Portland Sightseeing: Best Tours & Day Trips

Portland Sightseeing: The 10 Best Portland Tours & Day Trips

Affectionately known as Rip City, Stumptown, and the City of Roses, Portland is one of the most eclectic cities in the USA. Bursting with personality and creative energy, this vibrant Pacific Northwest city seems to be on everyone’s must-visit list these days.

But with a dizzying array of microbreweries, trendy coffee shops, art galleries, and independent music venues, planning a trip to Portland can be overwhelming with so many sightseeing options.

Being from here, we’re always happy to point our friends and readers toward all of the weird things to do in Portland, but sometimes you just want to leave the planning and organization up to someone else. If so, then you’re in luck because we have compiled a list of the best Portland sightseeing tours.

Listed below are our top picks for the best Portland tours and Portland day trips – get ready for loads of fun sightseeing in one of the hippest cities in the USA!

And don’t miss our other posts about Portland to help you plan your trip:

How to Book Tours in Portland

GetYourGuide is our go-to for booking tours because you can compare all the tour options around Portland in one place and choose the excursion that is just right for you. Plus, they have an excellent cancellation policy in case your holiday plans change.

From haunted shanghai tunnels to craft beer and scrumptious street food, these GetYourGuide tours of Portland offer something for every type of traveler. Plus, Portland is one of the most pedestrian and bike-friendly cities in the USA, making it ideal for exploring on a walking tour or bicycle tour.

And if you feel the need to get out of the city, you’ll find several interesting Portland day trips that are ideal for seeing a bit more of the Pacific Northwest. With GetYourGuide you can skip the hassle of renting a car and leave the driving to someone else so you can just relax and enjoy the spectacular scenery that surrounds Portland. Consider taking a day trip to the Oregon Coast, Mount Hood, a Wine Tour to the Willamette Valley, or a day trip to beautiful Mount St. Helens.

The Best Tours of Portland, Oregon

1. Explore Portland on a 2-Hour Family Walking Tour

Portland Sightseeing: The Best Portland Walking Tour (Portlandia Statue)

The best way to quickly get a feel for the City of Roses is on this 2-hour family walking tour with a guide that explores many of Portland’s best sights. Starting in St. James Lutheran Church, you’ll be guided through downtown Portland by an entertaining and knowledgeable local who will provide plenty of insider tips and even share a few of Portland’s secret spots. 

On this Portland walking tour, you’ll visit the city’s most iconic sights and landmarks full of interesting facts and stories at an easy pace and fun for the whole family. You’ll discover how Portland received its name along with its many hidden secrets and off-the-beaten-path locations. Both adults and kids will have fun searching for all the miniature horses!

Your guide will end your walking tour by providing you with additional advice on what to do in Portland for the rest of your trip. By the end of the tour, you will have a better understanding of what makes Portland so unique, and you’ll be ready to explore more of the city on your own!

Book a Walking Tour of Portland

2. Get Spooked on the Portland Downtown Haunted Walking Tour

Go beyond the typical tourist sights and experience Portland’s seedy history on this seriously creepy haunted Portland tour. Portland has a dark side that many people are completely unaware of, even city residents. And on this offbeat tour, you’ll discover Portland’s legendary Shanghai tunnels on a guided walk full of intrigue and dark history. 

Originally constructed in the 19th century under Portland’s Chinatown neighborhood, these spooky underground tunnels connected hotels and taverns to the Willamette River. The intended purpose of the Shanghai tunnels was to transport goods from ships docked along the river, but these secret tunnels also lent themselves to plenty of nefarious activities and organized crime.

You’ll start your tour at the Lan Su Chinese Garden and the route will take you to eight locations in the downtown area. While exploring Portland, you will learn about the city’s sinful past – full of gambling, crime, and corruption. If you’re a fan of ghost tours or spooky experiences then this is the perfect Portland tour for you!

Book an Underground Portland Walking Tour

Like this post?! How about...
56 Weird & Wonderful Things to do in Portland, Oregon

3. Visit Majestic Mt. Hood

Portland Sightseeing: Best Portland Day Trips (Multnomah Falls)

Experience the epic landscape of Mt. Hood and the Columbia River Gorge on this full-day Mt. Hood excursion from Portland. Your tour will begin with a hotel pickup followed by a spectacular scenic drive through the Columbia River Gorge. This day trip from Portland includes a visit to Multnomah Falls, the second tallest waterfall in the USA, and you’ll enjoy lunch and wine tasting in the quaint town of Hood River.

This is one of the best day trips from Portland, and over the course of your 8.5-hour tour, you’ll experience beautiful mountain scenery, stunning waterfalls, fresh air, and panoramic views as you explore Oregon’s tallest mountain, Mt. Hood. Your knowledgeable guide will answer all of your questions about the flora, fauna, geology, climate, and history of this area.

This full-day tour from Portland offers a perfect escape from the city and a great introduction to the beauty of the Pacific Northwest. 

Book a Day Trip to Mt. Hood

4. Marvel at the Stunning Waterfalls of the Columbia River Gorge

Portland Sigtseeing: Best Portland Day Trips (Columbia River Gorge)

If you don’t have enough time for a full-day tour of Mt. Hood, you can still see the stunning waterfalls of Oregon’s famous Columbia River Gorge. This half-day Columbia River Gorge tour is ideal if you’re short on time, but want to see one of the most photographed areas in the entire United States.

Starting at 9 am, this tour takes you out of Portland and along the historic Columbia River Highway – a stunningly scenic route full of impressive waterfalls and sweeping views. 

Highlights include stops at Latourell Falls, Bridal Veil Falls, and the aforementioned Multnomah Falls (the 2nd tallest waterfall in the USA). You will stop for photos at the many viewpoints along the Columbia River Highway including the Crown Point Vista House. And the final stop on the tour is the Bonneville Fish Hatchery where you can see Herman the Sturgeon, an 11-foot-long fish that weighs 500 pounds!

Book a Tour of the Columbia River Gorge

Like this post?! How about...
14 Awesome and Adventurous Things to Do in Hood River, Oregon

5. Eat Your Way Through Portland on a Street Food Tour

Portland Sightseeing: Best Portland Tours - Food Carts

With over 500 food trucks and food carts in Portland, deciding where to eat can be one of the toughest choices you’ll face all day while sightseeing in the Rose City. So leave the decision-making up to the experts on a street food tour of Portland.

Taste the best curbside cuisine on a delectable tour of Portland’s best street food. On this 2-hour walking tour of Portland, you’ll be guided by a local who will introduce you to a few of the city’s finest mobile kitchens. You will sample 7 hand-selected tasty treats from Portland’s best food carts, hidden dining spots, and award-winning food trucks.

Even if you aren’t a self-proclaimed “foodie”, this tour is a great way to get acquainted with Portland’s funky neighborhoods and food-cart culture. 

Book a Portland Street Food Tour

6. Explore Portland’s Incredible Craft Beer Scene

Portland Sightseeing: Best Tours in Portland, Oregon - Brewery Tour

Find out why Portland is also known as “Beervana” on an epic craft beer tour! You’ll sample an assortment of craft beers, like sours, Belgians, wits, imperial IPAs, cider, and much, much more – all local brews made right here in Portland.

On this 2.5-hour beer tour, you’ll explore Portland’s eastside neighborhoods while learning about the origins of craft beer in the Rose City. A passionate guide will show you some of Portland’s best breweries and provide you with tailored beer recommendations based on your personal tastes and preferences.

You’ll walk nearly three miles, with plenty of stops for beer tastings, so come thirsty and wear comfortable shoes! By the end of this tour, you’ll know what your favorite Portland beers and breweries are so you can return later for another pint. If you’re a beer lover then there is no doubt that this is the best Portland tour for you! 

Book a Portland Craft Beer Tour

Like this post?! How about...
Portland Neighborhoods: A Complete Guide to Portland, Oregon

7. Discover Portland’s Best Kept Secrets by Bicycle

Portland Sightseeing: Best Tours in Portland, Oregon - Bike Tour

Portland is one of America’s most bikeable cities so why not explore it on a Portland bike tour? This unique tour will have you biking through some of Portland’s hippest neighborhoods, with plenty of fun stops at art collectives, one-of-a-kind markets, outdoor sculptures, and rose gardens. Don’t worry if you haven’t ridden a bike recently, this bike tour is laidback and suitable for all skill levels. 

Your bike tour begins just a few blocks from Portland’s trendy Hawthorne Avenue. Avoiding the typical tourist sights, you’ll ride through the art-heavy industrial neighborhood of Portland’s inner Eastside, visit hidden beaches along the Willamette River, ride across two of Portland’s lesser-known bridges, and stop for doughnuts at a local bakery.

From there, you’ll visit the Old Town, Chinatown, and the quaint neighborhood of Ladd’s Addition capping off 3 hours of touring around this beautiful bike-friendly city. 

Book a Bike Tour of Portland

8. Sample the World-Class Wines of the Willamette Valley

Portland SIghtseeing: Best Portland Day Trips (Willamette Valley Winery)

Taste the best wine that Oregon has to offer on this exceptional wine-tasting tour. Just a short drive from Portland sits the picturesque rolling hills and famous wineries of the Willamette Valley. Over 250 of Oregon’s wineries call the Willamette Valley home, so this tour is the perfect option to sample a few of the finest wines in the region. 

This 5-hour wine tasting tour visits three local vineyards that have been carefully selected, offering a range of ambiances from a hip modern winery to a small local vineyard that provides some of the world’s best Pinot Noir and Pinot Gris. To ensure you have the best wine-tasting experience possible, your wines will be perfectly paired with a selection of tasty cheeses, crackers, and chocolates. 

If you love wine then you simply can’t visit Portland without touring the wineries of the Willamette Valley!

Book a Willamette Valley Wine Tasting Tour

Like this post?! How about...
Oregon Road Trip: 15 Beautiful Places to Visit in the Pacific Northwest

9. Admire the Beauty of Oregon’s Rugged Coastline

Portland Sightseeing: Best Portland Day Trips (Cannon Beach)

Another one of the best day trips from Portland is a visit to Oregon’s beautiful and rugged coastline. On this unforgettable tour of the Oregon coast, you’ll visit secluded beaches, eccentric beachside towns, and two of Oregon’s best state parks – Ecola Park and Oswald West State Park. Both parks offer miles of breathtaking trails and scenic drives through impressive old-growth forests. 

Your first stop on the Oregon coast will be Neahkahnie Point. With its sweeping views of the Pacific Ocean, it’s one of the best places in the state for spotting whales! Your next stop is Short Sand Beach in Oswald West State Park – a wild, remote beach that’s popular with local surfers and bodyboarders.

You’ll continue following the Oregon Coastal Highway north to the seaside town of Cannon Beach. Full of cute restaurants, art galleries, and boutique shops, this picturesque town is best known for its massive sea stack, Haystack Rock, sitting just offshore. It’s one of Oregon’s most iconic landmarks.

Your final stop on the tour is at Ecola State Park where there is a good chance that you’ll spot seals, sea lions, and perhaps even whales if you’re lucky. This is definitely a day trip from Portland that you won’t soon forget.

Book an Oregon Coast Tour

10. Be Blown Away by Mount St. Helens

Portland Sightseeing: Best Portland Day Trips (Mount St. Helens)

Our final recommendation for sightseeing around Portland is a full-day trip to Mount St. Helens. Located about 50 miles northeast of Portland, Mount St. Helens became a household name on May 18, 1980, when a huge explosion killed 57 people. It was the deadliest volcanic eruption in US History.

This incredible tour allows you to hike in Mount St. Helens National Park and explore Ape Cave – one of the longest lava tubes in the world. You’ll also visit the Johnston Ridge Observatory Visitor Center where you can see into the still-steaming crater of Mount St. Helens and learn about the geology of an active volcano.

A day trip to Mount St. Helens is an unforgettable experience and will surely be one of the highlights of your trip to Portland. 

Book a Day Trip to Mount St. Helens

That’s it – the 10 best tours of Portland. We hope you have a great time sightseeing in the Rose City!

Planning a trip to Portland? Check out our favorite books and travel guides.


About the Author:

  • Nick Wheatley

    Nick took his first solo trip abroad to Ireland and Scotland when he was just 19. Since then he has visited over 70 countries around the world (plus 45 states in the USA).

    He coupled his passion for travel photography with Val’s passion for writing and thus Wandering Wheatleys was born. He now lives in Asheville with his two rambunctious kids, Humphrey and Wilhelminha.

    Besides photography, Nick loves eating the weirdest food he can find in a country (sheep’s brain currently sits in first place) and making Val get up an hour before sunrise to make sure he gets “the good light”.

Leave a Comment

Your email address will not be published. Required fields are marked *