Keep Portland Weird

We planned a trip to Portland for my mom’s 60th birthday because we wanted good food and wine and to visit place we have never been.  It was the perfect long girls weekend and we loved the experience!

We rented a car from the airport so we could drive to Astoria and Cannon beach to see all of the Goonies sites and visit the adorable towns along the way.  We could also use it to drive from the airport to our Airbnb in downtown Portland which was a plus.  We stayed at an Airbnb owned by a James Beard award winning chef and above his restaurant and bar in downtown which was perfect as we could walk to everything and it had free parking. The drive to Astoria was beautiful with all the Fall leaves changing color and the trip would have been worth it just for that scenery. They have a great brewery called Fort George you should make a stop at and a column you can climb up to see the views. It is an hour and a half drive and then from Astoria to Cannon Beach it is 40 minutes.  Have the dungeness crab at Wayfarer in Cannon Beach where you have a beautiful view of the ocean and can walk to the beach where Goonies was also filmed.  Here are the top Goonies sites to visit.

Willamette Valley

We wanted to make my moms birthday extra special and a big part of the reason we went to Portland was to try all the Pinot Noir Willamette Valley is famous for.  We booked a Tesla wine tour which I would highly recommend.  It was one of the more expensive tours but the Tesla added to the experience as it had carpool karoake which was really fun after all the winery tours. You could always visit the area yourself with a designated driver too. All of the wineries we visited were on top of narrow hills so I wouldn’t have wanted to drive.

We started the tour with a cupping experience at Caravan coffee where we learned how they make coffee as well as produce special blends. We then went to lunch at Rosmarino Italian food which truly tasted like you were in Italy. The chef is from Northern Italy and kept to his roots.

We chose this tour with Dr Corwynn Beals because it is custom and private, visiting boutique and hidden gem wineries. He was born and raised locally in the Valley and brings deep knowledge of the area and wine to enliven our experience. He took us to very unique wineries and you could tell each and every wine maker was extremely passionate about what they do.  These were not the big box popular wineries so we were able to meet the winemakers, owners and have a truly personalized experience.

This it the tour we chose and it was perfect.  Keep in mind when you do budget that it doesn’t include tastings, lunch or all the wine you will inevitably buy. This was the highlight of our trip and our guide did not disappoint!

“The unexamined wine is not worth drinking.”

— C. Beals


The last few days we spent were in Portland and it was one of my favorite places for culture, food and funky people. Here are a few highlights from our trip to Portland:


  • Brunch is HUGE in Portland.  Expect a line but it will be worth the wait. I would recommend checking out Tasty and Adler, Screen door, Jam, BeSaws and Breakside.
  • There are a ton of Asian inspired restaurants. We LOVED Pok Pok however I don’t think you can have a bad meal in Portland and Yelp and Thrillest has a ton of recommendations.
  • Make sure to stop at Voodoo Donuts and Blue Star Donuts



  • There are tons of breweries as well as distillery row. I would recommend Breakside or Ten Barrel Brewery rooftop if it is nice for breweries.
  • Teardrop cocktail lounge had amazing drinks!
  • Pepe Le moko- espresso martini is fantastic at this speakeasy style bar
  • Heart Coffee and Never were our favorite coffee shops with a great flat white

To Do:

  • We LOVED the Alberta Arts District which had a ton of clothing, art and jewelry shops as well as restaurants, food trucks and an amazing ice cream shop with wild flavors (Salt and Straw). Stop by the Kennedy School after which is an old school that every room was turned into a different type of bar or restaurant and the classrooms are hotel rooms. The detention room is a whiskey bar and home room is a cocktail bar. I would stay there one night next time I go. They have a great soaking pool you can bring your drinks to.
  • Portland Mercado (foster & powell)
  • First Thursday Art Galleries Pearl & Old Town/ Chinatown
  • Saturday and Sunday they have a fantastic farmers market to walk around to find clothes or jewelry
  • If we had more time we would have driven to Mutomah Falls which is supposed to be a nice hike and beautiful falls

Whatever you do in Portland, you don’t really need to plan. It is an early night type of place and very casual. No need to dress up or make reservations. It is a great place to explore!

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