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Oregon

10 day itinerary

Oregon

Personalized with:CoupleWinter activitiesDriving

Itinerary

Day 1: Arrival in Portland

Welcome to Oregon! Start your trip by flying into Portland and checking into your cozy accommodation. Spend the day exploring the vibrant city, known for its hipster culture, craft breweries, and delicious food scene. Visit the iconic , stroll through the beautiful , and indulge in some local cuisine at one of the many food carts scattered throughout the city.

Day 2:

Rent a car and head east to the stunning . Marvel at the breathtaking , hike along the scenic trails, and enjoy the panoramic views of the gorge. Don't forget to stop by the historic for a hot cocoa or a warm meal.

Day 3: and

Drive south to , a charming town nestled in the high desert. Spend the day exploring the city's unique shops, breweries, and art galleries. In the afternoon, head to , a popular ski resort, and enjoy some winter activities like skiing or snowboarding. End the day with a relaxing soak in one of the natural hot springs in the area.

Day 4:

Embark on a scenic drive to , one of Oregon's most iconic destinations. Marvel at the deep blue waters of the lake, formed in the caldera of an ancient volcano. Take a snowshoeing or cross-country skiing tour around the rim, and if weather permits, enjoy a breathtaking sunset over the lake.

Day 5:

Head south to the picturesque . Explore the charming town of , known for its Shakespeare Festival and vibrant arts scene. Take a leisurely stroll through , visit local wineries, and enjoy a romantic dinner at one of the cozy restaurants in town.

Day 6:

Drive west to the stunning . Explore the rugged coastline, visit iconic landmarks like , and take a scenic hike along the cliffs. Enjoy fresh seafood at one of the coastal towns and watch the sunset over the Pacific Ocean.

Day 7: and Yaquina Bay

Continue your coastal adventure by visiting . Explore the historic , visit the , and take a walk along the . If you're feeling adventurous, go on a whale-watching tour or try your hand at crabbing.

Day 8:

Head back inland to the beautiful Willamette Valley, known for its world-class wineries. Spend the day wine tasting and exploring the vineyards. Enjoy a leisurely lunch at one of the winery restaurants and take in the scenic views of the rolling hills.

Day 9: and

Return to Portland and spend the day exploring . Take a scenic drive up to and enjoy the winter wonderland. Go skiing or snowboarding on the slopes, or simply relax by the fireplace with a cup of hot cocoa.

Day 10: Portland Departure

On your last day, take some time to explore any remaining attractions in Portland. Visit the , browse the unique shops in the Pearl District, and indulge in some last-minute food cart treats. Bid farewell to Oregon as you head to the airport for your departure.

This itinerary offers a mix of winter activities, scenic drives, coastal exploration, and city adventures, ensuring you make the most of your 10 days in Oregon as a couple. Enjoy your trip!

Places of interest

Powell's City of Books Oregon

Powell's City of Books

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Washington Park Oregon

Washington Park

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Food carts in Portland Oregon

Food carts in Portland

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Columbia River Gorge Oregon

Columbia River Gorge

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Multnomah Falls Oregon

Multnomah Falls

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Timberline Lodge on Mount Hood Oregon

Timberline Lodge on Mount Hood

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Bend Oregon

Bend

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Mt. Bachelor Oregon

Mt. Bachelor

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Natural hot springs in Bend area Oregon

Natural hot springs in Bend area

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Crater Lake National Park Oregon

Crater Lake National Park

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Rogue River Valley Oregon

Rogue River Valley

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Ashland Oregon

Ashland

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Lithia Park Oregon

Lithia Park

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Wineries in the Willamette Valley Oregon

Wineries in the Willamette Valley

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Oregon Coast Oregon

Oregon Coast

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Haystack Rock in Cannon Beach Oregon

Haystack Rock in Cannon Beach

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Newport Oregon

Newport

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Yaquina Bay Lighthouse Oregon

Yaquina Bay Lighthouse

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Oregon Coast Aquarium Oregon

Oregon Coast Aquarium

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Newport Bayfront Oregon

Newport Bayfront

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Whale-watching tour in Newport Oregon

Whale-watching tour in Newport

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Willamette Valley Wine Country Oregon

Willamette Valley Wine Country

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Mount Hood Oregon

Mount Hood

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Timberline Lodge Oregon

Timberline Lodge

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Portland Japanese Garden Oregon

Portland Japanese Garden

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Pearl District shops in Portland Oregon

Pearl District shops in Portland

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