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Staying Classy in Portland, Oregon

Planning a trip to Portland means researching the city’s eclectic restaurants, bustling breweries and various parks and museums. Just outside of the city, discover hiking trails that lead to waterfalls and picturesque views of mountains in the distance. Portland just has this small-town vibe not found in other metropolises.

On top of all there is to do nearby, the progressive city puts a large emphasis on protecting its beautiful surroundings. From farm-to-table restaurants and sustainable seafood options to its cycling scene and open-minded community, it’s a unique spot that has attracted attention from travelers across the United States and beyond.

Despite the city’s laidback atmosphere, it’s possible to enjoy a one-of-a-kind luxury vacation in the so-called City of Roses.

Staying in European Style

When it comes to a classy stay in Portland, the hotel you choose is key. Kimpton’s Hotel Monaco is one of the most stunning hotels on the West Coast, offering plenty of personality. Boutique hotels tend to have the best décor, but this spot takes it to the next level.

Hotel Monaco lobby in Portland Oregon

The more than 220 guest rooms are eclectic in style, but each maintains a consistent level of comfort. The black-and-white bird-patterned wallpaper was a nice touch, accompanying vibrant carpeting and geometric curtains. The tufted, upholstered headboard on the bed was a rich orangey brown color, adding a bold display of color. Toss in the funky black and white furniture, and the green and white bathroom, and you’ve got an interesting space.

hotel room at Hotel Monaco in Portland

While the small yet spacious room, and the comfortable robes, thrilled us on our stay, it was the lobby that was one-of-a-kind. Groups will want to book more than one room, but don’t need to fear—the lobby is the perfect space to hang out together. The bright red walls are perfectly accented with white trim and velvet periwinkle chairs. Other elegant chairs, ottomans and cushions are perched on top of the hotel’s rich patterned rug, which features many of the same colors.

In this room, you’ll find a grand piano, a fireplace, a bookshelf filled with some fairly old titles and an oversize chessboard. Gather on the comfy seating to enjoy regular sessions of live music, wine or chocolate tasting events or other social hours.

group travel at Hotel Monaco in Portland Oregon

Elsewhere in the hotel, enjoy amenities for the furry friends of the family. A dog-shaped sign by the front door features the names of pets staying at the hotel. Water and treats are located at the front desk. An old-fashioned telephone sits near the lobby, not far from complimentary water, a stunning round mirror and live orchids. The hotel also has its own fish: Bassta Rhymes, Notorious F.I.N. and, of course, Swimmy Fallon. Know what else is great about this hotel in Portland? Tip the doorman—he offered the best service we’ve had, nearly anywhere, offering suggestions and help at every encounter.

A Wine-Centric Getaway

Groups looking for something different than the bright and elegant setting of Hotel Monaco should stay a few blocks away. Hotel Vintage Portland, another Kimpton property, is themed boutique hotel designed for wine lovers.

wine cork art in Portland Oregon

A beautiful cork art portrait greeted us as we opened the door to our spacious room with deep plum-colored walls. There were lights throughout, focused on specific parts of the walls, creating unique mood lighting and relaxing vibes. The sleek bedroom featured elegant glass lamps, and a smooth white bed with a carved wooden headboard and varied pillows. In the bathroom, a round mirror doubled as a makeup light, and the spa-sized bathtub provided us plenty of entertainment as we slipped on our bathing suits, grabbed the bottle of the wine left in the room and hopped in the hot water to warm up from the cold wind outside.

An additional space in our room offered a place for groups to recline, with a bright red sectional sofa and a television. The floor-to-ceiling windows were covered with blackout curtains that, when opened, revealed a bustling street scene below. There is also a small round table in the room, which was topped with the wine and Oregon truffle chocolates.

I’ll offer you another Portland tip: head downstairs to the bar with your whole group. While you can enjoy a variety of wines, there are also plenty of other spirits to keep your mood up.

Elsewhere in the hotel, enjoy special little touches that add to the wine theme. There were winery names on the door of each room (ours was Salem, Oregon-based Cristom Vineyards). The elevators also feature a unique corkscrew design on the doors. Take a look at the map of Oregon wineries and wine-themed quotes that decorate the walls. Or enjoy the social hours each night that feature tastings of local Oregon wines. And don’t forget to head up the spiral staircase from the lobby to visit the on-site game lounge. With shuffleboard, a pool table and various videogames, it’s a great way to enjoy time at the hotel together.

wine quote Portland Oregon

A Portland Tip: Immerse Yourself

While these two hotels offer incredible luxury stays in downtown Portland, venture out and you’ll find out upscale ways to enjoy the city. Enjoy fine dining at Portland City Grill, situated on the 30th floor of the second tallest building in the region, the U.S. Bancorp Tower. Savor dishes like crab-stuffed halibut, wagyu steak or seared scallops while taking in stunning views of the river below. The elegant restaurant also offers an extensive wine list, with the most expensive offerings running at nearly $250 per bottle.

Elizabeth Taylor at Tasty n Adler

Another Portland tip: After dinner, head to Salt & Straw for late-night dessert. The high-end ice cream parlor offers unique flavors like honey lavender, pear and bleu cheese, roasted strawberry coconut and olive oil in addition to series like the recent one focused on chocolatiers.

If it’s luxurious activities you seek, there are plenty of cultural options around town. The Portland Art Museum is internationally renowned, offering an outstanding permanent collection from ancient through modern times. Another option is attending a show at the Crystal Ballroom. The historic 1914 building has a “floating” dance floor, crafted with springs in the floor to make it feel like you’re dancing in the clouds. Other theaters, like the Newmark and the Keller, offer other stage shows and live music.

Portland lights skyline

To enjoy views from a different perspective, take a ride on the Portland Aerial Tramway. Whether you visit by day to see the vibrant colors of the city’s trees, or by night to take in the lights, it’s a gorgeous way to stay classy in Portland. Tip your hat to the beauty of the Pacific Northwest before returning to your hotel.

Staying Classy in Portland, Oregon, USA

What are some of your favorite places to visit on luxury vacations? Have you ever stayed at elegant boutique hotels? Or dined at fancy restaurants while traveling?

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Ashley Ryan

Author Ashley Ryan

Ashley Ryan is a southern California native with a background in journalism and anthropology. She loves learning about other cultures and combines her passions for traveling, writing and photography in her professional work. To learn more or get in touch, visit facebook.com/ashleyryantravel

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