Top Portland Cultural Tours

Immerse yourself in the beauty and culture of central Portland as a local would—by bike. On this bike tour, ride through Portland’s historic west side, exploring art galleries, food carts, iconic breweries and 19th-century architecture. Then head to Waterfront Park for great river views and bridge spotting.

Our tour provides the best of its category -- best bicycles, best guides, best vehicles, best snacks! We transport our guests and bikes in Mercedes Sprinters, and our guides ride with our very small groups. You'll get personal attention and the safest experience we can provide. Like no other active tour of the gorge, we tell the stories that are just beginning to awaken from this place. Beyond the 180 years of pioneers and loggers, before the century-old highway, this was the land of people with a rich mythology. We tell the stories that have been told to us by the indigenous people as best we can. But what's most important, we remember the long long history this place holds. Our tour also provides the most active hiking and visits waterfalls you will not see on other tours.

It's all about the bike ride! We like to spend more time riding in small groups, but always stopping to smell the roses. Start in the inner Eastside neighborhoods, where we will safely fit you for a bike and helmet, ready for a sweet 9-11 mile ride through a pretty residential neighborhood, to our favorite rose garden, into an art-heavy industrial district, across the sexy Tilikum Bridge, and onto Portland's waterfront. From there, it's a visit to Old Town, and tell the story of Voodoo, before we head back over another bridge back to our shop! You'll visit a total of 5 of the city's quadrants, ride over two bridges, and along the Willamette River. We'll visit almost-secret beaches, read poetry written in sidewalks and rocks, see public art of every shape, color and texture. And have you tried some of the city's best doughnuts? Learn our favorites! All along the way, we'll tell the stories of the city we love. Bikes, helmets and water provided. Please wear masks for bike sizing.

The 80 miles of the Columbia River Gorge’s steep rocky sides offer some of the most spectacular scenery in the world: pounding waterfalls, eagles, century-old trees, ferns, flowers, ancient rocks. This half-day of exploring and meditating on wonders with very short hikes and visits to overlooks and vistas will have you gasping in awe. We'll visit waterfalls and overlooks, selected by our guides to include both the most iconic, like the unmissable Latourell Falls, a stunning plunge-style falls that is one of the most iconic in Oregon, and the special. Depending on weather conditions, this could include a few small hidden waterfalls and another spectacular plunge-style falls with columnar basalt. We'll also tell you stories, not just of the geology and botany and the oft-repeated tales of pioneers and road-builders, but also the old stories we've learned, of gods and animal spirits and the Beaver princess tragically turned into a waterfall.

With more breweries than any other city in the US, Portland is a beer drinker’s dream. It can be hard to decide where to start, so this craft brewery tour takes you to a handful of the best on the city’s East Side, a neighborhood known for its innovation but off the radar of many tourists. Challenge your taste buds and find your new favorite brew, from West Coast IPAs to seasonal lagers and barrel-aged beers.

Portland’s famous food carts are scattered all over the city's five (now six) quadrants, over 600 in total, in over 60 pods — collections of food carts! Let us put you on one of our lightweight, beautiful bicycles and guide you on a 8-12 mile (11-17 km) culinary experience through some of our best-loved chefs and makers, sampling everything from Oregon farm-to-table delights to snacks appropriate to late-night cravings. Our focus is on locally-owned businesses with a great story; we’ll take you to our favorites, many of which were important in creating the food cart scene as it exists today. Without these unique and passionate people, we may not have even half of what Portland offers to residents and guests alike. Expect flavors and fusions that tell not only a culinary, but also a cultural, tale. Bikes, helmets and plentiful food samples provided. We keep groups very small, so you'll have an intimate experience with your passionate guides!

We'll take you to 3 tasting rooms representing a variety of settings, wines, and personalities. Your wine industry-honed guide will introduce you to the Willamette Valley AVA while camaraderie develops among your small group. You will be wafted away to wine country while we provide you with background on the history, terroir, and character of Willamette Valley wine. Your guide will feel out the desires of your group in selecting among the 500 Willamette Valley wineries, and specific requests may be accommodated. We'll wander through the rolling hills of multiple Willamette Valley sub-AVAs, passing through charming little villages, while making stops at some of the most unique boutique wineries. You'll visit vineyards and tasting rooms that stand out, not only for the views and the character of their wine, but the intriguing personalities (both human and canine) involved. Lunch is included, tasting fees are not.

Whether you love sours or Belgians, IPAs or ales, no beer fan should miss Portland's burgeoning brewery scene. You can experience some of the city's most creative beers on this Portland beer biking tour, complete with a bike, helmet, and guide to lead the way. Just meet your group and hop on a bike to cruise the Eastside of Portland. Visit four different breweries—with tastings included—and sample some of the best craft beers around.

Portland's chocolate scene is overwhelming; let us navigate you through its origins, passionate makers, and diversity with this walking tour that delves into what some call "decadence" but we call "delight." Chocolate is a virtue! Our tour hits both the well-known highlights and some of the secrets of the chocolate scene, with a few surprises we don't want to give away. You'll taste chocolate in myriad forms and styles; think of it as a chocolate education. Trust that you will not leave the tour wanting! The tour in total is about 2.5 miles (4km), mostly flat walking, with several tastings of chocolate -- just the right amount so you'll have the opportunity to truly taste every bite! We keep groups very small, so you'll have an intimate experience with your enthusiastic guides. (Contact us for larger groups or private experiences; we are happy to accommodate!)

Your day is guided by a native born Oregonian who has spent most of their life exploring the Oregon Coast. They know the history, the hidden gems and many personal stories about this beautiful scenic byway of the Pacific Northwest. Ask your guide as many questions as you want and PLEASE bring your camera. You'll want to take lots and lots of pictures. Your friends and family back home will have to see it to believe it.

Together with the professional guide, you will visit the most charming places in the city. You will have a chance to explore the city, while hearing fascinating facts and legends. Did you know that Portland has the most breweries than any other city and its name was decided by a flip of a coin? Why is it considered a paradise for eco-friendly and vegetarian residents? You will be surprised how many stories are hidden in the streets, buildings and corners of Portland. Your charming guide will tell you what is special and unique about living in this city. Perfect for those who are visiting the city for the first time and want to get the most of it!

More than just a basic city tour, Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown. Not only will you experience the best Portland sites, including Pioneer Courthouse Square, Pittock Mansion, Lan Su Chinese Gardens and the International Rose Test Garden, but you will also find out what makes the citizens of Portland so colorful, and learn the cultural history of this unique Pacific Northwest city. Today the 26th largest city in the US is known as one of the world’s most environmentally conscious cities: a hub for farm-to-table eateries, alternative lifestyles, a large community of cyclists, and high walkability. Our tour will take you into the heart of the city where you will experience what makes the City of Roses so unique. Hundreds of food carts, the world’s largest independent bookstore, and a huge urban forest are just a few points of interest that you will encounter.

The trolley tour is a two-hour, fully narrated City Tour featuring our famed open air Pink Trolleys. This tour includes a 30 minute stop at Portland’s world famous Rose Test Gardens. The tour also includes the waterfront neighborhoods, city center landmarks, a scenic drive through Washington Park and Hoyt Arboretum, and Portland’s Northwest neighborhoods, including the Pearl District.

An exclusive tour for all the romantics of the world! Together with the professional local guide, you will visit the most romantic places in the city. Portland is not only an environment-friendly city and a cultural hotspot, but also home to many breathtaking gardens and parks. You will feel spellbound in a charming atmosphere. What is considered as one of the best places to have a date in the city? Where can you make lovely photos? You will be surprised how many historical love stories are hidden in the streets, buildings, parks of the city. From heartbreaking and tragic, to the hilarious or spicy ones. What is the strange and fateful story of Mortimer Stump’s love that is connected to the haunting ,,Witch’s Castle”? This tour is especially recommended in the Saint Valentine period!

The trolley tour is a two-hour, fully narrated City Tour featuring our famed open air Pink Trolleys. This tour includes a 30 minute stop at Portland’s world famous Rose Test Gardens. The tour also includes the waterfront neighborhoods, city center landmarks, a scenic drive through Washington Park and Hoyt Arboretum, and Portland’s Northwest neighborhoods, including the Pearl District

Carved out of an old warehouse district in the 90s this neighborhood highlights the best that the city has to offer. With a wide variety of architecture, coffee shops, trendy restaurants and some of the best breweries in the world, this walk makes it easy to see what makes Portland so great.

An up-close and personal introduction to the mighty Willamette River cutting through the center of the city. You'll get right up to the water's edge and cross the historic Steel and Burnside Bridges that offer panoramic views of Old Town and the West Hills.

Come explore the unique history and diverse culture of the entertainingly eccentric city of Portland! Enjoy a fascinating and informative narration by your local guide, highlighting the colorful past and present of Portland’s many historic churches, diverse modern architectural wonders, abundant city parks, bountiful boutiques and world famous culinary hot spots.