Itineraries for Your Trip to Portland
3 Days in Portland for First Timers
It’s not an exaggeration to say that Portland, Oregon, is one of my favorite cities in the United States. As an avid reader, I can hardly tear myself away from beloved bookstores like Powell’s. As a food lover, I’m drawn to the city’s cooler-than-cool food cart pods like a moth to a flame. As a hiker, I’m convinced its nearby nature excursions—including the Columbia River Gorge and Mt. Hood—are some of the most beautiful in the country. And as an oenophile, I cherish its proximity to the vaunted Willamette Valley wine region.
In short, Portland is a pretty much unbeatable destination—and three days in town is the perfect amount of time to make the most of its offerings. Here’s how to plan your itinerary.
With its classic Pacific Northwest climate, Portland often experiences cool, overcast, or changeable weather; bring layers.
If you only have time for one thing, make it a time-saving walking tour of the city’s key attractions.
One of Portland’s top attractions isn’t a landmark but a scene—its food cart pods. These clusters of food trucks offer dozens of eclectic dishes from varying cuisines, and they’re an absolute must-try when you’re in Rose City. Start your 3-day trip with a wide-ranging, late-morning food tour to get acquainted.
Once you’re feeling satiated, dedicate the rest of your first day in town to an introductory walking tour. Exploring on two feet is a great way to learn about Portland’s history while discovering the highlights of its city center—and soaking up its artsy, eclectic atmosphere.
Portland is surrounded by Cascade Mountain peaks, river gorges, and thundering waterfalls—little wonder that taking a nature excursion is a must while in town. Set off on a day trip to the absurdly photogenic Columbia River Gorge; look out for combination tours that visit nearby Mt. Hood, too.
After a full day of getting rugged, unwind with a drink when you return to Portland proper—well, kind of. On an after-dark ghost tour, you’ll learn about a frightful side of the city’s history and see some of its spookiest corners. Afterward, take the edge off with top-notch, Portland-made craft beer.
Portland is celebrated as one of the country’s top craft beer destinations—but its wine scene is just as worthy of acclaim. Three days in town gives you the time to book a wine-tasting trip to the nearby Willamette Valley. Primarily known for its world-class pinot noir, the region is an oenophile’s dream.
After a busy day sipping and swirling, wind your trip down with a celebratory river cruise and dinner. As you kick back and indulge, you’ll also enjoy one of the most magical perspectives of the city—now that’s worth toasting to.
