“West Coast” and “cheap” rarely share the same sentence — but one city is proudly proving there are exceptions to every rule.
Famous for embracing its weirdness (by its own slogan, no less), this offbeat hotspot is suddenly just as surprising for its prices as its quirky personality.
I had the pleasure of visiting for the first time almost a year ago as of this writing. I won’t lie, I had some hesitations flying solo — not because of its off-the-wall vibes, but because of its often negative headlines.
But it turns out you can’t believe everything you see on the news. Who would’ve thought?!
There was never a dull moment, unless you wanted there to be, as there’s arguably no better city to pop a squat with a good book and sip sensationally crafted coffee in a trendy cafe.
The reality is it’s one of the best U.S. cities for solo trips, but that shouldn’t stop couples, friend-cations, and nomads on the go from carving out their own adventure here.
Just revealed as one of America’s most affordable spring getaways, the misunderstood city of Portland, Oregon may not be your typical West Coast vacay, but it just might be the one your wallet and wanderlust have been waiting for.
Normalcy Not Allowed: Portland Is America’s Last ‘Weird’ City
If you can’t find your tribe in Portland, you might need to reevaluate your life. I’ve told this story before, but within half an hour of checking into my hotel and hitting downtown, I witnessed slam poetry in vacant parking lots, graffiti promoting entertainment I would probably get fired for mentioning, drag shows taking over food truck parks, and ‘Karaoke from Hell’ at one of the city’s most popular cabarets.
There is no shame in Portland’s game, especially being home to the most strip clubs per capita — and they don’t try to hide it.
As other bizarro locales like Austin and Marfa have fallen prey to corporate greed, Portland still lets their freak flag fly, but it’s not a place that feels grungy or overly edgy despite some unsightly headlines.
So, let’s tackle it.
Portland has a homelessness problem. There’s no doubt about it, but so do many West Coast cities, even some venturing away from the coast and into the desert like Vegas.
But people are still flocking in record numbers to West Coast destinations that struggle with zombie-land eyesores dispersed around the city, such as my hometown of San Diego.
Portland is a phenomenal place — and one that will never bore you, whether you’re into arts, food, nature, or judgement-free late nights, where even DJ booths take over donut shops.
I saw that with my own eyes too.
Is Portland Unsafe Or Just Unabashedly Free?
There was only one moment I felt my Spidey Sense activating, saying, “Sam, it’s time to cross the street”.
That was around midnight, making a food run to a part of downtown not well-lit and turning into “Tent City” for the night.
In fairness to Portland, most major cities have areas like this. I should’ve done more research instead of aimlessly wandering around late at night on a weekend.
That said, I spoke with locals about this very issue. Sometimes a friendly chat with bartenders and baristas gives me a better feel for the city, but this topic was about a 50/50 split…
Dirty, uninviting encampments hurt local business, but non-business owners seem to take the side of the homeless, stating they deserve to be in public space just as much as the next person, as long as they’re being respectful.
No matter your personal belief, if there’s one thing anyone visiting Portland should know is you will encounter this problem — it’s unavoidable. Even CVS stores lock up soft drinks to minimize theft.
It’s something you just have to expect when visiting any major West Coast city. It doesn’t matter if it’s Los Angeles, San Francisco, or Portland — that’s just the way it is.
But is it really as unsafe as mainstream news portrays and local business owners claim?
One 2025 report revealed Portland came in 72nd place for violent crimes per 100,000 people. Not terrible, right?
The city’s negative headlines tend to reflect more about unsightly protests, petty crime, and the way the government tackles its homeless crisis with back-and-forth decriminalization policies.
That said, let us know what you think by clicking on our new Safety Index tool above. It’s designed to showcase real-time data for any chosen destination.
It’s been a year since I visited. I would’ve voted “I Felt Safe” back then.
Let us know if Portland has changed for better or worse.
Portland’s Biggest Surprise: A Wallet-Friendly West Coaster
A West Coast getaway that’s wallet-friendly? You bet!
No, that’s not us making light that your wallet might get snatched…
According to expert number-crunchers at GoBankingRates, Portland is the #1 most affordable spring getaway in terms of hotels, with rates averaging in the $130s, which beats our own estimates.
When you see reports like this, it’s important to remember a keyword: averaging.
That means you can find rates even lower than the mean. So, we did some digging for you.
These are Portland’s 5 best-value hotels through March and April, just in time to witness the vibrant waterfront bloom with Cherry Blossoms.
But Portland isn’t a one-trick pony either. It’s affordable across the board. Well, maybe not if you buy a house…
These are my top 3 picks for budget-friendly food actually worth eating:
- Fuller’s Coffee Shop (amazing diner-style breakfast!)
- Hana Sushi and Izakaya Pearl (rotating sushi bar; go for happy hour!)
- Dan & Louis Oyster Bar (you can’t go wrong with any of their stews!)
Additionally, a day pass for TriMet transit is only $5.60. Make use and head to Washington Park for a gorgeous hike with fresh, pine air and hop aboard their free shuttle.
Oh, and Powell’s City of Books is a destination unto itself.
