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5 Days Exploring Portland and Mount Hood

5 Days Exploring Portland and Mount Hood Itinerary

Last updated: 2024 Jun 14

Discovering Portland's Icons

Morning
Start your day with a visit to Pioneer Square, often referred to as Portland's living room. This bustling square is the perfect place to get a feel for the city's vibe. After soaking in the atmosphere, head over to Mother's Bistro & Bar for a hearty breakfast that will fuel you for the day's adventures.
Afternoon
In the afternoon, explore Powell’s City of Books, one of the largest independent bookstores in the world. Lose yourself among millions of books and unique literary finds. For lunch, make your way to Lardo, known for its delicious sandwiches and casual atmosphere.
Evening
Conclude your day with a visit to Portland Pearl District. This vibrant neighborhood is filled with art galleries, boutiques, and trendy bars. Enjoy dinner at Andina, a highly-rated Peruvian restaurant offering an array of flavorful dishes.
Bedtime
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Nature and Culture in Portland

Morning
Begin your morning with a serene walk through Portland Japanese Garden, considered one of the most authentic Japanese gardens outside of Japan. Follow this peaceful experience with breakfast at Tin Shed Garden Cafe, which offers delicious farm-to-table options.
Afternoon
Spend your afternoon at Portland Art Museum, where you can explore an extensive collection of Native American artifacts, contemporary art, and more. For lunch, head over to Tasty n Alder, known for its innovative small plates and lively atmosphere.
Evening
Wrap up your day by visiting International Rose Test Garden in Washington Park. As you stroll through thousands of rose varieties, you'll understand why Portland is known as the City of Roses. Dinner awaits at Le Pigeon, where you can enjoy French-inspired cuisine in an intimate setting.
Bedtime
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Waterfalls and Wine

Morning
Kick off your day with the Portland Columbia River Gorge Waterfalls Morning Tour. This tour will take you to some of the most stunning waterfalls in the Columbia River Gorge, including Multnomah Falls. Begin with a hearty breakfast at Pine State Biscuits, known for its Southern-style biscuits and gravy.
Afternoon
After a morning of waterfall exploration, head back to Portland for lunch at Grassa, which offers delectable handmade pasta dishes. Post-lunch, enjoy a leisurely stroll through Hoyt Arboretum, where you can explore a diverse collection of trees and plants from around the world.
Evening
In the evening, indulge in the Portland Mount Hood Wine and Waterfalls Full-Day Tour. This tour combines visits to local wineries with scenic views of waterfalls, providing a perfect blend of relaxation and adventure. Conclude your day with dinner at Nostrana, an Italian restaurant renowned for its wood-fired pizzas and seasonal dishes.
Bedtime
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Urban Exploration and Farewell

Morning
Start your final day in Portland with a visit to Lan Su Chinese Garden, an authentic Ming Dynasty-style garden that offers tranquility amidst the urban hustle. Enjoy breakfast at Voodoo Doughnut, famous for its quirky and delicious doughnuts.
Afternoon
Spend your afternoon on the Portland Food Walking Tour, where you'll get to sample some of Portland's best culinary offerings while learning about the city's food culture. For lunch, make sure to try out one of the food carts recommended during the tour.
Evening
End your trip with a relaxing evening cruise on the Willamette River. The Portland Willamette River 2.5-hour Dinner Cruise offers stunning views of Portland's skyline as you enjoy a gourmet meal onboard. Reflect on your adventures while dining on delicious cuisine prepared by top chefs.
Bedtime
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Adventures Beyond Portland

Morning
Embark on an exciting journey with the Portland Mt. Hood Day Tour. This full-day tour will take you from Portland to Mount Hood, offering breathtaking views and numerous photo opportunities along the way. Start your adventure early with breakfast at Screen Door, famous for its Southern-style comfort food.
Afternoon
Continue exploring Mount Hood's scenic beauty as part of your tour. You'll have time to enjoy activities such as hiking or simply taking in the stunning landscapes. A packed lunch will be provided during the tour so you can dine amidst nature.
Evening
Return to Portland in the evening after a fulfilling day at Mount Hood. Relax and unwind with dinner at Ox Restaurant, where you can savor Argentine-inspired dishes prepared on an open wood-fired grill.
Bedtime
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