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5 Days in Portland Oregon Adventure

5 Days in Portland Oregon Adventure Itinerary

Last updated: 2024 Jun 30

Exploring the Heart of Portland

Morning
Start your day with a visit to Pioneer Square, often referred to as Portland's living room. This bustling square is the perfect spot to get a feel for the city's vibe. After soaking in the atmosphere, head over to Powell’s City of Books, one of the largest independent bookstores in the world. Lose yourself among the endless shelves and perhaps pick up a book or two as souvenirs. For breakfast, enjoy a delicious meal at Mother’s Bistro & Bar, known for its comfort food and welcoming ambiance.
Afternoon
In the afternoon, take part in Portland: Pink Trolley City Tour. This tour will give you an excellent overview of Portland's main attractions and neighborhoods. Afterward, visit Portland Art Museum, where you can explore an impressive collection of Native American artifacts and contemporary art pieces. For lunch, stop by Tasty n Alder, a popular spot offering innovative dishes and a vibrant atmosphere.
Evening
Conclude your day with a relaxing stroll through South Park Blocks. These historic park blocks are lined with beautiful trees and sculptures. As evening falls, head to Departure Restaurant + Lounge for dinner. This rooftop restaurant offers stunning views of the city skyline along with delectable Asian-inspired cuisine.
Bedtime
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Pioneer Square

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Powell’s City of Books

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Portland Pink Trolley City Tour

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Portland Art Museum

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South Park Blocks

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Nature and Gardens Galore

Morning
Begin your second day with a visit to Washington Park, one of Portland's most beloved green spaces. Within the park, you'll find several attractions including the famous International Rose Test Garden. Spend some time wandering through rows upon rows of beautiful roses in every color imaginable. For breakfast, enjoy fresh pastries and coffee at St. Honoré Bakery, located nearby.
Afternoon
In the afternoon, explore another gem within Washington Park: the serene Portland Japanese Garden. Known as one of the most authentic Japanese gardens outside Japan, it's a peaceful retreat from city life. Following this tranquil experience, embark on an exciting adventure with Portland: Columbia River Gorge 3-Hour Small Group Tour. This tour will take you through breathtaking landscapes along the Columbia River Gorge. For lunch before your tour departs, try out some local flavors at Kenny & Zuke’s Delicatessen, famous for its delicious sandwiches.
Evening
End your day by visiting Pittock Mansion, which offers panoramic views over Portland from its hilltop location. The mansion itself is also worth exploring for its rich history and stunning architecture. For dinner tonight, dine at Andina Restaurant, where you can savor exquisite Peruvian cuisine in an elegant setting.
Bedtime
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Washington Park

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International Rose Test Garden

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Portland Japanese Garden

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Portland Columbia River Gorge 3-Hour Small Group Tour

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Pittock Mansion

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Cultural Insights and Scenic Views

Morning
Kick off your third day by visiting one of Portland's hidden gems: Lan Su Chinese Garden. This walled garden is an oasis of tranquility amidst downtown hustle-bustle; don't miss their traditional tea house either! Afterward head towards Old Town Chinatown district exploring historical landmarks including iconic gate marking entrance into this vibrant neighborhood filled cultural significance plus unique shops eateries galore! Breakfast recommendation goes out Voodoo Doughnut iconic spot offering quirky creative doughnuts sure satisfy sweet tooth cravings any traveler!
Afternoon
Post-lunch delve deeper into local culture via engaging experience offered through participation on intriguing tour namely: 'Portland Underground Shanghai Tunnel Tour Beer Tasting' (ID#435163). Uncover fascinating stories behind infamous tunnels used during early 20th century while enjoying samples craft beers provided knowledgeable guides throughout journey beneath streets city itself truly unforgettable way spend afternoon indeed! Lunchtime suggestion includes hearty meal served up Pine State Biscuits renowned biscuits gravy fried chicken more comfort food classics sure leave feeling satisfied ready next adventure awaits ahead...
Evening
Wrap up third eventful day taking leisurely walk around picturesque Alphabet District (ID#16069) charming neighborhood boasts historic homes tree-lined streets boutique shops cafes perfect place unwind after busy sightseeing schedule earlier parts today finally cap off wonderful evening dining Clyde Common trendy eatery known inventive cocktails farm-to-table dishes crafted using locally sourced ingredients ensuring memorable culinary experience fitting end another fantastic exploration-filled day spent discovering all beauty charm vibrant Pacific Northwest metropolis like none other...
Bedtime
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Lan Su Chinese Garden

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Historic Sites and River Adventures

Morning
Start your fourth day with a visit to Oregon Museum of Science and Industry (OMSI). This interactive museum is perfect for both adults and children, offering hands-on exhibits that cover a wide range of scientific topics. Don't miss the planetarium shows or the submarine tour! For breakfast, head to Pine State Biscuits, where you can enjoy hearty Southern-style biscuits with various delicious toppings.
Afternoon
In the afternoon, embark on an exciting river adventure with Portland: Willamette River 2.5-hour Dinner Cruise. This cruise offers stunning views of Portland's skyline from the water while you enjoy a delectable meal. Before your cruise, have lunch at Little Bird Bistro, known for its French-inspired cuisine and charming atmosphere.
Evening
Conclude your day by exploring Portland Pearl District, one of Portland's trendiest neighborhoods. Stroll through its cobblestone streets lined with art galleries, boutiques, and cafes. For dinner, dine at Deschutes Brewery Portland Public House, where you can sample local craft beers along with delicious pub fare.
Bedtime
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Oregon Museum of Science and Industry (OMSI)

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Portland Willamette River 2.5-hour Dinner Cruise

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Portland Pearl District

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Gardens and Scenic Flights

Morning
Hoyt Arboretum is the perfect place to start your final day in Portland. This living museum features over 2,300 species of trees and plants from around the world. Enjoy a peaceful morning walk through its well-maintained trails. For breakfast, visit Screen Door, famous for its Southern-style brunch dishes.
Afternoon
Portland: Columbia Gorge Waterfalls Afternoon Tour will be the highlight of your afternoon. This tour takes you to some of the most breathtaking waterfalls in the Columbia River Gorge area. Before heading out on this adventure, have lunch at Lardo, known for its gourmet sandwiches and laid-back vibe.
Evening
Forest Park is an excellent spot to spend your last evening in Portland. As one of the largest urban forests in the United States, it offers numerous trails for hiking and enjoying nature. End your trip with a memorable dinner at Le Pigeon, where you can indulge in innovative French-inspired dishes crafted by renowned chefs.
Bedtime
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Hoyt Arboretum

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Portland Columbia River Gorge Waterfalls Afternoon Tour

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Forest Park

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