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Portland's Diverse Delights: 5-Day Adventure Itinerary
Last updated: 2024 Jun 14City Highlights and Culinary Delights
Morning
Start your Portland journey with a delightful breakfast at Flying Elephants at Fox Tower, known for its fresh pastries and artisanal coffee. Afterward, immerse yourself in the literary paradise of Powell’s City of Books, the world's largest independent bookstore.
Afternoon
For lunch, savor the eclectic flavors at The Woodsman Tavern, offering a menu inspired by the Pacific Northwest. Post lunch, take a leisurely stroll through the serene landscapes of the Portland Japanese Garden, considered one of the most authentic outside of Japan.
Evening
Dine at Expatriate, a cozy spot with a global menu and inventive cocktails. Afterward, enjoy the vibrant atmosphere of the Portland Pearl District, known for its art galleries, boutiques, and excellent dining options.
Bedtime
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4.60Powell’s City of Books
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4.60Powell’s City of Books
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4.87Portland Japanese Garden
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4.87Portland Japanese Garden
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Waterfalls and Wine
Morning
Enjoy a hearty breakfast at The Observatory before embarking on the breathtaking Columbia River Gorge Waterfalls Morning Tour. Witness the majestic Multnomah Falls and other natural wonders.
Afternoon
Indulge in a wine and waterfall adventure with the Portland Mount Hood Wine and Waterfalls Full-Day Tour. Experience the beauty of the region's wineries and the cascading waters of the Columbia River Gorge.
Evening
For dinner, head to There Be Monsters, a gastropub with a laid-back vibe and a menu that highlights local produce and meats. Conclude your day with a leisurely walk across the historic Portland Steel Bridge.
Bedtime
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4.76Columbia River Gorge Waterfalls Morning Tour
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4.76Columbia River Gorge Waterfalls Morning Tour
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4.91Portland Mount Hood Wine and Waterfalls Full-Day Tour
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4.91Portland Mount Hood Wine and Waterfalls Full-Day Tour
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Cultural Immersion and Haunted History
Morning
Begin with a classic Portland breakfast at Radio Room, known for its retro ambiance and comfort food. Post breakfast, explore the interactive exhibits at the Oregon Museum of Science and Industry (OMSI), a perfect spot for science enthusiasts.
Afternoon
Enjoy a guided tour of the Portland Underground Shanghai Tunnel Tour with Beer Tasting, a unique experience that delves into the city's intriguing history. For lunch, visit McMenamins Market Street Pub, a local favorite with a diverse menu and craft beers.
Evening
Delve into the darker side of Portland with the Portland Ghosts, Poltergeists, and Psychopaths Walking Tour. Afterward, lighten the mood with dinner at The Knock Back, a neighborhood bar and kitchen offering a relaxed dining experience.
Bedtime
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4.65Oregon Museum of Science and Industry (OMSI)
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4.65Oregon Museum of Science and Industry (OMSI)
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4.41Portland Underground Shanghai Tunnel Tour with Beer Tasting
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4.41Portland Underground Shanghai Tunnel Tour with Beer Tasting
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Day of Discovery and River Cruises
Morning
Enjoy a morning bike ride through the city with the Bike Portland Bridges, Neighborhoods, Poetry, and Roses tour. Take in the scenic views and learn about Portland's vibrant neighborhoods.
Afternoon
For lunch, experience the diverse flavors of the city with the Portland Food Carts of the Eastside Bike Tour. Sample a variety of cuisines from the famous food carts scattered across the Eastside.
Evening
Relax and unwind on the water with the Portland Willamette River 2.5-hour Dinner Cruise. Indulge in a sumptuous meal while enjoying the city skyline from the river. After the cruise, continue the nautical theme with drinks at Virginia Cafe, a historic bar with a lively atmosphere.
Bedtime
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4.69Bike Portland Bridges, Neighborhoods, Poetry, and Roses
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4.69Bike Portland Bridges, Neighborhoods, Poetry, and Roses
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4.36Portland Food Carts of the Eastside Bike Tour
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4.36Portland Food Carts of the Eastside Bike Tour
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Iconic Sights and Christmas Cheer
Morning
Begin your day with a festive breakfast at Flying Elephants at Fox Tower. Then, take a guided tour to visit the City of Roses Tour Historical and Iconic Portland Sights, including the International Rose Test Garden and other iconic landmarks.
Afternoon
Enjoy a holiday-themed lunch at Paddy's, an Irish pub with a warm and welcoming ambiance. Spend the afternoon exploring the Pittock Mansion, beautifully decorated for the Christmas season, and take in panoramic views of the city.
Evening
Conclude your trip with the Portland Ghosts Boos and Booze Haunted Pub Crawl, a fun and spirited way to experience Portland's nightlife. End the evening with a memorable dinner at C-Bar PDX, known for its elegant setting and innovative cuisine.
Bedtime
Find amazing hotels in Portland.
4.90City of Roses Tour Historical and Iconic Portland Sights
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4.90City of Roses Tour Historical and Iconic Portland Sights
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4.93Pittock Mansion
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4.93Pittock Mansion
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