Steel Bridge and Cherry Blossom Trees in Portland Oregon United States

Updated: June 20, 2026

15 Best Things to do in Portland, Oregon 

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Planning a trip to Portland, Oregon? You’re in the right place!

We loved exploring the City of Roses. From its quirky history and thriving food scene to its breathtaking waterfalls and scenic coastline, Portland is packed with unforgettable experiences. But with so much to see and do, figuring out where to start can feel overwhelming! 

After plenty of time wandering Portland’s streets, hiking its trails, and indulging in its famous donuts, we’ve put together this guide to help you make the most of your visit. Whether you want to uncover the city’s offbeat past, hike to Multnomah Falls, or soak up the beauty of Cannon Beach, we’ve got you covered. Let’s dive in!

Don’t miss out!

Our Top Choice

multnomah falls seen on a tour from Portland Oregon

The tour we loved the most and suggest booking ASAP is this one!

Our FAVORITE thing we did near Portland was this waterfall tour! We got to visit the Columbia River Gorge, Multnomah Falls, and several hidden spots, all without the hassle of driving.

The views were unreal, and the short hikes made it feel like a real adventure!

Check the 2,000+ reviews and book this tour here.

Portland at a Glance

Daniel-and-Bailey-take-a-selfie-while-walking-in-Portland Oregon
Bring layers! You can thank me later
Bailey-drinks-a-beer-in Portland Oregon
Some of Portland’s best spots are outside of downtown so be sure to explore!

Portland is a super easy city to explore, but a few local tips can make your trip even smoother. After several visits, we found these things especially helpful!

Important tip: Plan for rain and use public transit!

TriMet, Uber, and Google Maps: The MAX Light Rail, buses, and streetcars connect most of the city’s top attractions, and Google Maps works really well for planning routes. Unless you’re taking day trips to places like Cannon Beach or Multnomah Falls on your own, you may not need a rental car at all. Uber can help fill in the gaps, and I’d recommend using it at night over public transportation.

Bring layers—even in summer: Portland weather can change quickly. We visited during sunny summer days and still found ourselves reaching for a light jacket in the evenings. Packing layers will keep you comfortable whether you’re exploring the city, visiting waterfalls, or heading to the coast.

Explore beyond downtown: Some of Portland’s best neighborhoods aren’t in the city center. Areas like the Pearl District, Mississippi Avenue, and Alberta Arts District are packed with great restaurants, breweries, coffee shops, and local character, so leave some time in your itinerary to wander.

How I would spend 3 days in Portland

Haystack Rock at Cannon Beach seen on a tour from Portland Oregon
Visit the incredible Cannon Beach
Daniel-eats-ramen-in-Portland Oregon
Taste Portland’s legendary food culture on a guided tour

Three days in Portland is just enough time to experience the best of this quirky Pacific Northwest city. We packed our itinerary with incredible food, local breweries, stunning waterfalls, and even a day trip to the Oregon Coast. So, whether it’s your first visit or a return trip, here’s how we’d spend three days in Portland!

Day 1: Start your time in Rose City with an e-bike tour to all of its top sites, then follow it up with the BEST food tour in Portland! Afterward, grab a craft beer at the world-famous Deschutes Brewery or 10 Barrel Brewing before exploring the upscale Pearl District neighborhood.

Day 2: See one of the West Coast’s most impressive waterfalls, Multnomah Falls, while hiking the Columbia River Gorge. Then, spend your afternoon wandering through the Japanese Gardens and the world’s largest independent bookstore, Powell’s! End the day on Mississippi Ave, famous for cool bars, restaurants, and live music. 

Day 3: Take a full-day tour to Oregon’s most beautiful beaches, such as Cannon Beach, Ecola State Park, and Haystack Rock with a naturalist guide. Back in Portland, see a comedy show at the city’s best comedy club, and enjoy a farewell drink at the Library Bar.

For even more details, see our 3-day Portland itinerary with our personal recommendations!

Things to do in Portland, Oregon

1. Discover Portland’s quirky history with a local guide

The Portland sign on the Arlene Schnitzer Concert Hall in Portland Oregon
The famous Portland sign at the Arlene Schnitzer Concert Hall
World Landmarks Directional Signpost in Pioneer Courthouse Square in Portland Oregon
World Landmarks Directional Signpost in Pioneer Courthouse Square

Tour Details

  • Duration: 3 hours 
  • Time: 9:30 am or 1 pm 
  • Highlights: Explore Portland’s top sights with a local guide, visit Pittock Mansion and the International Rose Test Garden, cross the Willamette River, and discover the city’s history, neighborhoods, and best viewpoints
  • Inclusions: Pick up and drop off, bottled water, small group tour 
  • Rating: 4.8 stars (check 200+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

If it’s your first time in Portland, this city tour is a fantastic introduction. It covers many of the city’s most iconic sights, including Pittock Mansion and the International Rose Test Garden, while giving you insight into Portland’s unique history and culture along the way.

Right off the bat, you’ll visit Pittock Mansion to wander the incredibly preserved estate. Originally home to the famous publisher Henry Pittock, the French Renaissance-style mansion impresses with its grand architecture, ornate interiors, and sweeping views of Portland.

You’ll pass by several Portland staples like Powell’s City of Books, Old Town, and Pearl District, hearing all about the city’s rough history and beginnings. No wonder it’s so quirky and charming; the city definitely has some grit to it! 

One of the most memorable stops on the tour is the International Rose Test Garden. Rows upon rows of vibrant roses fill the 5-acre garden with color and fragrance, making it easy to see why it’s one of Portland’s most beloved attractions. Take your time wandering the paths, admiring the different varieties, and soaking in the views of the city beyond.

Shakespeare fans will get a kick out of the garden’s dedicated Shakespeare Garden section. Here, you’ll find roses and fruit trees named after characters from some of William Shakespeare’s most famous works. Yes, Romeo and Juliet have their own roses here—a tragic love story and all! 

This tour feels like discovering the heart of Portland while sightseeing comfortably and getting a history lesson all in one. 

2. Go hiking at Multnomah Falls and the Columbia River Gorge

People standing at multnomah falls on a tour from Portland Oregon
Multnomah Falls is stunning
The Columbia River Gorge seen on a tour from Portland Oregon
This view of the Columbia River Gorge took my breath away

Tour Details

  • Duration: 4 hours 
  • Time: 8:30 am or 2 pm 
  • Highlights: Exploring the Columbia River Gorge area, hiking at Multnomah Falls, visiting Latourell, seeing the iconic Vista House, Portland Women’s Forum State Scenic Viewpoint, exploring Bridal Veil Falls State Park
  • Inclusions: Air-conditioned transport, bottled water, snacks, professional guide
  • Rating: 5 stars (check 2,200+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

Not for nothing is this Columbia River Gorge tour our top pick for things to do in Portland! We had the best time exploring this scenic area, and booking a guided tour meant that we didn’t have to deal with the hassle of hiring a driver ourselves. 

We were especially glad to have Ana as our guide—she knew all the best stops and had so many fun stories to share. At Multnomah Falls, Oregon’s tallest waterfall, we had plenty of time to snap photos and take in just how massive it is up close.

Next up was Latourell Falls, where we hiked a beautiful 2-mile (3.2-kilometer) loop through mossy forest while Ana kept us entertained with the legend of the Beaver princess. At Vista House, her storytelling brought the Columbia River Gorge’s history to life, from Indigenous traditions to the early road builders who carved this route through the cliffs.

We wrapped things up with a short hike down to Bridal Veil Falls—a dreamy cascade framed by lush greenery. The whole morning was the perfect mix of adventure, scenery, and local insight.

By the time we returned to Portland, I felt like I had truly experienced the wild beauty of Oregon. If you want to explore the Gorge without the hassle of driving, this tour is the way to go! After all, 2,000+ 5-star reviews can’t be wrong!

Related Read: For more info on this tour (including pros and cons!), check out our honest review of this Multnomah Falls and Columbia River Gorge Tour!

3. Explore Powell’s City of Books

Powell's Books, Inc. in Portland Oregon
Photo credit: Powell’s Books, Inc.
Powell's Books, Inc. in Portland Oregon 1
Photo credit: Powell’s Books, Inc.

Powell’s City of Books is a true Portland institution, and something locals are incredibly proud of. As the largest independent bookstore in the world, it spans an entire city block and feels almost like its own little city of books tucked into the Pearl District.

Inside, you can spend hours wandering its four floors of shelves, with thousands of sections and genres to get lost in. It’s the kind of place that perfectly captures Portland’s quirky, independent spirit, complete with an on-site coffee bar and plenty of quiet corners to linger in, especially on a rainy day.

On the third floor, you’ll find the coolest part of the whole store: the Rare Book Room. Filled with first editions, signed copies, and high-cost rare prints, this room is a can’t-miss when visiting. 

Open daily from 10 am to 9 pm, it’s the perfect place to spend a few hours relaxing and reading. You can access the Rare Book Room from 10 am to 5 pm by getting a pass from the Pearl Room Information Center. 

4. Visit the beautiful Cannon Beach

Haystack rock on cannon beach on a tour from Portland Oregon
Haystack Rock is iconic
Cannon beach seen on a tour from Portland Oregon
Amazing!

Tour Details

  • Duration: 8–9 hours
  • Time: 9 am
  • Highlights: Enjoying ocean views and wildlife at Ecola State Park, exploring the town of Cannon Beach, free time for lunch, looking for nesting seabirds at Haystack Rock, stopping at Hug Point State Park or Oswald West State Park (time permitting)
  • Inclusions: Air-conditioned vehicle, professional guide, bottled water, light snacks
  • Rating: 4.9 stars (check 900+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

The best part about this Oregon Coast tour is definitely the flexibility! The guides know exactly how to tailor the day based on the weather, tides, and your group’s energy, making sure that you have the best experience possible.

You’ll start your adventure by visiting Ecola State Park, where you can watch the mist roll in over the Pacific. You may also get to peep at a secret spot where you can catch a glimpse of bald eagles flying overhead! Depending on the conditions, you may get a short hike here, or choose extra time at Cannon Beach instead.

At Cannon Beach, you can wander through charming shops, grab a fresh seafood lunch, and marvel at Haystack Rock, where puffins often nest. If the tide is low, you’ll get to explore the tide pools, which are teeming with colorful sea stars and anemones. How cool is that?

Next up, you’ll visit Hug Point to see hidden sea caves and a seasonal waterfall that cascades right onto the sand. Then the final stop, Neahkahnie Mountain, which offers a panoramic view of the coastline. What an incredible way to end the day!

This tour feels like a really personalized experience, even though it’s a shared tour. If you want to see the best of the Oregon Coast without stressing about logistics, this is the way to do it!

5. Find Portland’s best donuts

Bailey-eating-a-donut-on-a-tour-in-Portland Oregon
Oh, how I love a good donut
Donuts-on-a-donut-tour-in-Portland Oregon
Yummy!

Tour Details

  • Duration: 2 hours 
  • Time: Various slots between 9 am and 3 pm 
  • Highlights: Visiting Portland’s best donut shops, trying out famous spots, discovering locally beloved hidden gems, sampling the best options at each location
  • Inclusions: Local guide, all donut tastings, vegan and gluten-free options available at some stops
  • Rating: 4.9 stars (check 500+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

Whether you’re a foodie or just someone who appreciates a little sugar-fueled adventure, this donut tour is a must! But trust me, you should book it in advance because this one ALWAYS sells out.

We signed up for this tour for all of the delicious donuts, but it ended up being an awesome way to get to know Portland’s offbeat, quirky character as well. Not only did we hit the iconic Voodoo Doughnuts (because how could we not?), but we also got to discover some hidden gems that locals swear by and tourists usually miss. 

Our guide, Kayla, had an infectious energy that made the tour even better. She shared hilarious tales from Portland’s history, some lesser-known donut lore, and even a few conspiracy theories about why this city is so obsessed with fried dough!

Along the way, we got to sample some perfectly glazed classic donuts as well as some local artisanal specialties. I even tasted a blueberry basil donut! We also got to try some “doughssants”, which are essentially what would happen if a croissant and a donut had a baby. They were amazing!

Along with devouring our weight in donuts, we explored Portland’s coolest neighborhoods and got great local tips, especially on coffee spots! Whether you’re a donut fanatic or just want a fun way to see the city, this tour’s a hit. Just make sure to book early because this tour is super popular and you don’t want to miss out!

6. Find some beauty at the Portland Japanese Gardens and Rose Test Gardens

If I had to describe the climate in Portland, “lush” is the first word that comes to mind. While there are plenty of natural green spaces to escape to beyond the city, there’s a combo of manicured gardens that deserve a standing ovation for their beauty: The Portland Japanese Gardens and the International Rose Test Garden.

Starting at the Japanese Garden, you’ll feel the immediate onset of calming surroundings. Intentional designs of balance with water, shapes, blooms, and pathways truly seem to alleviate any worries as you stroll through this majestic space.

After finding zen at the Japanese Gardens, I love to take the short walk over to the Rose Test Gardens to wander through over 10,000 blooms and the best aromas on earth. You’ll find seemingly endless gardens of every color rose imaginable and get to experience different varieties getting tested out for commercial use in real time. We even saw a bright golden rose that seemed to glow in the sunlight.

Tickets to the Japanese Gardens are $22.50 USD and can be purchased online, and admission to the Rose Test Gardens is completely free!

7. See Portland’s best sights on a bicycle tour 

Daniel-and-Bailey-ride-bikes-on-a-tour-in-Portland Oregon
We love a good bike tour!
The Steel Bridge in Portland Oregon
Taking in the views along the waterfront

Tour Details

  • Duration: 2 hours 
  • Time: 10 am or 1 pm 
  • Highlights: Cruising around the city on a multi-speed cruiser bike or e-bike, Waterfront Esplanade, Park Clocks, Pearl District, learning about the spirit of Portland, seeing the Willamette River
  • Inclusions: Local guide, use of bike or e-bike, helmet, rain gear (if necessary)
  • Rating: 4.9 stars (check 470+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

If you want to experience Portland like a true local, then you’ll need to hop on a bike. After all, Portland is one of the most bike-friendly cities in America! But it can be tough to know where to start when it’s your first time in a new place, which is why we highly recommend this bicycle tour!

You can choose between a multi-speed cruiser bike or an e-bike if you’d like a little more assistance with the pedaling! Either way, this tour is one of the best ways to explore the city. 

We kicked things off in Old Town, where our guide gave us a crash course on the city’s past with tales of Portland’s wild early days. From there, we cruised along the scenic Waterfront Park and the floating bike paths of the Eastbank Esplanade. We even caught a glimpse of Mount Hood in the distance as we crossed the Tilikum Bridge!

One of the highlights of this tour was definitely gliding through the Park Blocks. If you book the Saturday morning tour, you’ll even get to hit the legendary Portland Farmers Market!

Our tour wrapped up in the trendy Pearl District, which is home to cool cafes, shops, and the city’s thriving art scene. Needless to say, we were very happy about this!

If you’re looking for a fun, active way to see the city, this is a must-do. Just be sure to book in advance. There is a reason this one sells out so fast!

Why We Book Tours with Viator

Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:

  • Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
  • Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
  • Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
  • Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
  • Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.

8. Take a day trip to Mt Hood and Hood River

View from Rowena Crest Viewpoint on a tour from Portland Oregon
The iconic shot from Rowena Crest Viewpoint
Trillium Lake and Mount Hood seen on a tour from Portland Oregon
Trillium Lake has one of the best views of Mt Hood

Tour Details

  • Duration: 8.5 hours 
  • Time: 9 am 
  • Highlights: Multnomah Falls, Timberline Lodge, free time for lunch in Hood River, driving through the Columbia River Gorge, Benson Bridge viewpoint, Vista House, Rowena Crest Viewpoint, Draper Girls Country Farm
  • Inclusions: Hotel pick up and drop-off from downtown, local guide, luxury sprinter van transport, bottled water
  • Rating: 4.8 stars (check 700+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

If you’re in Portland and want to experience the absolute best of Oregon’s natural beauty, this Mt. Hood day trip is an absolute must. It’s a jam-packed adventure through waterfalls, mountain views, charming small towns, and the iconic Timberline Lodge.

The day begins with an early morning pickup, and before you know it, you’re cruising along the breathtaking Columbia River Gorge. Your first stop is the famous Multnomah Falls. Guides take you to the Benson Bridge, which offers insane views of the towering falls. It’s an absolutely stunning sight. 

From there, you’ll continue along the Historic Columbia River Highway and make a quick stop at the Rowena Crest Viewpoint. Then, enjoy some free time in Hood River for lunch, before getting to experience the flavors of Oregon’s famous “Fruit Loop” drive. This portion is filled with multiple u-pick fruit orchards and street stands! If you’ve never experienced Oregon-grown fruit, you’re in for a real treat. 

On your way to the mountain, you’ll stop at Trillium Lake to get some scenic shots before making your way to the legendary Timberline Lodge. Perched on the south side of Mt. Hood at 6,000 feet (1,828 meters) above sea level, the views here are epic, but that’s not the only reason it’s famous. The lodge was also used for the Overlook Hotel in The Shining

With over 550 5-star reviews, this tour is certainly popular. It always sells out, so book ASAP to avoid missing out!

9. Visit the Grotto

The Grotto in Portland Oregon
The Grotto

There’s so much running around involved when trying to discover new sights. It can be completely exhausting; that’s why I love to visit the Grotto while in Portland for some much-needed peace in nature. 

Officially known as The National Sanctuary of Our Sorrowful Mother, The Grotto is a Catholic shrine and botanical garden nestled in the heart of the city. The sanctuary is 62 acres (25 hectares) of lush forest land. Its focal point is an impressive Catholic shrine carved out of a 110-foot (35.5-meter) high cliff, which houses a large marble replica of Michelangelo’s Pieta. Regardless of religious affiliation, it feels remarkably quiet and secluded, a rare sense of calm within the city. 

Surrounding the chapel and outdoor shrine, you’ll find multiple walking paths and hiking trails with stunning gardens, breathtaking views, and ornate statues made of marble, wood, and bronze.

Admission to the lower-level gardens is completely free, including parking. However, we recommend purchasing an admission ticket to the upper gardens as well. It’s only $10.95 USD and includes access to the meditation chapel with floor-to-ceiling windows and panoramic views of the Columbia River and Mount Saint Helens on clear days. 

10. Enjoy a dinner cruise on the Willamette River

Dinner on a cruise in Portland Oregon
The food was fantastic
Portland Skyline Along Willamette River in Portland Oregon
So were the views

Tour Details

  • Duration: 2.5 hours
  • Time: 6 pm or 7 pm (changes seasonally)
  • Highlights: Enjoy a 3-course dinner while taking in views of Portland and the Willamette River
  • Inclusions: Dinner, live piano music, historical narration on the outer decks, private reserved table
  • Rating: 4.4 stars (check 500+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

Want a totally unique perspective of Portland? This dinner cruise on the Willamette River is a wonderful way to spend an evening relaxing in the city. 

Climb aboard The Portland Spirit, a small cruise ship equipped with space for up to 280 passengers. You’ll get a reserved table, and although window seats are not guaranteed, you can still enjoy the views on the outer deck before and after dinner! While you’re out there, take a listen to the historical narration provided; it’s full of Portland tidbits about the landmarks you’re actively passing. 

You’ll pass under several of Portland’s most iconic bridges, including the Hawthorne, Marquam, Morrison, and Burnside, each with its own distinct design and skyline views worth stopping for a photo. Other highlights include cruising by a barbel-class submarine in the U.S. Navy, Oaks amusement park, Elk Island, and Moda Center, home to Portland’s biggest concerts and sports events. 

A full, 3-course, freshly prepared meal is served while you glide along the Willamette. Live piano accents the already special ambiance, making it a truly romantic evening to enjoy Portland along the water. 

If you’ve never experienced a dinner cruise, make this one your first! The whole experience is quite memorable, and over 500 other travelers agree

11. Hike to Pittock Mansion from Forest Park

Trail in Forest Park, Portland Oregon
The Forest Park trail leading to Pittock Mansion
The view of Portland from Pittock Mansion in Portland Oregon
The view of Portland from Pittock Mansion

City days in Portland are never dull, but sometimes, you need a little fresh air. Forest Park is the perfect place to get it! Covering 5,200 acres (2,104 hectares), it’s a vast network of trails with lush forested cover, wildflowers, and the occasional hidden structure along the way.

With over 80 miles (129 km) of trails, it can be difficult to choose just one to explore, so we narrowed it down to our favorite route: the hike from Lower Macleay Park up to Pittock Mansion, a scenic trail that naturally ends at one of the city’s most iconic viewpoints and the historic mansion above it. 

This 2.5–3 mile (4–5 km) trail winds through dense forest before gradually opening up to sweeping views of Mt. Hood and downtown Portland from Pittock Viewpoint. From here, it’s a short final stretch to Pittock Mansion itself, perched high above the city.

Originally built in 1914, the mansion features 23 uniquely styled rooms and an elegant circular marble staircase. After taking in the views from the grounds, you can step inside to explore the interior, which feels like a reward after the climb. Tickets are $16 USD per adult and can be purchased in advance or on site.

From here, you have a couple of options: either retrace your steps and hike back down through the forest (mostly downhill on the return), or make things easier and grab an Uber or rideshare back into the city, if you don’t feel like going the extra distance.

12. Taste your way around Portland

Bailey-and-Daniel-take-a-selfie-with-their-fresh-pretzels-during-a-food-tour-in-Portland Oregon
Enjoying our pretzels!
Ramen eaten on a food tour in Portland Oregon
The ramen was so good

Tour Details

  • Duration: 3.5 hours 
  • Time: 11 am or 1 pm 
  • Highlights: Exploring Portland’s coolest neighborhoods with a local guide, sampling Portland’s specialty treats, visiting locally beloved hotspots and Pine Street Market, exploring the fashionable Pearl District 
  • Inclusions: All food samples amounting to a full lunch, local foodie guide, drinks
  • Rating: 4.8 stars (check 220+ reviews here)
  • Free Cancellation: Yes
  • Price: Check prices here!

Portland’s food scene has a reputation for being one of the best in the country, and this walking food tour really showed us why! We had so much fun exploring Portland’s coolest neighborhoods, and it was such a great way to avoid the tourist traps and visit the spots that Portlanders love! 

We started on a high with a house-made sausage and fried egg sandwich on buttery sourdough. Then, as we walked through the charming Pearl District, we stopped for a local drink and a soft, chewy pretzel with a yummy dipping sauce. We were in heaven!

Next up, we tried some rich tonkotsu ramen, and then just when we thought we couldn’t eat any more, our guide revealed the secret dish. We won’t spoil the surprise, but we promise you’re in for a treat! We capped off the tour with a bright pink Simpsons-themed donut and finished up with a coffee at a cozy cafe.

Beyond the food, I loved how our guide wove in stories about Portland’s history, architecture, and vibrant food culture. It felt like getting an insider’s tour of the city while eating my way through its best bites. If you’re visiting Portland, this tour is a must, but please come hungry, because you’ll leave absolutely stuffed!

13. See Portland from above on a scenic flight

Aerial view of Downtown Portland Oregon
What a view!

Tour Details

  • Duration: 20 minutes (flight time)
  • Time: Multiple times available from 9 am–9 pm
  • Highlights: Take a scenic flight over iconic landmarks, including the Moda Center, Rose Quarter, and Providence Park
  • Inclusions: Pick up and drop off, bottled water 
  • Rating: 4.9 stars (check 100+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

Whenever I’m flying into a city, I pop open the shade and study the land before me. Little lives are all hustling around down there while I’m soaring above. I’ve always appreciated these views and wished for just a little longer to observe. That’s why when I found this downtown Portland air tour, I knew I just had to experience it! 

This tour has multiple timing options, but I wanted to catch the sunset, so 9 pm was the deciding take-off time. Arriving promptly 20 minutes prior to flight time, the jitters and anticipation were primed! After check-in and a quick safety video and introduction, it was time to fly. 

The flight time is only about 20 minutes, but it was pure bliss being able to soar over popular landmarks like Moda Center, Providence Park, and the Portland, Oregon, sign. Each pass by was met with fun facts and history from our guide. 

I felt like a pilot for those 20 minutes of communicating through the headsets they provided! The views offer incredible opportunities for photography that you couldn’t possibly capture from a jetliner. 

Flying above Portland at sunset makes an excellent date night, family outing, or solo adventure!

14. Go wine tasting in Oregon’s famous Willamette Valley region

Daniel-and-Bailey-take-a-selfie-while-drinking-wine-in the Willamette Valley region on a tour from Portland Oregon
The wine was incredible!
Grape-vine-in-the-Willamette Valley region on a tour from Portland Oregon
Wandering through the vineyard

Tour Details

  • Duration: 7.5 hours 
  • Time: 9 am 
  • Highlights: Exploring the Willamette Valley wine country, visiting up to three different vineyards, sampling local wines, learning about grape production, and a picnic-style lunch at a winery
  • Inclusions: Hotel pick up and drop-off, lunch, professional guide, all transport, bottled water
  • Rating: 4.9 stars (check 500+ reviews here)
  • Free Cancellation: Yes
  • Price: Check price here!

Whether you’re a wine lover like me or a casual enthusiast, this full-day tour of Willamette Valley wine country promises an epic experience. We had the best day ever cruising through the rolling hills and lush vineyards of this famous wine region, and we loved hearing stories about the valley’s winemaking history.

We visited three incredible wineries, each of which offered a unique tasting experience. The wine samples were on our own account, but we actually appreciated this as it meant we got to pick the tastings that we wanted to try!

At every stop, we tasted a wide range of wines, including pinots, chardonnays, and rieslings, each with distinct notes and characteristics that showcased the valley’s terroir.

Best of all, we enjoyed a gourmet picnic-style lunch of artisan produce at one of the wineries, with amazing views to boot. With fresh bread, local cheeses, and lots of fresh fruit, we really couldn’t have asked for more!

Each stop on this tour not only introduced us to fantastic wines but also provided a deeper understanding of sustainable viticulture and the art of winemaking in Oregon. We moved at a leisurely pace so we never felt rushed, and we had plenty of time to savor the wine and soak in the beautiful scenery.

We would do this tour again in a heartbeat, and judging from the glowing reviews, we’re not the only ones.

15. Find your favorite food cart and craft beer

Hawthorne Asylum in Portland Oregon (3)
Photo credit: Hawthorne Asylum
Hinterland Beer and Carts in Portland Oregon
Photo credit: Hinterland Beer and Carts

No visit to Portland is complete without eating at a food cart pod. The city essentially pioneered the modern food truck movement, with food carts becoming a major part of Portland culture in the early 2000s. 

Today, Portland is widely considered one of the best food truck cities in the country, and these aren’t just random trucks parked on a street corner. Most pods have dozens of vendors, plenty of covered seating, and even bars pouring local beer, cider, and wine.

One of our favorite stops is Hawthorne Asylum, a bustling food cart pod on Portland’s east side near the Hawthorne District, where you can sample everything from Ukrainian and Burmese dishes to Korean and Lebanese specialties. Hinterland Bar & Food Carts, located in southeast Portland, offers a more local and relaxed vibe with plenty of great food options. Piedmont Station is another excellent choice if you’re spending time in northeast Portland.

The best part? Many food cart pods double as a great introduction to Portland’s famous craft beer scene. Grab a meal and pair it with a locally brewed IPA, lager, or cider while you soak up the atmosphere. 

Beer lovers looking to dive deeper should check out iconic breweries like Great Notion, Wayfinder, and the rising star Brujos. Not a beer fan? Portland’s cider scene is just as impressive, with Portland Cider Co. being one of our favorite stops. You’ll love their rotating seasonal ciders!

Related Read: Make the most of your time and follow our 3-day Portland itinerary. It includes these top activities, and a few of our favorite hidden gems!

Where to Stay in Portland, Oregon

The Ritz-Carlton, Portland in Portland Oregon 1
Photo credit: The Ritz-Carlton, Portland
The Ritz-Carlton, Portland in Portland Oregon
Photo credit: The Ritz-Carlton, Portland

Now that you’re all caught up on the best things to do in Portland, you just need to figure out where to stay! In our opinion, Downtown Portland is the best area to stay in because it’s a lively and walkable area that’s home to most of the city’s top attractions!

The Downtown area is also incredibly convenient for getting around. Many tours offer free pickup from the area, and you’ll have easy access to Portland’s extensive public transport network, so getting out to explore other areas won’t be a problem. To make your stay even easier, we’ve listed some of the best hotel options in Downtown Portland for every budget.

Luxury – $$$ 

The Ritz-Carlton, Portland is a luxurious 5-star hotel ideally located just a short walk from some of the city’s top attractions, like the Portland Art Museum and Lan Su Chinese Garden. The hotel boasts elegant rooms featuring air-conditioning, private bathrooms, and modern amenities. But my favorite thing about this hotel is the stunning indoor rooftop infinity pool, which offers spectacular city views through its floor-to-ceiling window. Trust me, you’ll struggle to tear yourself away!

Prices at The Ritz-Carlton, Portland start from $500 per night. Check out all of the options and book this luxurious stay on Booking.com now!

Mid-range – $$ 

The Heathman Hotel is a charming hotel located in the heart of Portland’s vibrant Downtown, just a short walk from the Portland Art Museum and Powell’s City of Books. It offers modern spacious rooms, and we love the library-themed hotel restaurant! Plus, with a 24-hour gym, free WiFi, and some pet-friendly rooms, you’ve really got everything you need here!

Rooms at the Heathman Hotel typically range between $150 and $250 during peak season. Check availability and reserve your stay on Booking.com!

Budget – $ 

The Moxy Portland Downtown hotel offers an amazing location at an affordable price. We think that this hotel is modern and fun, with comfortable rooms and even a quirky on-site coworking space and bar. We love its industrial-chic design and the fact that there’s free WiFi, a games room, and a fitness center on site. It really is a home from home! 

Prices at Moxy Portland Downtown start at $100 per night. Check out all the options and this hotel’s availability on Booking.com now!

Check out all of Portland’s listed hotels here!

Related Read: Want more options beyond Downtown? Check out our full guide to the best areas and hotels in Portland, Oregon, here to find the perfect neighborhood for your stay.

Renting a Car in the USA

Car rental photo for the United States

The United States is a vast country with diverse landscapes, from bustling cities to scenic national parks. While public transportation exists in major cities, renting a car is often the best way to explore the country’s wide-open spaces and hidden gems.

We always book with Discover Cars and can’t recommend them enough. It’s super easy to compare prices, check company ratings, find the right vehicle for your needs, and add affordable full coverage insurance. If you want a full breakdown, check out our Discover Cars review here.

Tips for Renting a Car in the USA

  • Drive on the right: In the U.S., vehicles drive on the right-hand side of the road, and the driver’s seat is on the left. If this is different than your home country, take some time to adjust before hitting busy streets!
  • Know the local rules: Speed limits, road signs, and driving laws can differ between states. For example, turning right on red is generally allowed after a complete stop, unless a sign indicates otherwise. Always check the specific rules for the states you’ll be driving in.
  • Add full insurance: We always recommend full coverage rental insurance, especially in the U.S., where long distances, varying road conditions, and unpredictable weather can lead to unexpected situations. Discover Cars makes it easy (and affordable!) to add this peace of mind when you book.
  • Choose the right car: Consider the nature of your trip. For city driving, a compact car is convenient, while for road trips or national park visits, an SUV might be more comfortable. With Discover Cars, it’s easy to filter by vehicle type, transmission, fuel efficiency, and more to find the perfect fit.

What You Need to Rent a Car in the USA

  • A valid driver’s license from your home country.
  • An International Driving Permit (IDP) is recommended if your license is not in English or uses a non-Roman alphabet. Some rental companies may require it, so it’s best to check in advance.
  • A credit card in the driver’s name is typically required for the security deposit.
  • Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.

Ready to hit the road and discover the freedom of exploring the USA on your own terms?

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Thanks for reading!

Daniel-and-Bailey-take-a-selfie-drinking-a-beer-in-Portland Oregon
Thanks for reading!

That’s our complete guide to the best things to do in Portland, Oregon! From waterfall hikes and coast day trips to donuts and underground tunnels, this city truly has something for everyone. We had an amazing time uncovering both the well-known highlights and the quirky corners that give Portland its charm.

If you’re planning more trips around the Pacific Northwest or beyond, be sure to check out our other USA travel blogs for more ideas. We’ve also linked a few favorite nearby destinations below to help you keep the adventure going!

10 Best Things to do in Los Angeles

10 FUN & EXCITING Things to do in Las Vegas

9 Best Things to do in Palm Springs, California

How to Spend THREE DAYS in Seattle, Washington: 3-Day Itinerary

The Services We Recommend

From hotels to guided tours, we only recommend services we know and trust. Here are our recommended partners so you can explore Costa Rica with confidence.

Bailey and Daniel are the married couple who started this blog. They’re endlessly curious, always planning the next adventure, and happiest when they’re on the move. Travel isn’t something they do once or twice a year — it’s the way they’ve chosen to live their lives.

Learn more about Dan & Bailey

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