What You Can Expect From Us

We know it can be overwhelming thinking about planning a trip to an unfamiliar place. Our first international trip together was to Chile and Torres del Paine National Park, which was a logistical nightmare compared to some of the more recent trips we’ve taken.

We’ll do our best to proactively think about all the questions you might have about visiting Oregon  – how many days do you need in Portland, where should you stay, what should you absolutely not miss, how do you get between cities/places, what to expect in each season, etc. – and answer them in the guide we’re putting together.

Crucially, our guides are based on our own personal experiences in the places we’ve visited, which is something that’s surprisingly rare in travel writing these days.

Throughout our guides, you’ll find the little details that make the difference between an okay trip and an amazing trip. Like which route to take on a hike, or the specific breweries / wineries we love.

Oh, and in addition to doing the legwork of planning our trips, we also pay for everything ourselves. No sponsored content here! 

We see a lot of guides and posts out there on the internet that are sponsored, but you’d only know it if you read all the way to the bottom of the post and read the small, italicized text buried there. It drives us NUTS.

We strongly believe that this is important for a couple of reasons.

First, it allows us to accurately decide whether something is worth the price. Is the $20 walking tour worth the upgrade from the free tour (spoiler: the answer is almost always yes)?

It also allows us to have a more objective view of the things we’re writing about without outside pressure to give a good review.

Last, and arguably most important, it means we’re paying the (ideally local) businesses we’re writing about – the walking tour companies, the cooking class providers, the bars and restaurants – for their products and services, which in turn helps them build their businesses and continue to serve you!

Like we mentioned before, supporting small businesses is important to us, and we do our best to make sure our dollars are going to the businesses we love (and by extension, their owners). 

At the end of the day, we’re a small business pursuing our craft too!

Our Story

Now that we’ve covered why we started this site, let’s go back in time and talk about all the events that led us to this very moment. 

Neither of us grew up in Oregon, but Matt grew up in the Seattle area and his love of the Pacific Northwest – the dense evergreen forests, the unbeatable long summer days, and the diversity of landscapes to explore – is what brought us back.  

Alysha grew up in rural Northern California, where she was exposed to the outdoors from a very young age (there are pictures of her in a makeshift cardboard playpen in Joshua Tree as a baby). Matt was a suburban kid who hated the very idea of going on a hike (he chose to finish Harry Potter and the Goblet of Fire in the car instead of going on a hike in Bryce Canyon National Park in middle school). 

Fast forward a few years to 2014. We met on a boat cruise on the San Francisco Bay. Matt was in town interviewing for a job (he lived in Seattle at that point), Alysha lived in San Francisco working in the non-profit sector. 

We hit it off, kept in touch, and went on seven dates in seven days when Matt took the job and made the move to San Francisco that summer. 

We lived in San Francisco for almost a decade, moving into an apartment in Nob Hill together for the last three years, and while we loved (and still love) the city, Matt had always had his eye on moving back to the Pacific Northwest. 

We spent many weekends in Portland over that time, mostly because it has an excellent gluten free scene and Matt has Celiac Disease and loves gluten free beer and doughnuts, which are two categories that Portland excels in. 

In February of 2020, after a few years of small but steady growth of our original site (Wheatless Wanderlust, if you’re curious), we decided to quit our jobs in San Francisco and bet it all on a travel business. 

That timing was, uh, not great. We ended up moving in with Alysha’s mom for several months and made basically zero money for a couple of years as we slowly ate through the money we had saved up for a year-long trip over the previous few years. 

While that time was a challenging and uncertain one, it had one major benefit for us. 

It cemented our love of the state of Oregon. 

After four months cooped up in a relatively small house in rural Northern California, we packed up Homer the Honda Odyssey (the minivan we inherited from Alysha’s dad, with a homemade bed platform in the back) and hit the road to Oregon. 

Now, while we had actually spent a fair amount of time in Portland, we had never left the area within about an hour of the city before. 

To us at that point, Oregon was almost a flyover state that we passed through on our way up to Seattle to visit Matt’s family, or passed over as we daydreamed about sexier international destinations like New Zealand and the Canadian Rockies.

2024 update: It was actually a recent trip to New Zealand in early 2024 that made us realize just how lucky we are to live in this beautiful corner of the world. We flew 14 hours halfway around the world only to realize that we have places that are just as beautiful within two hours of our front door. 

Why Oregon? The reason is pretty simple, actually. 

Oregon was the first state to open up campgrounds in State Parks in 2020, and as soon as that happened we made a beeline for the Oregon border. 

We spent two months on the road in Oregon, making a big loop through the western half of the state starting in Crater Lake, heading up through central Oregon through Bend and Hood River, stopping in Portland, and heading back down the Oregon Coast. 

We spent our days hiking in the quintessential Oregon summer weather, and our evenings hanging out at camp, reading or chatting over an Oregon cider. 

That two month road trip is when we fell in love with Oregon, but we had a lot of traveling to do before we moved here! We spent the next 18 months on a road trip around the western United States, hitting all of the national parks west of the Rocky Mountains. 

Then we spent three blissful months in Europe, exploring Spain, Portugal, and Italy as what seemed like the only Americans around (it was fall/winter of 2021, and it was MAGICAL). 

By the time we got home from that trip, it was early 2022 and we had spent two years traveling full time. 

While being on the road full time sounds very cool and sexy AF (and it is, to an extent), there is one aspect that started to get to us. 

We were craving a home base. 

Matt grew up in Seattle and always wanted to return to the Pacific Northwest, and we had decided (after that Oregon adventure in 2020) that Portland, Oregon was the place for us thanks to the combination of an amazing gluten free food scene and the proximity to both the mountains and the coast. 

We moved to Portland in July of 2022, and adopted a new member of the family shortly thereafter – a 30 pound border collie mix we named “Lupine” after the purple flowers that light up the slopes of Mount Rainier in the early summer (we joke that we had the name well before we had the dog). 

Now, we’ve made Portland our home, and we couldn’t be happier with our decision.

Yes, Portland as a city has its problems (as every person we meet loves to tell us as soon as we say that we’re from Portland – even in New Zealand!). 

But, frankly, as two people who have lived in San Francisco and Seattle over the past decade, Portland’s issues are not particularly unique. And every city has its issues. 

For us, Portland’s pros – the thriving small business culture that constantly has us saying “I wish I was that creative / passionate about / good at literally anything”, the unparalleled access to both a great city and natural beauty, and the food and drink scene that punches well above its weight – far outweigh its cons. 

And zooming out from Portland, the diversity of landscapes that Oregon has to offer are what initially drew us here, years ago in our van, and are ultimately what keep us excited about exploring new corners of the state in future years.