22 Hours in Portland, or an Exercise in Improvisational Travel

My default mindset for travel (and perhaps in general) is a structured one. A case in point would be my family’s recent mini-vacation to Vermont. Leading up to our trip, I studied Vermont maps, researched possible destinations, and drafted a spreadsheet-style itinerary with addresses, estimated driving times, etc., all customizable based on weather changes.

I “mixed it up” yesterday on my one-day solo trip to Portland. Aside from getting a handful of personal recommendations, I decided I would “wing it” with the 22 hours I would have in the city. It took some effort to figure out the city layout and transit system, and I had a couple moments of self-doubt — (“am I skipping out on something I should be seeing?”) — but in the end, I left Portland satisfied, and I gained a dose of confidence in my ability to wander, or to go unscripted. It was an exercise in forced spontaneity, which is something I’d like to try more often.

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