3 Days in Portland Travel Guide

3 Days in Portland Travel Guide

I couldn’t wait to write my Portland Travel Guide for you! This is half because we had a great time, but also largely because Portland wasn’t at all what I expected and I wanted to share my experience with you. Based on how media talks abut Portland and it being a major west coast hub, I expected it to be much larger. In reality, it’s a sleepy little city where it takes 10 minutes or less to drive anywhere you want to. By the middle of the first day, I had the downtown area memorized because it’s that small. Not a bad thing, but not what I expected. Good thing we planned a whole day outside of the city in the woods, or I would have gotten a little stir crazy.

My friend Justina and I visited for three days on a girl’s trip and this is what we did! I hope this guide will help you plan your own trip to Portland/Oregon.


We landed around 10:20, rented a car and drove to Hotel Monaco, where we were staying. This place is so freaking cute. Think fun wallpaper, bright colors, classy decor and dogs to make friends with because it’s a pet friendly hotel. The valet was super quick and we were in our room by 11:15pm. You can read more about Hotel Monaco here. We shared some wine and then headed out to grab a slice of late night pizza. Just the beginning of our food journey here in Portland.Portland Travel Guide Portland Travel GuidePortland Travel Guide


We woke up around 7am, grabbed some fresh coffee in the lobby and got ready for the day. We borrowed uber cute vintage-style bikes from Hotel Monaco and opted to explore the city that way for the morning. Vintage bikes are kind of tricky to ride the first time, but you’ll get used to it. They have about 7ish bikes and it’s first come, first serve, so make sure you claim one early if you want it. Our first stop was Blue Star Donuts, about 7 blocks down. Robin has been talking about Blue Star’s Bourbon Blueberry Basil donut for months now and I must say, the flavor lived up to the hype. They have outstanding donuts and frostings. I also tried the passion fruit with coco nips and holy cow! I’ve never tasted a more flavorful donut in my entire life. Voodoo is that famous place you always hear about, but every local knows their donuts look pretty, but don’t taste as good as Blue Star.

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After breakfast, we biked around the city for a couple of hours. We went to the base of Washington Park, looped down through the Pearl District to the riverfront, weaved through Chinatown and Downtown back to Hotel Monaco around Noon. The city is very peaceful and there wasn’t s many cars downtown as I thought there would be. This was great for biking – I didn’t really worry about getting hit by a car and when we got lot and had to stop in the middle of the road like idiots, it was fine. We took a little break at the hotel before heading out to lunch at Tasty n Alders, a restaurant on Alder and 12th street. For some reason, at 1pm on a normal Friday afternoon, the waitlist was over an hour. People here love to eat! While waiting for our table, we walked around the local shops and checked out the food cart squares. This city is all about their food carts — think a food truck, but in a permanent cart fashion, and hundreds of them dotted around the city. This is something truly unique to Portland and I loved it. We also stopped by Heart, a cute local chain coffee shop with the best spicy chia I’e ever tasted.

At Tasty on Alders, we just grabbed food, but looked like they had a great tap menu and wonderful sides to try as well. We got back to our hotel a little before 4pm and spent the next hour relaxing and getting ready for a night on the town. Hotel Monaco offers a free social happy hour to guests every day from 5pm-6pm, so when that started, we headed down stairs to start the night out with some free drinks. They have cocktails, beer, wine and bites plus a piano player to tie the whole mood together.

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For happy hour round two, we headed to the Portland City Bar Grill which is on like the 30th floor or something. As someone who loves drinking on tall places, this was a favorite of mind. I didn’t think we’d be able to find a table next to the window, but we lucked out and a couple was just about to leave and let us have their table. I recommend heading there closer to 4pm when it starts. Watch the sunset over the city and stay for the evening. They have jazzy piano music and a very classy, romantic vibe. Date night done right. Coming from San Francisco, I found their prices to be very cheap for a nice place- happy hour beers were under $5 and I got Mac n Cheese for $6. A steal! Afterward, we headed to the Whisky Library to try and sample some fabulous whisky in a fabulous spot. Sadly, they had a waitlist of 2 hours and we weren’t able to get in. We did stop by on Sunday and saw just how amazing the decor was.

By 8pm, we had realized that the Portland crowd is an earlier one then we’re used to. There was also just less people out than there would be in San Francisco. Because of this, the “west side” of Portland felt a bit dead to us. We hit up another cocktail bar, which was full of old people, then moved onto Kelly’s, a dive with motorcycles handing from the ceiling. This was more my scene-  cheap but good beer, tasty bar food, cozy booths and people watching. We ended the night at around midnight.


We were feeling bit hungover to be honest, so we moved a bit slowly on Saturday but our yummy room service at Hotel Monaco helped a lot. I got the eggs and chickpea cakes which was just what I wanted after a heavy night of drinking. I’d recommend trying their breakfast its least once when staying! By 10am we were out the door and headed out of the city for a drive in the wilderness. I detailed out exactly where we went HERE, so check that our for a recap on Mount Hood and Mulnotham Falls.

When we got back, we caught the end of the social happy hour and headed out to Ron Toms right away. This is a bar our valets kept recommending and was clearly a local favorite. And I don’t blame them. The inside is wide open with lounge seating, but the outside patio is the best. it’s covered and has fires going, so it was a cozy, which place to sip on drinks. Ron Toms was on the East Side of the river on Burnside street and this is clearly where the locals hang out. After drinks, we headed next door to grab pizza by the slice. Since we were in Oregon, where weed is legal, we wanted to check out a dispensary, but sadly we thought of it too late. Dispensaries close at 10pm in Portland, if not earlier, so if you are visiting and want to get lit, plan ahead.

We lifted for the night since it was raining, though we could have walked. It was about 1.7 miles from our hotel.Portland Travel GuidePortland Travel GuidePortland Travel Guide


We were craving a good brunch and headed out to Screen Door on the East Side around 11am. They also had an hour wait, so we wandered around the area and grabbed another spicy chia at the east side Heart coffee shop. The guy at Screen Door told us it would be at least an hour before we get a table and to check back then — we checked back a little before an hour only to learn they decided to move some names around and already gave our table away. And instead of putting our names right back on the top, we had to wait for another 3-5 tables before we got seated. This bothered us a lot, but the lesson is to not walk away from Screen Door even if they tell you that you can. I’m happy we waited even longer than we should have because I loved my brunch. I got the Garden Grits which were perfectly cheesy and savory. Justina had the oyster sandwich and it tasted so fresh. People around us were having the fried chicken and waffles. Be warned, this dish is meant to serve two people because it’s stacked with 3 HUGE pieces of chicken on top. Everything on the menu looked so great and is a place to go for southern food in the city.

Our next foodie stop of Salt and Straw, about a 5 minute drive from Screen Door. We opted to do an ice-cream flight and tired their olive oil, lavender, strawberry basil and brittle flavors. My favorite was the olive oil. You wouldn’t think it would be good, but it was!! So unique and nothing I’ve ever had before. They had fun Halloween flavors we weren’t brave enough to try, like the Dracula’s Pudding with real chicken liver in it. No thanks.

Afterward feeling even more full, we headed to the Japanese Botanical Garden which we’ve heard great things about. I’m going to be honest – it was beautiful, but really small. I don’t feel like it was worth the $10 to enter. We tried taking our time walking around it and it still only took about 25 minutes to walk around the whole thing. It was pretty in the fall with the changing leaves, but I imagine it’s drop-dead gorgeous in the spring with the trees blossoming. If you really love gardens and/or need to kill a half hour in Portland, then head to the gardens. If not, maybe save some money and avoid them.Portland Travel Guide Portland Travel Guide Portland Travel GuidePortland Travel GuidePortland Travel GuidePortland Travel GuidePortland Travel Guide Portland Travel GuidePortland Travel Guide Portland Travel GuidePortland Travel Guide Portland Travel GuidePortland Travel Guide

Since we were done a lot earlier than we expected, we headed to the Whisky Library to grab drinks before returning to the airport. And that concludes our Portland trip! I hope these detailed tips will help you plan your own trip to Portland. Please leave a comment below if you have questions or any recommendations to add!




  1. November 8, 2016 / 8:01 am

    Such a gorgeous guide. I’m actually heading to Portland tomorrow for a mini vacay. Bummer about the Japanese Botanical Garden; guess I can avoid it! :]

    // ▲ itsCarmen.com ▲

    • Kara
      November 9, 2016 / 8:03 am

      If you’re into gardens, you should still check it out! Just don’t plan on staying there for long.
      Have fun in Portland!


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