16 days in Oregon Itinerary

16 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary maker

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Route & dates

16 days in Oregon Itinerary

Start: Sao Paulo
Fly:  19​h 15​min
1
Portland
— 1 night
bus:  1​h 15​min
2
Hood River
— 2 nights
Drive:  3​h 15​min
3
Bend
— 2 nights
Drive:  4​h 30​min
4
Ashland
— 1 night
Drive:  4​h 45​min
5
Yachats
— 3 nights
Drive:  2​h 15​min
6
Tillamook
— 1 night
Drive:  1​h 45​min
7
Astoria
— 3 nights
+2
bus + tram + Fly:  22​h
End: Sao Paulo

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.
Kick off your visit on the 2nd (Mon): take in nature's colorful creations at Lan Su Chinese Garden, tour the pleasant surroundings at Forest Park, then contemplate the long history of Pittock Mansion, then admire the natural beauty at International Rose Test Garden, and finally take in nature's colorful creations at Portland Japanese Garden. On the 3rd (Tue), you'll have a packed day of sightseeing: indulge your taste buds at Food & Drink, stop by Powell's City of Books, and then admire the sheer force of Multnomah Falls.

For photos, maps, more things to do, and more tourist information, refer to the Portland online trip itinerary planner .

Sao Paulo, Brazil to Portland is an approximately 19.5-hour flight. You can also do a combination of bus and flight; or do a combination of flight, bus, and train. Due to the time zone difference, you'll gain 5 hours traveling from Sao Paulo to Portland. Traveling from Sao Paulo in September, expect little chillier with lows of 15°C in Portland. Wrap up your sightseeing on the 3rd (Tue) to allow time to drive to Hood River.

Things to do in Portland

Parks Tours Nature

Side Trip

Multnomah Falls
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Powell's City of Books ©
Powell's City of Books
International Rose Test Garden ©
International Rose Test Garden

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Start off your visit on the 4th (Wed): see the interesting displays at Columbia Gorge Discovery Center & Museum, contemplate the waterfront views at Columbia River Gorge National Scenic Area, and then do a tasting at Marchesi Vineyards. Keep things going the next day: examine the collection at Western Antique Aeroplane & Automobile Museum, take in the dramatic scenery at Starvation Creek State Park, and then fly down the slopes at Mount Hood.

For more things to do, other places to visit, photos, and more tourist information, you can read our Hood River trip planning website .

You can drive from Portland to Hood River in 1.5 hours. Other options are to take a bus; or take a train. Traveling from Portland in September, you will find days in Hood River are little chillier (25°C), and nights are about the same (16°C). Finish your sightseeing early on the 5th (Thu) to allow enough time to drive to Bend.

Things to do in Hood River

Parks Nature Wildlife

Side Trips

Starvation Creek State Park, Columbia River Gorge National Scenic Area, Columbia Gorge Discovery Center & Museum
Highlights from your plan
Mount Hood ©
Mount Hood

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 6th (Fri): savor the flavors at Food & Drink and then get impressive views of Newberry National Volcanic Monument. Here are some ideas for day two: let the river carry you with a rafting and tubing tour, indulge your thirst for a good beer at Deschutes Brewery, and then hike along Pilot Butte State Scenic Viewpoint.

Start your trip to Bend by creating a personalized itinerary on Inspirock.

You can drive from Hood River to Bend in 3.5 hours. Other options are to do a combination of taxi and bus; or do a combination of bus and flight. Traveling from Hood River in September, Bend is little chillier at night with lows of 7°C. Finish your sightseeing early on the 7th (Sat) so you can drive to Ashland.

Things to do in Bend

Outdoors Parks Tours
Highlights from your plan
Pilot Butte State Scenic Viewpoint ©
Newberry National Volcanic Monument ©
Deschutes Brewery ©
Deschutes Brewery

1
night
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 8th (Sun): look for gifts at Tudor Guild Shop, then see a show at Oregon Shakespeare Festival, and then let the river carry you with a rafting and tubing tour.

For reviews, photos, traveler tips, and tourist information, read our Ashland day trip planner .

Getting from Bend to Ashland by car takes about 4.5 hours. Other options: do a combination of bus and flight; or do a combination of bus and train. Expect somewhat warmer temperatures when traveling from Bend in September; daily highs in Ashland reach 33°C and lows reach 13°C. Finish your sightseeing early on the 8th (Sun) so you can drive to Yachats.

Things to do in Ashland

Tours Outdoors Adventure
Highlights from your plan
River Rafting & Tubing
Oregon Shakespeare Festival ©
Oregon Shakespeare Festival
Tudor Guild Shop ©
Tudor Guild Shop

3
nights
Yachats

Yachats ©
Yachats is a small coastal city in Lincoln County, Oregon, United States. You'll explore the less-touristy side of things at Sandland Adventures and Nye Beach. Change things up with these side-trips from Yachats: Siuslaw River Bridge (in Florence), Boiler Bay State Wayside (in Depoe Bay) and Newport (Yaquina Bay Bridge, Hatfield Marine Science Center, & more). There's still lots to do: take a leisurely stroll along Yachats coastline and explore the striking landscape at Devil's Churn.

For more things to do, other places to visit, and tourist information, use the Yachats online trip planner .

Traveling by car from Ashland to Yachats takes 5 hours. Alternatively, you can take a bus; or do a combination of bus, train, and taxi. When traveling from Ashland in September, plan for little chillier days and about the same nights in Yachats: temperatures range from 20°C by day to 11°C at night. Wrap up your sightseeing on the 11th (Wed) to allow time to drive to Tillamook.

Things to do in Yachats

Parks Outdoors Beaches

Side Trips

Newport, Florence, Boiler Bay State Wayside
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sandland Adventures ©
Sandland Adventures
Devil's Churn ©
Devil's Churn

1
night
Tillamook

Tillamook ©
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Start off your visit on the 12th (Thu): look for gifts at Blue Heron Cheese & Wine Company, then enjoy the sea views from Cape Meares Lighthouse, then steep yourself in history at Tillamook Air Museum, and finally immerse yourself in nature at Cape Lookout State Park.

To find other places to visit, more things to do, and tourist information, go to the Tillamook trip builder tool .

You can drive from Yachats to Tillamook in 2.5 hours. Alternatively, you can take a bus. The time zone difference moving from Pacific Standard Time (PST) to Mountain Standard Time (MST) is 1 hour. In September, daytime highs in Tillamook are 24°C, while nighttime lows are 10°C. Cap off your sightseeing on the 12th (Thu) early enough to go by car to Astoria.

Things to do in Tillamook

Historic Sites Parks Nature
Highlights from your plan
Cape Meares Lighthouse ©
Cape Meares Lighthouse
Cape Lookout State Park ©
Cape Lookout State Park
Tillamook Air Museum ©
Tillamook Air Museum

3
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
You'll explore the less-touristy side of things at Fort Clatsop National Memorial and Hug Point State Park. You'll find plenty of places to visit near Astoria: Cannon Beach (Haystack Rock, Cannon Beach, & more). There's still lots to do: snap pictures at Astoria-Megler Bridge, stop by Beach Books, and appreciate the history behind Astoria Column.

To see reviews, traveler tips, more things to do, and tourist information, you can read our Astoria road trip planner.

Traveling by car from Tillamook to Astoria takes 2 hours. Alternatively, you can take a bus. The time zone difference moving from Mountain Standard Time (MST) to Pacific Standard Time (PST) is minus 1 hour. Expect a daytime high around 24°C in September, and nighttime lows around 13°C. Cap off your sightseeing on the 15th (Sun) early enough to travel back home.

Things to do in Astoria

Parks Nature Historic Sites

Side Trips

Cannon Beach, Beach Books
Highlights from your plan
Fort Clatsop National Memorial ©
Fort Clatsop National Memorial
Hug Point State Park ©
Hug Point State Park
Haystack Rock ©
Haystack Rock

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