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5 Days in Portland with Snow Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Portland

Morning

Start your day with a hearty breakfast at Pine State Biscuits, known for its delicious Southern-style biscuits. After breakfast, head to Pioneer Square, often referred to as Portland's living room. This is a great spot to get a feel for the city and enjoy some people-watching.

Afternoon

For lunch, make your way to Lardo, famous for its sandwiches and casual atmosphere. Afterward, visit the iconic Powell’s City of Books, the largest independent bookstore in the world. Spend some time exploring its many rooms and perhaps pick up a book or two.

Evening

Enjoy dinner at Le Pigeon, known for its innovative French cuisine. End your day with a visit to Portland Art Museum, which houses an impressive collection of art from around the world.

Bedtime

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4.72
Pioneer Square
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4.60
Powell’s City of Books
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Nature and Gardens

Morning

Begin your day with breakfast at Mother's Bistro & Bar, offering comfort food made from scratch. Then head over to Portland Japanese Garden, considered one of the most authentic Japanese gardens outside of Japan.

Afternoon

For lunch, stop by Nong's Khao Man Gai for some delicious Thai chicken and rice. Afterward, explore the beautiful International Rose Test Garden nearby, where you can see thousands of rose varieties in bloom.

Evening

Dine at Andina Restaurant, which offers Peruvian cuisine in a vibrant setting. Conclude your evening with a stroll through the charming streets of the Alphabet District.

Bedtime

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4.87
Portland Japanese Garden
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4.76
International Rose Test Garden
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Waterfalls and Wine

Morning

Kick off your morning with breakfast at Screen Door Eastside, known for its Southern comfort food. Then embark on an adventure with the From Portland Half Day Columbia River Gorge Waterfalls Tour. This tour will take you to some of the most stunning waterfalls in the region.

Afternoon

After returning from your tour, have lunch at Kachka, which serves Russian-inspired dishes. Spend your afternoon visiting local wineries on an organized tour like the Outside Portland Wine, Waterfalls, and Timberline Tour. Enjoy tastings while taking in beautiful vineyard views.

Evening

Have dinner at Toro Bravo, offering Spanish tapas in a lively atmosphere. Finish off your day by exploring more of Portland’s nightlife or relaxing back at your accommodation.

Bedtime

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5.00
From Portland Half Day Columbia River Gorge Waterfalls Tour
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5.00
Outside Portland Wine, Waterfalls, and Timberline Tour
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Cultural Immersion

Morning

Start with breakfast at Tasty n Alder, known for its eclectic brunch menu. Visit the historic mansion turned museum, Pittock Mansion, which offers panoramic views of Portland and insights into its history.

Afternoon

For lunch, try out some Vietnamese flavors at Luc Lac Vietnamese Kitchen. Post-lunch, explore more cultural sites like the serene Lan Su Chinese Garden. This classical Chinese garden is an oasis in downtown Portland.

Evening

Dine at one of Portland’s top restaurants, Ox Restaurant, which offers Argentine-inspired dishes cooked over an open flame. End your evening by taking part in a unique local experience such as the guided foodie bike tour: Portland Guided Foodie Bike Tour.

Bedtime

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4.93
Pittock Mansion
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4.57
Lan Su Chinese Garden
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Adventure and Farewell

Morning

Begin your final day with coffee and donuts from the famous Blue Star Donuts. Head out on an exciting aerial adventure with Portland Flightseeing Tour Mount Hood. The flight offers breathtaking views of Mount Hood covered in snow.

Afternoon

After landing back in Portland have lunch at Grassa known for their handmade pasta dishes then visit Oregon Museum of Science and Industry (OMSI) where you can engage with interactive exhibits that are fun for all ages.

Evening

Conclude your trip with dinner reservations at Departure Restaurant and Lounge where you can enjoy Asian fusion cuisine while taking in panoramic views of downtown Portland from their rooftop lounge.

Bedtime

Find amazing hotels in Portland, Oregon.