Our Favorite Places: Portland, Oregon

By Eric Hrubant, Founder & CEO of CIRE Travel

A city of delightful complexities, Portland celebrates its contradictions with unapologetic confidence. Here’s a place that has figured out how to be simultaneously gritty and refined, bookish and bohemian, craft-obsessed and refreshingly unpretentious. “Weird” isn’t just a marketing slogan—it’s a way of life that somehow makes perfect sense once you’re here.

We love Portland for the opportunity it gives us to browse a bookstore that spans an entire city block in the morning, catch sight of the nation’s second-largest bronze statue (Portlandia, but not to be confused with the TV show!) by afternoon, and cap off our evening at a festival celebrating everything from Polish heritage to cutting-edge breweries.

Call it Bridge City, Stumptown, Beervana, or the City of Roses, but just let yourself soak up the cool vibes of a cultural crossroads where film and forestry museums coexist, where the locals drink coffee and read voraciously, and where creation is fearless. However you describe it, Portland shows that sometimes the best way to stay relevant is to never take yourself too seriously.

Stay: Luxury Hotels in Vancouver

1. The Nines, a Luxury Collection Hotel

Elevate your Portland stay, quite literally, at The Nines. Set on the eighth floor and above in the historic Meier & Frank Building, this LEED Silver-certified hotel embodies the essence of Portland: art, culture, great food, a commitment to sustainability, and an inviting personality that’s both historic and contemporary. Every room is literally “dressed to the nines,” with over-scaled tufted ivory leather headboards, winding mercury lamps, and ivory-colored satin draperies. More than 400 carefully curated pieces grace the atrium, restaurant, library, lobby, and guest rooms, from sculptures and paintings to custom installations.  Shop in the nearby Pearl District (no sales tax!), or hop on the eco-friendly MAX Light Rail to go farther afield. Head back to The Nines for happy hour at the Urban Farmer Bar or Living Room, and dinner at Departure (nab a table on one of the two rooftop patios).

2. The Ritz-Carlton, Portland

Surprised by a Ritz-Carlton in a city as funky and outdoorsy as Portland? Then you haven’t experienced this iteration of the luxury icon’s urban offerings. Rising high above the city’s quirky indie boutiques, cozy coffee shops, and food cart pods is a modern glass skyscraper that affords spectacular views of the city, the Willamette River, and the Cascades. It’s a perfect blend of contemporary-classic and the Pacific Northwest’s natural side. Everywhere you turn, you’re reminded of Portland’s history, landscape, and pioneering spirit, whether you’re soaking in the infinity pool next to floor-to-ceiling windows, dining on regional bounty at the 20th-floor Bellpine, where locally sourced entrees are served alongside panoramic views, or relaxing in a Flora & Fauna Suite, where your sightline includes Mount Hood or Mount St. Helens.

Eat: Best Restaurants in Portland, Oregon

Portland’s food scene is legit. Where else can you kickstart the morning with locally roasted coffee and sinful, gluten-free donuts, pick up a food cart waffle sandwich for lunch, and, later, sit down to a dinner of high-end Thai with natural wine pairings. For a modest-sized city, its culinary game packs a punch. Start with our suggestions, then do a little more homework to make the most of Portland’s mouthwatering adventures, building time into your schedule for the happy hour lifestyle that falls upon the city from 4-7 PM daily. Regional pride plays a big part in the local menus, as chefs primarily work with area farmers, producers, and purveyors in their attempt to always try something no one else is doing.

1.     Chelo

Pop-up restaurants are almost as ubiquitous as Portland’s famous food carts, and Chelo was born of one of those ideas. Chef Luna Contreas designs her menus in accordance with her own whims and what’s in season, but you’ll typically find blue corn empanadas, ricotta-stuffed chilaquiles rellenos in mole Amarillo, branzino a la plancha with miso-brothy beans, and a tres leches cake that morphs with the calendar from matcha to strawberry to whatever Contreras is feeling. Check her out on social media and you’ll get an immediate taste for her and her restaurant’s strong sense of identity and whimsical ways.

2.     Pasar

For all its globally influenced cuisine in such a foodie-friendly city, Portland hasn’t previously offered much in the way of Indonesian fare. Pasar, which translates to market, is changing that. Owner and chef Feny shares street food-inspired, shareable favorites, from the gorengan combo of fried snacks and rujak serut (spicy pineapple, papaya, and cucumber salad), menu staple longton cap go meh, a coconut broth with chewy rice cakes, and babi goreng, or crispy pork belly. Sweet tooths, don’t miss kue, delicate, colorful Indonesian desserts made of chewy tapioca or rice flour and lightly sweetened with jackfruit, pandan, and other regional flavors.

3.     Screen Door

We wouldn’t be doing justice to the Portland food scene if we didn’t mention a tried-and-true brunch spot. Portland loves its leisurely weekend (or even a random Tuesday) brunch as much as its craft beer. The buttermilk-battered fried chicken and waffles are well worth it. Other favorites: a Creole bloody Mary with pickled okra, cheesy cheddar grits, and the Cajun scramble.

Do: Best Things to Do in Portland, Oregon

1.     Spend the Day in the Park

The exquisite Portland Japanese Garden, the International Rose Test Garden, the Hoyt Arboretum, and even a “Witch’s Castle.” What do they all have in common? They’re all part of Portland’s immense park system, including Washington Park and Forest Park. Take a stroll through the serene Japanese garden, with its trickling waterfalls, a teahouse, and eight gardens in distinctive Japanese gardening styles. Then, visit the International Rose Test Garden, the country’s oldest testing ground for new rose varieties. More than 10,000 rose bushes represent over 600 colorful varieties. The best rose-viewing is May through September, and you’ll get fantastic city and Mount Hood views year-round.

Want a longer walk? Head to Forest Park and hike the 5-mile Macleay Park Trail to Pittock Mansion, or the short, but eerie walk to the lichen-coated, graffiti’d stone structure known as the “Witch’s Castle.”

2.     Browse (and Eat) Your Way Through the Portland Farmers Market

The city’s flagship farmers market is located at Portland State University and runs year-round, so you’re bound to find something in season. Think leafy greens in the winter, rhubarb in the spring, Maryhill peaches, and locally grown apples in the fall. Even if you’re not stocking up on fresh produce to take home to cook with, you’ll want to bring an appetite for the myriad food stalls at either end of the market. Look for Mio’s Delectables, where you can munch on an Earl Grey Swiss roll with Oregon-grown pears, and Enchanted Sun, where the long line gives away how delicious their New Mexico–style breakfast burritos are.

3.     Get Lost in a Book (or 50)

If you’re a bibliophile, plan ahead and bring an extra suitcase for the haul of pages you’ll take away from Powell’s Books, the world’s largest independent bookstore. It’s hard enough to get past the display tables in the cavernous entrance to this beloved store. New releases, employee favorites, old classics you haven’t thought about since college, regionally authored books, and all manner of literature-related souvenirs await. Wander deeper, room by room, all organized by color, and get lost in the stacks. Here, a floor-to-ceiling bookshelf of romantasy; there, a wall of cookbooks that span global cuisine. Grab a coffee in house at Guilder and plan to spend a good hour or two browsing. If you’d like to check out the Rare Book Room (you should), visit Friday through Sunday.

4.     Get Cultured

Overcast skies and drizzle don’t keep Portlandians from getting their cultural fix. Grab a raincoat and a warm beverage and follow the locals to the Alberta Arts District’s many galleries, art collectives, print-making studios, and smaller art exhibitions. Learn local history from the Black Heritage Markers on the sidewalk between Northeast 11th and 24th Avenues. Take the mile-long, audio-guided Albina Soul Walk tour to discover an iconic era of Portland soul music.

Downtown, make a trip to the Portland Art Museum for Impressionist paintings, 19th-century Japanese woodblock prints, and Oregon artists like Mickalene Thomas and Robert Colescott. Want more art? Pick up The Portland Art Map, which points you to more than 60 local galleries and museums.

5. Have a Hyper-Local Moment

Do like the locals do and head 20 minutes out of town on a summer evening to Topaz Farm for a concert or farm-to-plate dinner. The farm is located on Sauvie Island and hosts live concerts, from indie folk to bluegrass, regionally sourced dinners and farm drinks, silent reading parties (for those titles you picked up at Powell’s!), and berry picking. Fall brings harvest dinners and pumpkin hunting. For the prime summer season, get your tickets early.

CIRE Is Here to Help

Ready to discover Portland’s quirky, undeniably addictive appeal? Our expert luxury travel planners can help you make the most of your time there. Contact us now for a hassle-free way to stay and enjoy this captivating Pacific Northwest city.