Portland: Attempt One

Before I visit a new place I often get travel ideas/get giddy by talking to people I know who have already visited my destination. I become obsessed with reading online city guides and scrolling through bloggers’ trip summaries. I get a sense of things to do, “it” places to go, and ways to wander off the beaten path. Sometimes, this preparation pans out really well. Other times, the intoxication of overly positive nostalgia and gorgeously curated guides set me up for unrealistic expectations. I must admit, I definitely have a tendency of building up most things up in my mind, not just trips. Things can end up going more or less how I imagined, but, more often than not, life and all its unfiltered and unexpected glory leads to the hilarious, imperfect, and therefore memorable. Such was the case with my first “vacation” since having Frankie.
My husband, son, sister, soon-to-be-brother-in-law, baby niece, and I all made the trek to the “City of Roses” with the naive intention of a picture perfect weekend (or at least my naive intention). Things quickly shifted. It rained the entire time we were there. (Coming from Vancouver, rain is something we can generally handle, but it can sometimes be tough to take when on holiday). For some reason, despite Portland being a bike and transit friendly place, we walked EVERYWHERE, with babies in strollers. What were we thinking?! We stayed in a classic Airbnb that was Gatsby themed, came equipped with a fish tank overlooking the master bed, and a Jesus statue overlooking the hot tub (apparently the building was formerly a church?)
We sort of saw the sights: I managed to take a photo of Voodoo donuts, but we didn’t actually manage to eat Voodoo donuts. We wandered through one of the Powell’s Books, but didn’t manage to take a tour of the famous flagship store. Oddly enough, one of the biggest highlights of the trip was my husband taking a picture of my sister and I that we both agree is ugliest photo we have ever seen of either one of us (she hasn’t given the go-ahead to share that pic). It warms my heart whenever I look at that photo because it reminds me of how fun and funny a travel fiasco can be.
We have agreed there will definitely be a second attempt. Our hope is to do/see some of the following places:
And if we go in September, it’d be incredible to see this:
Any other suggestions?

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