For many people, Portland is fondly associated with food trucks, craft beer, and the hilarious antics of Carrie Brownstein and Fred Armisen. (Oh, and that recent head-scratching occupation by ICE agents.)
It’s an eclectic, artistic city with no shortage of fermented pickles and IPAs. To peg Portland as just a fun and funky place, however, would be to miss out on the high level of finesse and intention operating there on multiple levels.
If you’re eager to see the city’s posher side, this is the weekend itinerary you need.
A guest room at Portland's The Ritz-Carlton(Courtesy of The Ritz-Carlton, Portland)
Friday in Portland
If you’re flying out of SFO—a major hub for Alaska Airlines, the main carrier to Portland International Airport (PDX)—the luxe life can start before you get there. The new Alaska lounge, which opened in July 2024 as part of the airport’s expansion of Harvey Milk Terminal 1, is spacious and airy, with 11,000 square feet in which to snack, sip, and indulge in those famous Alaska Air pancakes. Partnerships with Ritual Coffee and Salt & Stone bath products are nice touches, as well.
On such a short route (under two hours), it’s easy to opt for a first class ticket. The price isn’t a giant leap for kicking off a fancy weekend, and the extra space and free canned Oregon Old Fashioned from Portland company Straightaway Cocktails served in actual glassware makes it a treat.
Once you land, take a car from the lofty PDX, which just underwent a massive $2 billion renovation, adding a nine-acre roof made from local timber over the main terminal, plus 300,000 square feet of new space.
Check in to The Ritz-Carlton, Portland (900 SW Washington St.) downtown. This new luxury hotel (and residences) opened in 2023 and is decorated with elements from the area, including crystal-bedecked chandeliers, wood-grain patterned wall panels, and a living plant wall at the entrance. Word is that the designers had a giant, 300-page design deck to guide the project with intentionality.
Have an afternoon oyster pick-me-up at French-Norwegian bistro, Maurice.(Courtesy of @maurice_pdx)
Settle into your room, one of 251 within 35 stories with great views of the Cascade Range and the Willamette River below, then head out to explore downtown. Pop into nearby shops like Frances May (521 SW 10th Ave.) and the upscale Kiriko Made (1001 SW Morrison St.) for Japanese denim. If your legs get tired, stop for a glass of wine and some oysters at Maurice (921 SW Oak St.), a French- and Norwegian-inspired cafe.
Dinner is back at the hotel, up on the 20th floor at Bellpine. New chef de cuisine Jocelyn Chacón arrived at the property this year and is revved up about using all the great Pacific Northwest ingredients. Her menu pulls from her Mexican roots, plus years of experience working in restaurants all over the world, and features dishes like pork belly tamal with marionberry adobo and hazelnut crema, and salmon aguachile with apple kimchi. The glittering cityscape below is magic.
If you are up for more, grab a nightcap down at Meadowrue, the forest-inspired lobby bar where twinkling lights and Japanese-influenced small plates set the scene for crafty cocktails and mocktails.
Wineries like Alloro Vineyard are just a short drive from downtown Portland.(Courtesy of @alloro_vineyard)
Saturday in Portland
Right next door to the Ritz is the The Flock food hall (917 SW Adler St.), which opened in 2025 and features a bunch of vendors all in one place. It’s a fun spot to check out, and an easy place to grab some coffee and a pastry before the day’s adventures begin.
The hotel works with partner First Nature Tours to offer exclusive, curated excursions to Ritz guests. They also arrange special tours to Oregon’s Willamette Valley, with stops at three wineries for tastings and lunch. It’s a deeper dive into the taste of this region than you’d find easily on your own, with stops at wineries like the pioneering Ponzi Vineyards (19500 SW Mountain Home Rd., Sherwood), where you can tour the cellar and check out historic barrels salvaged from a Coca-Cola plant, to wine- and olive-oil-producing Durant Vineyards (5430 NE Breyman Orchards Rd., Dayton).
In between, find yourself on the beautiful grounds of Allorro Vineyard (22185 SW Lebeau Rd., Sherwood), a brand that seems to take inspiration from Italy’s agritourism tradition. This is where lunch happens, and it’s outstanding: fresh focaccia, abundant local cheese and charcuterie boards, and handmade pasta all made by executive chef Denali Whaley. The food is thoughtfully paired with Laurelwood District estate wines, like sparkling Brut Rosé and cool-climate riesling, all enjoyed in the tasting room that feels like a cozy trattoria. Afterward, stroll across the street to visit the animals (pigs! ducks! lambs!).
James Beard Award-winning chef Gregory Gourdet combines Hatian and PNW flavors at Kann.(Courtesy of @kannrestaurant)
The wine tour takes several hours, so you will be ready to relax and refresh back at the hotel. Don’t nap too long, though: This is a food city and you need to get out to experience some of its most elevated cuisine.
It is hard to choose where to go in just one weekend here, as countless restaurants level up to stay in the game. Chefs are pushing boundaries and it is a benefit to us diners. Kann (548 SE Ash St.), one of North America's 50 Best Restaurants of 2025, is where James Beard Award-winning chef Gregory Gourdet brings his Haitian heritage together with regional ingredients in a live-fire format. The flavors are bold, distinct, and different than expected. The space is buzzy, welcoming, vibrant, and colorful, yet also feels classy and refined. A very interesting cocktail program features drinks like the Evergreen Dream—made with douglas fir brandy, melon liqueur, amaro, lime, wasabi, and egg whites—as well as non-alcoholic options that don’t feel like a passive addition.
Walk three blocks to end the night at Scotch Lodge (215 SE 9th Ave. #102), the 2026 James Beard winner for Outstanding Bar. The discreet entrance leads you into what feels like a cool basement hideaway with artful wallpaper, glowing lights, and excellent cocktails. Try the Pandan Old Fashioned with mezcal and coconut-oolong demerara. If you still have room, definitely order food as well; word is the pickle-spiced fries and pappardelle with seaweed butter and candied duck are out of this world.
Portland Art Museum recently added 100,000 square feet of new and renovated space.(Courtesy of @portlandartmuseum)
Sunday in Portland
Start the morning with some spa time up at Cloudbreak on Nineteen, the Ritz’s aptly named 19th-floor retreat. It is a serene perch, decorated in neutral tones and set above the city with panoramic views. In lieu of a cold plunge, the spa features a large ice shower, if you can handle that kind of thing. You can also opt for a steam room, dry sauna, or all three.
This is also where you’ll find the indoor infinity pool and hot tub, as well as the giant 4,000-square-foot fitness center. Portland gets a lot of professional athletes coming through (it’s home to three major league sports teams: the Portland Trail Blazers, the Portland Timbers, and Portland Thorns FC of the National Women's Soccer League), and many of them stay here, so the gym is equipped with performance technology favored by folks of a higher level of athleticism than the rest of us. Just notice the 100-pound dumbbells in the mix.
Don’t leave the city without a visit to the newly expanded Portland Art Museum (1219 SW Park Ave.), less than a 10-minute walk from the hotel. It reopened this past November with 100,000 square feet of new and renovated space to exhibit its impressive collection of sculpture, Native American works, and modern art. The new pavilion area is named for artist Mark Rothko, who grew up in Portland.
After exploring the museum, head into the wonderful gift shop for some souvenirs, then sit down for lunch at the new on-site café, Coquelico, run by the team behind local favorite Providore Fine Foods. Baked goods, fancy tea blends, and an afternoon apéritif menu happen here in a bright and cheerful space full of orange and red tones. Don’t skip desserts like the multicolored Rothko cake.
Don't forget to leave enough time at PDX to stop by Blue Star Donuts for an apple cider fritter.(Courtesy of @bluestardonuts)
This weekend visit is just the tip of the iceberg, so make plans to return for more exploring. Allow enough time before flying back to enjoy the PDX though, stopping at Tender Loving Empire—the brand and mercantile that features and supports all local makers—as well as Blue Star Donuts, because you can’t go wrong with an apple cider fritter for the flight home.
