17 days in Oregon Itinerary

17 days in Oregon Itinerary

Created using Inspirock Oregon trip builder

Make it your trip
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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Portland

— 5 nights

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 Oregon Museum of Science and Industry. Explore Portland's surroundings by going to Dayton (Archery Summit Winery, Domaine Serene, &more), Carlton (Carlton Winemakers Studio & K&M Wines) and Bravuro Cellars (in Newberg). Dedicate the 5th (Sat) to wine at some of the top wineries in the area. Next up on the itinerary: take a peaceful walk through The Grotto - National Sanctuary of Our Sorrowful Mother, see the interesting displays at Oregon Maritime Museum, have fun and explore at Portland Children's Museum, and take in the exciting artwork at Live Laugh Love Art.

To see reviews, traveler tips, photos, and tourist information, use the Portland day trip website.

Santiago, Chile to Portland is an approximately 18-hour flight. The time zone changes from Chile Standard Time to Pacific Standard Time, which is usually a -4 hour difference. In December in Portland, expect temperatures between 8°C during the day and 1°C at night. Finish up your sightseeing early on the 6th (Sun) so you can go by car to Albany.

Things to do in Portland

Wineries · Museums · Tours · Shopping

Side Trips

Albany

— 2 nights
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

Cannon Beach

— 4 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. Do some cultural sightseeing at Tillamook Air Museum and Tillamook Rock Light. You'll enjoy a bit of beach vacationing at Cannon Beach and Haystack Rock. 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: admire the majestic nature at Ecola State Park, view the masterpieces at Bronze Coast Gallery, kick back and relax at Short Sands Beach, and get a taste of the local shopping with Cannon Beach Gallery.

To find traveler tips, other places to visit, photos, and other tourist information, read our Cannon Beach travel route builder site.

You can drive from Albany to Cannon Beach in 2.5 hours. In December, daytime highs in Cannon Beach are 11°C, while nighttime lows are 3°C. Finish your sightseeing early on the 12th (Sat) so you can drive to Hood River.

Things to do in Cannon Beach

Parks · Outdoors · Beaches · Nature

Side Trips

Hood River

— 3 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Western Antique Aeroplane & Automobile Museum and Fire Museum in City Hall are good opportunities to explore the local culture. Next up on the itinerary: look for all kinds of wild species at Columbia River Gorge National Scenic Area, take in the exciting artwork at Art on Oak, learn about winemaking at Cathedral Ridge Winery, and examine the collection at Columbia Gorge Discovery Center & Museum.

For other places to visit, photos, maps, and more tourist information, read our Hood River trip itinerary planner.

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 up your sightseeing early on the 15th (Tue) so you can go by car to Timberline Lodge.

Things to do in Hood River

Wineries · Museums · Nature · Wildlife

Side Trips

Timberline Lodge

— 1 night
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 · Trails · Outdoors

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.