Sometimes I wonder what it would be like to live somewhere else. I’ve lived in San Francisco for almost 20 years and I absolutely love this city, so it’s hard to imagine what this life would be like. Where would I go anyway? Would I still be able to do Broke-Ass Stuart? Most importantly, would there be good burritos?

Somehow, over the past 10 days, I’ve had a chance to explore this concept.

To celebrate full vaccination, Kayla and I decided to take my parents on a road trip through Northern California and Oregon. They pulled up from San Diego in late May and we got in the car. First stop, Humboldt County.

One of my best friends from junior high and high school has lived in Arcata and / or Eureka since college, so it was a great place to stay for a night. Wedged between the sea and sequoia trees and speckled with fog, these small towns are charmingly picturesque and yet lively. My buddy Jon and his wife, Amy, built a great life for themselves, becoming small business owners and highly dedicated members of the local community. Your hotel / bar / cafe, the Humboldt Bay Social Club, became a serious community hub during the pandemic, partly because of the atmosphere they created and partly because of the huge outdoor space your kids can frolic in while you eat delicious things and drink.

Recently, Jon and Amy teamed up with one of Humboldt’s biggest cannabis brands to bring what may be the next big thing in cannabis tourism and hospitality. Papa & Barkley Social is a luxury day spa, pharmacy, consumer lounge with a food truck on site. Concepts like this could be the future of cannabis culture in California.

After spending about 24 hours in Humboldt and seeing what a cool, blooming life my friends lead there, I thought about what it would be like to live there. The area is beautiful and the people are nice and friendly. I was also very impressed with the innovative thinking in the emerging cannabis industry. It could definitely be a great place to build a future. Even so, I knew it was too small to ever settle in there, and I didn’t have that electrical zeal that keeps San Francisco flowing through my veins.

Next up was a visit to my mother’s oldest friend outside of Stayton, Ore. They live in a rural area with breathtaking views and plenty of space for their horses. It was a nice, relaxing place to spend a night, but I never imagined ending up in the sticks deep in Trump land … even though horses are pretty cool.

From there we drove to Bend, Oregon to visit my cousin Rachel. Upon checking in at the hotel, we found that the last blockbuster video in the world was just a few blocks away! Of course we had to visit that and get some T-shirts.

At nearly 100,000 people, Bend was the biggest place we’ve been since leaving San Francisco. The people were nice, the food was good, and the natural beauty was amazing. But when I was looking for things to do there, it was almost entirely wilderness-related, and I’m more likely inside. So there is no way I can end up there. One of the great things about San Francisco is that you only have to cross one bridge if you want to be in nature.

After winding our way through heavenly mountains and forests, we ended up in our ultimate destination: Portland.

I had only been to Portland once, but since that trip five years ago, the city had been high on my list of possible places to live. What is special about Portland is that it feels like a series of college towns surrounding a big city. The neighborhoods are full of brilliantly creative restaurants, quirky bars, funky bookstores, gorgeous artisan houses, and adorable crank. And downtown are full of skyscrapers, professional sports teams, and even more adorable weirdos. To top it off, everything is a lot cheaper than San Francisco. Plus, dozens of my friends from the Bay Area have moved there over the past 10 years.

We arrived exactly when the world was finally starting to open up again and it was a wonderful time to be in Portland. We spent hours shopping at thrift stores in Hawthorne. We went to a backyard barbecue in our friend Miranda’s big beautiful craft house that she bought for half the price of a one-bedroom in SF. We spent the day on a boat cruising the Willamette River with old SF friends. We have eaten food from places like Malka and Eem which create incredibly inventive top class food at medium prices. We saw the inspiring neighborhood food fridges and pantries put up for people in need of food during the pandemic. We explored the myriad waterfalls of the Columbia River Gorge, which is just 30 minutes outside of town.

Portland feels so perfect that every time a friend asked Kayla and me when we moved there we sighed before saying it wasn’t us.

Because as great as Portland is, it will never be San Francisco. After 10 days of traveling through Northern California and Oregon, I missed being able to go almost anywhere I wanted to go. I missed the diversity and heard Spanish or Tagalog or Cantonese while wandering around. I missed the sizzling energy North Beach had, even during the pandemic. I’ve missed the camaraderie of seeing people I know everywhere I go. And of course I missed Mission Burritos.

While it’s tempting to think that one day I could afford a house in a place as wonderful as Portland, San Francisco still isn’t. Who knows, things may change in the future, but as far as I can tell there is nothing I love more than being a San Franciscan.

Stuart Schuffman is a travel writer, television presenter, and poet. Follow him on and join his mailing list at He is a visiting columnist and his point of view is not necessarily that of The Examiner.

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