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How to Spend 3 Days in Portland

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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6 Tours and Activities

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Mt Hood Day Trip from Portland to Multnomah Falls and Hood River
Likely to Sell OutLikely to Sell Out

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

star-5
298
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
$120.00
Price varies by group size
From
$120.00
Price varies by group size
Taking safety measures

Oregon Coast Day Trip: Cannon Beach and Haystack Rock
Likely to Sell OutLikely to Sell Out

Oregon Coast Day Trip: Cannon Beach and Haystack Rock

star-4.5
248
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
$120.00
Price varies by group size
From
$120.00
Price varies by group size
Taking safety measures

2.5-Hour Dinner Cruise Through Downtown Portland

2.5-Hour Dinner Cruise Through Downtown Portland

star-4.5
80
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
$110.00
From
$110.00

Portland Brewery Bike Tour
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Portland Brewery Bike Tour

star-5
235
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
  • Taking safety measures
From
$70.77
From
$70.77
Taking safety measures

Willamette Valley Wine Tour from Portland with Lunch
Likely to Sell OutLikely to Sell Out

Willamette Valley Wine Tour from Portland with Lunch

star-5
234
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
$190.00
From
$190.00
Taking safety measures

Essential Portland Bike Tour

Essential Portland Bike Tour

star-5
135
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
$39.75
From
$39.75
Taking safety measures