14 days in Oregon Itinerary

14 days in Oregon Itinerary

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Route & dates

14 days in Oregon Itinerary

Start: Tampa
Fly:  10​h
1
Portland
— 4 nights
Drive:  2​h
2
Astoria
— 3 nights
Drive:  3​h
3
Hood River
— 3 nights
Drive:  3​h 15​min
4
Bend
— 2 nights
Fly:  11​h
End: Tampa

4
nights
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.
Willamette Valley Vineyards and Oregon Museum of Science and Industry are good opportunities to explore the local culture. Museum-lovers will get to explore Evergreen Aviation & Space Museum and Portland Art Museum. You'll find plenty of places to visit near Portland: Carlton Winemakers Studio (in Carlton), Adelsheim Vineyard (in Newberg) and Mount Angel Abbey (in Saint Benedict). There's lots more to do: look for gifts at Powell's City of Books, steep yourself in history at Columbia River Highway, sample the tasty concoctions at Clear Creek Distillery, and examine the collection at Oregon Maritime Museum.

Plan a Portland trip in moments using our itinerary builder.

Tampa to Portland is an approximately 10-hour combination of bus and flight. You can also fly; or drive. You'll gain 3 hours traveling from Tampa to Portland due to the time zone difference. Expect cooler weather when traveling from Tampa in January: highs in Portland hover around 46°F, while lows dip to 35°F. Finish up your sightseeing early on the 12th (Sat) so you can go by car to Astoria.

Things to do in Portland

Museums Wineries Historic Sites

Side Trips

Ardiri Winery and Vineyards, Evergreen Aviation & Space Museum, Carlton Winemakers Studio, Adelsheim Vineyard, Mount Angel Abbey
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Columbia River Highway ©
Columbia River Highway

3
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Get a sense of the local culture at Columbia River Maritime Museum and Fort Clatsop National Memorial. You'll enjoy a bit of beach vacationing at Haystack Rock and Cannon Beach. Step out of Astoria to go to Cannon Beach and see Ecola State Park, which is approximately 50 minutes away. There's more to do: examine the collection at Seaside Inverted Experience and look for gifts at Beach Books.

To find where to stay, photos, and tourist information, read our Astoria attractions planning website .

Getting from Portland to Astoria by car takes about 2 hours. Other options: do a combination of train, taxi, and bus; or take a bus. In January in Astoria, expect temperatures between 50°F during the day and 38°F at night. Wrap up your sightseeing on the 15th (Tue) early enough to drive to Hood River.

Things to do in Astoria

Parks Nature Historic Sites

Side Trips

Cannon Beach, Seaside
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Ecola State Park ©
Ecola State Park

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. You'll explore and learn at Western Antique Aeroplane & Automobile Museum and Fort Dalles Museum and Anderson Homestead. Do some cultural sightseeing at Columbia Gorge Discovery Center & Museum and Fire Museum in City Hall. Take a break from Hood River with a short trip to Multnomah Falls in Bridal Veil, about 40 minutes away. The adventure continues: contemplate the waterfront views at Columbia River Gorge National Scenic Area, learn about winemaking at Sunshine Mill Winery, look for gifts at Foothills Yarn and Fiber, and experience rural life at The Gorge White House.

To find reviews, maps, and more tourist information, read our Hood River online itinerary planner .

Drive from Astoria to Hood River in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Astoria in January, things will get a bit cooler in Hood River: highs are around 38°F and lows about 32°F. Cap off your sightseeing on the 18th (Fri) early enough to go by car to Bend.

Things to do in Hood River

Parks Nature Museums

Side Trips

The Dalles, Multnomah Falls, Columbia River Gorge National Scenic Area
Highlights from your plan
Multnomah Falls ©
Multnomah Falls

2
nights
Bend

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.
Kick off your visit on the 19th (Sat): learn more about the world around you at High Desert Museum and then relax and rejuvenate at some of the top local wellness centers. Get ready for a full day of sightseeing on the 20th (Sun): shop like a local with The Art of Alfred A. Dolezal Gallery, then stop by Crescent Moon Ranch, and then immerse yourself in nature at Smith Rock State Park.

For where to stay, other places to visit, traveler tips, and other tourist information, read our Bend travel route tool .

Traveling by car from Hood River to Bend takes 3.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Traveling from Hood River in January, expect little chillier with lows of 24°F in Bend. Finish up your sightseeing early on the 20th (Sun) so you can travel back home.

Things to do in Bend

Parks Museums Wildlife

Side Trips

Redmond, Crescent Moon Ranch
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
The Art of Alfred A. Dolezal Gallery ©

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