With my boyfriend doing an internship for a few months this summer in Chicago, I didn’t really feel much of a need to leave the city.  That being said- the minute he went back to law school, I was looking up flights to my next destination!

Since I had a holiday weekend over Labor Day, I decided to go visit my friend Jake in Portland, Oregon.  I had visited him a few years ago when he had first moved there and loved it so much that I knew it wouldn’t be my last.

Honesty time- I have been feeling a lot of anxiety lately between changes at work, life decisions and new friend dynamics which led me to have a mini panic attack before boarding the flight.  However, I called some of my favorite people who reminded me that life is for the brave and if you don’t get on the plane now, you might never get on.

Needless to say, I boarded the flight and ended up having a spectacular time in Portland!

Ever since I visited my 2 best friends abroad I have loved traveling to destinations where my friends live.  It is so much more fun to live like a local and hit up all the best restaurants, shops and bars and skip all the boring sh*t that everyone’s seen on Google.

However, if you don’t have a couch to crash on- I totally recommend checking out Airbnb.  What I love about Portland is everything is so unique and one of a kind.  Each small shop, restaurant and art gallery is thoughtfully curated and done with passion.  <3


After tossing down my carry on and splashing some cold water on my face, it was time to hit up the “big city.”  My friend Jake who goes by Jame was performing with his band at the bar Firkin Tavern.  Since I hadn’t eaten all day due to my anxious mind, I was feeling like I could eat a house.  So while he was doing his mic check, I went down the street to get some food at Virtuous Pie.

Needless to say I did NOT know it was a vegan pizzeria until I was halfway done with my personal pie.  Being from NY I can be kind of a snob about good pizza and let’s just say that cashew cheese wasn’t foolin’ anyone!  But after I got over the initial shock and doused it in sriracha it was actually pretty good.  🙂

I was blown away by my friend’s voice and if you haven’t already, you should definitely check him out HERE!


After a night of some *light* partying,  brunch was definitely in order.  We ended up getting a table at the super cute restaurant Milk Glass Market.  I ordered the bacon and egg cheddar biscuit and we got some focaccia and snack eggs for the table.  YUM. 🙂

Once breakfast was finished we decided to partake in a few of my favorite activities- looking at plants and thrifting.  🙂

First we hit up Solabee which had been on my to-do list since my last visit to Portland.  It was soo cute but luckily for my bank account I didn’t live around the block or I would have spent all my money there!

We then hit up a few thrift stores on Sandy Blvd- Hollywood Lux Blvd and Rerun2 🙂

My friend Jake, like myself, loves his pet cats.  He was invited to this Facebook event titled “Caturdays in the Park” in which case I thought, “When in Rome…”

Side note: Another thing that I love about Portland is the weather.  Every morning it was about 55 degrees and by 6 pm it would get up to 75!  So so perfect.

The cat event was in Laurelhurst Park which was so stunning!  It is the perfect place for a picnic or afternoon nap.  After getting lost in the park for a bit we came across the group of about 8 people awkwardly holding their pet cats in a circle.  It was perfect.  <3

After Caturday’s we got some some delicious Fro-Yo from Nectar.  If you go there, definitely get the banana flambe!

We almost headed home after that but we decided to go to the Lan Su Chinese Garden and I am so happy we did!  The designer of the garden built it so that you wouldn’t feel like you were in the middle of a city and I seriously felt like I was in a different country.  From the gorgeous koi fish to the stunning architecture, it was the perfect afternoon stop!

We were pretty exhausted after our long day so we decided to head back to the apartment, regroup and take a nap.  🙂

Once we were well rested we changed our clothes and went out for drinks to Jackknife where I got the cocktail- Oaxacan National which had Los Javis Mezcal, Pineapple Gomme, Lime, and Apricot.  I am a sucker for anything with pineapple and mezcal so it was obviously delicious.  We also went to Shift Drinks which was another awesome cocktail bar!

Drinks and cocktails in Portland typically range from $4 to $10 which is UNHEARD of in Chicago!


We called it an early night and woke up extremely refreshed and ready to take on the day.  First we headed to St. Honore Boulangerie where I got the most incredible vegetarian quiche!

After breakfast we stopped at the market and got some more cheese and bread to bring with us to the Vineyard we were heading to!

P.S- I highly suggest renting a car if you don’t already have one while you are there. 🙂

The Vineyard we went to was called Maysara and it was possibly one of the most gorgeous places I have ever been.  The Vineyard is family owned and is 146 acres full of pinot grapes!  The wine was delicious and I seriously felt like I was in Italy.

After we tried 7 of the seasonal Pinot Noirs we got back in the car and headed to the Coast.  When I pictured “the Coast” I pictured a beach with people tanning in their bikinis and swimming in the water like they do in California or the Jersey shore.

Turns out it wasn’t like that at all.

The temperature is about 10 degrees cooler and the water is freezing cold.  Everyone on the beach was wearing jackets and NO ONE was in in the water!  But once I understood that’s how it is there, I quickly realized how beautiful it is.

Look familiar?  Have you ever seen The Goonies…

Jake’s family friend had an apartment on the beach that she let us stay at and it was soo gorgeous and literally steps from the water!  The sunset was magic.

After we had a delicious seafood dinner we watched a movie and waited for the sky to get completely pitch black which happens in Oregon around 12 am.  Being from New York and living in Chicago, I had never really seen a starry night.   It was unbelievable!  Sitting on the beach at night and looking up at the huge sky full of stars was bliss.  I even saw my first shooting star! 😉


We woke up and made a family sized brunch right away.  After that it was time to enjoy my last full day in Oregon!   We spent most of the day hanging out on the beach and hitting up the local stores in the town we were in which was called Rockaway.  It’s about a 2 and a half hour ride to Portland so we were in no rush to get back to city life.

After we got some fresh salmon for lunch we packed the car and headed back to the city.  My flight was at midnight and I knew there was one place in Portland that I had to go before my trip was over…

For those of you who do not know, Salt and Straw is one of Portland’s most famous ice cream shops that usually has an hour long wait.  The line stretches around the block at any given time because they let each customer try as many flavors as they want!

The flavors are pretty out there and include ingredients such as bone marrow, olive oil and blood sausage!  It may sound weird but I personally love things like that and the flavors are so good when paired with the right things.  I ended up getting Peach Vanilla Bean Crumble and Strawberry Balsamic Glaze and it did not disappoint!

So- there you have it.  My full guide to Portland!  For those of you who made it this far, congratulations.  I hope this post inspired you to buy that plane ticket and head out West!

Ciao for now,


You may also like

Leave a Reply

Your email address will not be published. Required fields are marked *