Top Portland Likely To Sell Out in 2026

Discover the history and legends behind Portland’s Shanghai Tunnels on a small-group walking tour. Follow your guide beneath a restaurant to the tunnels, which once connected local businesses and hotels to the Willamette River. Learn about subterranean historic events and perhaps catch a glimpse of Nina, the resident ghost. Afterwards, resurface and enjoy three tastings and a full pint of locally produced beer.

Learn about the haunted past of Portland, Oregon's Old Town with this guided ghost tour. Your guide will regale you with tales of the past as you walk to different allegedly haunted locations, wrapping up at Kells Irish Restaurant & Pub, believed to be haunted by a long-dead fire captain.

The Columbia River Gorge is known for its dramatic waterfalls and impressive vistas—but if you don't have car, planning a trip from Portland can be tricky. Instead, enjoy a hassle-free way to check off many top attractions in just half a day, all thanks to this small-group sightseeing tour. Visit the historic Vista House, admire Latourell Falls, stop at Multnomah Falls, and more, all while your guide shares insider stories.

Immerse yourself in the beauty and bounty of Willamette Valley's renowned wine country on this full-day, small-group tour from Portland. Perfect for all levels of wine enthusiasts—from newcomers to connoisseurs—this tour whisks you to three or four top-rated vineyards. Sample a range of varietals (tasting fees own expense), enjoy a picnic lunch, and benefit from door-to-door service.

Head out to the Columbia River Gorge for half a day of visiting cascading waterfalls and scenic overlooks with this tour from Portland. You'll visit Multnomah Falls, the highest waterfall in the state, as well as lesser-known falls throughout the region. You'll also have the chance to take mini-hikes in the area to get better views of waterfalls and the surrounding scenery.

Immerse yourself in the scenery and story of Portland on this small-group sightseeing tour. With your naturalist guide, visit verdant urban parks, eclectic neighborhoods, and some of the city’s most treasured landmarks including the famous Powell’s Books. Enjoy a breakfast of tea and pastries as you traverse the city in style.

Forest Park and Washington Park Small-Group Hike Hike from the city and up into massive Forest Park and the adjacent Washington Park with a guided hike. The morning tour will take you through Northwest Portland and up into the International Rose Test Garden, while the afternoon tour starts in the Goose Hollow neighborhood near downtown. Both will pass by some of the parks' prettiest spots, including the Japanese Garden and the Witch's Castle.

See a side of Portland many people miss with this haunted evening walking tour. In addition to visiting many of the city's most haunted historic sites, including the Shanghai Tunnels and Roseland Theater, hear creepy tales from your guide that bring each attraction to life. A walking tour also lets you see each spot up close.

On this day-long excursion you’ll explore the northern stretch of shore between Astoria and Cannon Beach as your guide leads you through an oceans-worth of American history, coastal culture, and pristine nature. Start your day in the bustling seaport of Astoria, where the Columbia River feeds into the Pacific, and Lewis & Clark and John Jacob Astor concluded their epic expeditions. Wander the town’s docks, wind up the Astoria Column, and walk through Fort Clatsop, before continuing south along beaches and bluffs to Cannon Beach. A quintessential beach town, the savory smell of chowder houses meets the briny ocean air on Cannon Beach’s picturesque streets. After meandering through the town, you’ll take to the beach for an interpretative nature walk to Haystack Rock with your naturalist guide. Complete your day by traversing through a maze of Sitka spruce in Ecola State Park. The forest opens to a secluded beach where you’ll cap off your tour with an amazing view of the crashing waves.

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 the highlights of Portland in just one afternoon, without having to sort out transportation on this tour. 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 and the surrounding area unique with stops at the International Rose Test Garden (seasonally), Pioneer Courthouse Square, NW 23rd Avenue, and more.

Experience the unrivaled beauty of the Columbia River Gorge, Cascade Mountain Range, and Mount Hood—and see them all in one hassle-free, time-saving excursion—on this full-day tour from Portland. In the comfort of a luxury vehicle, travel with just your guide and a small group for company. Enjoy a guided tour of the Gorge’s top destinations, including Vista House, Multnomah Falls, Timberline Lodge, Hood River, and more.

Get off the beaten path to explore Portland's Kerns neighborhood with this guided food tour. You'll head up to the stretch of NE 28th Avenue known as "Restaurant Row," for a 1.2-mile-long walk with a guide, with stops at six different eateries along the way to sample local flavors.

Portland takes pizza seriously—and this tour is the easiest, most fun way to taste the scene in one walk. You’ll hit four pizzerias on a relaxed route with short walks in between (about ~1 mile total), tasting a curated progression of styles and signatures. This is a full-meal experience: each guest gets a full slice at each stop (four slices total). Your guide keeps it laid-back and social while sharing quick, useful pizza insight—what makes a great slice, what to order, and where to go next depending on what you loved most. Pizza and drinks are included. Rain or shine, come hungry and ready to eat like a local.

Immerse yourself in waterfall hiking in one of the most unique geologic formations in Oregon! Over the course of the three hours we are in the canyon, we will discovering South Falls' stunning amphitheater and history as the centerpiece of a failed attempt to become Oregon's first National Park. From here we will descend into the up-and-down trails that make up the gorgeous canyon, encountering century-plus-old trees, wildflowers in season, mosses, lichens, and mushrooms and a variety of fantastic rock formations. We will experience up-close encounters with some of the state's most unusual and impressive waterfall formations. On this hiking experience we will explore 4-6 waterfalls and enjoy snacks with the option to purchase a light breakfast or lunch from the cafe. Our hike will be between three and eight miles (5 - 13 km) depending on group energy and desire.

Visit the top attractions in the Columbia River Gorge National Scenic Area and Mt. Hood National Forest on this day trip from Portland. After spending the morning chasing waterfalls and marveling at 500-pound fish at Bonneville Fish Hatchery, enjoy free time for lunch in historic downtown Hood River. After lunch, we will visit a vineyard in the region for a wine tasting and drive more than halfway up the side of Mt. Hood to explore Timberline Lodge

The Northern Willamette Valley's close proximity to Portland creates a perfect opportunity to join others on a small group public tour of Oregon’s wine country with Sea to Summit Tours, Portland Oregon's original tour and adventure company. Experienced, knowledgeable guides, providing fun and informative tours with unparalleled customer service, while operating the nicest and most comfortable, custom equipped 4x4 Mercedes-Benz vehicles in Portland’s tour industry. We set an itinerary with outstanding wine, great hospitality, and beautiful scenery with wine tasting fees included – all the keys to creating a unforgettable Willamette Valley Wine Tour for our clients... Created, owned and operated by native Portland Oregonian's, since 2001

This is not a tiny-spoon tasting tour. At every stop, guests sample every available flavor and receive a full scoop per person — all included in the ticket price. There’s no choosing just one flavor, no standing in lines, and no additional purchases. The entire experience is fully hosted by entertaining local guides who handle ordering, keep things moving, and make it fun. You’ll enjoy laughs, insider food recommendations, and a relaxed walk through the heart of Portland. With multiple flavors plus full scoops at each stop, many guests say this feels closer to an almost all-you-can-eat ice cream crawl than a traditional food tour — just without the chaos or rushing. Created by Portland locals with a genuine love for ice cream and their city, this tour is designed to be generous, easy, and unforgettable — perfect for families, visitors, and serious ice-cream lovers.

Cross state lines into Washington on this full-day trip from Portland to Mount St. Helens, led by a professional naturalist guide with extensive knowledge about the local geology and ecosystem. Learn about the Pacific Northwest’s most famous active volcano through nature walks and exhibitions, and then make it back to Portland by evening.

Oregon’s Willamette Valley is known for its fantastic wine, and while it’s easy to get to from Portland by car, driving yourself means limiting your consumption. This small-group tours includes the services of a driver so you can taste wine without worrying about designating a driver, showcasing off-the-beaten-path wineries that you might otherwise miss.

Being short on time doesn’t mean you can’t see the best of Portland. This morning tour showcases some of the city’s most popular attractions in just half a day, including Pioneer Courthouse Square, shopping areas such as the Pearl District and NW 23rd, the Lan Su Chinese Garden, and more. Seasonal stops at the International Rose Test Garden and the World Forestry Center add to the fun.

Discover Mount Saint Helens from a unique vantage point on a private flight tour from Troutdale. Once airborne, soar over the Colombia River Gorge and Portland. Have your camera ready as the plane flies above and around Mt. Saint Helens' crater and see the destruction from its 1980 eruption. Note: The flight route is dependent on weather and may change last minute.

Eat your way through Portland's best food carts on this guided van tour. See some of the city's favorite food cart "pods," and pass through many of Portland's coolest neighborhoods on the way. Stops include the Alberta Arts District, North Mississippi Avenue, and the hippie-meets-hipster neighborhood of Hawthorne.