27 days in Oregon Itinerary

27 days in Oregon Itinerary

Created using Inspirock Oregon sightseeing planner

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Route & dates

27 days in Oregon Itinerary

Start: Sao Paulo
Fly:  19​h 15​min
1
Portland
— 2 nights
bus:  1​h 15​min
2
Hood River
— 3 nights
Drive:  3​h 15​min
3
Bend
— 3 nights
Drive:  2​h 45​min
4
Crater Lake National Park
— 3 nights
Drive:  2​h 15​min
5
Ashland
— 2 nights
Drive:  3​h
6
Coos Bay
— 2 nights
Drive:  1​h 15​min
7
Florence
— 3 nights
Drive:  3​h
8
Tillamook
— 2 nights
Drive:  1​h 45​min
9
Astoria
— 4 nights
+2
bus + tram + Fly:  22​h
End: Sao Paulo

2
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.
Discover out-of-the-way places like Silver Falls State Park and Beer Tastings & Tours. Step out of Portland with an excursion to Multnomah Falls in Bridal Veil--about 46 minutes away. There's still lots to do: admire the natural beauty at Portland Japanese Garden, tour the pleasant surroundings at Willamette Valley, steep yourself in history at Pittock Mansion, and look for gifts at Powell's City of Books.

To see where to stay, maps, ratings, and more tourist information, refer to the Portland holiday planning site .

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. The time zone changes from Brasilia Time to Pacific Standard Time, which is usually a -5 hour difference. Expect slightly colder evenings in Portland when traveling from Sao Paulo in September, with lows around 15°C. Finish your sightseeing early on the 4th (Wed) so you can drive to Hood River.

Things to do in Portland

Parks Nature Tours

Side Trips

Silver Falls State Park, 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

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Explore hidden gems such as Mount Hood and Columbia Gorge Discovery Center & Museum. Change things up with these side-trips from Hood River: Trillium Lake (in Government Camp), Fire Museum in City Hall (in The Dalles) and River Rafting & Tubing (in Maupin). There's much more to do: explore the activities along Columbia River Gorge National Scenic Area, stroll through Port Marina Park, and see the interesting displays at Western Antique Aeroplane & Automobile Museum.

To find out how to plan a trip to Hood River, use our trip itinerary maker.

Getting from Portland to Hood River by car takes about 1.5 hours. Other options: take a bus; or take a train. Expect a bit cooler weather when traveling from Portland in September: highs in Hood River hover around 25°C, while lows dip to 16°C. Wrap up your sightseeing on the 7th (Sat) early enough to drive to Bend.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

The Dalles, Trillium Lake, River Rafting & Tubing, Columbia River Gorge National Scenic Area
Highlights from your plan
Mount Hood ©
Mount Hood

3
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.
Step off the beaten path and head to Newberry National Volcanic Monument and Tumalo Falls. Go for a jaunt from Bend to Sisters to see McKenzie Pass-Santiam Pass loop about 58 minutes away. There's much more to do: savor the flavors at Food & Drink, sample the tasty concoctions at Deschutes Brewery, hike along Pilot Butte State Scenic Viewpoint, and tour the pleasant surroundings at Drake Park.

For traveler tips, maps, more things to do, and more tourist information, read Bend tour itinerary builder site .

Drive from Hood River to Bend in 3.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of bus and flight. Traveling from Hood River in September, you can expect nighttime temperatures to be little chillier in Bend, with lows of 7°C. Finish your sightseeing early on the 10th (Tue) to allow enough time to drive to Crater Lake National Park.

Things to do in Bend

Outdoors Parks Nature

Side Trip

McKenzie Pass-Santiam Pass loop
Highlights from your plan
Pilot Butte State Scenic Viewpoint ©
Newberry National Volcanic Monument ©
McKenzie Pass-Santiam Pass loop ©
McKenzie Pass-Santiam Pass loop

3
nights
Crater Lake National Park

Crater Lake National Park ©
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Step off the beaten path and head to Rim Dr and Cleetwood Cove Trail. Step out of Crater Lake National Park with an excursion to National Creek Falls in Prospect--about 46 minutes away. Spend the 12th (Thu) exploring nature at Crater Lake National Park. There's lots more to do: step off the mainland to explore Wizard Island, look for all kinds of wild species at Rogue River Gorge Viewpoint, trek along Garfield Peak, and steep yourself in history at Rim Village Visitor Center.

For ratings, reviews, other places to visit, and more tourist information, you can read our Crater Lake National Park trip builder website .

Traveling by car from Bend to Crater Lake National Park takes 3 hours. Alternatively, you can do a combination of bus and taxi. Expect somewhat warmer temperatures when traveling from Bend in September; daily highs in Crater Lake National Park reach 33°C and lows reach 13°C. Wrap up your sightseeing on the 13th (Fri) to allow time to drive to Ashland.

Things to do in Crater Lake National Park

Parks Nature Outdoors

Side Trip

Prospect
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Rim Dr ©
Rim Dr
Cleetwood Cove Trail ©
Cleetwood Cove Trail

2
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Start off your visit on the 14th (Sat): stop by Rogue Creamery, contemplate the waterfront views at Rogue River, and then let the river carry you with a rafting and tubing tour. On the 15th (Sun), you'll have a packed day of sightseeing: get curious at ScienceWorks Hands-on Museum, stroll through Lithia Park, and then see a show at Oregon Shakespeare Festival.

To find ratings, reviews, and tourist information, you can read our Ashland online travel route planner .

Getting from Crater Lake National Park to Ashland by car takes about 2.5 hours. Other options: do a combination of taxi and bus. In September in Ashland, expect temperatures between 33°C during the day and 13°C at night. Wrap up your sightseeing on the 15th (Sun) early enough to travel to Coos Bay.

Things to do in Ashland

Parks Outdoors Tours

Side Trips

Rogue Creamery, Rogue River
Highlights from your plan
River Rafting & Tubing
Rogue River ©
Rogue River
ScienceWorks Hands-On Museum ©
ScienceWorks Hands-On Museum

2
nights
Coos Bay

Coos Bay ©
Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. Kick off your visit on the 16th (Mon): play a few rounds at Bandon Dunes Golf Resort, then explore the striking landscape at Face Rock State Scenic Viewpoint, and then stop by Face Rock Creamery. On your second day here, admire the majestic nature at Shore Acres State Park and then admire the majestic nature at Cape Arago State Park.

Plan a Coos Bay trip in moments using our itinerary builder.

Drive from Ashland to Coos Bay in 3.5 hours. Traveling from Ashland in September, expect nights in Coos Bay to be about the same, around 13°C, while days are little chillier, around 23°C. Finish your sightseeing early on the 17th (Tue) so you can travel to Florence.

Things to do in Coos Bay

Nature Parks Outdoors

Side Trip

Bandon
Highlights from your plan
Shore Acres State Park ©
Shore Acres State Park
Face Rock State Scenic Viewpoint ©
Face Rock State Scenic Viewpoint
Cape Arago State Park ©
Cape Arago State Park

3
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. You'll explore the less-touristy side of things at Sandland Adventures and Yachats coastline. Venture out of the city with trips to Yachats (Smelt Sands State Park & Devil's Churn) and Newport (Devils Punchbowl State Natural Area, Nye Beach, & more). The adventure continues: take in the views from Siuslaw River Bridge and explore the striking landscape at Thor's Well.

For photos, more things to do, reviews, and other tourist information, go to the Florence holiday builder app .

You can drive from Coos Bay to Florence in 1.5 hours. In September, daily temperatures in Florence can reach 23°C, while at night they dip to 13°C. Finish up your sightseeing early on the 20th (Fri) so you can go by car to Tillamook.

Things to do in Florence

Parks Nature Outdoors

Side Trips

Yachats, Newport
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sandland Adventures ©
Sandland Adventures
Devil's Churn ©
Devil's Churn

2
nights
Tillamook

Tillamook ©
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. On the 21st (Sat), look for gifts at Blue Heron Cheese & Wine Company, then admire the majestic nature at Cape Lookout State Park, then examine the collection at Tillamook Air Museum, and finally visit a coastal fixture at Cape Meares Lighthouse. Keep things going the next day: take in the waterfront activity at Kelly's Brighton Marina, then tour the pleasant surroundings at Manzanita Beach, then stop by Cloud and Leaf Bookstore, and finally look for gifts at Flamingo Jim's.

To see maps, photos, other places to visit, and tourist information, use the Tillamook trip maker .

Traveling by car from Florence to Tillamook takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. The time zone difference moving from Pacific Standard Time (PST) to Mountain Standard Time (MST) is 1 hour. September in Tillamook sees daily highs of 24°C and lows of 10°C at night. Wrap up your sightseeing on the 22nd (Sun) to allow time to drive to Astoria.

Things to do in Tillamook

Parks Outdoors Beaches

Side Trips

Rockaway Beach, Manzanita
Highlights from your plan
Cape Lookout State Park ©
Cape Lookout State Park
Cape Meares Lighthouse ©
Cape Meares Lighthouse
Kelly's Brighton Marina ©
Kelly's Brighton Marina

4
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Explore hidden gems such as Fort Clatsop National Memorial and Astoria-Megler Bridge. Get out of town with these interesting Astoria side-trips: Cannon Beach (Hug Point State Park, Haystack Rock, & more) and Turnaround at Seaside (in Seaside). And it doesn't end there: examine the collection at Flavel House Museum, appreciate the history behind Astoria Column, and trek along Astoria Oregon Riverwalk.

To see where to stay, photos, reviews, and tourist information, refer to the Astoria trip itinerary tool .

Traveling by car from Tillamook to Astoria takes 2 hours. Alternatively, you can take a bus. The time zone changes from Mountain Standard Time (MST) to Pacific Standard Time (PST), which is usually a -1 hour difference. Expect a daytime high around 24°C in September, and nighttime lows around 13°C. Finish your sightseeing early on the 26th (Thu) so you can travel back home.

Things to do in Astoria

Parks Nature Outdoors

Side Trips

Cannon Beach, Turnaround at Seaside
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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