14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon tour planner

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Route & dates

14 days in Oregon Itinerary

Start: Bologna
Fly:  16​h 30​min
1
Portland
— 3 nights
Bus:  1​h 15​min
2
Hood River
— 2 nights
Drive:  3​h 15​min
3
Bend
— 1 night
Drive:  2​h 45​min
4
Crater Lake National Park
— 1 night
Drive:  5​h
5
Florence
— 1 night
Drive:  1​h 15​min
6
Newport
— 2 nights
Drive:  2​h 45​min
7
Cannon Beach
— 2 nights
Drive + Fly:  19​h 15​min
End: Bologna

3
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.
Dedicate the 16th (Tue) to wine at some of the top wineries in the area. Next up on the itinerary: take in nature's colorful creations at Portland Japanese Garden, identify plant and animal life at Oaks Bottom Wildlife Refuge, meet the residents at Oregon Zoo, and hike along Forest Park.

To see other places to visit, traveler tips, more things to do, and other tourist information, use the Portland trip builder site .

Bologna, Italy to Portland is an approximately 16.5-hour flight. You can also do a combination of train and flight. The time zone difference when traveling from Bologna to Portland is minus 9 hours. In July, Portland is a bit cooler than Bologna - with highs of 33°C and lows of 17°C. Finish your sightseeing early on the 17th (Wed) so you can drive to Hood River.

Things to do in Portland

Tours Parks Zoos & Aquariums
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
International Rose Test Garden ©
International Rose Test Garden
Powell's City of Books ©
Powell's City of Books

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 18th (Thu): see the interesting displays at Western Antique Aeroplane & Automobile Museum, then learn about winemaking at Marchesi Vineyards, and then look for all kinds of wild species at Columbia River Gorge National Scenic Area. Get ready for a full day of sightseeing on the next day: admire the engineering at Bonneville Lock & Dam, take in the dramatic scenery at Multnomah Falls, and then hike along Horsetail Falls- Columbia River Gorge.

For other places to visit, where to stay, photos, and other tourist information, go to the Hood River attractions app .

Traveling by car from Portland to Hood River takes 1.5 hours. Alternatively, you can take a bus; or take a train. In July in Hood River, expect temperatures between 30°C during the day and 17°C at night. Wrap up your sightseeing on the 19th (Fri) to allow time to drive to Bend.

Things to do in Hood River

Parks Nature Wildlife

Side Trips

Multnomah Falls, Columbia River Gorge National Scenic Area, Bonneville Lock & Dam
Highlights from your plan
Multnomah Falls ©
Multnomah Falls

1
night
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.
On the 20th (Sat), get a new perspective on nature at High Desert Museum, then explore the activities along Deschutes River, and then tour the pleasant surroundings at Drake Park.

To find ratings, other places to visit, maps, and tourist information, read our Bend online road trip planner .

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 July, expect nights in Bend to be little chillier, around 13°C, while days are a bit warmer, around 34°C. Finish up your sightseeing early on the 20th (Sat) so you can go by car to Crater Lake National Park.

Things to do in Bend

Parks Wildlife Museums
Highlights from your plan
High Desert Museum ©
High Desert Museum
Drake Park ©
Drake Park

1
night
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.
Kick off your visit on the 21st (Sun): explore the striking landscape of Crater Lake National Park.

To see maps, reviews, other places to visit, and other tourist information, you can read our Crater Lake National Park route website .

Traveling by car from Bend to Crater Lake National Park takes 3 hours. Alternatively, you can do a combination of bus and taxi. Prepare for a bit warmer weather when traveling from Bend in July: high temperatures in Crater Lake National Park hover around 40°C and lows are around 19°C. Finish your sightseeing early on the 21st (Sun) so you can drive to Florence.

Things to do in Crater Lake National Park

Parks Nature
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park

1
night
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Start off your visit on the 22nd (Mon): take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, then visit a coastal fixture at Heceta Head Lighthouse, and then putt your heart out at Sandland Adventures.

To find where to stay, photos, and more tourist information, refer to the Florence online trip builder .

Getting from Crater Lake National Park to Florence by car takes about 5 hours. Other options: do a combination of taxi, train, and bus. Expect colder weather when traveling from Crater Lake National Park in July: highs in Florence hover around 22°C, while lows dip to 14°C. Finish your sightseeing early on the 22nd (Mon) to allow enough time to drive to Newport.

Things to do in Florence

Parks Nature Outdoors

Side Trip

Cape Perpetua Visitor Center - Siuslaw National Forest
Highlights from your plan
Sandland Adventures ©
Sandland Adventures
Heceta Head Lighthouse ©
Heceta Head Lighthouse

2
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Kick off your visit on the 23rd (Tue): hike along Devils Punchbowl State Natural Area, then admire nature's wide array of creatures at Oregon Coast Aquarium, and then take a leisurely stroll along Yachats coastline. Get ready for a full day of sightseeing on the 24th (Wed): identify plant and animal life at Yaquina Head Outstanding Natural Area, take in the exciting artwork at Lincoln City Glass Center, then visit a coastal fixture at Yaquina Head Lighthouse, and finally take in the waterfront at Newport's Historic Bayfront.

To find ratings, reviews, other places to visit, and tourist information, refer to the Newport itinerary maker tool .

Drive from Florence to Newport in 1.5 hours. Alternatively, you can take a bus. In July, daytime highs in Newport are 20°C, while nighttime lows are 11°C. Finish your sightseeing early on the 24th (Wed) so you can drive to Cannon Beach.

Things to do in Newport

Parks Nature Outdoors

Side Trips

Yachats coastline, Lincoln City Glass Center
Highlights from your plan
Yachats coastline ©
Yachats coastline
Yaquina Head Outstanding Natural Area ©
Oregon Coast Aquarium ©
Oregon Coast Aquarium

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 25th (Thu), admire the majestic nature at Ecola State Park, immerse yourself in nature at Hug Point State Park, and then take in the dramatic natural features at Haystack Rock. Get ready for a full day of sightseeing on the next day: soothe aching muscles at some of the top local wellness centers, then admire the majestic nature at Oswald West State Park, and then enjoy the sand and surf at Cannon Beach.

For ratings, other places to visit, traveler tips, and tourist information, read our Cannon Beach journey builder tool .

Traveling by car from Newport to Cannon Beach takes 3 hours. Alternatively, you can take a bus. Traveling from Newport in July, expect nights in Cannon Beach to be about the same, around 15°C, while days are a bit warmer, around 24°C. Finish your sightseeing early on the 26th (Fri) so you can travel back home.

Things to do in Cannon Beach

Parks Nature Outdoors
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

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