The Best of Portland: Private Half-Day Driving Tour

Known as the largest city in Oregon and the second largest in the Pacific Northwest, Portland was founded in 1851 and has since become one of the most important cities on the West Coast. The historic and cultural epicentre is the Central City area, and there’s no better way to explore it than with a local expert guide on this private half-day highlights tour.

On this private half-day driving tour, you will:

• Get a comprehensive initiation to Portland’s charming Central City;
• Make the most of your time in Portland with pick up and drop off from your central hotel;
• Explore all of the major neighbourhoods of inner Portland on both sides of the river;
• Wander through the grounds of Pittock Mansion, the stunning Victorian manor nestled in the hills of west Portland;
• Capture the best views of the city and keep an eye out for the five stratovolcanos visible on a clear day. 
• Stop and smell the roses at the world-famous International Rose Test Gardens;
• Learn about Portland’s intriguing history and the evolution of its current vibrant and quirky culture scene;
• Pass by Portland’s most iconic sites, including the First Presbyterian Church, Crystal Ballroom, and Portland Art Museum;
• Admire the iconic Portland Oregon Sign, a beloved symbol of the city's downtown skyline, welcoming visitors with its vintage charm;
• See Portland’s iconic bridges in the heart of the city, including the steel marvel of Hawthorne Bridge, the double-decked Steel Bridge, and the towering Fremont Bridge.

Thanks to its strategic position near major trade routes and geographical features, including its proximity to the Columbia River and the Pacific Ocean, Portland is an important economic, cultural, and transportation hub for the Pacific Northwest. It is beloved by locals and visitors alike thanks to its scenic beauty, eco-friendly urban planning, and incredible beer, wine, and food scene. It is also celebrated for its progressive and eccentric spirit, spawning the slogan ‘Keep Portland Weird,’ and immortalized in the acclaimed television series Portlandia.

Your introduction to enthralling and unusual Portland will take place at your central hotel, where your driver-guide will pick you up for an exhilarating itinerary around the city’s most famous spots. After introductions, you will set off for your first stop: the beautiful International Rose Test Gardens. Located within the lush Washington Park, the site spans 4.5 acres and contains over 10,000 Rose Bushes. As you stroll this colourful and fragrant section of the park, you will see a wide variety of roses from around the world (there are thought to be over 600 different species on display). You will learn about how the garden was created during WWI as a haven to preserve hybrid roses grown in Europe since it was feared they would not be wiped out by bombing raids.

You will also get a chance to visit the grounds of the famed Pittock Mansion, an impressive French Renaissance-style château. Nestled in the hills of West Portland, the mansion was built over 100 years ago and is remarkably well-preserved. From this viewpoint, you will admire breathtaking panoramic views of the Portland skyline and if conditions are clear enough, you’ll also see Mt. Hood, Mt. St. Helens, Mt. Adams, Mt. Rainier, and Mt. Jefferson.

You will then embark on a picturesque drive around some of the city’s celebrated green spaces, such as the Hoyt Arboretum, Oregon Zoo, Providence Park, and the serene Japanese Gardens. You will soon see why Portland is known for its urban planning policies that prioritize these green spaces and promote sustainability. Your guide will also show you Portland’s exquisite 19th-century buildings and tell you the fascinating stories behind them, including the First Presbyterian Church, Simon Benson house, and the Pioneer Courthouse.

No visit to Portland would be complete without seeing the legendary Powell’s City of Books. Occupying an entire city block, it is the world’s largest independent bookstore and stocks over a million books across thousands of genres. As you go deeper into the city’s history and urban landscape, you will visit as many of Portland’s emblematic plazas, bridges, and fountains as time allows and traverse well-known streets like Hawthorne Boulevard, the locus of Portland’s hippy culture in the 1970s. Your final stop will be one of Portland’s most vibrant and culturally diverse streets: North Mississippi Avenue. This renowned street is thought by many to epitomize the ‘weird’ hipster culture of Portland humorously showcased in Portlandia. It also houses Sunlan Lighting Inc., an eclectic lighting store and local icon where we may enter to observe its nostalgic atmosphere and extensive collection of light bulbs of all shapes and sizes.

Once your voyage of discovery around Portland reaches its conclusion, you will doubt be left with a deep appreciation for this weird and wonderful city. You will have the option to return to your hotel or another location of your choosing in Central Portland, and your guide will be happy to recommend other local attractions to visit on your own, as well as authentic bars and restaurants to experience Portland’s marvellous craft beer, wine, and gastronomy.