Begin your tour with a pickup in central downtown Portland at Director Park. Drive up Portland’s north/south dividing line, passing Powell’s Books, the biggest independent bookstore in the world, as well as some of the city’s bike art and historical buildings.
Once you reach the summit of King’s Heights, walk around the grounds of the mansion built by a newspaper baron to the view that was once available only to the city’s elite. It's one of the best places to develop the context by which to experience this city.
Walk through the mansion’s grounds and back to the van, where you will drive into the SW Portland neighborhood of Arlington Heights, on the edge of Washington Park. Take a walk through a secret garden and into the International Rose Test Garden, learning the story of the rose city. After photos and (in season) inhaling the scent of the roses, get into the van for your next stop. (When roses aren't in season, you may make an alternative stop at the Hoyt Arboretum.)
From here, head back into the city center, driving through what Portland calls the cultural district — once the literal heart of the city, the center line along which once the merchants and lumber barons lived, and now institutions like the Portland Art Museum, the Oregon Historical Society and Portland State University dominate.
It wouldn't be Portland without a stop for doughnuts, so discuss the history of the city's foundation and the design of these blocks after you duck into one of the favorite shops and grab a treat.
After this, drive along Portland's South Waterfront and the waterfront park, telling the story of the shining Swiss Alps-style engineering of the Aerial Tram and the development of this brand-new neighborhood and its beautiful, one-of-a-kind Tilikum Crossing bridge.
Time and interest allowing, jaunt across one of the oldest bridges in the city to the inner Eastside neighborhood of Ladd's Addition, a jewel box of sorts where you can be introduced to some of the best coffee, food carts, restaurants and breweries the city of foodies has to offer.
