11 days in Oregon Itinerary

11 days in Oregon Itinerary

Created using Inspirock Oregon visit planner

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Route & dates

11 days in Oregon Itinerary

Start: Dallas
Fly:  6​h 30​min
1
Portland
— 1 night
Drive:  2​h
2
Cannon Beach
— 2 nights
Drive:  2​h 45​min
3
Newport
— 2 nights
Drive:  1​h 15​min
4
Florence
— 1 night
Drive:  2​h
5
Bandon
— 1 night
Drive:  1​h 30​min
6
Winston
— 1 night
Drive:  3​h 30​min
7
Bend
— 2 nights
Fly:  9​h 15​min
End: Dallas

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.
On the 2nd (Thu), admire the natural beauty at Portland Japanese Garden, then admire the natural beauty at International Rose Test Garden, and then look for gifts at Powell's City of Books. Get ready for a full day of sightseeing on the 3rd (Fri): contemplate the long history of Pittock Mansion, stroll through Oregon Zoo, then explore the engaging exhibits at Portland Children's Museum, and finally learn the secrets of beer at a beer tour and tasting.

For ratings, reviews, photos, and tourist information, you can read our Portland trip itinerary builder .

Dallas to Portland is an approximately 6.5-hour flight. You can also drive; or take a bus. You'll gain 2 hours traveling from Dallas to Portland due to the time zone difference. Expect slightly colder temperatures when traveling from Dallas in May; daily highs in Portland reach 70°F and lows reach 51°F. Cap off your sightseeing on the 3rd (Fri) early enough to go by car to Cannon Beach.

Things to do in Portland

Tours Parks Zoos & Aquariums
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Portland Children's Museum ©
Portland Children's Museum
Oregon Zoo ©
Oregon Zoo

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 4th (Sat): tour the pleasant surroundings at Cannon Beach, then stop by Cloud and Leaf Bookstore, then enjoy the sand and surf at Manzanita Beach, and finally explore the striking landscape at Haystack Rock. On the 5th (Sun), you'll have a packed day of sightseeing: immerse yourself in nature at Hug Point State Park, admire the majestic nature at Ecola State Park, and then stroll through Hug Point State Recreation Site.

For maps, more things to do, where to stay, and more tourist information, you can read our Cannon Beach trip itinerary website .

Drive from Portland to Cannon Beach in 2 hours. Alternatively, you can take a bus. Traveling from Portland in May, expect nights in Cannon Beach to be about the same, around 48°F, while days are little chillier, around 62°F. Finish up your sightseeing early on the 5th (Sun) so you can go by car to Newport.

Things to do in Cannon Beach

Parks Outdoors Beaches

Side Trips

Manzanita, Hug Point State Recreation Site
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Hug Point State Recreation Site ©
Hug Point State Recreation Site

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.
On the 6th (Mon), take in the waterfront at Yachats coastline, take in the exciting artwork at Earthworks Gallery, then browse the exhibits of Hatfield Marine Science Center, then take in the views from Yaquina Bay Bridge, and finally kick back and relax at Nye Beach. On your second day here, take a tour by water with Boat Tours & Water Sports, identify plant and animal life at Yaquina Head Outstanding Natural Area, and then kick back and relax at Devils Punchbowl State Natural Area.

To see where to stay, other places to visit, traveler tips, and other tourist information, refer to the Newport trip planner .

You can drive from Cannon Beach to Newport in 3 hours. Another option is to take a bus. In May, daytime highs in Newport are 58°F, while nighttime lows are 46°F. Wrap up your sightseeing on the 7th (Tue) early enough to drive to Florence.

Things to do in Newport

Outdoors Parks Wildlife

Side Trips

Yachats, Dolphin & Whale Watching
Highlights from your plan
Nye Beach ©
Nye Beach
Hatfield Marine Science Center ©
Hatfield Marine Science Center
Devils Punchbowl State Natural Area ©

1
night
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Start off your visit on the 8th (Wed): have fun at Sand Master Park, kick back and relax at Heceta Beach, then make a trip to Siuslaw River Bridge, and finally putt your heart out at Sandland Adventures.

For maps, where to stay, traveler tips, and tourist information, you can read our Florence trip itinerary planning website .

Getting from Newport to Florence by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 62°F in May, and nighttime lows around 49°F. Wrap up your sightseeing on the 8th (Wed) to allow time to drive to Bandon.

Things to do in Florence

Fun & Games Outdoors Beaches
Highlights from your plan
Sandland Adventures ©
Sandland Adventures
Sand Master Park - Sandboarding ©
Sand Master Park - Sandboarding
Heceta Beach ©
Heceta Beach

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. On the 9th (Thu), look for gifts at Face Rock Creamery, identify plant and animal life at Face Rock State Scenic Viewpoint, immerse yourself in nature at Bandon State Park, then identify plant and animal life at Coquille Point, and finally visit a coastal fixture at Coquille River Lighthouse.

For where to stay, photos, more things to do, and other tourist information, go to the Bandon vacation maker tool .

You can drive from Florence to Bandon in 2 hours. Alternatively, you can take a bus. In May, plan for daily highs up to 62°F, and evening lows to 49°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to travel to Winston.

Things to do in Bandon

Parks Nature Wildlife
Highlights from your plan
Face Rock State Scenic Viewpoint ©
Face Rock State Scenic Viewpoint
Bandon State Park ©
Bandon State Park
Coquille Point ©
Coquille Point

1
night
Winston

Winston ©
Winston is a city in Douglas County, Oregon, United States. Kick off your visit on the 10th (Fri): identify plant and animal life at Wildlife Safari.

To see photos, other places to visit, ratings, and tourist information, read our Winston online vacation planner .

Traveling by car from Bandon to Winston takes 2 hours. When traveling from Bandon in May, plan for a bit warmer days in Winston, with highs around 73°F, while nights are about the same with lows around 50°F. On the 10th (Fri), wrap the sightseeing up by early afternoon so you can travel to Bend.

Things to do in Winston

Wildlife Parks
Highlights from your plan
Wildlife Safari ©
Wildlife Safari

2
nights
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.
Start off your visit on the 11th (Sat): learn more about the world around you at Sunriver Nature Center, see the sky in a new way at Oregon Observatory, then explore the fascinating underground world of Lava River Cave, and finally take a tour by water with Boat Tours & Water Sports.

For ratings, other places to visit, more things to do, and more tourist information, read Bend trip maker app .

Getting from Winston to Bend by car takes about 3.5 hours. Traveling from Winston in May, things will get a bit cooler in Bend: highs are around 67°F and lows about 40°F. Wrap up your sightseeing by early afternoon on the 12th (Sun) to allow time for travel back home.

Things to do in Bend

Outdoors Parks Tours

Side Trip

Sunriver
Highlights from your plan
River Rafting & Tubing
Oregon Observatory ©
Oregon Observatory
Lava River Cave ©
Lava River Cave

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