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 don’t worry, I’m actually from Oregon! With my local tips, I’m 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 trip 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!
My Top Choice
The tour I loved the most and suggest booking ASAP is this one!
My personal FAVORITE thing I did was this half-day tour to Multnomah Falls! Seeing Oregon’s tallest waterfall and the stunning Columbia River Gorge was a bucket-list experience, and this tour made it easy!
Itinerary Overview
🚲Day 1: Start your time in Rose City with an e-bike tour to all of its top sites. Then, wander 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 2: See one of the West Coast’s most impressive waterfalls, Multnomah Falls, while hiking the Columbia River Gorge. Refuel in the afternoon with this food cart tour around the city, and spend the night enjoying the Pearl District.
🌊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
Exploring a city on two wheels is one of my favorite ways to experience it. You cover so much more ground and get to see it from a totally different perspective. Plus, riding a bike is just fun! This Portland bike tour checked all those boxes and more, and even as an Oregon native, I learned so much about the city.
You can choose between an e-bike or a multi-speed. I opted for the e-bike, but honestly, the multi-speed would have been just fine. We never faced any hills, and since it’s city biking, I really didn’t pick up much speed. I booked the 10 am to 12 pm tour, which operates rain or shine, so hopefully you get a nice day as I did!
After meeting the tour and getting acquainted with our bikes, we cruised through Old Town and towards Waterfront Park. This is where the famous Portland Farmer’s Market is located! From there, we crossed the historic Steel Bridge, which is one of the few in the country that operates with a vertical lift.
This tour was cool because the river splits Portland into quadrants, and we hit all four. Besides historic buildings, we saw street art, the best food cart pods, and rolled through a charming little neighborhood. Our guide even had us stop to smell the roses planted in community gardens all around the city. No wonder Portland is nicknamed the “City of Roses”.
We finished by crossing Tilikum Bridge and spotting Mount Hood in the distance – iconic Portland!
This tour was relaxed and packed with information. It’s accessible to most travelers, as long as you can ride a bike! I’d definitely recommend it for anyone who wants to make the most of their time in Portland and really get to know the city.
Lunch – Backwoods Brewing
After all that pedaling, we were ready for lunch! As a self-proclaimed craft beer enthusiast, I made sure to stop by a brewery at least once in this itinerary (okay, maybe more than once!). Backwoods Brewing is just a 10-minute walk from the end of the bike tour, so it was an easy option for lunch.
This stop wasn’t anything fancy, but it definitely hit the spot, especially with their burger and beer lunch combo. They even had gluten-free options for my mom, so everyone was happy! There are a handful of other breweries around this area if anything else catches your eye, but don’t wander too far because our next stop is right around the block.
Afternoon – Visit Powell’s Books, gardens, or a museum
The rest of the day is relatively unscheduled, so move at your own pace. I have a few iconic Portland spots that can’t be missed!
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, and there really is something for everyone – even if you’re not a bookworm!
This is less than a five-minute walk from Backwoods Brewing, and depending on your level of interest, you could spend twenty minutes here or a few hours – up to you!
Gardens
Portland is known as the City of Roses, and just a 7-minute Uber ride from Powell’s, 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, the $22 USD admission is well worth it. Both gardens showcase Portland’s natural beauty and are a lovely way to slow down and soak it all in.
Museums
If you have extra time or the weather turns sour, visiting a museum is a great addition to your itinerary!
The Portland Art Museum is on the same side of the river, so it’s easy to get to, just a 5-minute drive from Powell’s or a 10-minute drive from the Rose Garden. It’s the oldest art museum in the Northwest, with a massive collection of local artifacts and art. It’s open until 5 pm every day except Monday.
Another one of my favorite museums is the Oregon Museum of Science and Industry, or OMSI. I frequently visited this museum growing up, and it’s just as fun as an adult. There are some amazing rotating exhibits, like Bodyworks and dinosaurs, as well as hands-on labs, a planetarium, and a submarine. This is across the river, so a slightly longer drive, and is open until 5:30 pm every day except Monday.
Evening – Mississippi Ave
After you’re done with your afternoon activities, head back to your hotel to freshen up. I 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 2
Morning – Go hiking at Multnomah Falls and the Columbia River Gorge
As an Oregonian, I’m a bit spoiled for the outdoors, but I can’t deny how iconic Oregon’s tallest waterfall is! Luckily for you, it’s just a short drive from Portland, and this half-day tour makes it easy to reach.
This tour is great because you can visit four waterfalls and see the stunning Columbia River Gorge without the hassle of renting a car or figuring out the logistics yourself. It leaves at 9 am and returns promptly at 12:30 pm.
Our first stop was the Vista House, which our guide told us the local nickname is the “$100,000 outhouse.” Regardless of the name, the views over the Columbia River were stunning, and the marble structure was also beautiful.
The next three stops were all about waterfalls, each one higher than the last. Latourell Falls is 225 feet (69 meters), Shepherd Dell Falls is a 300-foot-long waterfall (91 meters), and Wakeena Falls is 500 feet (152 meters) tall! All of these “hikes” were more like strolls, all less than 0.25 miles (400 meters) each way and nothing too strenuous. Our guide, James, was a wealth of information, explaining history, ecology, foraging, and all sorts of tidbits of knowledge.
Finally, we made it to the main event: Multnomah Falls! Here, we had about 40 minutes to explore on our own. There are trails that weave up towards the 620-foot (189-meter) waterfall, as well as a gift shop and coffee shop. While you could easily spend a full day hiking here, a short visit is enough to enjoy the scenery and stand in awe at the size of this waterfall!
If you’re looking for a short, sweet, jam-packed afternoon outside the city, don’t hesitate to book this tour!
A quick note: The closest meeting point to downtown is a 20-minute drive/Uber, but you can also reach out to the tour operator ahead of time and see if you can get a closer pickup spot if that is too far.
Related Read: For more details on our experience (including pros and cons!), check out my honest review of this Multnomah Falls and Columbia River Gorge Tour!
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:
Afternoon – Taste your way around Portland
Normally, I don’t like to plan back-to-back tours, but these are both can’t-miss experiences in my book! After a morning of waterfalls and hiking, you’ll probably be pretty hungry, so this food cart food tour is the best way to refuel.
This tour starts at 1:30 pm and is a 20-minute drive from the endpoint of the Multnomah Falls tour to the meeting point of this tour. I know that sounds a bit tight, but the waterfalls tour is known for being quite punctual, so you should have no problems with timing.
Portland is known as the pioneer of food truck pods. If you’ve never experienced them before, they are so fun! These “pods” are a handful of food trucks grouped together, usually with varying cuisines, and in Portland, you’ll almost always find craft beer, cider, or wine. There are plenty of food carts around, so this tour shows you the ropes.
You’ll visit a few different pods, including two of the famous ones: Cartopia and Hawthorne Asylum. I loved that all food and drinks were included, so we showed up, and our guide already had some of the tastiest foods ordered. This was a great way to try some new cuisines, like Burmese noodles and Ukrainian dumplings!
By the end, I tried almost seven different foods, plus local beer and a sweet treat. Since we walked from pod to pod, it was a great way to get to know the city, see iconic sights, and enjoy Portland!
Evening – Explore the Pearl District
The food tour will wrap up around 4:30 pm, and since you’ve had a busy day, the evening is yours to use as you’d like! I recommend going back to your hotel to rest and freshen up, then heading out to the Pearl District for an evening wander.
The heart of the Pearl District is NW 23rd, aka Nob Hill. It’s a classy area, full of trendy restaurants and bars, boutiques, and galleries. The architecture here is also really beautiful, with historic homes and tree-lined streets. It feels different from other gritty, quirky parts of Portland!
The best way to experience this area is to wander around and see what stands out to you. However, Bar Diane is a great option for small bites and great cocktails if you’re feeling a bit peckish. And if you’re ready for a full dinner after that food tour, Papa Haydn is well loved in the neighborhood.
For dessert, Salt & Straw offers 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 day!
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 pickup, the adventure started with a visit to 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 got a glimpse of bald eagles flying overhead! He said that, depending on conditions, he sometimes takes groups on a short hike here, but our group spent 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 visited Hug Point to see hidden sea caves and a seasonal waterfall that cascaded onto the sand. Then our final stop, Neahkahnie Mountain, offered a panoramic view of the coastline. Even as an Oregon native, I had never been to these last two stops, so they were a fun addition to an already amazing day.
I loved how Jim adjusted the itinerary to make the most of the conditions. It felt truly personalized, 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!
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 my favorite 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! I 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 – $$$
The Ritz-Carlton, Portland is a luxurious 5-star hotel ideally located just a short walk from some of the city’s top attractions, like the Portland Art Museum and Lan Su Chinese Garden. The hotel boasts elegant rooms featuring air-conditioning, private bathrooms, and modern amenities. But my favorite thing about this hotel is the stunning indoor rooftop infinity pool, which offers spectacular city views through its floor-to-ceiling windows. Trust me, you’ll struggle to tear yourself away!
Prices at The Ritz-Carlton, Portland start from $500 per night. Check out all of the options and book this luxurious stay on Booking.com now!
Mid-range – $$
The Mark Spencer Hotel is comfortable and full of character. It sits right on the edge of Downtown and the Pearl District, so it’s in a top-notch location within walking distance of some of the best shops, restaurants, and attractions in the city.
The hotel has a classic, elegant feel, with spacious rooms and a welcoming atmosphere. It’s a really solid choice if you want a reliable stay in a great location without spending too much. Rooms here usually start at around $200 USD per night. Check availability and book your stay here.
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 my full guide to the best areas and hotels in Portland, Oregon, to find the perfect neighborhood for your stay.
Book your Airport Taxi in advance
Start your trip stress-free by booking your airport taxi before you arrive. You’ll skip the long lines, avoid overpriced fares and scams, and won’t have to worry about explaining your hotel address to a driver. Simply prebook your airport pickup online here, and your driver will be ready to take you directly to your hotel!
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
What You Need to Rent a Car in the USA
Ready to hit the road and discover the freedom of exploring the USA on your own terms?
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Thanks for reading!
Three days is the perfect amount of time to experience Portland. This city perfectly blends outdoor adventure with quirky 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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The Services We Recommend
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Meghan is a slow traveler and meticulous planner, who fell in love with traveling while exploring North and Central America on motorcycle and backpacking through Asia. Now based in Cambodia, she specializes in crafting seamless itineraries that balance must-see sights with spontaneity—favoring mountains, history, craft beer, and experiences that go a little off script.
