Whether you call it Stumptown, the City of Roses, PDX, or Beervana, the city of Portland has a ton to offer its residents: easy access to outdoor fun, a burgeoning food scene, plenty of arts and cultural opportunities and much, much more.

Now, we won’t sugar coat it: If you’re coming from sunny Hawaii, you might start missing the state’s 240 average sunny days each year. Portland has about 144 on average, and the U.S. average is 205. That being said, Portland life has its perks, and we’ll give you a brief tour of them in this article. We’ll also give you a leg up on your research around where to live—and what to do once you make the move.

Why Make the Move Between Hawaii and Portland?

Portland recently became the U.S.’s 25th largest city, and its population has been growing steadily since 2010 when it occupied the 29th spot on this list. By the way, this isn’t the first boom that the city of Portland has experienced. During a period of rapid growth in the 1840s, the city was growing so fast that there wasn’t time to remove the stumps from the land they were clearing to accommodate the city’s expansion. Thus, one of the city’s nicknames, Stumptown, was born.

Today, many people move to Portland to enjoy:

1. The PNW Outdoor Lifestyle

The coastline, lakes, mountains, forests, and rivers throughout the Pacific Northwest create a veritable playground for outdoor enthusiasts. Whether you want to hike, bike, ski, kayak, swim, or climb, you’ll find plenty of opportunities to enjoy in the surrounding areas. If you love the ease and facilities that parks provide, the area has plenty of city, state and national parkland to enjoy. If you yearn for the wilderness, you can find that, too, in just a few hours’ drive from Portland. If you loved the outdoor life in Hawaii, you’ll find a ton of new possibilities to explore in Oregon.

2. Temperate Weather and Glorious Summers

Yes, moving to Portland from Hawaii means a return to seasonal weather. However, because of its location, Portland experiences much milder winters than many other locations in the U.S. It might dip below freezing for a couple of days, but not much more than that. Additionally, ask a resident what summers are like in Portland, and you’ll hear them wax poetic: pleasantly warm weather, low humidity, sunlight until late in the day and very little rain. Finally, you’ll also get to experience a unique PNW phenomenon: a sun break, which is when the sun pierces the cloud cover, creating some very real feelings of joy (and maybe even a rush outside to bask in the light)!

3. A Flourishing Food Scene

Although the Hawaiian islands have their share of delicious food, the Portland food scene is on a whole different level. Portland has plentiful access to all kinds of fresh, local ingredients, including vegetables, fruit and seafood. The variety, the quality, and the attention to detail that many of Portland’s best restaurants offer will knock the socks off most foodies. And don’t forget to check out Portland’s food trucks! If you enjoyed sampling what Hawaii had to offer in this arena, you’ll love the way Portland wholeheartedly embraces the food truck phenomenon.

4. A Focus on Arts & Culture

Museums, music venues, symphonies, art galleries, drama, and dance are just a few of the arts and cultural resources you’ll find in Portland—along with the west coast’s oldest art museum, the Portland Art Museum. The city’s vibrant arts scene can keep even the most enthusiastic patron busy. And don’t forget to check out some of the festivals you’ll find in and around Oregon, like the LEGO Convention, the Chainsaw Carving Championship, and the Airshow of the Cascades.

By now, if you’ve got your heart set on moving from Hawaii to Portland, you’ve probably started looking at the kinds of neighborhoods you’d like to call home. We’ve got some ideas to kickstart your research.

What’s the Best Place to Live in Portland?

Portland has a ton of charming neighborhoods, each with its own features to recommend them. Maybe you’ve already looked at areas like Laurelhurst, Arlington Heights, Sellwood-Moreland, Nob Hill, Goose Hollow, or one of Portland’s many other enclaves. There’s one neighborhood, in particular, we’d love to call your attention to Southwest Hills.

You’ll find Southwest Hills perched just above the city, offering easy access to all that downtown Portland has to offer. Its location also offers stunning views that can even include glimpses of Mt. Hood, Mt. Adams or Mt. Saint Helens on a clear day. Although you’re just a few minutes from the central business district, the windy roads, the lush landscape, and plentiful parkland in the area make Southwest Hills a quiet, verdant enclave. Add a great school district, and this is a neighborhood that many families would flock to.

The neighborhood is primarily made up of single-family homes in a variety of styles of architecture: Craftsman, colonial, Victorian, and contemporary. Southwest Hills is also home to one of Portland’s notable historic homes, the 1918 Frank J. Cobbs House, which is listed on the National Register of Historic Places.

Because the neighborhood is fully residential, you will have to drive to reach amenities like grocery stores, restaurants, and Portland’s famous coffee shops. However, if you crave life in a peaceful neighborhood, the trade-off will feel more than worth it to you.

Once you’ve got a bead on where you want to live in Portland, you might be wondering what life is like for PDX residents—and what they like to do in their leisure time.

7 Ways to Enjoy Living in Portland

When you move to Portland, you’ll have all the resources of a city right at your fingertips, plus easy access to other surrounding metropolitan areas, like Seattle and Bend, Oregon, home of the University of Oregon. But just in case you need a few ideas on how to spend your first days in Portland, we’ve got some suggestions for you.

1. Spend a Morning in the Largest Used and New Bookstore in the World

As bookstores become few and far between, Powell’s City of Books is holding strong in downtown Portland’s Pearl District. You’ll probably need the whole morning to thoroughly explore the store, which takes up an entire city block. Grab a cup of coffee from the café, take in the heady smell of the store’s books and get lost in a tome or two.

2. Stroll Portland’s Otherworldly Japanese Garden

Even though it’s just a short drive from the heart of downtown Portland, the city’s Japanese Garden feels like it could be miles away from the nearest city. Stroll the beautifully-maintained grounds and enjoy the serenity of 5.5 acres of trees, flowers, bridges, streams, and pools. If the crush of the city ever becomes too much for you, the Japanese Garden is always waiting to offer you a moment of Zen.

3. Drink Your Way Through the Craft Beer Scene

Like San Diego, Portland has more than its share of craft breweries, and you could easily spend a weekend tasting your way through each one. Every Portlander has their favorites, so ask your new neighbors for their recommendations. Ours include:

  • Great Notion – If you’re an adventurous beer-lover, get a flight at Great Notion to try out their hazy IPAs and culinary-inspired sours and stouts.
  • Breakside Brewery – This brewery recently won 12 medals at the 2020 Oregon Beer Awards—no mean feat since the competition is so fierce in the state. Enjoy their classic IPA with a plate of nachos at their Slabtown location.
  • Deschutes – Although their main brewery is in Bend, Deschutes recently opened a second brewpub in Portland. The Portland location offers a tasty menu and an extensive set of taps so you can enjoy some of the brewery’s classic offerings, as well as seasonal and small-batch creations.
  • Von Ebert Brewing – Modeled after a German beer hall, Von Ebert’s airy, open space is perfect for a gathering with a bunch of new friends. Although the brewery focuses on German, Belgian and Czech styles, they’ve also got some experimental offerings to interest those who like their beers a little left of center.

4. Explore Portland’s Museums

If you’re a museum lover who’s toured all of Hawaii’s museums—twice—then you’ve got some fun waiting for you in Portland. In addition to the Portland Art Museum, check out the Oregon Museum of Science and Industry, which features a planetarium as well as laser shows. If you’re interested in the history of the Pacific Northwest, don’t miss the Oregon Historical Society, which will give you a solid background on how the city of Portland came to be, as well as insights into the native American people who occupied these areas before settlers moved west.

5. Dip into Portland’s Coffee Culture

Portlanders take their coffee seriously as the venues in which they drink it. After all, is there a better way to spend a cloudy, drizzly day than by lingering over a great cup of coffee as you page through the day’s newspaper? Like its craft breweries, every coffee shop in Portland is unique, so you can make a sport of trying every unique bean blends and atmosphere.

6. Take a Day Trip to the Willamette Valley

If you love wine—specifically cool-climate varieties, such as Pinot noir, Pinot Gris, Chardonnay, and Pinot blanc—then you’ve hit the jackpot. Just an hour south of Portland lies the Willamette Valley, home to several award-winning wineries. Make a day of it (or a weekend outing!) and head south to sip some of Oregon’s finest wines. Consider stopping by Alloro for its annual farm-to-table dinner in September or Lenné for its unique blind tasting classes, which will give you a whole new perspective on the wine you drink.

Relocating to the City of Roses

Moving to Portland from Hawaii will mean a bit of a change in both weather and culture. However, after taking a quick tour of all that Portland has to offer, we hope you’re feeling excited for all that awaits you in the City of Roses. Those who crave culture, love the outdoors, and take their food and wine seriously will find it easy to settle into the Portland lifestyle. (And remember, Hawaii is just a quick flight away when you need a taste of island life!)


Thinking of making the move to/from Portland? We’ve helped thousands of families move from Hawaii to the Pacific Northwest, and we’d be happy to help you! Just get in touch with us for a complimentary quote to get started.

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