We may receive a commission if you make purchases through affiliate links (at no extra cost to you). Read why our approach to travel is different.
A few years ago, Oregon’s largest city came on to the radar of trendsetting travelers. No longer was Portland a stopping off point for road trippers working their way along the West Coast from San Diego to Seattle.
The reason: Portland reinvented itself as hipster central. Craft breweries cropped up on every corner, food trucks appeared en masse and quirky coffee shops filled the gaps between them. Alternative, edgy and as indie as it gets, Portland has always been vying with Seattle to take the crown as the Pacific North West’s crown. It might not quite compete in terms of viewpoints, but when it comes to things to do and cultural experiences, the City of Roses can certainly hold her own.

On top of these curious new draws, Portland packs plenty of history. Add in gorgeous river views, top eats and an eclectic nightlife scene and a trip to Oregon becomes even more of a good idea. Our itinerary for Portland will help you to explore the old, the new and the downright bizarre.
Getting to Portland
By land
If you are traversing the West Coast, the chances are you’ll have brought or rented a car. Thankfully, Portland traffic is nowhere nearly as bad as Seattle’s, let alone Los Angeles and many hotels offer self or valet parking.
If you’re not driving, several Amtrak trains serve Portland’s Union Station which is within walking distance of Downtown. The Coast Starlight runs daily between Seattle and Los Angeles, the Empire Builder connects Portland with Chicago. Amtrak Cascades offers a frequent service between Eugene, Portland, Seattle and Vancouver. Greyhound and Flixbus also serve Portland from Seattle and Sacramento.


By air
Portland International Airport (PDX) is 12 miles north of Downtown. The MAX Red Line light rail system runs frequently between the two; taxis and rideshares such as Uber and Lyft are also available.
PDX is a hub for Alaska Airlines who provide connections across the United States along with all the major U.S. airlines. If you’re coming from Europe, year round services are offered by British Airways from London Heathrow and KLM from Amsterdam Schiphol. There are a number of additional seasonal routes plus year round services to Mexico and Canada. To find the best option for your itinerary for Portland, compare flights before you book.
Where to stay in Portland
Downtown Portland is fairly compact, so whichever area you choose to stay in, it won’t be hard to get around. Public transport is exceptionally good by U.S. standards and a day ticket for the bus and light rail network offers great value.

Around Pioneer Courthouse Square
The most central area to base yourself on this itinerary for Portland, Pioneer Courthouse Square is flanked by the impressive Pioneer Courthouse. Staying in the heart of Downtown is ideal for shopping, exploring museums and dining.
Unequivocally our top pick here is The Paramount Hotel. The grand lobby sets the tone for extremely spacious, well-appointed rooms. There’s a gym, a dimly-lit bar serving exceptional cocktails and, better still, the rates are shockingly low.
For the most luxurious accommodation on this itinerary for Portland, Dossier Hotel on bustling SW Alder Street won’t disappoint. Perfectly positioned between Pioneer Courthouse Square and the Old Town, the Dossier is where old school charm meets modern comfort.

For a slightly lighter-on-the-wallet stay, look no further than The Clyde Hotel. Opened in 1912, it’s strategic location is perfect for seeing the sights on this itinerary for Portland.
The Old Town
Portland’s historic Old Town is packed with buildings from bygone years and is right by the Willamette River. This is the ideal area to soak up the city’s indie vibes and has the best food trucks.
Our top pick here is the chic Hoxton Portland. Slap bang in the middle of the Old Town, the snug and cozy rooms feature stylish décor and modern amenities. Another excellent choice, The Society Hotel has a beautiful rooftop bar with river views. It’s a great spot to unwind after working through your itinerary for Portland.

Around Portland State University
Just south of Downtown, staying in the university district can often help you save on accommodation. It’s quiet, safe and still within walking distance of all the top sights and restaurants.
University Place Hotel offers plenty of comfort and astonishingly good value. This itinerary for Portland will keep you busy but there’s always time to take a breather and relax by their outdoor pool. Breakfast is always free and the rooms are beyond spacious. Just north of the university you’ll find another of Portland’s top boutiques: Hotel Zags. Modern industrial-chic décor, brightly furnished rooms and a free breakfast await if you opt to stay here.
2-Day Itinerary for Portland
Day 1
9 am: Breakfast
You’ll soon see that this itinerary for Portland isn’t lacking in food, and in a city famous for food trucks, where better to have your first taste of Portland? Fried Egg I’m In Love, and I confess my love of The Cure is lending to a little bias here, is the place to be.

Although they have three locations, we recommend heading to their truck on Pioneer Courthouse Square for breakfast with a view. It’s always buzzing no matter what time of day and you can tick off one of Portland’s most iconic landmarks in the process.
10 am: Get to grips with Portland at the Oregon Historical Society
The number one museum in Portland, Oregon Historical Society is a history museum with a difference. Immersive and interesting, this is the kind of museum you can lose yourself in and walk out three hours later wondering where the time’s gone.

From Native Americans to white settlers and statehood, the museum documents the story of Oregon from the very beginning. Special exhibits include a photo gallery of Portland through the ages and regularly changing guest exhibitions.
The museum is open daily and tickets can be purchased on arrival.
1 pm: More food trucks than you’ve ever seen
Learning about history is sure to make you hungry. Thankfully, Food Truck Park, home to Portland’s largest collection of food trucks is only a ten minute walk away.



From classic American Philly Cheesesteaks to Mexican, Thai and Indian, there’s options for every taste. Thanks to the communal seating, if you’re tackling this itinerary for Portland as a group, everyone can order from a different truck and you can all eat together.
2 pm: An Afternoon tipple in a London Bus
I’m not saying you need an excuse for daytime drinking when you’re on vacation, but if you do, stumbling across an old red London double decker bus converted to a bar seems like a pretty good one. Rachel & Rose is quirky if nothing else.

The bus (if you’re as nerdy as I am, you’ll instantly recognize it as a Leyland Olympian) spent its life as a London sightseeing bus before being shipped across the Atlantic to see out its days serving wine and cocktails. If ever there was a perfect retirement, this is it!
3 pm: A book lover’s dream
Just a minute’s walk along West Burnside, Powell’s City of Books is an unmissable stop on any itinerary for Portland. Famous the world over, Powell’s flagship store has an inventory of over four million books. Split into 3,500 sections across nine rooms, every genre is represented.

A highlight of any visit is a trip to the Rare Book Room on the top floor. Only fourteen people are allowed in at any one time and you’ll need to obtain a pass from the information desk to enter. There’s an excellent, and always busy, little café on the ground floor who serve amazing coffees, pastries and beer and wine. If you’ve added to your book collection, grab a drink and start reading.
5 pm: Under the Old Town
Walk due east from Powell’s and you’ll find yourself in the Old Town. Head down to the Williamette River to take in the view of the bridges and get a snap of the iconic White Stag Sign. Then, walk a couple of blocks north to Old Town Pizza & Brewing.

One of Portland’s countless craft breweries, Old Town Pizza do more than just pizza and beer. Built on top of the Shanghai tunnels, they’ve worked tirelessly to renovate their section of tunnels into safe enough shape for visitors to explore.
Join a tour with a knowledgeable guide as you dive deep underground and hear stories of ghosts, women of ill-repute and seedy goings on. You’ll also learn what it means to “get Shanghai’d”. I could tell you, but it’s much more fun to go on the tour and find out yourself.


At the end of your tour you’ll also get a free pint of house-brewed beer. Grab a can to take back to your hotel or enjoy it at the bar whilst taking the chance to get to know your new friends from the tour whilst finally being able to see them.
8 pm: Dinner at Portland’s oldest
Established in 1879, Huber’s is Portland’s oldest restaurant. The saying goes that if you’d visited in the nineteenth century, “you’d have seen patrons conversing with a drink in one hand and a turkey sandwich in the other.” In all honesty, not much has changed since.

Famous for their turkey dinners, the menu covers all bases. Equally impressive is the wine list and whatever you do, don’t miss the chance to try a Spanish Coffee.
9:30 pm: Indulge in Portland’s nightlife scene
We couldn’t pen an itinerary for Portland without making mention of its fun, and frankly wild, nightlife. Dante’s has shows every night. There’s karaoke every Monday, a happy hour on Sundays and regular open mic nights. If you stay late and get peckish at closing time, they have a great hole-in-the-wall pizza takeaway by the exit.

If you want to dive into Portland’s craft beer revolution, head along to Loyal Legion. Open until midnight on weekdays and later at weekends, Loyal Legion’s ever-changing tap list has beers features the latest local brews as well as guest beers from across the country.
Day 2
9 am: A leisurely breakfast
Kick off the second day of your itinerary for Portland with a break from food trucks. Finch Restaurant at the side of the Royal Sonesta hotel dish up freshly cooked delights every morning. Divine eggs, succulent sausages and healthy muesli all make an appearance with the option to add on a cheeky morning cocktail.
10 am: Step back in time at Pittock Mansion
Built in 1914, Pittock Mansion is just ten minutes from Downtown Portland yet somehow feels as if you’ve left the city miles behind.
Travel tip: Bus 20 runs frequently from Downtown to W Burnside & NW Barnes from where it’s a 15-minute walk to Pittock.

Designed in French Renaissance style, Pittock was built as a family home for Henry Pittock, the London-born publisher of the Oregonian newspaper. He lived in the house for almost 5 years until his death in 1919, a year after his wife Georgina passed away.
The mansion has been beautifully restored and retains much of the original furniture. There are several interesting exhibits, including one on how the City of Roses got its name. Tickets can be purchased on arrival and there is a small gift shop which sells light refreshments.


1 pm: The beautiful Columbia River Gorge
Grab a quick lunch to go from Food Truck Park before embarking on a tour of the Columbia River Gorge. Running east along the Oregon-Washington border, a trip to the waterfalls along the Columbia Gorge is a must on any itinerary for Portland. See the spectacular Multnomah Falls which, at 189m, are the tallest in Oregon.

During your tour, you’ll get to see a number of waterfalls along the Gorge as well as historic lodges. The scenery along the way is unbeatable and a stark contrast to the buzzing streets of Portland.
5:30 pm: Riverside walks
Back in the big city, make the most of this itinerary for Portland with a wander along the Williamette River. On the west bank, riverside parks stretch the length of the city. With sweeping panoramas of the 12 bridges, the walk will be a slow one. Stop off at Mill Ends Park, the smallest park anywhere in the world.

6:30 pm: Dinner at Luc Lac
Over the years, thousands of Vietnamese migrants have made Portland their home resulting in a number of top-notch Vietnamese restaurants. Luc Lac is the best of the best. Start off by sampling their delicious Viet-street food style small plates before moving on to pho and bahn mi.

The drinks menu is impressive and their cocktail list is particularly strong. To be transported to South Asia, go for the Blood of Tiger, a delicious concoction of tequila, canh chau and lime.
8 pm: Visit the Pearl District
Once the city’s industrial heartland, no itinerary for Portland would be complete without a visit to the Pearl District. Recently rejuvenated and brimming with art galleries and boutique eateries, the Pearl District is living proof that Portland is a city on the up.
Make The Triple Lindy your final stop on your itinerary for Portland. This classic dive bar has always stayed with it. When Portland evolved from Bud Light to local crafts, The Triple Lindy evolved with it. Gone is the musky haze, that’s been replaced with handcrafted cocktails and fancy small plates. This may be a dive bar at heart, but in 2024, The Triple Lindy is about as Portland as Portland gets.
Share This Article

Traveling soon? Subscribe to The Insight below and get exclusive access to our personalized travel advice community via WhatsApp so you can ask all your burning travel questions.
Looking for the best comprehensive travel insurance? SafetyWing has you covered.
And for your eSIM in every country, there is only one option we recommend: Airalo.
Read more of our best insights from around the world