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Travel AI

Ultimate 5-Day Portland Adventure Itinerary

Last updated: 2024 Jun 14

Portland City Highlights & Waterfront

Morning

Start your day with a delicious breakfast at Mother's Bistro & Bar, known for its homestyle cooking. Afterward, embark on the City of Portland Tour Historic and Iconic Sights to get an overview of the city's history and landmarks.

Afternoon

For lunch, head to Lardo for their famous sandwiches. Afterward, take a leisurely stroll through the Portland Pearl District, known for its art galleries and boutiques. Don't miss a visit to the iconic Powell’s City of Books, a book lover's paradise.

Evening

Enjoy a sophisticated dinner at Departure Restaurant + Lounge, offering panoramic city views. End the evening with a relaxing Portland Willamette River 2.5-hour Dinner Cruise, where you can savor a gourmet meal while cruising along the river.

Bedtime

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4.90
City of Portland Tour Historic and Iconic Sights
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4.72
Portland Pearl District
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Columbia River Gorge & Waterfalls

Morning

Indulge in a delightful brunch at Tasty n Alder, known for its innovative dishes. Then, embark on the From Portland Columbia Gorge Waterfalls Tour to witness the breathtaking beauty of the Multnomah Falls and other stunning waterfalls.

Afternoon

For a quick snack, visit Blue Star Donuts for their unique flavors. Afterward, explore the Columbia River Gorge and make a stop at the Vista House for panoramic views of the gorge.

Evening

Enjoy a cozy dinner at Little Bird Bistro, known for its French-inspired cuisine. End the day with a relaxing evening at your hotel or explore the vibrant nightlife of Portland.

Bedtime

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4.93
From Portland Columbia Gorge Waterfalls Tour
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4.83
Multnomah Falls
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Portland's Culinary Delights

Morning

Start your day with a guided Portland Secret Food Tour with Local Guide, where you'll discover hidden culinary gems and taste a variety of local specialties.

Afternoon

For lunch, head to Grassa for their delicious pasta dishes. Afterward, explore the Portland Art Museum to admire its impressive collection of art.

Evening

Indulge in a memorable dining experience at Le Pigeon, known for its innovative and seasonal menu. After dinner, take a leisurely walk through the Portland Japanese Garden, a serene oasis in the city.

Bedtime

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5.00
Portland Secret Food Tour with Local Guide
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4.82
Portland Art Museum
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Portland's Unique Experiences

Morning

Enjoy a hearty breakfast at Sweedeedee, known for its delicious baked goods. Then, embark on the Portland Underground Shanghai Tunnel Tour with Beer Tasting to learn about the city's intriguing history.

Afternoon

For lunch, head to Nong's Khao Man Gai for their signature dish. Afterward, explore the International Rose Test Garden and the Pittock Mansion, offering stunning views of the city.

Evening

Experience the Portland Ghosts Boos and Booze Haunted Pub Crawl, where you'll hear spooky stories and enjoy drinks at haunted pubs. End the night with a late dinner at Clyde Common, known for its communal dining experience.

Bedtime

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4.41
Portland Underground Shanghai Tunnel Tour with Beer Tasting
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4.76
International Rose Test Garden
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Mt. Hood & Farewell to Portland

Morning

Enjoy a leisurely breakfast at Ava Gene's, known for its farm-to-table cuisine. Then, embark on the Portland Mt. Hood Day Tour to explore the majestic Mt. Hood and its surrounding areas.

Afternoon

For lunch, savor the flavors of the Mediterranean at Andina Restaurant. Afterward, visit the Mt. Hood National Forest for a peaceful nature walk.

Evening

Conclude your Portland adventure with a farewell dinner at Imperial Restaurant, known for its Pacific Northwest cuisine. Reflect on your trip and savor the memories before heading back home.

Bedtime

Find amazing hotels in Portland, Oregon.