Top Portland Sightseeing Tours

See the best Stumptown has to offer on a small-group tour of the city's top sights and attractions. Learn about local history, culture and everyday life while exploring downtown and its surrounds. Peruse the revamped Pearl District and visit Pioneer Square. Experience what makes Portland unique with stops at the International Portland Rose Garden, Pittock Mansion and Lan Su Chinese Garden. Walk away with a better appreciation for and knowledge of Oregon's largest city.

Explore Portland on a 3.5-hour city sightseeing tour that travels from downtown Portland to the Pearl District to Nob Hill. Take a tour of the Pittock Mansion and see Lan Su Chinese Garden, a collaboration between Portland and sister-city Suzhou, China. Stroll through the International Rose Test Garden, located in Washington Park and boasting more than 7,000 rose plants with 550 varieties represented. Learn about the history and culture of Portland, which has been growing rapidly in recent years. Your tour includes pickup and drop-off from downtown Portland hotels.

Experience highlights of the Portland area on this full-day sightseeing tour, including the blossoming food cart culture, diverse neighborhoods, Pioneer Courthouse Square, and the unspoiled beauty of the Columbia River Gorge. Immerse yourself in a guided tour of Portland’s fascinating history and quirky contemporary culture.

See the best of the Pacific Northwest on this guided Portland city tour. Pass top attractions including the Lan Su Chinese Garden, Pittock Mansion, the International Rose Test Gardens, and Powell’s Books. Your guide will provide commentary, beverages, and snacks while you take in views of nearby Mount Adams, Mount Hood, Mount St. Helens, and Mount Rainier.

On this 3.5-hour tour, you'll get a broad overview of the Central City. We'll make stops at Pittock Mansion, the International Rose Test Gardens, and the Portland Aerial Tram. At Pittock Mansion, you'll get pictures of the best views of the city, and the five stratovolcanoes that are visible on a clear day. You'll have plenty of time to smell the roses at the Rose City's most famous garden. You'll get another great view of the city riding the Aerial Tram (*PORTLAND AERIAL TRAM CURRENTLY CLOSED TO PUBLIC DUE TO COVID-19*). Your expert guide will provide background on the sites and city history, while navigating through city traffic, so you don't have to. You'll meander through all of the major neighborhoods of inner Portland on both sides of the river while gaining views of 14 of Bridgetown's 22 notable bridges. Your guide will return you to your departure location at the end of the tour. Book our Explore Columbia River Gorge Half-Day Small-Group Tour as well, and receive $10 cash back.

Want to check out Portland's hot thrift shop scene? You just have to know where to go! Come along with me for a tour of shops that include everything from items plucked out of the dump to high-end Prada at a second hand boutique! Portland's thrifting culture is rooted in our respect for the environment and a commitment to re-use and recycle useable goods rather than send them to the landfill. Consequently, we have many thrift shops of every kind and category! There's no place better to begin than SE Hawthorne Ave., a vibrant street of secondhand shops, as well as a food carts, coffee shops, and small businesses selling made-in-portland goods. It's my treat for coffee or cocktails as we meet to get acquainted and caffeinated! This is a team experience so we can share what we're looking for and act as scouts for each other (me: Frye boots, color brown, size 10). I look forward to going thrifting with you in Portland!

Whether you want to relax after a long day of sightseeing or need to unwind at the end of your workweek, a sunset dinner cruise along the Willamette River is sure to do the trick. The journey offers spectacular views of the Portland skyline and city’s main landmarks. Listen to live music while you enjoy a freshly cooked Pacific Northwest meal.

Meet downtown and head to the Columbia Gorge to enjoy 3 amazing waterfalls. All of the waterfalls are located in the Columbia Gorge which is about 30 mins outside Portland. Each of the hikes will be about a mile or less. We will visit the most famous and some also lesser known waterfalls.

Take a spin around the City of Roses with this bike tour of essential Portland. Pedal through the city's historic Old Town, along the river on the Waterfront Esplanade, through the Park Blocks with their many green spaces and the hip Pearl District. Learn about the spirit of Portland from knowledgeable guides as you see the city as many of the locals do—by bike.

Start your day off right with a 2-hour brunch cruise along the Willamette River. Board the boat in the late morning and soak in the scenery of northern Oregon as your boat glides away from Portland. When you’re ready, help yourself to a buffet brunch accompanied by sparkling wine or apple cider. You can walk around the deck or sit near the cabin windows to view the stunning landscape.

See Oregon’s infamous waterfalls from above on a private airplane tour through the Columbia River Gorge. Get 360-degree views as you soar over the Vista House, Booneville Dam, the Bridge of the Gods near Cascade Locks, and more. This private experience allows you to customize your itinerary to fit your preferences. 

If you’ve never flown on a private plane before, this 20-minute ride over the Columbia River Gorge will be an unforgettable experience and a thrilling overview of the natural beauty of the Pacific Northwest. Your knowledgeable pilot will take you east through the Gorge toward the Vista House viewpoint, past the waterfalls and cliffs of the Gorge.

Maximize your beach time while at the Oregon Coast! Oregon’s coastline is graced with unforgettable vistas: dramatic cliffs, offshore rocks and sea lions, wide sandy beaches, majestic capes, historic lighthouses, enchanted forests and lovely small beach towns which artists and artisans make their home. Locations we may visit include: Cannon Beach, Haystack Rock, Short Sand Beach at Oswald West State Park, Neahkahnie Point, and Manzanita while enjoying spectacular views of the dramatic Oregon Coastline.

Join us on our full day guided tour from Portland to Mt. Hood. By visiting Mount Hood with our enthusiastic and knowledgeable guides, you will have multiple opportunities to get the best photographs of the awe-inspiring scenery, and to learn about the history and heritage of Portland’s iconic mountain. Our tour will depart the hustle and bustle of downtown Portland by first taking you into the wonders of the Columbia River Gorge. We will follow the Columbia River east to the town of Hood River for lunch before driving up through the Hood River Valley to the south side of Mt. Hood. The sites that we may visit include: Multnomah Falls, Rowena Crest, a farm stand (seasonally), and Timberline Lodge. Your route may vary based on weather and road conditions but our guides will make necessary changes to enhance your Mt Hood Loop tour experience.

Along the Northern Oregon Coast, you will find old-growth forests, pristine beaches, majestic capes and stunning views. Wander in the footsteps of Lewis and Clark as you explore the beach and majestic Haystack Rock. Have lunch in Cannon Beach and browse in the many quaint stores and shops. Pass through a preserved old-growth forest on the way to Ecola state park and hike out to view the sea lions and seabirds.

See Portland your own way on this private customizable tour of downtown Portland and other city highlights. Travel in a comfortable vehicle to the attractions that you most want to see, like the Moda Center and Hawthorne District, while learning about Portland history and contemporary culture alike. This small-group tour is limited to four people or fewer and includes all transportation, bottled water, and snacks.

Experience Oregon from the sky with this aerial tour above some of the state’s most dramatic scenery. This flight for up to three people will take you above the Columbia Gorge, over the Mt. Hood National Forest and back. Note that prices are for the entire plane ride, so bring a couple friends and make a day of it.

In this Portland food tour, we will explore the charming streets of the Kerns neighborhood where we will sample some of the tastiest bites that Portland has to offer. This once sleepy neighborhood has blossomed into a Portland bazaar for diverse and delicious treats. Our six stops will create a varied and scrumptious meal and whet your appetite for what the Kerns has to offer. Examples will include ethnic contributions such as Cuban & Israeli food, as well as a visit to an eclectic food cart pod, charcuterie, and dessert and an artisanal ice cream shop. You will not leave hungry! While the Kerns extends more broadly, its core is centered on Restaurant Row, on NE 28th between Burnside and Glisan St. We will walk a total of 1.2 miles through tree lined streets and hipster hangouts while we visit six foodie hot spots in the Kerns neighborhood. Along the way we will also talk about the history of the Kerns and take in some classical Portland residential architecture. All ages welcome.

Explore Portland from above on a private flight. See the city’s skyline and natural landscapes as you fly low over the Columbia River Gorge, and industrial cityscapes. See Bridgetown from a new perspective as you soar through the sky and hear historical and geographical insights from your pilot. The small-lightweight plane can hold 1-3 passengers plus the pilot. Forget about traffic and see the city from the sky on an airborne adventure.

Visit the lush trails of Portland's gargantuan Forest Park, the only urban wilderness park in the U.S. Your guide will take you along forested trails, telling you about the plants, animals, and history of the park—and the region—as you walk. And if you feel like turning back, there's no pressure. The hike is a moderate 3–5 miles (5–8 kilometers) long, but can be shortened or adjusted to meet your needs.

A short drive east of Portland, the Columbia Gorge is one of the most breathtaking scenic routes in the Pacific Northwest.Spanning along the Columbia River that separates Northwestern Oregon from Southwestern Washington, this beautiful area is characterized by gorgeous forests, towering waterfalls, ample hiking opportunities, and world-class wines. With this customizable private tour, you'll get to experience it on your own terms, with a focus on nature, wine tastings, or both.

We will experience local Portland culture together as I drive you and your guests around in a classic 1971 VW Bus The Tour group size is intimate and the locations we go to give you a true feel of the Portland Culture We will travel to 3-4 distinct local spots as well as several unique districts. You will have the opportunity to sip a variety of craft beer as well as pop into some of the best shops in the Hawthorne District. You and your fellow travelers will trade stories and laugh as the VW Bus whisks you around town. The tour encompasses a wide swath of what makes Portland Unique, the neighborhood culture, the craft beer, unique shops, the tasty food, incredible parks as well as the niche architecture. You won't just see Portland, you'll experience it!

Portland's downtown is dotted with outdoor sculptures. Some immense and famous, some hidden in plain sight. The outdoor sculptures of Portland exemplify Portland's unique character, charm, and history in a number of ways. Take a self-guided GPS audio walk and discover Portland in a new and interesting way! Downtown Portland is a busy place on a weekday, but people are friendly. You may run into street musicians, homeless people, food carts, and more! The tour starts in the middle of Pioneer Square, known as "Portland's Living Room." The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.

Discover four of Willamette Valley’s top wineries on a private 8-hour tour.  Your chauffeur takes your group from your Portland hotel into Oregon's wine country. Private transportation saves you the trouble of navigating on your own and relieves your group of needing a designated driver. Available for two people or more, the tour is great for a romantic weekend, family vacation, or special outing for your wedding party.