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The ultimate Portland itinerary for first-time visitors

Portland sign

If you want to visit Portland, sure, you can get a good sense of the city in two or three days. But there’s SO MUCH to see just outside the city that you really need to spend a bit more time if you want to do it all. Unlike my weekend itinerary for Portland, which focuses almost exclusively on the city itself, this Portland itinerary works in some of the top day trips (the coast! Wine country!) to really give you a good idea of what the region’s all about.

THE ULTIMATE PORTLAND ITINERARY FOR FIRST-TIME VISITORS

Portland skyline
Chinatown gate

DAY 1

Welcome to Portland! Unless you’re coming from the West Coast, it’s likely you had a long flight, so after checking into your accommodations (I have lots of recommendations in my Portland city guide!), take it easy. If you need coffee, your options are nearly endless—try grabbing one at Good Coffee, Coava Coffee, Upper Left or the iconic Stumptown, to name a few. Then, stroll around the city to get your bearings. 

There are lots of shops to check out downtown (housed within beautiful historic buildings) near Pioneer Courthouse Square, or if you head north, you’ll wind up in the Pearl District, where shops now inhabit old red-brick warehouses. Powell’s City of Books, the world’s largest independent bookstore, is a must in the Pearl!

For dinner, keep it local by checking out Tasty n Alder, one of the city’s most renowned restaurants. (Can’t get in? Mediterranean Exploration Company, its sister restaurant, is a great fallback!)

If you’re not totally spent afterward, downtown Portland has great cocktail bar options for a nightcap, one of which might even be in your hotel. Abigail Hall (inside the Woodlark) and Pepe Le Moko (inside the Ace Hotel) are both low-key options. If it’s a weekend, though, you’ll run less chance of extreme crowding at Abigail Hall.

Pittock Mansion
Pittock Mansion

DAY 2

MORNING

You’ve got a lot of ground to cover over the next few days when it comes to exploring the region, so use this day to hit the real highlights in Portland proper. Start the day off at the impressive and beautiful International Rose Test Garden, which will help explain Portland’s “City of Roses” nickname. Not visiting during the blooming season? The nearby Portland Japanese Garden is worth a visit whether or not you hit the rose garden.

After the gardens, make the short hop over to Pittock Mansion, a historical-home-turned-museum that once belonged to a wealthy local family. Whether you choose to go inside for a tour (you’ll need to pay admission) or just roam the grounds (for free!), you’ll learn about the city’s journey to industrialization. Oh, and the Portland city skyline views from Pittock Mansion can’t be beat (unless maybe you ride the Portland Aerial Tram—it’s a tossup for me!). 

Tusk salad
Tusk

AFTERNOON/EVENING

Make your way back downtown for lunch, where options include French luncheonette Maurice, local favorite sandwich spot Lardo, low-key Boxer Ramen and multi-option food hall Pine Street Market.

Then, cross the Willamette River for the first time to hit up Portland’s east side, which many will call the “authentic Portland” (or the more “Portlandia” side). Hawthorne and Division are two lively business districts with plenty of shops, cafes, independent businesses and more to check out, so give yourself some time to wander. Definitely stay for dinner, too: Afuri Izakaya, Oui Wine Bar, Tusk and Ava Gene’s are all fantastic options in this quadrant of the city.

If you think the night is over, think again. YOU MUST go to Hale Pele if the idea of a world-class tiki bar—complete with a divey vibe, flaming drinks and a fog machine/sound effects—sounds even remotely entertaining. There is almost always a wait for a table here, but they’ll serve you drinks while you pass the time!

Canon Beach
Ecola State Park

DAY 3

MORNING/AFTERNOON

It’s time to hit the road! Head for the Oregon Coast, and in particular, Canon Beach. The ride should take about an hour and a half, so if you want to maximize your time on the coast, you might want to get an early start.

Once there, head straight down to the beach itself, home of the famous Haystack Rock (I’ve never seen Goonies, but I’m told that if you have, it might look familiar!). While the beach is too cold for swimming (at least sans-wetsuit), there’s still plenty to do there. In addition to admiring the rock formations, you can check out the tide pools filled with tons of tiny crustaceans, interesting plant life and more. It’ll keep you busy for at least an hour, trust me (and if you’re into photography, you may well want to stay longer). 

After your beach walk, you’ll find lots to explore in Canon Beach itself. Despite the cooler temperatures (which to me separate it from other beach towns I’ve visited), it still manages to capture that quintessential beach-town vibe. There’s no shortage of fudge, candy and ice cream shops lining the streets, and picturesque, flower-clad houses to admire. Depending on timing, you can grab lunch either before or after browsing what the town has to offer. Cap off the day with a beer or an ice cream before heading out.

But before you go back to Portland, there’s one more must-see stop: Ecola State Park. Right from the parking lot, you’ll find can’t miss views of the beautiful Canon Beach scenery, meaning that it’s worth a stop even if time is limited. Yes, you’ll pay an entrance fee, but it’s well worth it even for a quick drop-in!

Beer
Kachkan

EVENING

Whether or not you like beer, you’d be remiss to come to Portland and not go to at least one brewery. The city prides itself on its brewery scene, which includes larger operations that distribute nationally all the way down to much tinier businesses. Either Base Camp Brewing (which has fire pits outside!) or Cascade Brewing (famous for its fruity sours) will put you in walking distance of Kachka, a must-visit restaurant for even moderately adventurous eaters. Don’t let unfamiliar items on this menu of modern Russian food scare you away; everything at Kachka is incredible, and the novelty will help make for an unforgettable dining experience. Go hard on the pelmeni (dumplings) and thank me later.

Wine
Domaine Serene

DAY 4

MORNING/AFTERNOON

Time for day trip No. 2! Today you’ve got a choice to make between the Willamette Valley (wine country world-famous for its pinot noirs) or Mt. Hood (with or without a stop or two in the Columbia River Gorge). It’s a tough decision to make, but you really can’t go wrong.

If you opt for wine country, map to Babica Hen Cafe in Dundee, as many of the wineries don’t have as robust a food menu as you might expect. Babica Hen has all the brunchy items you could want, including hashes, decadent pancakes and more. Then, pick a couple of wineries that suit your fancy and go! You’ll find all sorts of experiences in the Willamette Valley, from small, laid-back wineries with picnic tables to larger, fancier ones that make you feel like you’re in an Italian villa (with price points to match). Note that some wineries require advance reservations for tastings.

If the mountains are calling, head for Mt. Hood, a year-round ski destination and a great place to hike during the summer. There are tons of trails in the area for hiking and snowshoeing (I like the Tom Dick and Harry Mountain Trail for hikes), but if you do go all the way to the mountain itself, stop into Timberline Lodge, which makes a great place to grab a drink, enjoy the view or sit by a fire.

If you choose a shorter summer hike but still want to make a day of it, consider stopping in Hood River—a fun town on the Columbia River chock-full of breweries—or by a pick-your-own fruit/flower farm nearby. On the way from Hood River back to Portland, you’ll pass the beautiful Multnomah Falls, which are definitely worth at least a quick stop.

Portland

EVENING

After what’s almost certainly been a busy day, there’s no better way to unwind than with rooftop tacos at Tope, located on the top floor of the The Hoxton hotel. On a clear night, you can see both Mt. Hood and Mt. St. Helens from the restaurant, so make sure to arrive before sunset. And get the queso fundido!

If you’re not wiped out (or alcohol-ed out, if you went to wine country) at this point, The Hoxton has a speakeasy in the basement that’s worth a visit. But if it’s a nice evening, you could also just stay at Tope and have another spicy margarita. Your call.

DAY 5

MORNING

It’s back to the east side to start your last day in Portland, which should definitely include the Alberta Arts District. Grab brunch at Australian cafe Proud Mary and then wander NE Alberta, popping into boutiques, record stores and bakeries along the way. There’s plenty of street art to admire, too!

Waterfall
St. Johns Bridge

AFTERNOON/EVENING

Later on, if you’re up for another small excursion, drive out to Multnomah Falls, about 30 minutes outside the city (if you haven’t done so already). The falls themselves are gorgeous, and you’ll get spectacular Columbia River Gorge views on the way there and back, too.

If you want to stay close for your last day in town—and particularly if you didn’t do any hiking yesterday—get your nature fix by heading to the 5,200-acre Forest Park, one of the country’s largest urban forests. Find a trail there that meets your desired difficulty level, from all-out hike to casual stroll. Afterward, if you want, you can pop over to nearby Cathedral Park to view the St. Johns Bridge in all its glory.

For dinner, head back to Southeast Portland and make sure to get in a visit to either Tusk or Ava Gene’s, particularly if you haven’t hit one or the other already. Afterward, cap off your trip with ice cream from Cloud City!

For more on Portland, check out my complete guide to the city and my day-trip guide. Need a shorter itinerary for Portland that covers city only? I’ve got that right here! And for info on how to visit the city for free, check out the 52 Cities free resource library or register to join me on an upcoming masterclass!

Hope you enjoyed this Portland itinerary! What are you planning to check out in the city? Let me know in the comments! >>

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Portland itinerary
Portland itinerary
Portland itinerary

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