Travel Diary: 2 Days in Portland


As I mentioned in my San Francisco Travel Diary, we spent one day in San Francisco and two days in Portland when we were on the West Coast back in October. Both cities were a lot of fun and each had its own vibe. But Portland? It’s definitely unique. The slogan “Keep Portland Weird”, which can be seen plastered on the side of buildings and bumper stickers, seems very appropriate. I can kind of see where some of the inspiration behind Portlandia came from. When I say that, I mean it in the best way possible. Portland is home to many local bars, restaurants, and shops, each one with its own personality. There were not many chains, which made sampling the local fair even more fun and interesting. Here’s where we stayed, ate, drank, visited, and shopped.


Where we stayed

We’re slowly becoming Airbnb pros. This time, we stayed in one of the rooms of a beautiful historic house. We had a private bathroom and kitchenette with a microwave and small fridge. The house is located right in Nob Hill and within walking distance of the Pearl District, a fun place to shop and eat. I don’t think we could have chosen a more perfectly located place to stay at such a great price.


Where we visited

One of the must-see attractions in Portland is their Japanese Garden. According to the website, it has been described as one of the most authentic Japanese Gardens outside of Japan. Simply walking through will definitely make you feel more at peace. Every tree, bush, and stone seems to contribute to the beauty of the setting around you. We especially loved the Strolling Pond Garden, complete with waterfalls, bridges, and coy fish, and the calming effect of the Sand and Stone Garden. We were so lucky to visit during the fall when the Japanese maples were showing off their vibrant reds and oranges.

After our visit, we meandered over to the Rose Garden, which is right across the street. It’s a free attraction located in Washington Park that contains more than 10,000 individual rose bushes and 610 different rose varieties. It’s amazing because with that many varieties, it’s not just red and pink roses. You start to see color combinations you wouldn’t expect like blue and purple. I found myself taking photos of the name plates just so I could remember my favorites. Nestled at the far side of the Rose Garden is the Shakespeare Garden. It’s walled off by brushes and shrubs, making it the perfect place to get away and enjoy a good book or sonnet.

There are of course many other attractions to enjoy, but because we only had two days, were limited in what we could do. One of our Uber drivers recommended visiting one of the many strip clubs for dinner and a show. Apparently that’s a thing in Portland and apparently the food is very good and affordable. He also recommended visiting one of the many cannabis shops. We were not that adventurous!


Where we shopped

The Pearl District is a great place to get started on your shopping endeavor as it is home to Powell’s City of Books, a store with nine different rooms and 3,500 sections of books. It seemed endless and overwhelming, but definitely an experience worth having. This area also features many other local shops like Portland Gear and dfrntpigeon for cool Portland wears as well as a variety of furniture stores and outdoor gear and clothing shops. There’s a Toms Shoes and a lululemon for those looking for something a little more mainstream. As much as I love all of the independent shops, I still love to visit my forever favorite store to browse: Anthropologie. The one in Portland’s Pearl District is one of the biggest Anthros I’ve ever been to. It has a second floor, giant sale room, and an entire section devoted to their BHLDN line.

NW 23rd street in the North West District is maybe one of the cutest stretches of street in Portland. Every shop is independent and they all sit right next to each other in a tight little row so perusing each of them can be done in a few hours. The street is also dotted with cute coffee shops, bars, and restaurants to give you many options for shopping fuel. I especially loved Blush Beauty Bar and Will Leather Goods.


Where we ate and drank

Portland is a great place to visit if you love beer and coffee. It’s home to more than a few breweries and coffees shops. We visited Rogue Pearl Public House and Deschutes Brewery and had a great time sampling the beers on tap and yummy pub food.

If you’re looking for a bar, restaurant, hotel, or theater with a lot of character, I would highly recommend checking out any of the family-owned McMenamins venues. They specialize in renovating historic buildings and transforming them into these entertainment spaces. They also have their own breweries. We tried Blue Moon Tavern and Grill for lunch and Ringlers Pub at the Crystal Ballroom for drinks and had great experiences at both.

Our one fancy dinner of the trip was at Jake’s Famous Crawfish. The menu is filled with classic seafood dishes and the restaurant is dripping with old-school charm and sophistication. One of our favorite dishes was their seafood sampler. I think I hogged all of the oysters and shrimp to myself, and I have no regrets.

We ended our stay in Portland with a drink and great view of the city from 30 stories up at the Portland City Grill. If you’re lucky enough to snag one of the booths along the window, those are the best seats in the house.


Portland is a low-key cool place to visit. It has a lot of character, socially conscious businesses, and some very unique experiences, but it doesn’t take itself too seriously. If you are ever on the West Coast and have the time, I would recommend stopping. Our flight from San Francisco to Portland was only $50!

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