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Planning a trip to Portland? You’re in the right place!
The City of Roses is packed with fun things to do and surrounded by some of the most beautiful nature in the United States. With so much to see, it can be hard to know where to start—but after spending plenty of time here, we’re confident the itinerary below is the best way to experience Portland in just 3 days.
From Multnomah Falls and Cannon Beach to top-rated food tours and the world’s largest independent bookstore, this itinerary will have you falling in love with one of the West Coast’s most beloved cities. So keep reading for the perfect 3-day Portland adventure!
Don’t Miss Out On Our Top Choice!
The tour we loved the most and suggest booking ASAP is this one!
Our personal FAVORITE thing we did was this half-day tour to Multnomah Falls! Exploring Oregon’s most famous waterfall and the stunning Columbia River Gorge was easy with our guide. It’s a sight you can’t miss!
Check out the 1,700+ 5-star reviews and book this tour here!
Itinerary Overview
Three days in Portland is the perfect amount of time to make the most of this creative, green, and ever-so-slightly quirky city (in a good way!). Split by the Willamette River, Portland’s East and West sides each bring their own flavor—and it’s easy to explore both without a rental car thanks to the MAX light rail, rideshares, and a super walkable layout.
From biking past murals and historic buildings to sampling award-winning food, sipping local brews, and venturing out to stunning natural spots like Multnomah Falls and Cannon Beach, this itinerary blends urban cool with Pacific Northwest wilderness. Expect leafy neighborhoods, indie vibes, and a whole lot of delicious surprises along the way.
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.
Day 1
Breakfast – Cheryl’s on 12th
Cheryl’s on 12th is a breakfast joint that offers a lot of variety and does all of it just right. From hearty classics like breakfast burritos to lighter options like rice with fried egg and sausage, you can’t go wrong with any of it.
It’s also only a 15-minute walk from today’s first tour, which starts at 10 am, so you’ll have plenty of time to fuel up before heading out for the day! Plan on leaving Cheryl’s on 12th at 9:30 am to give you time to walk over to the tour start and check in.
Morning – Explore Portland on an e-bike
If you want to experience Portland like a true local and understand what makes this city so unique, then you’ll need to hop on a bike. After all, Portland is one of the most bike-friendly cities in America! However, it can be challenging to know where to begin, and without a guide, Portland’s most interesting stops may not be as engaging as they could be. That’s why we highly recommend this bicycle tour!
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 the Shanghai Tunnels under the city to its role in the punk rock music scene in the 70’s there was a lot of hidden history here.
From there, we cruised along the scenic Waterfront Park and its cherry blossoms and the floating bike paths of the Eastbank Esplanade. 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. Once Portland’s most run-down, grungy neighborhood, this area has seen a huge change over the years. Our guide even gave some recommendations for places to check out after the tour!
Book your spot for this Portland essentials bike tour here!
Afternoon – Taste your way around Portland
After your bike tour, you’ll only be a 15-minute walk from the upcoming food tour at 1 pm, but you’ll have an hour to kill before then. To pass the time, head to the trendy Pine Street Market to look around and grab a cup of Portland’s finest locally brewed coffee. You can thank me later!
Now that you’re good and hungry, it’s time for you to taste firsthand why Portland is known as one of the best cities in the US for food lovers. This walking food tour took us to Portland’s best local spots for five incredible dishes (including a secret one!) and avoided the overpriced tourist traps most people fall into.
We started on a high with a housemade sausage and fried egg sandwich on buttery sourdough. Then, as we walked through the 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 tonkatsu 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!
Grab your spot on this top-rated food tour here!
Brewery stop – Deschutes Brewery or 10 Barrel Brewing
The food tour will finish up in Southwest Portland, so before you can get your hands on some great beer, you’ll need to catch a ride back toward the Pearl District. I highly recommend just booking a 5-minute Uber ride instead of a 40-minute bus ride, but if you want to save some money, the bus system is a great alternative to Uber.
Now let’s drink some beer!
Deschutes Brewery is the largest and most popular brewery in Oregon for a good reason. Their flagship beers are Black Butte Porter, Fresh Squeezed IPA, and Mirror Pond Pale Ale, which are all certified Oregonian classics. You’ll find all these classics as well as seasonal beers at their Portland location, which boasts over 26 taps.
10 Barrel Brewing also serves some of Oregon’s most iconic brews like the Apocalypse IPA, Cucumber Crush, and Pray For Snow. Their Portland location has some excellent rooftop seating (in the summer months) and an impressive 20-tap lineup.
Both of these breweries are right around the corner from each other, so why not stop at both for a flight? When in Oregon, drink beer as the Oregonians do!
Evening – Explore the Pearl District
By now, you’ve passed through the Pearl District on two different tours and will probably have a pretty good feel for the area. However, neither of the tours has taken you to NW 23rd (aka Nob Hill), so I recommend heading there to experience Portland’s upscale boutiques, retailers, and food scene.
It’s a great area to explore on foot, and that’s a good thing since you’ll probably still be a little full from the food tour and beer. So, take some time to explore the area and soak up this gorgeous Portland neighborhood. When you’re ready for dinner, we have one of our favorite spots for you to check out next!
Dinner – Top Burmese
Portland is known for its amazing multicultural cuisine, and Top Burmese is a great example of that. Whether you’re digging into tea leaf salad, mohinga (a traditional noodle soup), or flavorful curries, everything here tastes homemade and authentic. It’s a great place to try something new without breaking the bank!
If you still have room for dessert, head to Salt & Straw—just a short drive or walk away. They’re Portland-famous for a reason, offering creative ice cream flavors like Pear & Blue Cheese or Sourdough with Olive Oil Chocolate. It’s the perfect sweet (and slightly weird—in a good way!) ending to your meal.
Day 2
Morning – Go hiking at Multnomah Falls and the Columbia River Gorge
Today’s tour starts at 8:30 am, so wake up plenty early to get ready and meet at the tour start point. It will be about 4 hours of non-stop scenery and some hiking, so grab a quick breakfast and get ready for adventure!
Between the beauty of the Pacific Northwest and the convenience of having a driver there’s a reason this Columbia River Gorge hiking tour is our top pick for Portland. 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, 1,700+ 5-star reviews can’t be wrong!
Book this popular tour here and get FREE cancellation 24 hours before you go.
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.
Check out the Viator website here! Or, for more info, read our detailed review about Viator here.
Lunch – Hawthorne Asylum Food Cart Pod
Right around the corner from where the tour ends, the Hawthorne Asylum Food Cart Pod is a great place to grab a casual bite. Food carts are a staple of the Portland experience, and this spot has dozens of options—from Thai noodles to loaded tater tots—all set in a funky, open-air space with covered seating.
So enjoy a delicious quick lunch before we move on to our next activities!
Afternoon – Visit famous gardens and Powell’s Books
Gardens
Portland is known as the City of Roses, and just a 15-minute Uber ride from the food cart pod, you’ll find the beautiful International Rose Test Garden. Open daily with free admission, this popular spot is perfect for a casual stroll among thousands of blooming roses, with postcard-worthy views of Mt. Hood and the city skyline. You can easily spend an hour or more here, but an hour is a good overview of the gardens!
Right next door are the Portland Japanese Gardens, which are equally stunning and offer a peaceful, meticulously designed space to explore. If you have extra time, it’s well worth the $22 USD admission. Both gardens showcase Portland’s natural beauty and are a lovely way to slow down and soak it all in.
Powell’s Books
Visiting Powell’s City of Books is about as classic Portland as it gets. Open since 1971, it’s the world’s largest independent bookstore (seriously!), taking up an entire city block and offering over a million new and used titles. With its colorful rooms, quirky staff picks, and endless shelves, it’s easy to spend hours getting lost inside. Just a 7-minute Uber drive from the rose gardens, it’s the perfect next stop to unwind and browse at your own pace.
Evening – Mississippi Ave
After you’re done at the gardens and browsing the books at Powell’s, head back to your hotel to freshen up. We have a night out at Mississippi Ave scheduled to finish out the day!
Known for its diverse community and laid-back vibe, this area is packed with unique restaurants, cozy bars, and live music venues. To start, grab dinner at Prost!, a lively German pub serving hearty plates and local beer. Afterward, head to The Rambler for a nightcap in a warm, inviting space that feels more like someone’s living room than a bar. If you’re in the mood for music, The 1905 offers fantastic live jazz in an intimate setting—perfect for ending the night on a high note.
This is another iconic area so head there earlier if you can to really soak up the vibe and see what Portland is all about!
Day 3
Full day – Visit the Oregon Coast
Our final day in Portland is really going to blow you away, especially if you love the beach! This guided tour to the Oregon coast will take you to several of the most beautiful beaches in Oregon. Even better, it includes pickup (starting around 9 am) so you can have a laid back morning before you go. Make sure to eat a big breakfast!
After being picked up our adventure started by visiting Ecola State Park, where we watched the mist roll in over the Pacific. Our guide Jim also took us to a secret spot where we were able to get a glimpse of some bald eagles flying overhead! He said that, depending on the conditions, he sometimes takes groups on a short hike here, but our group went for extra time at Cannon Beach instead.
There, we wandered through charming shops, grabbed a fresh seafood lunch, and marveled at Haystack Rock, where puffins were nesting. Since the tide was low, we even got to explore the tide pools, which were teeming with colorful sea stars and anemones. How cool is that?
Next up, we went to visit Hug Point to see hidden sea caves and a seasonal waterfall that cascaded right onto the sand. Then our final stop, Neahkahnie Mountain, offered a panoramic view of the coastline. It was the perfect ending to an unforgettable day!
I loved how Jim adjusted the itinerary to make the most of the conditions. It felt like a really personalized experience, even though it was 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!
Check out the HUNDREDS of 5-star reviews and book this tour here!
Evening – Comedy at Helium Comedy Club or Multnomah Whiskey Library
If you’re up for some laughs to end the night, catch a show at Helium Comedy Club—one of Portland’s top spots for live stand-up. Located in Southeast Portland, this club hosts performances every night of the week, featuring both big-name comedians and rising local talent.
Most shows start around 7 pm, which lines up perfectly with the end of your Oregon Coast trip. There’s a full dinner and drink menu available during the show, so you can simply eat dinner here. Be sure to check their schedule ahead of time to see who’s performing during your visit.
Have a drink at Multnomah Whiskey Library
If you’d rather have a laid-back evening sipping whiskey (or other cocktails) than rushing off to the comedy show, head to Multnomah Whiskey Library. Portland certainly has an affinity for the finer things in life, and this bar is no different. Here, you can find some of the finest whiskeys in the world, unique creations, a cozy vibe, and walls filled with various types of whiskey and spirits. This makes for a fantastic way to toast to your trip and close out an epic three days in Portland!
Related Read: If you find yourself with more time, check out our 10 Best Things to do in Portland and add a few more activities to your itinerary!
Where to Stay in Portland, Oregon
Now that you have the perfect itinerary, you need somewhere to stay! We recommend staying in downtown Portland, as it’s 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. If these hotels are still available, they are my top recommendations for a luxury, mid-range, or budget stay.
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!
Renting a Car in the USA
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? Book your car with Discover Cars here and discover the freedom of exploring the USA on your own terms!
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Thanks for reading!
We absolutely loved our three days in Portland. It perfectly blends outdoor adventure with city charm, highlighting the best of the Pacific Northwest. Stick to this itinerary and you’ll fall in love with Portland, just as we did!
Need help planning more of your travels? Check out our other USA blogs here. We have top things to do, guides on where to stay, and more city itineraries to inspire your next getaway. Here are a few related blogs to get you started – cheers!
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