternoon isn’t enough time to see them all, but some of my favorite include Ecliptic Brewing and Culmination Brewing.

Get dinner at Akadi

A lot of people will tell you to go to Kann, a Haitian restaurant owned by celebrity chef Gregory Gourget from Top Chef. Kann is very good, but it’s expensive and hard to get into. So I prefer Akadi, a West African spot not too far away.

You can expect to find African classics like egusi stew and akara, but don’t miss the goat meat jollof. It’s so richly flavored and is like a hug on a plate.

Pro tip: Buy one or three of their Akadi sauces to go. Trust me, you’ll want to slather it on everything!

Get dessert at Fifty Licks

Fifty Licks has a few different locations, making it an easy spot to close out your second day in PDX. You’ll find awesome handmade ice cream, including a lot of vegan options. I swear my favorite is the vegan mango ice cream. It’s so creamy you’d never know it doesn’t have dairy!

Day 3: Parks and wine tasting

Close out your Portland itinerary with an easy-going day exploring Rose City.

Get breakfast at Matt’s BBQ Tacos

Matt’s BBQ Tacos is a food cart with two locations. You can order ahead and pick up a piping hot breakfast taco with eggs, meats, and fixings. My go-to is the brisket egg taco, followed by pulled pork.

Visit Washington Park

Washington Park is a large park worth adding to your Portland itinerary. It has so much to see, with more than 400 acres and 15 miles of trails. Here are some of the not-to-miss attractions, which I recommend visiting on a weekday.

Keep an eye out for the 150-foot-tall Redwood Trees in Hoyt Arboretum. Most people don’t expect to see them outside of the Redwood Forest north of San Francisco, but they grow right in PDX!

Check out Pittock Mansion

Pittock Mansion is a historic building on the top of a big hill overlooking Portland. On a sunny day you’ll see Mt. Hood looming in the distance, so it’s worth a stop for stunning bird’s eye views of the city!

You can also tour the mansion built in the early 1900s by Henry Pittock, known as the man who made the Oregonian newspaper successful.

If you want to get some exercise, do the 4-mile hike from Washington Park on the Wildwood Trail to Pittock Mansion.

Get lunch at Eem Thai BBQ & Cocktails

Eem Thai BBQ & Cocktails is a hipster Thai restaurant serving mean cocktails (yes, it’s appropriate to get noon-time libations). I really enjoy their lamb massaman curry. The lamb is smoked so it has that backyard barbecue taste, but mixed with earthy and spicy Thai flavors.

Go wine tasting

There are a bunch of wine tasting rooms in Portland, my favorite being Division Wine Making Co. You’re also within a 20-30 minute drive of some of the best wineries in Willamette Valley. So you have a lot of options!

One of my favorite under-the-radar wineries is Villa Catalana in Oregon City just 15 minutes southeast of Portland. It was opened by a sweet older couple who own a rare plant nursery. Their winery grounds prove they have a green thumb. There are beautiful landscape scenes and nooks for sipping wine throughout the property. Don’t miss the hidden conservatory with tropical plants!

Get dinner at Langbaan

Langbaan is one of my more recent Portland restaurant discoveries and it absolutely blew my mind. It’s a Thai restaurant, but not your typical Thai restaurant with comforting curries and pad Thai. Langbaan creates a multi-course tasting menu featuring authentic Thai flavors reimagined into award-winning-worthy dishes. We honestly couldn’t stop gushing during our whole meal!

Get drinks at Expatriate

I’d finish my Portland itinerary with drinks at Expatriate, a cocktail bar by the husband of James Beard-winning celebrity chef Naomi Pomeroy’s. It’s got dark and moody vibes, perfect for enjoying a night cap after a whirlwind of eating and exploring using my Portland itinerary. I also hear they have great nachos if you need a little midnight snack.

How I’d spend one day in Portland

If you only have one day in Portland, here are the stops from the above Portland itinerary I wouldn’t miss:

Breakfast at Matt’s BBQ Tacos
Washington Park
Food cart pods for lunch
Shopping (and farmers market if it’s Saturday)
Tusk or Langbaan for dinner

My map of Portland, Oregon

Want more ideas to add to your Portland itinerary? Here’s my map of Portland that I frequently update with new places I discover or want to try. You’ll find places to eat, drink, shop, and sightsee, along with my review of each place I’ve been but didn’t think was special enough to add to your Portland itinerary.

More to explore near PDX

If you have more time to explore Oregon or want to customize your Portland itinerary, here are more guides to nearby areas.

And there you have it, my ultimate Portland itinerary depending on if you have one, two, three, or more days in Portland, Oregon. I’ll add more ideas to this guide as I continue to explore Portland, so pin this for later!

The Perfect Portland Itinerary You’ll Want to Steal