How to Spend an Indulgent Weekend in Portland, Oregon

From bustling outdoor markets and plenty of food carts to lazy afternoons by the Willamette River running through the center of town, Portland during the summertime is a haven for outdoor enthusiasts, foodies and oenophiles.

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Given Portland’s laid-back nature, luxury isn’t the first word one might use to describe a vacation in Oregon’s largest city. But even with its hipster reputation, Portland has a sophisticated side. Surrounded by spectacular natural beauty, Portland offers visitors a creative journey through its arts and outdoor scenes, all set against the sublime backdrop of Mount Hood.

While it still has that quirky charm, Portland has no shortage of fine dining and craft cocktail bars. It’s also a great home base for exploring the luxurious wine regions just south of the city in the Willamette Valley. 

Summer is arguably the best time to visit the Pacific Northwest, and that is especially true for Portland. Sure, the city has a reputation for rather dreary weather, but from May through September, the skies truly open up to the most abundant sunshine—and without the humidity. The warmer months offer a unique opportunity to experience the city at its most vibrant. From bustling outdoor markets and plenty of food carts to lazy afternoons by the Willamette River running through the center of town, Portland during the summertime is a haven for outdoor enthusiasts, foodies and oenophiles.

In a locale that effortlessly blends natural beauty with urban cool, it’s easier than ever to plan out an opulent weekend in the City of Roses.

Where to Eat


  • 250 NW 13th Avenue, Portland, OR 97209

One of Portland's most exciting and lauded openings of the last couple years, Janken is a culinary journey through Japanese-Korean fusion cuisine curated by executive chef Rodrigo Ochoa. A true gem in the Pearl District, Janken focuses on sharing plates, handcrafted cocktails and embracing a traditional-contemporary blend to create a comfortable yet upscale dining experience. Even the simplest dishes, like a veggie maki roll, will leave you in awe and asking for more. Other can’t-miss items include the mushroom bao buns with truffle and pickled onions; the japchae sweet potato noodles with mushrooms, carrot, red pepper, and egg; the matcha tiramisu with ladyfingers and rum mascarpone cream; and the “Pineapple Express” cocktail—a presentation experience you must see for yourself without spoilers.

Janken. Rachel King


  • 960 SE 11th Avenue, Portland, OR 97214

One of Portland’s most beloved restaurants just celebrated its 10th anniversary in April 2024, and it’s been an eventful decade, to say the least. Owners Bonnie and Israel Morales were both already  industry veterans when they opened Kachka in 2014, and one of the more common themes to their establishment is educating diners about what kind of food they serve. It’s not just Russian food, and it’s not just European food. Think of it more as cuisine from all over nations previously part of the Soviet Union, as well as those of Central Asia. Open for lunch and dinner, among some of the most popular dishes are vareniki (dumplings) filled with farmer’s cheese, chives and scallions; and mushroom shila plavi, a risotto-esque Georgian dish with local mushrooms and smoked sulguni cheese. (It’s also sometimes referred to as “funeral rice,” as it is usually served to uplift those in mourning.)

Kachka’s location in southeast Portland’s Goat Blocks consists of three dining spaces: a lounge, a larger dining room and a private dining hall seating up to 40 for dinner parties. Each space encourages sharing of food and drink, exemplified by the restaurant’s motto: “Clink. Drink. Eat. Repeat.” The Morales duo also added a Russian deli, Lavka, where guests can sample Kachka's line of vodka infusions and purchase grab-and-go housemade dumplings and other delicacies to cook at home.

Kachka. Rachel King

Fools and Horses

  • 226 NW 12th Avenue, Portland, OR 97209

This buzzy cocktail-focused restaurant opened in October 2022, welcoming guests with western flair, custom wallpaper from Lonesome Pictopia and a pressed tin backbar illuminating the extensive spirit collection. The culinary program draws inspiration from a point of view unique to the islands of Hawaii—The Paniolo Cowboys—alongside chef Alex Wong’s childhood on Oahu and his time living across parts of Europe and the western United States. The beverage program places a strong emphasis on cocktails and a wide variety of worldly spirits, featuring not only fresh, seasonal elements in bright, shaken recipes but also expressive, rich, spirit-forward offerings that lend themselves to an inspired and intentional menu.

Fools and Horses. Fools and Horses


  • 678 SW 12th Avenue, Portland, OR 97205

Tanaka’s menu is a blend of Japanese comfort food and artisanal baking, with a special focus on katsu, a breaded and deep-fried cutlet dish. Inspired by Osaka, Japan, Tanaka brings a taste of the city's culinary scene to Portland. But the menu is full of international twists, from the “dirty fries” with pulled pork and American cheese to the spam curry dip sandwiches. And anyone with a sweet tooth will be delighted by the fresh doughnuts, made on-site daily with locally sourced ingredients that represent flavors commonly found in Japanese cuisine.



  • 921 SW Oak Street, Portland, OR 97205

Self-touted as a “modern pastry luncheonette,” Maurice’s menu (and the vibe—especially the vibes) represent the amalgam of chef Kristen Murray’s French and Norwegian heritage. The eatery’s menu offers a creative marriage of French techniques with Nordic ingredients and sensibilities. Expect light bites like French breakfast radishes with butter and salt, in addition to heartier fare like the “I Dream of Sweden,” composed of egg salad on toast with pickled herring, beets and alp blossom cheese. The wine list is also an adventure, with a healthy sampling of natural wines as well as a bevy of options produced around the Pacific Northwest.

Where to Drink

Multnomah Whiskey Library

  • 1124 SW Alder Street, Portland, OR 97205

If you’re looking for a nightcap, there is nowhere quite like the Multnomah Whiskey Library (or “whisky,” depending on what exactly you’re drinking). Named for the nearby majestic waterfall, Multnomah is a membership-based social club, bar and restaurant and home to one of the most extensive collections of spirits in North America—boasting more than 1,000 bottles of whiskey from around the world, in addition to other liquors such as cognac, tequila, mezcal, rum and Italian amaro. And while the menu is extensive, to say the least, the point isn’t to overwhelm, but to educate. Even just ordering a Whistlepig on the rocks is an experience, with tableside bar carts circling the room and pulling up to your table with your order.

Multnomah Whiskey Library. NashCO/Travel Portland

Teardrop Lounge

  • 1015 NW Everett Street, Portland, OR 97209

Open since 2007, the award-winning Teardrop Cocktail Lounge offers a broad spectrum of cocktails inspired by the seasons of the Pacific Northwest, as well as historical drink recipes from the last centuries. The menu also includes a page of original drinks created by industry friends from around the country, emphasizing the greater community-at-large and the collaborative spirit for which Portland is known.

Teardrop. Teardrop

Too Soon

  • 18 NE 28th Avenue, Portland, OR 97232

Too Soon is one of the newest additions to the Portland nightlife scene. Inside, the sleek and contemporary furnishings are bathed in soft lighting, creating a cozy yet upscale ambiance. But the drinks are the real stars here. Fans of savory cocktails will enjoy the House Special, a concoction infused with fragrant curry spices and bell pepper. On the lighter side, the bar’s highballs come in variations like apple and horseradish, celery and shiso, or mango and chili using ice-cold Haku vodka on tap. And anyone who makes it to last call (just before 1 a.m.) is treated with a warm chocolate chip cookie on the house.

Too Soon. Too Soon

What to Do

Knot Springs

  • 33 NE 3rd Avenue, Suite 365, Portland, OR 97232

Knot Springs, just overlooking the Willamette River, is an urban oasis catering to those seeking a holistic approach to wellness, combining soaking in natural geothermal springs with fitness classes, massage therapies and a focus on mindfulness. The centerpiece of Knot Springs is undoubtedly the mineral-rich geothermal springs, where guests can unwind in the warm waters, letting the natural minerals soothe tired muscles and ease tension. Knot Springs offers day passes and packages for anyone seeking a day of pampering.

Knot Springs. Knot Springs
  • 529 SW 3rd Avenue, Suite 100, Portland, OR 97204

Perhaps only in Portland will you find a contemporary art gallery and a bespoke tailoring shop all in one unit. Upon entering, guests will first find themselves in Day in the Life, which showcases works for sale from dozens of artists from all over the country—but especially the Pacific Northwest—in glassblowing, ceramics, weaving and more. The space, which used to be a Chinese restaurant, hosts numerous events, including artist demonstrations, whiskey tastings and fashion shows. But step into the backroom and you’ll find yourself in a custom suiting shop fit for Savile Row—but without any of the attitude. Wildwood is far more inclusive, too; co-founder Joe Mueller tells Observer many of his clients include women and members of the trans community, and he welcomes anyone to make an appointment for a consultation, even if they’re not ready to make a purchase. Within the walnut-hued wood walls of the back room, Mueller and his team creates custom suits, fanciful accent pieces and made-to-measure shoes fit for James Bond, but with far more flair. 

Afterwards, definitely take the time to walk over to Powell's City of Books at Burnside—it’s less than a 15-minute stroll to the world’s largest independent bookstore. 

Wildwood & Company/Day in the Life Gallery. Rachel King

Willamette Valley

Spanning approximately 5,372 square miles (much larger than California’s Napa Valley down south), the Willamette Valley is home to more than 700 craft wineries. It’s a West Coast wine lover’s paradise, especially for pinot noir enthusiasts. The region is also on the map for some of the best domestic cheeses, and fresh farm-to-table dining has long been the status quo in the restaurant scene here. Among some of the wineries you should add to your day trip to-do list are Gran Moraine Wines, a jewel in the middle of the valley with indoor and outdoor tasting rooms and some of the most gorgeous views around, and Penner-Ash Wine Cellars, a family-owned winery tucked away up on a winding mountain road that looks straight out of a storybook. 

For dinner, Okta, in the town of McMinnville, is a culinary destination in its own right. Michelin-starred chef Matthew Lightner crafts a highly progressive (and frequently changing) tasting menu finely tuned to the terroir of the region and its micro-climates. Most of the elements on the plate come from the restaurant’s nearby fermentation lab and proprietary farm, where the outdoor wood fire stove is also used for all the house-made breads and pastries. If you’re more of a craft beer enthusiast, there are plenty of breweries within Portland proper. 

Willamette Valley. Dan Meyers/Unsplash

Take a Helicopter Ride

There are few natural landscapes in North America, let alone the United States, as breathtaking as those in the Pacific Northwest. And what better way to take in those vistas than from the beautiful (and sometimes clear!) skies above. Oregon Helicopters offers tours over many of the local wonders, including the Columbia River Gorge, Forest Park, Mount Saint Helens and Multnomah Falls—the most visited natural recreation site in the Pacific Northwest with more than 2 million visitors, according to the U.S. Forest Service.

Multnomah Falls. Ethan Dow/Unsplash

Where to Stay

The Ritz-Carlton, Portland

  • 900 SW Washington Street, Portland, OR 97205

The first Ritz-Carlton property in the Pacific Northwest opened in October 2023, and it’s arguably one of the company’s best locations yet, with an ultra-modern interior design and state-of-the-art facilities. The 35-story tower hosts 251 rooms, and many of the suites are configured with a full bedroom, a cozy seating area and white marble bathrooms with freestanding eggshell bathtubs. Even from your bathtub, you have spectacular views of the city.

The lobby area—decorated with original work by local artists—was designed to resemble walking through a forest, with features like columnar drapery resembling bark and dappled light filtering through the folds. And the giant tree stump in the hotel’s street-level bar and restaurant, Meadowrue (make sure to try the exclusive blend served here from coffee roasters cafe Coava), was salvaged after a fire in the Eagle Creek Forest.
The hotel's signature restaurant, Bellpine, is on the 20th floor, offering panoramic views of Portland and Mount Hood. Operated by Michelin-starred chef Pedro Almeida, the menu showcases the bounty of local produce and proteins, with a drinks menu that includes beers from local distilleries.

Just below the restaurant is what the hotel staff has coined as “Cloudbreak 19,” as it sits above the clouds, or sometimes just among them given the famous mercurial weather of the Pacific Northwest. It’s essentially the wellness floor, starting with the spa, which takes inspiration from the lines and shape of the curves and folds of a Portland rose, complete with rejuvenating treatments in the facility’s five treatment rooms. Just adjacent to the spa is arguably one of the best hotel gyms you will ever find, with all of the cardio machines and weights you could want during a short or long stay, as well as an indoor fitness center and an infinity pool.

Ritz-Carlton, Portland. Ritz Carlton

The Nines

  • 525 SW Morrison Street, Portland, OR 97204

Located in downtown Portland just near Pioneer Square, this LEED Silver-certified Luxury Collection hotel occupies the top nine floors of the iconic Meier & Frank building, which was previously a department store before being transformed into high-end, mixed-use space. The Nines was Portland's first true five-star hotel; the interiors pay homage to its retail history with a blend of classic elegance with contemporary art installations and subtle nods to Portland's vibrant cultural scene. Each room is uniquely designed, featuring artwork by local Oregon artists.

The Nines. The Nines


  • 1150 NE Alberta Street, Portland, OR 97211

One might not look toward Portland’s residential neighborhoods for a five-star hotel and wellness resort, but true to the city’s spirit, expect the unexpected. Slated to open in summer 2024, the Cascada is located in Portland’s growing Alberta Arts District, halfway between the PDX airport and downtown Portland, making it only a 15-minute drive from each. 

The minds behind the hotel describe the theme as “hedonistic wellness,” and guests who want to stick to a specific dietary and wellness program can plan personalized menus with the hotel concierge ahead of their trip. The hotel will have top-of-the line fitness and wellness facilities, including Portland’s first underground hot springs, complete with a hydrothermal circuit and an infrared Halotherapy salt sauna. There will also be several on-site dining options, including a health-forward program, but there will also be a full bar with a cocktail menu. 

Cascada. Cascada

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