A Luxury Weekend Getaway in Portland, Oregon

One of my favorite vacations was spent in Portland, Oregon before Will and I were married. We loved the city. I remember making him walk like 20 blocks in order to eat flan that I read about in a guide. It's been awhile since I've been there so when Andy Hayes, a resident of Portland, contacted me about guest posting, I happily agreed. Here are some of Andy's favorites in the city. 

A Luxury Weekend Getaway in Portland, Oregon

Considered by some newspapers to be the best place in the world to live, Portland is so much more than the hipster slice of Oregon portrayed on the popular TV show Portlandia.  Home to a quirky counter-culture that prides itself on local food and drink, Portland marches to its own beat (literally).

As a lover of all things luxe, I think Portland makes for the perfect luxury weekend getaway.  However, before I moved to Portland, I found it a little hard to find those luxurious experiences.  Below, I’d like to share with you some of my personal favorites.

The Great Outdoors

You might assume that it rains all the time here, and there’s nothing of interest outside.  It does rain, but not as much as you think; if the weather suits, try renting a bike and heading for a ride along the Willamette River.  You can ride on both sides of the river, and your hotel concierge will be able to give you directions/recommendations.

Not up for the bike?  Then head over to my favorite local’s spot, The Grotto. This botantical garden sits atop a cliff, and is a wonderful place to walk and reflect, even on a rainy day.   Another clifftop park is the International Test Garden, which offers incredible views of downtown – even if the roses are not in bloom, it’s a must-see.

Tip: If you have a car, I highly suggest a drive out to Multnomah Falls, located in the Columbia River Gorge.  In just an hour you’ll reach some of the most dramatic scenery in the whole state. 

Food and Wine

Portland is the most epicurean city I have ever lived in, by far.  Giving restaurant tips is almost painful, because I could rattle off a huge list.  I’ll make it easier by suggesting a visit to foodcartsportland.com and find a couple of carts near you.  The food cart scene here is still exploding, and it’s a great way to do some sampling throughout your visit – there are carts everywhere.

Once you’ve picked out some carts, followup with a visit to one of the Portland Urban wineries.  These winemakers have quirky tasting rooms and very good, locally produced wines (great for souvenirs, too).  Two favorites include Hip Chicks Do Wine and ENSO Winery – the link above has a full map to all the tasting rooms and opening hours.


Portland is home to many, many makers; most of the shops you’ll see throughout the city are locally owned – there are few chains.  Instead of recommending specific shops, I’d like to recommend some areas of town great for going on a shopping stroll, followed by a cocktail or glass of wine:

·         NW 23rd & Overton:  23rd is lined with shops and eateries on both sides, from quilting to gourmet popcorn, along with a popular distillery.
·         SE Hawthorne & 34th: A hip and fun area full of clothing shops, a foodie version of Powell’s Books, and other unique finds.
·         N Mississippi Ave & Fremont: Food carts, restaurants, and shops with very interesting combinations (salt and flowers, anyone?)

Trimet is Portland’s public transport provider, and for $5/day you can travel as much as you want to any of the city’s neighborhoods via tram, bus, or train.

Where to Stay

Portland has so many options for accommodation, and yet, on busy weekends you’ll find everything is booked (a reminder we are still a small city), so plan ahead.  The newly renovated Riverplace Hotel is in a wonderful quiet spot by the river, and is now owned by Kimpton so you can enjoy loyalty perks if you are a member.

For a central downtown spot, head for Hotel Lucia.  This art-themed property is a short walk to pretty much everything, from food and drink to a tour of Powell’s Books, and their luxe rooms are some of the best value you can find in town.

It’s Portland, so I leave you with an out-of-the-box suggestion:  splash out on a carefully restored home on AirBnB. I suggest looking in southeast Portland, where you’ll find a home-away-from-home that will make you feel like a king (or queen).

All photos are copyright by the author, used with permission.

Andy Hayes is based in sunny Portland, Oregon and he’s the founder of Plum Deluxe, a community of friends and family who enjoy life’s luxuries, big and small. 

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