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Portland, Oregon, USA

5-Day Portland Adventure: Waterfalls, Wine, and Urban Delights Itinerary

Published: 2024 Jan 04
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Waterfalls and Gorge Wonders

Morning
Begin your Portland journey with a hearty breakfast at Flying Elephants at Fox Tower, known for its fresh pastries and coffee. Afterward, embark on a scenic drive to the majestic Multnomah Falls, one of the most iconic waterfalls in the Pacific Northwest. Take a leisurely hike to the Benson Bridge for a stunning view of the cascading waters.
Afternoon
For lunch, head to The Observatory, where you can enjoy a meal with a view. Afterward, continue your waterfall exploration with a visit to Latourell Falls, known for its unique columnar basalt formations and the beautiful veil of water that drops 249 feet.
Evening
Conclude your day with a delightful dinner at The Woodsman Tavern, offering a cozy ambiance and a menu featuring Pacific Northwest cuisine. After dinner, take a relaxing stroll through the Portland Pearl District, known for its art galleries, boutiques, and vibrant atmosphere.
Bedtime
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Gorge History and Wine Tasting

Morning
Start with breakfast at The Solo Club, a spot known for its unique offerings. Then, journey east to the Bonneville Dam, where you can learn about the history of the Columbia River and its impact on the region. Take a guided tour to gain insights into the engineering marvel and its role in providing power to the Pacific Northwest.
Afternoon
After the dam, enjoy a scenic drive along the historic Columbia River Highway to the Vista House. This iconic structure offers panoramic views of the Gorge. For lunch, stop at C-Bar PDX, a local favorite with a diverse menu. Post-lunch, continue to the award-winning wineries of the Willamette Valley for an afternoon of wine tasting and vineyard tours.
Evening
Return to Portland and savor a sumptuous dinner at Expatriate, known for its globally inspired cuisine and innovative cocktails. Cap off the evening with a visit to the Portland Japanese Garden, considered one of the most authentic Japanese gardens outside of Japan. The serene atmosphere is perfect for a post-dinner walk.
Bedtime
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Urban Delights and Evening Cruise

Morning
Enjoy a Portland-style breakfast at Powell’s City of Books [13305], a unique spot where you can browse books while sipping on your coffee. Then, immerse yourself in the literary world at the Portland Art Museum, home to an impressive collection of art spanning diverse periods and styles.
Afternoon
For lunch, head to Paddy's, an Irish pub with a lively atmosphere and a menu featuring classic pub fare. Post-lunch, take a guided tour of the Portland Underground Shanghai Tunnel with Beer Tasting. Learn about the city's shanghaiing history and enjoy a cold brew in the subterranean passages.
Evening
Dine in style aboard the Portland Willamette River 2.5-hour Dinner Cruise. Indulge in a delicious meal while taking in the city skyline and the lights reflecting on the water. After the cruise, if you're up for more, consider the Portland Ghosts, Poltergeists, and Psychopaths Walking Tour for a different perspective of the city's history.
Bedtime
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Mountains and History

Morning
Start your day with breakfast at McMenamins Market Street Pub, a local chain known for its brews and pub food. Then, venture to the towering peak of Mt. Hood, where you can choose to ski, snowboard, or simply enjoy the alpine scenery. If you prefer a more relaxed morning, opt for the Portland Mt. Hood Day Tour for a guided experience.
Afternoon
After your mountain adventure, have a late lunch at Library Taphouse & Kitchen, a spot with a vast beer selection and a menu to match. Then, visit the historic Pittock Mansion, an architectural gem with panoramic views of the city and the surrounding landscape. Explore the mansion and its gardens while learning about Portland's past.
Evening
For dinner, experience the vibrant atmosphere of Radio Room, a restaurant with a diverse menu and a hip vibe. Afterward, if the weather permits, take a scenic drive along Mulholland Drive and enjoy breathtaking views of the city lights and the starry sky.
Bedtime
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Gardens, Books, and Farewell

Morning
Begin with breakfast at The Fireside, a cozy spot with a menu that highlights local ingredients. Then, spend the morning at the International Rose Test Garden, where you can stroll among thousands of blooming roses and enjoy the panoramic views of the city.
Afternoon
For lunch, head to Bar Maven, a gastropub with a creative menu and a wide selection of drinks. Afterward, visit the iconic Pioneer Square, also known as "Portland's living room," and take in the vibrant street performances and the unique architecture.
Evening
Conclude your Portland adventure with a visit to There Be Monsters, a spot with a laid-back atmosphere and a menu that caters to all tastes. Raise a glass to the memories made in Portland and enjoy a leisurely evening before bidding the city farewell.
Bedtime
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