5 days in Oregon Itinerary

5 days in Oregon Itinerary

Created using Inspirock Oregon itinerary maker

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Route & dates

5 days in Oregon Itinerary

Start: San Diego
Fly:  4​h 30​min
1
Portland
— 1 night
Drive:  2​h 45​min
2
Newport
— 1 night
Drive:  4​h 30​min
3
Bend
— 2 nights
Fly:  7​h
End: San Diego

1
night
Portland

Portland ©
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.
Start off your visit on the 6th (Thu): steep yourself in history at Pittock Mansion and then steep yourself in history at Officers' Row.

For other places to visit, reviews, traveler tips, and other tourist information, you can read our Portland day trip site .

San Diego to Portland is an approximately 4.5-hour flight. You can also drive; or take a bus. Plan for slightly colder nights when traveling from San Diego in June since evenings lows in Portland dip to 56°F. Wrap up your sightseeing on the 7th (Fri) to allow time to drive to Newport.

Things to do in Portland

Museums Historic Sites Parks

Side Trips

Sokol Blosser Winery, Hyland Forest Park, Officers' Row, Evergreen Aviation & Space Museum
Highlights from your plan
Officers' Row ©
Officers' Row
Sokol Blosser Winery ©
Sokol Blosser Winery
Evergreen Aviation & Space Museum ©

1
night
Newport

Newport
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
For other places to visit, ratings, reviews, and more tourist information, refer to the Newport day trip planner.

Drive from Portland to Newport in 3 hours. Alternatively, you can take a bus. Traveling from Portland in June, expect Newport to be a bit cooler, temps between 61°F and 48°F. On the 8th (Sat), you'll travel to Bend.

Things to do in Newport

Parks Outdoors Nature

2
nights
Bend

An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.
Let the collections at High Desert Museum and Dee Wright Observatory capture your imagination. You'll discover tucked-away gems like River Rafting & Tubing and Artists Gallery Sunriver. Venture out of the city with trips to Sisters (Proxy Falls & City of Sisters). Next up on the itinerary: take in the awesome beauty at South Sister, explore the striking landscape at Balancing Rocks, sample the tasty concoctions at Boneyard Beer, and take an in-depth tour of Des Chutes Historical Museum.

To find traveler tips, maps, reviews, and more tourist information, go to the Bend travel route planning website .

You can drive from Newport to Bend in 4.5 hours. Alternatively, you can take a bus. Traveling from Newport in June, expect nights in Bend to be about the same, around 45°F, while days are a bit warmer, around 75°F. Wrap up your sightseeing on the 10th (Mon) early enough to travel back home.

Things to do in Bend

Parks Museums Nature

Side Trips

Sisters, Dee Wright Observatory, Artists Gallery Sunriver
Highlights from your plan
River Rafting & Tubing
Dee Wright Observatory ©
Dee Wright Observatory
City of Sisters ©
City of Sisters

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