Did you catch the news? We've launched our very first video travel series, 'Go, Be You,' in collaboration with Alaska Airlines! Over the past five weeks, we've spotlighted a new city each week, and there are three more on the horizon. This series goes beyond just the places we visit—it explores how particular cities can bring out the finest versions of who we are.
As you start planning your next adventure, we trust you'll appreciate the recommendations below. And be sure to watch the Portland episode featured at the bottom of this article!
Early this year, I made a vow to myself: I'd break up the year with quick getaways to destinations across the US that I'd never visited before.
Extended weekends are making a comeback as a travel trend—they're simpler to schedule away from work and offer just the right duration to truly disconnect.
My first booked trip was Portland. A short flight from Los Angeles, it turned out to be an ideal getaway with a small group of friends.
Portland's carefully curated collections of music and books form a vibrant mosaic of culture, feeling, and creativity. History resides in layered worlds of wonder waiting around each bend.
Below are a handful of spots to mark on your itinerary:
Portland: Unlock Your True Self
To Eat
Grassa PDX
After stepping in from the overcast chill, nothing beats a steaming bowl of fresh pasta. That ideal bowl awaits at Grassa, where I admittedly got emotional over their cacio e pepe. Our group played a game of musical pasta, passing dishes around to sample each one. The rigatoni features a bright, sweet acidity wrapped in a rich warmth—that's their Sunday pork ragu.
We visited Pok Pok twice in just three days. The first time was for the Vietnamese fish sauce chicken wings, whose size caught us off guard. The second trip made up for a sushi dinner that prioritized elegance over substance. Those sticky, crispy, caramelized wings were the perfect companion for a rainy movie night featuring 'Baby Driver.'
But the ultimate comfort food prize goes to the biscuits and gravy at Pine State Biscuits. If you're sharing a plate with friends to leave room for more Portland eats, it'll vanish fast. So be sure to order something sweet too—another biscuit slathered with local apple butter.
To Browse
From streetwear and outdoor gear to music and book collections, Portland is a pop-culture playground with a scholarly devotion to history and travel.
This spirit is embodied in the can't-miss Powell's City of Books, with its nine magnificent floors. Housing roughly one million volumes, I could go on about how towering the shelves are. Upon arrival, our group scattered and arranged to reconvene in about two hours. In my pursuit of becoming a true explorer, I sheepishly realized how little I enjoy solo travel—or solo browsing. But I pushed through, navigating every color-coded level, including the one simply labeled 'Coffee,' and walked out with two books and a zine.
Fun fact: Company President Emily Powell is the third-generation owner of this bookstore chain.
For additional reading, check out Portland's oldest bookstore, Cameron's Books and Magazines, which opened its doors in 1938.
Cameron's Books
'Hey, what did you think of the music last time?' the clerk at Canoe inquired. We also stopped in here twice—it's a mini-museum for modern design lovers, with wall descriptions noting each item's country of origin. You can shop and browse online, but only in-store can you test every lovely perfume they offer. I returned specifically for Bon Parfumeur 701.
For vintage enthusiasts, Urbanite is an antique mall that debuted last September. It's a genuine treasure trove featuring over 40 vendors, offering furniture, vintage signs, decor, stationery, and miscellaneous odds and ends.
Urbanite
Cargo Inc. feels like a collection your coolest aunt might gather over a lifetime of travels—which makes sense, since founder Patty Merrill is a ceramicist and folk art collector. Spanish music filled the air as my eyes darted across wonderful shift dresses, embroidered jackets, handmade papers, mahjong tiles, bangles, books, and scissors of every shape.
It's especially enchanting to visit at night, when lanterns light the steps leading up to the tall double doors. You'll step into another world upon entering, but watch out for the shop cat, Calla Lilly!
To Caffeinate
Naturally, Portland ranks among the best coffee cities, having gifted us Stumptown, Heart, and Coava. Prince Coffee and Good were new discoveries for me, and the beans I brought home from Good were fantastic.
You truly can't make a bad choice here, given how knowledgeable everyone is. But don't skip the Artist Fellowship exhibit at Stumptown's downtown outpost. Gallery owner and curator May Barruel, together with a small committee, grants selected artists $2,000 and a 6-to-8-week solo exhibition as a way to support local arts.
To Get Lost
In Portland, it doesn't take long to drive somewhere where you're completely surrounded by trees, the city fading from mind yet still within reach.
We stayed close to the urban area but felt worlds away in Marquam Park. If you can't venture as far as Mt. Hood or Trillium Lake, another excellent natural escape is Hoyt Arboretum. Portland is a weekend dream partly because you don't need half a day to reach a major attraction.
As an artist and writer, I aspire to a certain elegance, but Portland is disarming. It doesn't demand that. So I gladly shed that expectation for the weekend. That joy tastes like crisp, fresh air. Style and fun here are woven from music, weather, trade, and heritage. Portland isn't waiting to be discovered, but it does have a place for you.
Like any worthwhile destination, there is no single experience that defines 'Portland.' Yet there's something about this city—where art spills onto walls and front yards—that invites you to pause a little longer. It teaches, urges, and challenges you, but most warmly, it thanks you for listening.
This article was sponsored by Darling's airline partner, Alaska Airlines. All opinions and reviews are solely Darling's.
Stream the Portland Episode of 'Go, Be You'
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Photos by Lawrence Yong
