17 days in Oregon Itinerary

17 days in Oregon Itinerary

Created using Inspirock Oregon trip builder

Plan created by another user. Make it yours
Fly
1
Portland
— 5 nights
Drive
2
Albany
— 2 nights
Drive
3
Cannon Beach
— 4 nights
Drive
4
Hood River
— 3 nights
Drive
5
Timberline Lodge
— 1 night
Drive to Portland International Airport, Fly to Comodoro Arturo Merino Benítez International Airport

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5
nights
Portland

City of Roses

A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Your cultural itinerary includes sights like Evergreen Aviation & Space Museum and Wine Tours & Tastings. Explore Portland's surroundings by going to Carlton (Carlton Winemakers Studio & K&M Wines), Dayton (Archery Summit Winery, Domaine Serene, &more) and Bravuro Cellars (in Newberg). There's still lots to do: take a peaceful walk through The Grotto - National Sanctuary of Our Sorrowful Mother, view the masterpieces at Live Laugh Love Art, do a tasting at Willamette Valley Vineyards Wine Center, and examine the collection at Oregon Museum of Science and Industry.

To see other places to visit, traveler tips, photos, and tourist information, you can read our Portland trip itinerary planning tool.

Santiago, Chile to Portland is an approximately 18-hour flight. The time zone difference moving from Chile Standard Time to Pacific Standard Time is minus 4 hours. In December, daytime highs in Portland are 8°C, while nighttime lows are 1°C. Finish your sightseeing early on the 6th (Sun) to allow enough time to drive to Albany.

Things to do in Portland

Wineries · Museums · Tours · Shopping

Side Trips

2
nights
Albany

Albany is the county seat of Linn County, and the 11th largest city in the State of Oregon. On the 7th (Mon), see the interesting displays at The Historic Carousel and Museum, don't miss a visit to Downtown Historic District, then learn about winemaking at Airlie Winery, and finally make a splash at Osborn Aquatic Center. Keep things going the next day: see the interesting displays at Albany Regional Museum, learn about winemaking at Willamette Valley Vineyards, and then get to know the fascinating history of Monteith District.

To see other places to visit, reviews, photos, and tourist information, refer to the Albany trip planner.

You can drive from Portland to Albany in 1.5 hours. December in Albany sees daily highs of 8°C and lows of 1°C at night. Finish up your sightseeing early on the 8th (Tue) so you can travel to Cannon Beach.

Things to do in Albany

Historic Sites · Museums · Wineries · Theme Parks

Side Trips

4
nights
Cannon Beach

Cannon Beach is a city in Clatsop County, Oregon, United States. Do some cultural sightseeing at Tillamook Air Museum and Cannon Beach History Center and Museum. You'll enjoy a bit of beach vacationing at Cannon Beach and Hug Point State Recreation Site. When in Cannon Beach, make a side trip to see Rockaway Beach Wayside in Rockaway Beach, approximately Rockaway Beach away. There's much more to do: kick back and relax at Haystack Rock, view the masterpieces at Bronze Coast Gallery, tee off at Manzanita Golf Course, and tour the pleasant surroundings at Manzanita Beach.

For reviews, traveler tips, more things to do, and more tourist information, read Cannon Beach trip planner.

You can drive from Albany to Cannon Beach in 2.5 hours. Expect a daytime high around 11°C in December, and nighttime lows around 3°C. Wrap up your sightseeing on the 12th (Sat) to allow time to drive to Hood River.

Things to do in Cannon Beach

Outdoors · Parks · Beaches · Nature

Side Trips

3
nights
Hood River

The city of Hood River is the seat of Hood River County, Oregon, United States. Western Antique Aeroplane & Automobile Museum and Columbia Gorge Discovery Center & Museum are good opportunities to explore the local culture. The adventure continues: identify plant and animal life at Columbia River Gorge National Scenic Area, take in the exciting artwork at Art on Oak, learn about winemaking at Cathedral Ridge Winery, and brush up on your military savvy at Fort Dalles Museum and Anderson Homestead.

You can plan Hood River trip in no time by asking Inspirock to help create your itinerary.

Traveling by car from Cannon Beach to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect slightly colder temperatures when traveling from Cannon Beach in December; daily highs in Hood River reach 5°C and lows reach -1°C. Finish your sightseeing early on the 15th (Tue) so you can drive to Timberline Lodge.

Things to do in Hood River

Wineries · Museums · Wildlife · Nature

Side Trips

1
night
Timberline Lodge

Perched high on the south face of one of the most iconic peaks in the Pacific Northwest, Timberline Lodge is the ski and snowboarding area known for the eponymous historic lodge, the design of which emphasizes the area's natural beauty.
Kick off your visit on the 16th (Wed): take a peaceful walk through Ramona Falls Trail, delve into the lush surroundings at Mt. Hood National Forest, and then hit the slopes at Timberline Lodge and Ski Area.

To find more things to do, ratings, other places to visit, and tourist information, read Timberline Lodge online holiday planner.

Traveling by car from Hood River to Timberline Lodge takes 1.5 hours. In December, plan for daily highs up to 5°C, and evening lows to -1°C. Finish up your sightseeing early on the 16th (Wed) so you can travel back home.

Things to do in Timberline Lodge

Nature · Parks · Outdoors · Trails

Side Trips

Oregon travel guide

4.5
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.