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How to Spend 3 Days in Portland

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578 reviews
How to Spend 3 Days in Portland
A full Portland experience can be had in three days with an itinerary that combines the sights, culture, and adventures of Oregon’s largest city. Here are our top ideas for how to spend your time in Portland and its Pacific Northwest surroundings, including day trips to the mountains or wine country.
 
Day 1: See the City Sights
Explore Portland at your own pace on a hop-on hop-off trolley tour that allows you to visit the attractions that most interest you, such as Powell’s Books or Pioneer Courthouse Square. Allow time to discover Portland’s food scene: perhaps by taking a coffee and doughnuts tour, food cart tour, or a food tour of Mississippi Avenue. Beer and wine lovers can visit breweries or urban wineries on a bike tour, or skip food in favor of filming locations from the TV show Portlandia. More brews can be enjoyed in the evening on a haunted pub tour of the once-seedy Old Town district.
 
Day 2: Explore Portland Outdoors
Visit one of the largest urban forests in the country on a guided hike of Forest Park in northwest Portland, and then take to two wheels to explore Portland like a local with a bike tour along the Willamette River waterfront, through the green spaces of the Park Blocks, and into the popular Pearl District. For a more adventurous pursuit, head to the White Salmon River in Washington, a little over an hour north of Portland, for whitewater rafting. When evening rolls around, hop on a dinner cruise to admire the city from the waters of the Willamette, or perhaps ride through downtown on an evening Segway tour.
 
Day 3: Go Beyond the City Limits
Tucked among mountains, rivers, vineyards, and the Pacific Ocean, Portland is brimming with day trip options. Head west to visit the coastal towns of Cannon Beach and Manzanita, go south to enjoy pinot noir and other varietals in the Willamette Valley wine region, or travel north into Washington to see Mount St. Helens, an active volcano. The most popular day trip, however, is east of Portland along the Historic Columbia River Highway. Tours typically take you to several natural attractions including Multnomah Falls, the tallest waterfall in Oregon; the Columbia River Gorge, a popular windsurfing and kitesurfing destination; and Mt. Hood, the highest mountain in Oregon.
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Portland Tours & Activities (13)
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Mt Hood Day Trip from Portland to Multnomah Falls and Hood RiverDay Trips

Mt Hood Day Trip from Portland to Multnomah Falls and Hood River

star-4.5
Immerse yourself in the beauty of Columbia River Gorge on this full-day trip from Portland to Mount Hood! With your small group, take a guided tour of such iconic Oregon destinations as Multnomah Falls and the famous Timberline Lodge, and enjoy lunch in the charming city of Hood River.
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  • 8 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From  
US$105.00 
Price varies by group size
From  
US$105.00 
Price varies by group size
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  • 8 hours 30 minutes
  • Free Cancellation
  • Taking safety measures

Oregon Coast Day Trip: Cannon Beach and Haystack RockDay Trips

Oregon Coast Day Trip: Cannon Beach and Haystack Rock

star-4.5
Explore the stunning beaches and beautiful towns along Oregon’s northern coast on this full-day trip from Portland. Visit the charming towns of Manzanita and Cannon Beach—home of the famous Haystack Rock—browse antique shops and art galleries, and stop several beaches to maximize your time at the Oregon Coast.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From  
US$100.00 
Price varies by group size
From  
US$100.00 
Price varies by group size
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  • 8 hours
  • Free Cancellation
  • Taking safety measures

2.5-Hour Dinner Cruise Through Downtown PortlandDay Cruises

2.5-Hour Dinner Cruise Through Downtown Portland

star-4.5
Whether you want to relax after a long day of sightseeing or need to unwind at the end of your workweek, a sunset dinner cruise along the Willamette River is sure to do the trick. The journey offers spectacular views of the Portland skyline and city’s main landmarks. Listen to live music while you enjoy a freshly cooked Pacific Northwest meal.
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  • 2 hours 30 minutes
  • Free Cancellation
From  
US$107.89 
From  
US$107.89 
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  • 2 hours 30 minutes
  • Free Cancellation

Private Half-Day Whitewater Rafting in the GorgeRafting

Private Half-Day Whitewater Rafting in the Gorge

star-5
Portland is surrounded by wilderness, including some incredible rivers with great rapids. With this family-friendly whitewater rafting adventure, you'll get to learn to ride the rapids at the White Salmon River, just a short jaunt from downtown Portland. After getting fitted with safety equipment, you'll get a lesson in paddling and be ready to hit the waters! You'll even have the option of going down Husum Falls, one of the tallest rafted waterfalls in the nation!
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  • 3 hours 40 minutes
  • Free Cancellation
  • Taking safety measures
From  
US$66.67 
Price varies by group size
From  
US$66.67 
Price varies by group size
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  • 3 hours 40 minutes
  • Free Cancellation
  • Taking safety measures

Haunted Pub TourBeer & Brewery Tours

Haunted Pub Tour

star-4.5
Explore the eerie side of Old Town with this haunted pub tour in Portland. Learn about some of the city's scary history as you walk through 19th-century buildings. Sample seven local beers as you hear about Portland's era of kidnapping, gangs, prostitution and opium dens.
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  • 2 hours 30 minutes
  • Free Cancellation
From  
US$49.00 
From  
US$49.00 
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  • 2 hours 30 minutes
  • Free Cancellation

Portland Brewery Bike TourMountain Bike Tours

Portland Brewery Bike Tour

star-5
Explore beautiful central Portland and sample some of the city’s iconic brews on this afternoon bike tour. Accompany your expert guide on a leisurely bike ride to several classic Portland microbreweries, including Lucky Lab and Rogue, for some fun and informative beer tasting.
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  • 3 hours
  • Free Cancellation
From  
US$70.77 
From  
US$70.77 
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  • 3 hours
  • Free Cancellation

Portland Hop-On Hop-Off Tour with Gray LineCultural Tours

Portland Hop-On Hop-Off Tour with Gray Line

star-4
Explore Portland’s diverse cityscape on this hop-on hop-off sightseeing tour. With your 1- or 2-day trolley pass, create your own adventure with 13 possible stops, including the International Rose Test Garden, Powell’s Books and the Pearl District. En route, learn about the city’s history and culture from your expert guide.
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  • 2 hours
  • Free Cancellation
From  
US$37.95 
From  
US$37.95 
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  • 2 hours
  • Free Cancellation

Portland Segway TourSegway Tours

Portland Segway Tour

star-5
Zip through Portland's historic and developing west-side neighborhoods on this guided Segway tour! Select a 1.5-hour waterfront tour or a 2-hour historical downtown tour, and enjoy quality sightseeing aboard your electric Segway. Visit locations like the Steel Bridge, Pearl District, historic Chinatown and the Portland Art Museum for a window into the city’s industrial and cultural past.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From  
US$59.00 
From  
US$59.00 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures

Willamette Valley Wine Tour from Portland with LunchWine Tastings

Willamette Valley Wine Tour from Portland with Lunch

star-5
Immerse yourself in the beauty and bounty of Willamette Valley wine country on this full-day tour from Portland. Perfect for all level of wine enthusiast – from newcomers to connoisseurs – this 7.5-hour trip offers the insight of expertly trained guides and visits to 3-5 vineyards to sample unique varietals including renowned pinots, chardonnays and rieslings. Tasting fees are not included.
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  • 7 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From  
US$175.00 
From  
US$175.00 
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  • 7 hours 30 minutes
  • Free Cancellation
  • Taking safety measures

Essential Portland Bike TourMountain Bike Tours

Essential Portland Bike Tour

star-5
Take a spin around the City of Roses with this bike tour of essential Portland. Pedal through the city's historic Old Town, along the river on the Waterfront Esplanade, through the Park Blocks with their many green spaces and the hip Pearl District. Learn about the spirit of Portland from knowledgeable guides as you see the city as many of the locals do—by bike.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From  
US$39.75 
From  
US$39.75 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures

Mississippi Avenue Food TourPrivate and Luxury

Mississippi Avenue Food Tour

star-5
Indulge in the diverse flavors of Mississippi Avenue in Portland on a tasting extravaganza. This afternoon food tour takes your small-group to Mississippi’s many trendy eateries, brewpubs, and boutique cocktail joints. Enjoy the hip local scene while nibbling on dishes that may include burgers, fusion tacos, and ice cream sandwiches, complemented by local beer and wine or a creative cocktail.
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  • 2 hours 30 minutes
From  
US$91.29 
From  
US$91.29 
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  • 2 hours 30 minutes

Guided Hike in Portland's Forest Park! (Largest Urban Wilderness in the USA)Hiking

SPECIAL OFFER

Guided Hike in Portland's Forest Park! (Largest Urban Wilderness in the USA)

star-5
Visit the lush trails of Portland's gargantuan Forest Park, the only urban wilderness park in the U.S. Your guide will take you along forested trails, telling you about the plants, animals, and history of the park—and the region—as you walk. And if you feel like turning back, there's no pressure. The hike is a moderate 3–5 miles (5–8 kilometers) long, but can be shortened or adjusted to meet your needs.
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  • 3 hours
  • Free Cancellation
From  
US$68.00 
US$85.00
US$17.00 savings
From  
US$68.00 
US$85.00
US$17.00 savings
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  • 3 hours
  • Free Cancellation


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