Where can our companion pass take us next? Yes, Portland

It has been about 6 months since I first discovered travel hacking as a hobby. I’m surprised that a bargain-loving traveler like me didn’t figure it out sooner.  Even though the first part of this hobby has consisted of feverishly earning miles and points, we are already reaping the benefits with our Southwest Companion Pass. It’s going to let us travel around the US for the next 18 months for nearly free.

I’ve always wanted to travel to Boston, Philadelphia, and Atlanta but once we got the Companion Pass, the options seemed limitless. I stared at the Southwest route map on many occasions and reconsidered many places that are now much more affordable.

We took a trip to Chicago a few weeks back and decided to make Portland our second stop.  To tell you the truth, when I first picked Portland, I had no idea what to expect.  I figured it would be a second-rate Seattle.  But after a fantastic weekend (partially thanks to the wonderful weather we experienced), we’re completely sold on the city and love it even more than Seattle (which I think is fabulous).

Upon seeing all of the flannel-wearing, PBR-drinking, tattooed people, Henry was already thinking of how he could move there.  These Portland “hipsters” seem more genuine in their lifestyle than LA hipsters who are ironically trying to fit into this independent subculture. Anyway, once Henry found out that Portland gets even more rain than Seattle, his dreams of becoming an Oregonian were shattered.

All in all, we had an incredible vacation full of memorable moments. The first thing we did after leaving the airport was to head for the good food. It’s a good thing Henry loves to eat just as much as I do.

Our first stop was the incredible Waffle Window. For $4-$6, you can choose from an assortment of creative waffles. We had the 3B’s (Bacon, Brie, and Basil) the first day and returned the second day to try the Blueberry Cheesecake Waffle (amazing!!).

The Waffle Window

The Waffle Window

Next, we stopped at a couple of food cart pods and ate our way through those.  We have food trucks in LA but Portland has food carts. They’re smaller and probably cheaper to start up and they’re usually organized in pods throughout the city.

Food cart pod

Food cart pod

Eventually, we even made it to the famous Voodoo Doughnuts. It took 3 attempts.  Even though it’s open 24 hours a day, it always had a line.  I did enjoy the Bacon Maple Bar but the other “naughty” donuts didn’t really get me excited.

Henry has an obsession with Chinatowns; I don’t know what it is but he loves to check them out in every city he visits.  Portland’s Chinatown is particularly depressing. Even in the middle of day on a Saturday, there was no one walking around. No tourists, no Chinese people…well…no other Chinese people if you don’t count us.  It is, however, home to one of the few Chinese gardens in North America and it was built by the team from China who also did the garden at the Huntington Library.

Entrance of the Chinese Garden

Entrance of the Chinese Garden

By the Chinese Garden

By the Chinese Garden

Chinese Garden

Chinese Garden

We checked out the nearby Portland Saturday Market; full of holistic healers, hippies, and all of the other characters that keep Portland weird.  Benjamin was very popular there; as he usually is everywhere he goes.

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