Welcome to Downtown Portland

Never has there been a more unfortunate collision of weekend chaos, pedestrian congestion and Google Maps-induced road rage.

Downtown Portland welcomed us with open bridges. As we cross over one of the giant iron arches, tall buildings reached out of the beautiful landscape to say “hey, you made it, have a cool view.” Both sides of nearly every sidewalk seemed to be dotted with trees while the general style of the area was something straight out of a Pinterest search. Gorgeous views typically reserved for historic streets and buildings in tiny towns grabbed our eyes from every angle.

Then, the streets went one way.

For a chic that’s never driven in a town with street cars or light rail, I feel like I’m owed a bit of forgiveness. None-the-less, the combination of the crazed Google Map girl nagging “turn left, turn left, turn left, turn left” combined with unforgiving one ways at every intersection, streets full of packed cars, bustling pedestrians and those creepy “they’re going to run us over” rails in every street — I was beyond overwhelmed. Oh – and the street cars have their own weird go lights? What is that?! We’d entered downtown in the busiest time of a Sunday afternoon with zero idea of where we were going, only that we wanted to be near there. The result was mass confusion, lots of frustration and maybe a few tears.

Meanwhile, Derek snapped this:

Who’s the photographer here?

The morning’s wet-wipe bath wasn’t cutting it anymore. While we were no longer hangery, we both wanted to be clean, in fresh clothes and chugging some stiff drinks. The lack of any of those things was taking a turn for the worse. Our planless plan was catching up with us quickly and we hadn’t even started trying to find a place to stay.

A quick Google from a shockingly vacant lot in which we were probably illegally parked revealed that most downtown hotels were going to run us about $200 for the night. I’m cheap and that didn’t seem reasonable. Not knowing the rest of the week’s plan, being a bit more thrifty with our first night’s expenses couldn’t hurt. So, I turned to Hotwire.

Hotwire offers a pretty interesting service that could essentially be billed as hotel roulette. While it doesn’t require last-minute booking — waiting until the last minute can actual score you some awesome deals on amazing locations. The catch? You don’t know what you’re getting.

I entered the date — just one night — and the location that I needed a hotel in. In this case, “downtown Portland” included several blocks at the heart of the city along the Waterfront Park, Pearl District and more. Multiple listings popped up and I opted for one around $96 that claimed to be a 64% savings. Derek didn’t trust it. I blindly booked anyway.

Seconds later, we had a reservation…with a Pineapple hotel.