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Portland's Diverse Delights: 5-Day Adventure

Portland's Diverse Delights: 5-Day Adventure Itinerary

Last updated: 2024 Jun 14

City Icons and Waterfront Wonders

Morning
Start your Portland journey with a delightful breakfast at Urban Steel Kitchen + Bar, known for its local ingredients and innovative dishes. Afterward, take a serene morning stroll through the lush landscapes of the Portland Japanese Garden, a haven of tranquility in the heart of the city.
Afternoon
For lunch, savor the flavors of the city at the Portland Food Carts, Pods, & Patios Tour. This guided tour will introduce you to the diverse and vibrant food cart scene of Portland. Afterward, enjoy an afternoon of exploration at the Portland Pearl District, known for its art galleries, boutiques, and upscale dining.
Evening
As the sun sets, embark on the Portland Willamette River 2.5-hour Dinner Cruise. Indulge in a sumptuous meal while taking in the glittering skyline and the gentle waters of the Willamette River. It's a perfect way to cap off your first day in Portland.
Bedtime
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Visit Portland Japanese Garden in Portland
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Portland Japanese Garden

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Portland Food Carts, Pods, & Patios Tour

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Waterfalls and Wine Country

Morning
Fuel up for the day with a hearty breakfast at The Eastburn, a local favorite. Then, set out early for the Portland Columbia River Gorge Waterfalls Morning Tour. Witness the majestic Multnomah Falls and other natural wonders as you breathe in the fresh mountain air.
Afternoon
After the tour, enjoy a leisurely lunch at Noble Rot, where you can pair your meal with stunning views of the city. Post-lunch, continue to the scenic Vista House to take in panoramic vistas of the Columbia River Gorge.
Evening
Conclude your day with a visit to the Willamette Valley, Oregon's renowned wine country. Join the Mt. Hood Wine and Waterfalls Full-Day Tour to sample exquisite wines and witness the beauty of the region. Return to Portland with a satisfied palate and memories of the valley's rolling vineyards.
Bedtime
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Visit Portland Columbia River Gorge Waterfalls Morning Tour in Portland
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Portland Columbia River Gorge Waterfalls Morning Tour

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Visit Vista House in Portland
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Vista House

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Historic Haunts and Culinary Cycling

Morning
Start with a fresh cup of coffee at The Woodsman Tavern, known for its artisanal brews. Then, embark on the Portland Underground Shanghai Tunnel Tour with Beer Tasting. Explore the city's intriguing past and enjoy a unique beer tasting experience in the historic underground tunnels.
Afternoon
For lunch, hop on the Portland Food Carts of the Eastside Bike Tour. Cycle through the vibrant Eastside neighborhoods and sample a variety of local bites from the famous food carts. It's a fun and flavorful way to spend your afternoon.
Evening
As the night falls, join the Portland Ghosts Boos and Booze Haunted Pub Crawl. Delve into Portland's darker history while visiting some of its most haunted pubs. Enjoy spooky stories and a few drinks as you uncover the city's eerie past.
Bedtime
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Visit Portland Underground Shanghai Tunnel Tour with Beer Tasting in Portland
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Portland Underground Shanghai Tunnel Tour with Beer Tasting

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Visit Portland Food Carts of the Eastside Bike Tour in Portland
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Portland Food Carts of the Eastside Bike Tour

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Mountains, Museums, and Mouthwatering Donuts

Morning
Enjoy a classic Portland breakfast at Powell’s City of Books [13305], where you can browse the shelves of the world's largest independent bookstore and grab a pastry and coffee at their cafe. Post-breakfast, head out for the Portland Mt. Hood Day Tour. Explore the stunning landscapes of the Cascade Range and get up close to the iconic Mt. Hood.
Afternoon
After returning from the tour, have a late lunch at C-Bar PDX, a cozy spot with a menu featuring local and seasonal ingredients. Spend your afternoon at the Oregon Museum of Science and Industry (OMSI), where interactive exhibits and hands-on activities await, perfect for all ages.
Evening
For dinner, indulge in a variety of delicious donuts on the Portland Guided Delicious Donut Tour with Tastings. Learn about the city's donut culture and visit several renowned donut shops. Wrap up the evening with a visit to the Portland Steel Bridge, beautifully illuminated against the night sky.
Bedtime
Find amazing hotels in Portland.
Visit Portland Mt. Hood Day Tour in Portland
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Portland Mt. Hood Day Tour

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Visit Oregon Museum of Science and Industry (OMSI) in Portland
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Oregon Museum of Science and Industry (OMSI)

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Roses, Views, and Culinary Capstone

Morning
Begin with a delightful breakfast at The Observatory, known for its elegant ambiance and delectable dishes. Then, take a morning stroll through the vibrant blooms of the International Rose Test Garden, where you can immerse yourself in the beauty of over 10,000 rose bushes.
Afternoon
For lunch, enjoy the casual yet refined atmosphere of The Fields Bar & Grill, located in the heart of the Pearl District. Afterward, visit the Pittock Mansion to explore the historic house and take in panoramic views of the city and surrounding landscape.
Evening
Conclude your Portland adventure with a dinner at Departure Restaurant + Lounge, a modern Asian restaurant with stunning views of the city. Reflect on your journey as you savor the innovative cuisine and the memories of the past five days in the City of Roses.
Bedtime
Find amazing hotels in Portland.
Visit International Rose Test Garden in Portland
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International Rose Test Garden

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Visit Pittock Mansion in Portland
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Pittock Mansion

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