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Portland, Oregon: 5-Day Adventure Itinerary

Last updated: 2024 Jun 14

City Highlights and Culinary Delights

Morning

Start your day with a delicious breakfast at Pine State Biscuits, known for their mouthwatering biscuits and gravy. Afterward, embark on the "Portland City + Waterfall Combo" tour, which takes you to iconic city landmarks and breathtaking waterfalls. The tour includes a stop at the International Rose Test Garden, where you can admire the vibrant blooms and panoramic views of the city.

Afternoon

For lunch, head to Tasty n Alder, a popular spot offering a diverse menu of globally-inspired dishes. Afterward, explore the Portland Art Museum, home to an extensive collection of art from various periods and cultures. Take your time to appreciate the museum's diverse exhibits.

Evening

As the evening approaches, indulge in a memorable dining experience at Le Pigeon, a renowned restaurant known for its innovative and flavorful dishes. After dinner, take a leisurely stroll through the Pearl District, known for its art galleries, boutiques, and vibrant atmosphere.

Bedtime

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4.76
International Rose Test Garden
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4.82
Portland Art Museum
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Nature's Wonders and Urban Exploration

Morning

Enjoy a hearty breakfast at Screen Door, famous for its Southern-inspired cuisine. Then, embark on a day trip to the Columbia River Gorge, where you'll witness the majestic Multnomah Falls, Latourell Falls, and Vista House. Take in the natural beauty and enjoy the refreshing air.

Afternoon

For lunch, savor the flavors of the Pacific Northwest at Bamboo Sushi NW, known for its sustainable and creative sushi offerings. Afterward, visit the Bonneville Dam, a marvel of engineering that harnesses the power of the Columbia River. Learn about the dam's history and significance.

Evening

Return to Portland and unwind with a delightful dinner at Andina Restaurant, where you can savor authentic Peruvian cuisine. Afterward, take a leisurely walk along the Portland Steel Bridge, which offers stunning views of the city skyline and the Willamette River.

Bedtime

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4.90
Columbia River Gorge
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4.94
Bonneville Dam
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Culinary Exploration and River Cruises

Morning

Start your day with a delectable brunch at Imperial, known for its wood-fired dishes and locally-sourced ingredients. Then, embark on the "Portland All-Inclusive Walking Food Tour," where you'll sample a variety of culinary delights from the city's top eateries.

Afternoon

After the tour, take a relaxing 2-hour lunch cruise on the Willamette River, enjoying the scenic views and the onboard entertainment. For dinner, experience the city's vibrant food scene at Toro Bravo Inc, known for its Spanish-inspired small plates and lively ambiance.

Evening

Conclude your day with a unique experience on the "Portland Ghosts, Poltergeists, and Psychopaths Walking Tour," where you'll hear chilling tales of the city's haunted past. Afterward, unwind with a nightcap at Clyde Common, a stylish bar known for its craft cocktails and cozy atmosphere.

Bedtime

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Mount Hood Adventure and Cultural Immersion

Morning

Enjoy a leisurely breakfast at Pok Pok, a popular spot offering authentic Thai cuisine. Then, embark on a full-day tour to Mount Hood, where you'll explore the mountain's natural beauty and enjoy outdoor activities such as hiking or snowshoeing, depending on the season.

Afternoon

For lunch, visit Lardo, known for its delicious sandwiches and casual vibe. Afterward, immerse yourself in the local culture at the Portland Japanese Garden, a serene oasis that showcases traditional Japanese landscaping and design.

Evening

Return to the city and treat yourself to a memorable dinner at Kachka Russian Cuisine & Vodka Bar, where you can enjoy a modern take on traditional Russian dishes. Afterward, take a stroll through the Pioneer Square, known as the heart of downtown Portland.

Bedtime

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Portland Japanese Garden
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4.72
Pioneer Square
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Oregon Coast and Farewell Dinner

Morning

Enjoy a delightful breakfast at Nong's Khao Man Gai, known for its signature Thai chicken and rice dish. Then, embark on a day trip to the Oregon Coast, where you'll visit Cannon Beach and the iconic Haystack Rock, a natural wonder that's a must-see.

Afternoon

For lunch, savor the flavors of the coast at Departure Restaurant and Lounge, known for its Asian-inspired cuisine and panoramic views. Afterward, take a leisurely walk on the beach and breathe in the fresh ocean air.

Evening

Return to Portland and conclude your trip with a farewell dinner at Ox Restaurant, known for its innovative and bold flavors. Raise a glass to your unforgettable adventure in Portland and reminisce about the wonderful experiences you've had.

Bedtime

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