The Perfect 2 Days in Portland Itinerary
It had been 10 years since I set foot in eclectic, weird Portland and I have many fond memories of my visits there. However, Portland’s destination image has taken a major hit because of COVID-19, political violence, and public safety concerns over the last few years. This of course made me want to visit it even more (because I’m weird like that and love the underdog) to see how it’s changed, and how it has dealt with all the tourism blows. I planned 2 days in Portland to go back to some of my favorite places and to see for myself if Portland had lost its mojo.
When I think of Portland I think of its individualism, donuts, creators, food carts, and cute little neighborhoods. Did this Portland still exist? I would find out over the next two days…and even discover some new pieces to Portland I didn’t know existed!
Is Portland Safe to Visit?
Let’s jump right into it. I had a lot of people ask me if Portland was a safe place to visit. Somewhere along the line, Portland went from weird to scary in people’s eyes. It’s really unfortunate because Portland is a cute little city that is full of passion and promise. Sometimes – it’s just a little too much passion I suppose.
I understand how people got the impression that it might not be safe; the past few years it’s been in the news for demonstrations, riots, and homelessness (all things that many cities have struggled with since 2020). To many people, Portland appeared to be the epicenter of chaotic social and racial unrest. The area that was affected the most by this unfortunate image was downtown.
In an effort to dispel this idea Travel Portland ran full-page ads in the major newspapers in the US
It’s true – the only way to really understand what is happening in a place is to go there – so that’s what I did.
Here’s What I Found
A conference brought me to Portland, but I stayed an extra couple of days to just explore and experience the weird, wild Portland that I love. I stayed downtown and while there is definitely a homeless issue (similar to Denver), I still felt safe.
I walked by myself at night (even though some people warned against it) and just stayed alert – as you should do in any city. However, there were also plenty of rideshare options if you didn’t want to walk.
I was sad to see many downtown shops and restaurants closed, but I think every downtown city in the US is having those same issues.
However, my overwhelming observation was that during the pandemic, Portlanders raised their level of creativity; it opened the door to new chefs, creators, and makers with a resilience and drive that was exciting and energetic. Portland is as beautiful, colorful, accepting, tasty, fun, and weird as it ever was! I can’t wait to see how the city thrives in the post-pandemic world!
Perfect 2 Day Portland Itinerary
Now that you know that Portland is still wonderful to visit and is safe, what should you do? I focused my time on some old favorites – like donuts – and spent time exploring some new-to-me neighborhoods. I also tried some urban adventure which was surprisingly close to downtown. And of course, I ate…a lot…because Portland chefs are so incredible!
Map 2 Days in Portland
Day 1 in Portland
Morning – Donut Biking Tour
You might as well kick this vacation off right with an iconic Portland activity – eating donuts! If you are in Portland, you must get your donut on; after all the donut craze really all started here with the famous Voodoo Donuts.
I’ve always sort of wondered how Voodoo Donuts became such a phenomenon…I mean…it’s just donuts – but the key is – they are quirky donuts. The business actually started as a way to get around the liquor laws requiring any place that sells liquor must also sell food. So a couple of nightclub owners started making donuts in the kitchen that the nightclub was connected to. But what makes Voodoo great is the kitschy-ness of their donuts – and that’s been there from the beginning when the nightclub owners made ‘party donuts’ filled with things like Pepto Bismol and Nyquil to help partiers with their hangovers.
In an effort to feel better about eating delicious Portland donuts all morning, I took the bike and donut tour with Pedal Bike Tours. It takes you to 4 of the city’s most famous donut shops for a taste of Portland’s most delicious doughy delights!
Not only do you stop at Voodoo Donuts and get to skip the line for their famous bacon maple donut, but you also get to see how Portland has moved beyond the kitschy nostalgia donuts and has embraced all kinds of donuts. We stopped at a shop that specialized in mochi donuts, one that specializes in laminated donuts (think croissant dough…layers and layers of light goodness), and also at Blue Star Donuts. Blue Star was the polar opposite of Voodoo serving up high-quality concoctions worthy of any French bakery.
If you aren’t into biking, don’t worry, you can still sample some of Portland’s best donuts on an Underground Donut Tour
Each stop means another donut…which is exactly why I was thankful that I was at least on a bike and getting a little exercise! Not only do you learn about the spectrum and history of Portland donuts, but you’ll also learn all about the various neighborhoods and history of Portland as you bike through the different areas. It’s a great way to get a complete city tour of Portland…while also getting to eat donuts!
My guide even took some extra time to show me a neighborhood across the river with a bunch of really cool street art!
Pedal Bike Tours was a great operation with quality bikes and guides that had a love of biking – so it was a super way to spend a morning! The Donut tour was 3 hours and you will be on a sugar high when you are done. They also offer a general city tour and a brewery bike tour.
Lunch – Glisan Neighborhood
You will actually finish the donut tour around noon, and if by some miracle you are still hungry (how???) then I suggest you head on over to the NE Glisan Neighborhood along Sandy Blvd. Stop at Friendship Kitchen for some tasty Vietnamese food that will cut through all of that sugar you had all morning! You’ll find things like beef and cheese banh mi and bún bò huế, with a quirky and colorful cocktail menu leaning on Southeast Asian fruits and spices. Plus – they have a lovely outdoor space for some patio time.
Take a stroll around the NE Glisan Neighborhood and stop in at some of the little local shops. My favorite was Make & Mary. This mother-daughter-owned store will grab you from the sidewalk with its incredible aromas wafting from the store. Well – that’s at least how I ended up there! The beautifully designed shop focuses on holistic living, creativity, and community. Not only do they sell a number of tinctures, salves, and home décor; but they also have classes open to anyone who wants to get more in touch with their creative side.
Take a look at their current events and see if you can sign up for a class while you are visiting Portland – it’s a wonderful way to get even more immersed in the community! The classes range from tarot readings, tea events, fabric dyeing, and other wellness-focused classes.
Of course, if after morning biking and donuts and then lunch you just want to go back to the hotel and take a nap – I wouldn’t think any less of you! After all – you are on vacation!
Evening – A Cultural Dinner
I accidentally came across a colorful and cultural restaurant downtown as I was walking around called Dar Salam. The sign said they served Iraqi food which piqued my interest – it’s an ethnic food you don’t see that often.
I’ll admit, I was a little wary at first as the restaurant felt pretty empty thanks in part to the really high ceilings. However, as soon as I sat down and the waiter greeted me with a smile – the empty feeling disappeared I felt as if I had just walked into a warm middle eastern home.
I’ve written before about how I love the Middle Eastern people, they are some of the most welcoming people I’ve ever experienced in the world – and Dar Salam had somehow brought this feeling to Portland for me.
The Sahib Family owns and operates DarSalam, the first Iraqi Middle Eastern restaurant in Portland. The décor was fun, it transported me back to cultures I love. They had recreated a full wall mural of the famous Gate of Ishtar and its hanging gardens.
Ghaith, the founder, grew up in Bagdhad and was a refugee from the Iraqi War. After first living in North Holland in 2007, he then moved to Portland in 2010 where he has worked to share his culture with the community through food. He employs his entire family and has brought all of the family recipes with him.
The family struggled and worked hard to get through the pandemic – and they are still working through challenges with higher food costs, lack of employees, etc.
Not only is this a fascinating family-owned Iraqi restaurant, but the food was also incredible. First off I was giddy when I saw the Cardamom Gimlet on the menu. Cardamom is my favorite spice, and gin is my favorite liquor…I couldn’t imagine a better match! The waiter told me about how they make their own house-infused cardamon gin to make their Classic Gin Gimlet. I must admit – I plan on taking this ‘Iraqi family recipe’ home to Denver and making it myself!
This is classic Middle Eastern food made from the heart. It was SO GOOD! We tried the Mezze platter which had a little bit of everything; hummus, donut-shaped falafel, baba ganoush, and tzatziki with a choice of flatbread or raw veggie sticks. I also tried the shredded lamb platter with a delicious stewed chickpea dish.
I can’t believe I could eat more after a day of donuts, but Dar Salam is worth it. It brings the flavor – but most of all it oozes culture and hospitality.
Discover how to plan the perfect weekend in Portland, Oregon with these tips from a local
Day 2 in Portland
After all of that sugary goodness yesterday – today is all about cleansing. After all, you have to treat that body right! And today’s plan will also have you working off a few of those donuts from yesterday starting with a morning spent downtown.
Morning – Tea Time
I didn’t know about Smith’s Tea before coming to Portland. However, there were a few packets of them in my hotel room and I was intrigued by the beautiful packaging as well as the flavor mixtures. Upon trying it before bed…I was hooked.
Then I found out that Smith’s Tea is a Portland company with an interesting background. Founded by Steven Smith (original founder of Stash Tea which sold to Starbucks) started a 2nd tea company that focused on small, quality batches. “I have an idea for another tea company. But this time, we’re going to do it small and buy only the best tea on the market and blend it with total transparency in our hometown of Portland, Oregon.”
There’s a Smith’s Tea shop right downtown where you can try and purchase a variety of flavors. In addition, there is also a Smith’s Tea Café for a complete tea experience where they weave tea and food together. This new tea experience opened in 2021 at NW 23rd at Glisan in Northwest Portland.
Books, Books, Books
Take that tea to go and walk on over to Powell’s Books, the largest independent bookstore in the world, it is hard to pass up this behemoth of the shop when in Portland. However – don’t go into the bookstore if you are short on time. One, it’s easy to get lost in there, but two…there’s so much to look at and grab your attention – it’s overwhelming. I had to remind myself that I didn’t actually read books…else I would’ve walked away with at least 6!
If you are a book lover – plan to spend all morning there!
Shop Local and Support Local Makers
The light, bright airy displays caught my eye and drew me into Tender Loving Empire – a local gift shop highlighting local artists. This artist collective brings jewelers, printers, sculptors, apothecaries, painters, and rockers together in a beautiful display of Portland creativity.
As it started to rain I hurried my way to Ramen Ryoma – a classic and well-known ramen joint downtown that had been recommended strongly. Ramen Ryoma restaurant was simple and so delicious. They have classic offerings, including corn butter miso ramen, spicy umami ramen, and Japanese-style curry. But be sure to consider one of their specialty bowls of ramen. I had the Tamago Mayu Ramen; perfect for a rainy, chilly day!
Afternoon – Hiking in Forest Park
It’s time to get some exercise…out of downtown and into nature. I hopped in an Uber to go meet Around Portland Tours guide Sarah at Forest Park. To my surprise, it was only a 10-minute ride from downtown Portland and I was in a dense green forest.
Portland is not just a good biking city – it’s a fabulous hiking city…yes…hiking. I was expecting a city park, but what I got was real wilderness. The park is eight and a half miles long by about a mile and a half wide AND there is 80 miles total of trails! I felt like I was in another world. This wasn’t some city park…this was proper hiking, streams, and challenging terrain…and the trees…the trees were incredible.
We experienced sunshine, blue skies, rain, downpours, and even sleet over the course of our 3-hour hike…it was crazy…thank god for layers! Here are the layers I recommend for trips like this.
Krimson Klover Leggings
Clamber Hiking Pants
Krimson Klover base layer shirt
Marmot Rain/Wind Jacket
Fjallraven Pack Down Hoodie
I did a challenging and beautiful 5-mile hike with Sarah from Around Portland Tours. Sarah started the company 4 years ago and survived the pandemic with the government programs and a switch from tourism to bike repairs. Thankfully – she was able to keep afloat. I think it’s important to recognize that the government programs did help people – all too often we only hear of the people who abused the system and not enough good stories about the financial assistance.
She was born and raised in Portland – and I think that’s her special sauce. Sarah understands the city, knows the history, and has so many fascinating stories to tell. She helped me understand the activist history in Portland – it was fascinating to hear how that culture came about.
Sarah also provided the history of the park and how it was saved from logging, as well as told me stories of witches! The witch ‘castle’ was probably my favorite. We then hiked up, up, up to Pittock mansion to get the best views of the city.
We wrapped up our hike in the rose test garden in Washington Park, where Sarah told me the story of how Portland became known as the Rose City. This was a fabulous way to spend an afternoon in nature while also learning about Portland’s history from a local. Make sure you check out all of the Around Portland Tours offerings to find something that resonates with you if you aren’t into hiking.
Evening – Portland’s Restaurant of the Year
Time to get cleaned up and go out on the town for your last night in Portland. Why not go big and make a reservation at Portland’s 2021 Restaurant of the Year (via the Oregonian) – Magna Kusina. Owner and mastermind, Chef Carlo LaMagna, has introduced Portlanders to delicious Filipino cuisine in an elevated way.
One of my favorite things about travel in the Philippines is the street food, and Chef Carlo has taken it and introduced it to fine dining in his new small, cozy restaurant in the SE Division neighborhood. As soon as you walk in the door you feel welcome as if you’ve walked into a Filipino home oozing with typical Philippine hospitality. It was bright, laid back, and full of charm. I was able to sit at the bar where I could get a good view of all of the action in the kitchen and bar area.
Chef Carlo managed the kitchen like a casual conductor with a permanent smile on his face. He and his head bartender would joke around and I even caught them dancing and lip-syncing to the super fun 80s music that filled the restaurant.
This was no stuffy restaurant experience that you might expect from a chef who was named one of the Best New Chefs of 2021 by Food and Wine Magazine.
You might wonder what food from the Philipines is like – it’s not light. But they do play with a bunch of flavors that you may not be familiar with – starting with their cocktails. Drinks with tamarin and ube…playing off of classic flavors from the Philippines.
The food is meant to be shared – so plan on ordering a few snacks and mains for sharing with your group. Whatever you do, don’t skip the Lumpia (Philippino spring rolls – my fav!), and the Sisig – crispy pork bit with onion and chili, topped off with a poached egg that oozes goodness! The heat of the food was warming and so was the atmosphere and attitude of the entire cooking team.
Late Night Cocktail
Enjoy your last night in Portland with a special nightcap at Abigail Hall downtown. Located inside the Woodlark Hotel, Abigail Hall is an intimate cocktail bar full of history. The living-room-like bar is in the historical ‘women’s lounge’ where women would get together and talk politics and equal rights. Abigail Hall is named after Abigail Scott Duniway, Oregon’s “Mother of Equal Suffrage.”
The cocktails were so incredibly inventive – and many had a tea infusion of some sort that gave it a really unusual, but familiar flavor. Each was served in a vintage cocktail glass that took you back in time. I felt as if I should be conspiring with my fellow women patrons around me about women’s representation!
Be sure to try the Oolong Sazerac which includes an infusion of Oolong tea. This way you started your day with tea, and ended your day with tea!
I happened to be there during women’s history month when they had just put out a special cocktail menu in honor of women. Also, make sure you check out their Sunday high tea service! It’s said to be a little bit classic, and a little bit saucy, just like the women who inspired the cocktail bar. You’ll get a selection of classic savory and sweet snacks, vintage teacups filled with Smith Tea steeped at your table, specially crafted tea-themed cocktails, and a rotating playlist that features strong and prominent female performers.
For more ideas on things to do in Portland, check out these Get Your Guide popular Portland tours:
Portland Travel Tips
Where to stay in Portland
I stayed at Hotel Lucia – a great location and a beautifully designed hotel downtown.
Hotel Lucia was the perfect home base for my Portland weekend. The design of the lobby and rooms was so fun and packed with interesting art. In fact, the hotel has the world’s largest permanent collection of black-and-white photographs by Pulitzer prize-winning photographer and Oregon native, David Hume Kennerly. It was sort of like staying in a super cool museum where I found myself wandering the halls just to look at the collection!
Built in 1909 as the Imperial Hotel, this boutique hotel, listed on the National Register of Historic Places, was once where Eastern Oregon cattle ranchers congregated when they came into town.
True to its historic status the Bathrooms are small and water pressure is a little variable – but I personally feel like that’s the charm of a historic building.
The décor of Hotel Lucia was the star. Enjoy simply wandering the halls and looking at art. And it’s a hotel where you don’t even mind spending time in the lobby! Plus they have a daily complimentary craft beer and cider hour highlighting local brews…don’t miss that!
Read Hotel Lucia reviews on Trip Advisor | Book a room here | More hotels in Portland
Map of Other Portland Hotels
How to get around Portland
Uber and Lyft were plentiful, but you can also easily get around on a bike or by using the trolleys there very easily and economically. Or – of course, you can rent a car if you’d like to take some extra days and do day trips outside of Portland along the Oregon Coast. When I travel, I find the cheapest rental car rates at RentalCars.com. Check out their prices and compare.
Best Time to Visit Portland
Of course, the summer is lovely there; it’s green and lush. I went in early March and even though it was chilly – it was still very green – as you can see from my pictures of Forest Park! It’s the Pacific Northwest – so expect it to be moody and rainy at times at any time of the year.
What to Pack for Portland
I will admit – the weather during my 2 days in Portland was all over the place – which is why you’ll definitely want to pack layers at any time of year. And be prepared for rain; a good rain jacket in Oregon is always recommended. You’ll also want a good walking shoe that you can also take hiking; the Oboz Arete is my favorite in that category of city/hiking shoe. Don’t forget to bring your own water bottle to refill and a small daypack to bring with you for light hikes or biking.
Marmot EVODry Torreys Jacket
Great for a wind and rain barrier as a top layer for your adventures. EVODry Torreys Jacket offers the weather protection you need for unpredictable days and the lightweight breathability you want in a high-performance shell. I always have it with me in my pack.
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Oboz Arete Travel/Hiking Shoe
These are the perfect shoe for traveling. They are nice enough to wear out in a city, and provide enough support to walk around all day and even do light hikes. I love it when a product can serve dual purposes for travel and this Oboz Arete does it. I take mine on every trip!
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05/25/2022 12:14 am GMT
Overall, the city was a bit worn from the last two years, but it certainly appears that it’s ready to come back! I had an incredible solo trip there enjoying all of the colorful street art and trying the new up-and-coming restaurants that made it through the pandemic. It was clear to me that one thing this city will never lose is its creativity and passion. This summer is a great time to visit Portland and enjoy the city and all of the donuts, urban adventures, shops, food, and cocktails it offers!
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