35 days in Oregon Itinerary

35 days in Oregon Itinerary

Created using Inspirock Oregon attractions planner

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Route & dates

35 days in Oregon Itinerary

Start: Orlando
Fly:  8​h 30​min
1
Portland
— 4 nights
Drive:  2​h
2
Astoria
— 2 nights
Drive:  2​h 30​min
3
McMinnville
— 3 nights
Drive:  1​h 15​min
4
Lincoln City
— 2 nights
Drive:  1​h 45​min
5
Florence
— 1 night
Drive:  1​h 30​min
6
Bandon
— 2 nights
Drive:  1​h 15​min
7
Gold Beach
— 2 nights
Drive:  45​min
8
Brookings
— 4 nights
Drive:  2​h
9
Grants Pass
— 2 nights
Drive:  1​h 15​min
10
Prospect
— 2 nights
Drive:  2​h 30​min
11
Bend
— 5 nights
Drive:  3​h 15​min
12
Hood River
— 4 nights
+2
bus + tram + Fly:  10​h 45​min
End: Orlando

4
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.
Visiting Waterfront Renaissance Trail and Hyland Forest Park will get you outdoors. Get some cultural insight at Rice NW Museum of Rocks and Minerals and The Chehalis Centralia Railroad & Museum. Get out of town with these interesting Portland side-trips: Steigerwald Lake National Wildlife Refuge (in Washougal) and Ardiri Winery and Vineyards (in Cornelius). There's lots more to do: take in nature's colorful creations at Peninsula Park and Rose Gardens, get engrossed in the history at Wells Fargo Museum, tour the pleasant surroundings at Powell Butte Nature Park, and brush up on your knowledge of spirits at Westward Whiskey.

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

Orlando to Portland is an approximately 8.5-hour flight. You can also drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 3 hours traveling from Orlando to Portland. Prepare for a bit cooler weather when traveling from Orlando in May: high temperatures in Portland hover around 70°F and lows are around 51°F. Finish up your sightseeing early on the 19th (Tue) so you can go by car to Astoria.

Things to do in Portland

Parks Museums Wildlife

Side Trips

Hyland Forest Park, Ardiri Winery and Vineyards, Steigerwald Lake National Wildlife Refuge, The Chehalis Centralia Railroad & Museum, Rice NW Museum of Rocks and Minerals
Highlights from your plan
Audubon Society of Portland ©
Audubon Society of Portland
Rice NW Museum of Rocks and Minerals ©

2
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Kick off your visit on the 20th (Wed): admire the majestic nature at Oswald West State Park, examine the collection at Heritage Museum, and then learn about winemaking at Shallon Winery. On the 21st (Thu), you'll have a packed day of sightseeing: appreciate the extensive heritage of The Lewis And Clark National And State Historical Parks and then see the interesting displays at Flavel House Museum.

To find maps, traveler tips, other places to visit, and more tourist information, use the Astoria online trip itinerary builder .

You can drive from Portland to Astoria in 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Portland in May, expect nights in Astoria to be about the same, around 48°F, while days are a bit cooler, around 62°F. Finish your sightseeing early on the 21st (Thu) to allow enough time to travel to McMinnville.

Things to do in Astoria

Parks Nature Museums

Side Trip

Oswald West State Park
Highlights from your plan
Oswald West State Park ©
Oswald West State Park
Flavel House Museum ©
Flavel House Museum

3
nights
McMinnville

McMinnville ©
McMinnville is the county seat and largest city of Yamhill County, Oregon, United States. On the next day, do a tasting at Eyrie Vineyards, learn about winemaking at Remy Wines, do a tasting at R Stuart & Co., then do a tasting at Elizabeth Chambers Cellar, and finally learn about winemaking at Willamette Valley Vineyards Wine Center.

For maps, where to stay, photos, and more tourist information, refer to the McMinnville travel site .

You can drive from Astoria to McMinnville in 2.5 hours. Traveling from Astoria in May, you will find days in McMinnville are somewhat warmer (70°F), and nights are about the same (47°F). Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Lincoln City.

Things to do in McMinnville

Wineries Museums

Side Trips

Dayton, Brooks Wine, Powerland Heritage Park
Highlights from your plan
R Stuart & Co. ©
R Stuart & Co.
Powerland Heritage Park ©
Powerland Heritage Park
Brooks Wine ©
Brooks Wine

2
nights
Lincoln City

Lincoln City ©
Lincoln City is a city in Lincoln County, Oregon, United States. On the 24th (Sun), snap pictures at Drift Creek Covered Bridge, take in the exciting artwork at Artists's Co-op Gallery, take an in-depth tour of Prehistoric, take in the exciting artwork at Rock Your World: Pacific Northwest Gem & Jewelry Gallery, then shop like a local with Freed Gallery, and finally take in the exciting artwork at Mossy Creek Pottery. On the next day, walk around Siletz Bay Park, then experience rural life at Barking Dog Farm, then enjoy the sand and surf at Taft Bay, and finally admire the majestic nature at Fogarty Creek State Recreation Area.

To see where to stay, reviews, photos, and more tourist information, go to the Lincoln City trip maker tool .

Getting from McMinnville to Lincoln City by car takes about 1.5 hours. While traveling from McMinnville, expect a bit cooler days and about the same nights in Lincoln City, ranging from highs of 58°F to lows of 46°F. Finish up your sightseeing early on the 26th (Tue) so you can go by car to Florence.

Things to do in Lincoln City

Parks Museums Shopping

Side Trip

Fogarty Creek State Recreation Area
Highlights from your plan
Mossy Creek Pottery ©
Mossy Creek Pottery
Fogarty Creek State Recreation Area ©
Freed Gallery ©
Freed Gallery

1
night
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Start off your visit on the 26th (Tue): kick back and relax at Heceta Beach, then tee off at Ocean Dunes Golf Links, and then trek along Hobbit Trail.

To see traveler tips, ratings, photos, and more tourist information, go to the Florence route planner.

Traveling by car from Lincoln City to Florence takes 2 hours. Alternatively, you can take a bus. In May, daily temperatures in Florence can reach 62°F, while at night they dip to 49°F. Cap off your sightseeing on the 27th (Wed) early enough to go by car to Bandon.

Things to do in Florence

Outdoors Parks Golf
Highlights from your plan
Heceta Beach ©
Heceta Beach
Ocean Dunes Golf Links ©
Ocean Dunes Golf Links

2
nights
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 27th (Wed), admire the majestic nature at Port Orford Heads State Park, then examine the collection at Port Orford Lifeboat Station Museum, then look for gifts at Misty Meadows Jams, and finally immerse yourself in nature at Bandon State Park. Here are some ideas for day two: tour the pleasant surroundings at South Slough National Estuarine Research Reserve, then tee off at Pacific Dunes, and then tour the pleasant surroundings at Coquille Point.

To find reviews, photos, where to stay, and other tourist information, use the Bandon trip builder site .

Getting from Florence to Bandon by car takes about 1.5 hours. Other options: take a bus. In May, daily temperatures in Bandon can reach 62°F, while at night they dip to 49°F. Cap off your sightseeing on the 29th (Fri) early enough to go by car to Gold Beach.

Things to do in Bandon

Outdoors Parks Nature

Side Trips

Port Orford, South Slough National Estuarine Research Reserve
Highlights from your plan
Bandon State Park ©
Bandon State Park
Coquille Point ©
Coquille Point

2
nights
Gold Beach

Gold Beach ©
Gold Beach is a city in and the county seat of Curry County, Oregon, United States, on the Oregon Coast. Kick off your visit on the 29th (Fri): examine the collection at Curry Historical Museum, then look for gifts at Gold Beach Books, then kick back and relax at Ophir Beach, and finally tour the pleasant surroundings at Myers Creek Beach. Keep things going the next day: contemplate the waterfront views at Illinois River and then play a few rounds at Cedar Bend Golf Club.

Find out how to plan Gold Beach trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Bandon to Gold Beach takes 1.5 hours. Alternatively, you can take a bus. In May, daytime highs in Gold Beach are 63°F, while nighttime lows are 48°F. Finish your sightseeing early on the 31st (Sun) so you can drive to Brookings.

Things to do in Gold Beach

Outdoors Parks Beaches

Side Trips

Ophir Beach, Myers Creek Beach
Highlights from your plan
Ophir Beach ©
Ophir Beach
Curry Historical  Museum ©
Curry Historical Museum
Illinois River ©
Illinois River

4
nights
Brookings

Brookings ©
Brookings is a city in Curry County, Oregon, United States. Get outdoors at Samuel H. Boardman State Scenic Corridor and McVay Rock State Recreation Site. Explore hidden gems such as Lone Ranch Beach and End of the Trail Museum. Get out of town with these interesting Brookings side-trips: Enderts Beach (in Redwood National Park) and Crescent City (Point St George Park, Northcoast Marine Mammal Center, & more). The adventure continues: admire the majestic nature at Crissey Field State Park, stroll around Chetco Point Park, take a memorable drive along Welcome to California, and sample the tasty concoctions at Chetco Brewing Company.

To see ratings, reviews, photos, and other tourist information, read our Brookings trip planner .

Getting from Gold Beach to Brookings by car takes about an hour. In May, plan for daily highs up to 63°F, and evening lows to 48°F. Wrap up your sightseeing on the 4th (Thu) early enough to drive to Grants Pass.

Things to do in Brookings

Parks Outdoors Beaches

Side Trips

Crescent City, Enderts Beach, End of the Trail Museum
Highlights from your plan
Lone Ranch Beach ©
Lone Ranch Beach
Enderts Beach ©
Enderts Beach

2
nights
Grants Pass

Grants Pass ©
Grants Pass is a city in, and the county seat of, Josephine County, Oregon, United States. Kick off your visit on the 4th (Thu): learn about winemaking at Wooldridge Creek Winery, stroll the grounds of Jacksonville Cemetery, then learn about winemaking at Troon Vineyard, and finally walk around Schroeder County Park. On the 5th (Fri), you'll have a packed day of sightseeing: relax in the rural setting at Rogue Creamery Dairy Farm, admire the masterpieces at Grants Pass Museum of Art, examine the collection at Schmidt House Museum, examine the collection at Bear Hotel Artworks Museum, then appreciate the history behind Grants Pass Caveman, and finally stop by The Kitchen Company.

To see more things to do, reviews, traveler tips, and other tourist information, you can read our Grants Pass trip itinerary builder tool .

Traveling by car from Brookings to Grants Pass takes 2 hours. In June in Grants Pass, expect temperatures between 70°F during the day and 49°F at night. Finish your sightseeing early on the 6th (Sat) so you can drive to Prospect.

Things to do in Grants Pass

Museums Wineries Parks

Side Trip

Jacksonville Cemetery
Highlights from your plan
Grants Pass Museum of Art ©
Grants Pass Museum of Art
Jacksonville Cemetery ©
Jacksonville Cemetery
Troon Vineyard ©
Troon Vineyard

2
nights
Prospect

Prospect ©
Prospect is an unincorporated community in Jackson County, in the U.S. Start off your visit on the 6th (Sat): take in the dramatic scenery at Plaikni Falls, then stroll through Watchman Peak, then trek along Pinnacles Trail, and finally stroll through Castle Crest Wildflower Trail. Get ready for a full day of sightseeing on the next day: take some stellar pictures from Natural Bridge Viewpoint, stroll through Annie Creek Canyon, and then contemplate the geological forces at Mount Scott.

To find reviews, more things to do, and other tourist information, go to the Prospect day trip website .

You can drive from Grants Pass to Prospect in 1.5 hours. Traveling from Grants Pass in June, expect Prospect to be a bit warmer, temps between 86°F and 55°F. Wrap up your sightseeing on the 8th (Mon) early enough to travel to Bend.

Things to do in Prospect

Parks Outdoors Trails

Side Trip

Crater Lake National Park
Highlights from your plan
Plaikni Falls ©
Plaikni Falls
Mount Scott ©
Mount Scott
Watchman Peak ©
Watchman Peak

5
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.
You'll explore and learn at Dee Wright Observatory and Artists Gallery Sunriver. Visiting Shevlin Park and Oregon Badlands Wilderness Trails will get you outdoors. Change things up with these side-trips from Bend: Erickson Aircraft Collection (in Madras), Sisters (Peterson Ridge Trail & City of Sisters) and Tumalo Mountain (in Redmond). There's lots more to do: sample the tasty concoctions at Deschutes Brewery, take in the dramatic natural features at Balancing Rocks, contemplate the waterfront views at North and South Twin Lakes, and trek along Deschutes River Trail.

To find where to stay, reviews, more things to do, and more tourist information, refer to the Bend driving holiday planner .

Getting from Prospect to Bend by car takes about 2.5 hours. Expect slightly colder temperatures when traveling from Prospect in June; daily highs in Bend reach 75°F and lows reach 45°F. Wrap up your sightseeing on the 13th (Sat) early enough to drive to Hood River.

Things to do in Bend

Parks Nature Outdoors

Side Trips

Sisters, The Museum at Warm Springs, Dee Wright Observatory, Tumalo Mountain, Artists Gallery Sunriver
Highlights from your plan
Dee Wright Observatory ©
Dee Wright Observatory
City of Sisters ©
City of Sisters
The Museum at Warm Springs ©
The Museum at Warm Springs

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Step off the beaten path and head to Stonehenge Memorial and Columbia Hills State Park. Appreciate the collections at Presby Museum and Fire Museum in City Hall. There's still lots to do: do a tasting at Mt. Hood Winery, stroll around Panorama Point County Park, go for a walk through Rowena Crest Viewpoint, and relax in the rural setting at The Gorge White House.

For more things to do, traveler tips, where to stay, and tourist information, read Hood River trip builder tool .

Getting from Bend to Hood River by car takes about 3.5 hours. Other options: do a combination of flight and bus; or take a bus. Plan for somewhat warmer nights when traveling from Bend in June since evenings lows in Hood River dip to 55°F. Wrap up your sightseeing by early afternoon on the 17th (Wed) to allow enough time to travel back home.

Things to do in Hood River

Wineries Parks Nature

Side Trips

Goldendale, Columbia Hills State Park, Starvation Creek State Park, Fire Museum in City Hall, Rowena Crest Viewpoint
Highlights from your plan
Viento Wines ©
Viento Wines
Mt. Hood Winery ©
Mt. Hood Winery
Presby Museum ©
Presby Museum

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