16 days in Oregon Itinerary

16 days in Oregon Itinerary

Created using Inspirock Oregon route builder

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Route & dates

16 days in Oregon Itinerary

Start: Orlando
Fly:  9​h 30​min
1
Portland
— 1 night
bus:  1​h 30​min
2
Hood River
— 2 nights
Drive:  3​h 30​min
3
Bend
— 2 nights
Drive:  3​h
4
Crater Lake National Park
— 1 night
Drive:  3​h 30​min
5
Brookings
— 2 nights
Drive:  2​h 30​min
6
Bandon
— 1 night
Drive:  3​h
7
Newport
— 2 nights
Drive:  3​h
8
Cannon Beach
— 2 nights
+2
bus + tram + Fly:  12​h
End: Orlando

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.
Your day-by-day itinerary now includes Nation Tours - Portland Segway Tours.

To find other places to visit, where to stay, maps, and other tourist information, you can read our Portland tour itinerary planner .

Orlando to Portland is an approximately 8.5-hour flight. You can also drive; or do a combination of bus and train. The time zone changes from Eastern Standard Time to Pacific Standard Time, which is usually a -3 hour difference. Traveling from Orlando in June, expect Portland to be little chillier, temps between 77°F and 56°F. Cap off your sightseeing on the 27th (Thu) early enough to catcht the bus to Hood River.

Things to do in Portland

Parks Tours Nature

Side Trip

Wintler Community Park
Highlights from your plan
Mount Tabor Park ©
Mount Tabor Park
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. On the 27th (Thu), learn about winemaking at Sunshine Mill Winery. On the 28th (Fri), you'll have a packed day of sightseeing: hike along Eagle Creek Trail, take in the dramatic scenery at Starvation Creek State Park, learn about winemaking at Mt. Hood Winery, then learn about winemaking at Wy'East Vineyards, then head outdoors with Fox-Tail Cider, and finally learn about winemaking at Springhouse Cellar.

For traveler tips, where to stay, ratings, and more tourist information, refer to the Hood River trip itinerary app .

Traveling by bus from Portland to Hood River takes 1.5 hours. Alternatively, you can drive; or take a train. Traveling from Portland in June, you will find days in Hood River are a bit cooler (72°F), and nights are about the same (55°F). Finish your sightseeing early on the 29th (Sat) to allow enough time to drive to Bend.

Things to do in Hood River

Wineries Outdoors Parks

Side Trips

Cascade Locks, Wishram, Sunshine Mill Winery
Highlights from your plan
Mt. Hood Winery ©
Mt. Hood Winery
Jacob Williams Winery ©
Jacob Williams Winery
Cascade Cliffs Vineyard & Winery ©
Cascade Cliffs Vineyard & Winery

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.
On the 29th (Sat), indulge in some personalized pampering at some of the best spas. Here are some ideas for day two: go for a walk through Deschutes River Trail, contemplate the geological forces at Newberry National Volcanic Monument, tour the pleasant surroundings at Lava Cast Forest Trail, then let the river carry you with a rafting and tubing tour, and finally wander the streets of City of Sisters.

To see more things to do, reviews, photos, and tourist information, you can read our Bend trip planner.

You can drive from Hood River to Bend in 3.5 hours. Other options are to do a combination of bus and flight; or take a bus. Traveling from Hood River in June, Bend is a bit cooler at night with lows of 45°F. Finish your sightseeing early on the 1st (Mon) to allow enough time to drive to Crater Lake National Park.

Things to do in Bend

Outdoors Parks Trails

Side Trips

City of Sisters, Lava Cast Forest Trail
Highlights from your plan
Newberry National Volcanic Monument ©
Pilot Butte State Scenic Viewpoint ©
City of Sisters ©
City of Sisters

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.
On the 2nd (Tue), trek along Pinnacles Trail, steep yourself in history at Fort Klamath Museum, and then explore the wealth of natural beauty at Crater Lake National Park. On the 3rd (Wed), you'll have a packed day of sightseeing: take a memorable drive along Rim Dr, take in the awesome beauty at Watchman Peak, then hike along Garfield Peak, and finally delve into the lush surroundings at Umpqua National Forest.

To find traveler tips, other places to visit, and tourist information, go to the Crater Lake National Park driving holiday planner.

Traveling by car from Bend to Crater Lake National Park takes 3 hours. Alternatively, you can do a combination of bus and taxi. Expect a bit warmer temperatures when traveling from Bend in July; daily highs in Crater Lake National Park reach 94°F and lows reach 61°F. Finish up your sightseeing early on the 3rd (Wed) so you can travel to Brookings.

Things to do in Crater Lake National Park

Parks Nature Outdoors

Side Trips

Umpqua National Forest, Fort Klamath Museum
Highlights from your plan
Rim Dr ©
Rim Dr
Crater Lake National Park ©
Crater Lake National Park
Fort Klamath Museum ©
Fort Klamath Museum

2
nights
Brookings

Brookings ©
Brookings is a city in Curry County, Oregon, United States. Get ready for a full day of sightseeing on the next day: immerse yourself in nature at Harris Beach State Park, admire the majestic nature at Crissey Field State Park, then trek along Stout Grove, then contemplate the waterfront views at Point St George Park, and finally see the interesting displays at Battery Point Lighthouse.

For maps, traveler tips, ratings, and other tourist information, refer to the Brookings trip planner .

Traveling by car from Crater Lake National Park to Brookings takes 4 hours. When traveling from Crater Lake National Park in July, plan for much colder days and a bit cooler nights in Brookings: temperatures range from 67°F by day to 53°F at night. Finish your sightseeing early on the 5th (Fri) to allow enough time to travel to Bandon.

Things to do in Brookings

Parks Outdoors Nature

Side Trip

Crescent City
Highlights from your plan
Harris Beach State Park ©
Harris Beach State Park
Battery Point Lighthouse ©
Battery Point Lighthouse

1
night
Bandon

Bandon ©
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. To see photos, reviews, traveler tips, and more tourist information, refer to the Bandon trip itinerary planning app .

Drive from Brookings to Bandon in 2 hours. In July, plan for daily highs up to 67°F, and evening lows to 54°F. Finish your sightseeing early on the 6th (Sat) so you can drive to Newport.

Things to do in Bandon

Parks Wildlife Outdoors

Side Trip

South Slough National Estuarine Research Reserve
Highlights from your plan
Face Rock State Scenic Viewpoint ©
Coquille Point ©
Coquille Point
Whiskey Run Beach ©
Whiskey Run Beach

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.
Here are some ideas for day two: take in the waterfront at Newport's Historic Bayfront, look for all kinds of wild species at Yaquina Head Outstanding Natural Area, then visit a coastal fixture at Yaquina Head Lighthouse, then stroll through Devils Punchbowl State Natural Area, and finally admire the majestic nature at Agate Beach State Recreation Site.

To find traveler tips, reviews, and tourist information, go to the Newport trip maker app .

Getting from Bandon to Newport by car takes about 3 hours. Other options: do a combination of bus and taxi. In July, plan for daily highs up to 63°F, and evening lows to 50°F. Cap off your sightseeing on the 8th (Mon) early enough to go by car to Cannon Beach.

Things to do in Newport

Parks Nature Beaches

Side Trip

Seal Rock State Wayside
Highlights from your plan
Seal Rock State Wayside ©
Seal Rock State Wayside
Nye Beach ©
Nye Beach
Agate Beach State Recreation Site ©

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Get ready for a full day of sightseeing on the 9th (Tue): take in the dramatic natural features at Haystack Rock, admire the majestic nature at Hug Point State Park, take in the exciting artwork at Bronze Coast Gallery, view the masterpieces at Icefire Glassworks, then kick back and relax at Cannon Beach, and finally relax and rejuvenate at some of the best spas.

To see maps, reviews, where to stay, and tourist information, go to the Cannon Beach trip itinerary builder website .

Traveling by car from Newport to Cannon Beach takes 3 hours. Alternatively, you can take a bus. When traveling from Newport in July, plan for somewhat warmer days in Cannon Beach, with highs around 69°F, while nights are about the same with lows around 55°F. Finish your sightseeing early on the 10th (Wed) to allow enough time to travel back home.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Seaside Inverted Experience
Highlights from your plan
Haystack Rock ©
Haystack Rock
Oswald West State Park ©
Oswald West State Park
Lightship Columbia ©
Lightship Columbia

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