One of America’s pioneering hipster cities, Portland has a unique set of offerings—its metro area boasts 37,000 acres of green space and an incredible foodie scene. The perfect long weekend destination, especially when combined with a visit to Oregon’s winelands in the Willamette Valley, Portland offers opportunities for outdoor adventure with a dynamic artisan community and ever-friendly locals.
Perfect forAdventurers | Families | Foodies | Trailblazers
When to goYear-Round
Ideal length of stay3-5 Nights
Designing Your Journey
Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.
3 Days: Essential Portland
The best way to enjoy Portland is to do as the locals do; bike around the city, enjoy late afternoon drinks at one of the many local breweries or distilleries and soak in the relaxed pace. Here is just one example of what our destination experts can create for you.
Enjoy breakfast at a Portland institution known for its daily brunch, and then shop around the city’s downtown area. Don’t miss Powell’s City of Books, the largest independent bookstore in the world, or any of Indagare’s favorite shops hawking only made-in-Portland goods. After lunch at Pok Pok, perhaps Portland’s most famous eatery, spend the afternoon relaxing at a wellness spa with a great hot springs circuit, and then have dinner at a classic Italian restaurant.
Start your second day with a hike through the Columbia River Gorge to the 620-foot-high Multnomah Falls. For lunch, sample cuisine from Portland’s many food carts. The most famous block of carts is downtown; don’t miss the acclaimed Nong’s Khao Man Gai. In the afternoon, go shopping in Mississippi, a lively area with great shopping. Before dinner and drinks at a stylish speakeasy, visit the Portland Japanese Garden for beautiful sunset views of Mount Hood.
Get up early for a hike in Forest Park, more than 5,000 acres of woodland located just ten minutes by car from the downtown area. Then, grab a quick bite at a French-inspired bistro and embark on a guided Distillery Tour. Before packing up, grab a sweet treat at Portland’s most famous ice cream parlor, Salt + Straw.
Where To Stay
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities, including upgrades, early check-in, breakfast, spa credits and more. Look for the Indagare Plus logo in the reviews.
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Ace Hotel Portland
The flagship Ace Hotel is as much a part of Portland culture as coffee and food trucks; the hipster watering hole is a gathering space for locals as well as a great hotel option for those willing to stay in...
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The Nines, a Luxury Collection Hotel
This luxurious property in the heart of Portland is the city’s most contemporary, design-minded hotel and boasts a lauded rooftop restaurant.
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