27 days in Oregon Itinerary

Created using Inspirock Oregon planner
Make it your trip
Drive
1
Astoria
— 3 nights
Drive
2
Newport
— 4 nights
Drive
3
Florence
— 4 nights
Drive
4
Coos Bay
— 4 nights
Drive
5
Bend
— 3 nights
Fly
6
Hood River
— 3 nights
Drive
7
Portland
— 5 nights

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Astoria — 3 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Change things up with these side-trips from Astoria: Manzanita Beach (in Manzanita), Nehalem Bay State Park (in Nehalem) and Cannon Beach (Hug Point State Park, Haystack Rock, &more). There's lots more to do: pause for some photo ops at Astoria Column, examine the collection at Seaside Inverted Experience, explore the striking landscape of Fort Clatsop National Memorial, and immerse yourself in nature at Fort Stevens State Park.

To find where to stay, ratings, other places to visit, and more tourist information, you can read our Astoria trip builder website.

Portland to Astoria is an approximately 2-hour car ride. You can also take a bus. In November, daily temperatures in Astoria can reach 55°F, while at night they dip to 42°F. Finish your sightseeing early on the 28th (Mon) so you can drive to Newport.
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Parks · Nature · Historic Sites · Beaches
Side Trips

Newport — 4 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Change things up with these side-trips from Newport: Yachats coastline (in Yachats) and Lincoln City (Prehistoric & Lincoln City Glass Center). There's much more to do: look for all kinds of wild species at Yaquina Head Outstanding Natural Area, kick back and relax at Nye Beach, get up close and personal with brilliant marine life at Oregon Coast Aquarium, and take a leisurely stroll along Newport's Historic Bayfront.

For photos, ratings, other places to visit, and other tourist information, read Newport tour planner.

You can drive from Astoria to Newport in 3.5 hours. Another option is to take a bus. In November, daytime highs in Newport are 54°F, while nighttime lows are 43°F. Finish your sightseeing early on the 2nd (Fri) so you can drive to Florence.
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Parks · Nature · Outdoors · Beaches
Side Trips

Florence — 4 nights

Florence is a coastal city in Lane County, in the U.S. state of Oregon. Change things up with these side-trips from Florence: Dean Creek Elk Viewing Area (in Reedsport), Cape Perpetua Visitor Center - Siuslaw National Forest (in Yachats) and Butterfly Pavilion & Gardens at ECEC (in Elkton). Next up on the itinerary: have fun at Sandland Adventures, explore and take pictures at Oregon Coast Hwy, visit a coastal fixture at Heceta Head Lighthouse, and explore the fascinating underground world of Sea Lion Caves.

To find where to stay, other places to visit, and more tourist information, read our Florence tour planner.

Traveling by car from Newport to Florence takes 1.5 hours. Alternatively, you can take a bus. In December, daily temperatures in Florence can reach 53°F, while at night they dip to 40°F. Wrap up your sightseeing on the 6th (Tue) early enough to drive to Coos Bay.
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Parks · Outdoors · Nature · Scenic Drive
Side Trips

Coos Bay — 4 nights

Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. Get out of town with these interesting Coos Bay side-trips: Bandon (Second Street Gallery, Circles in the Sand, &more). There's still lots to do: admire the majestic nature at Shore Acres State Park, take an in-depth tour of Coos History Museum, make a trip to Steve Prefontaine Murals, and observe the fascinating underwater world at Charleston Marine Life Center.

For ratings, photos, maps, and other tourist information, refer to the Coos Bay trip itinerary planning app.

Drive from Florence to Coos Bay in 1.5 hours. Expect a daytime high around 53°F in December, and nighttime lows around 40°F. Finish up your sightseeing early on the 10th (Sat) so you can go by car to Bend.
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Parks · Nature · Museums · Shopping
Side Trips

Bend — 3 nights

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 out of Bend to go to Redmond and see Smith Rock State Park, which is approximately 38 minutes away. There's much more to do: examine the collection at High Desert Museum, hike along Pilot Butte State Scenic Viewpoint, brush up on your knowledge of spirits at Oregon Spirit Distillers, and admire the sheer force of Tumalo Falls.

To see traveler tips, where to stay, other places to visit, and tourist information, use the Bend journey maker tool.

You can drive from Coos Bay to Bend in 5 hours. Plan for little chillier temperatures traveling from Coos Bay in December, with highs in Bend at 40°F and lows at 22°F. Cap off your sightseeing on the 13th (Tue) early enough to catch the flight to Hood River.
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Parks · Nature · Museums · Outdoors
Side Trips

Hood River — 3 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. Hood River is known for wineries, nature, and trails. Your trip includes some of its best attractions: contemplate the waterfront views at Columbia River Gorge National Scenic Area, examine the collection at Columbia Gorge Discovery Center & Museum, do a tasting at Sunshine Mill Winery, and hike along Historic Columbia River Highway State Trail.

For traveler tips, more things to do, reviews, and more tourist information, read Hood River vacation maker website.

Traveling by flight from Bend to Hood River takes 2.5 hours. Alternatively, you can drive; or take a bus. Plan for somewhat warmer nights when traveling from Bend in December since evenings lows in Hood River dip to 30°F. Finish your sightseeing early on the 16th (Fri) so you can drive to Portland.
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Parks · Outdoors · Nature · Museums
Side Trips

Portland — 5 nights

City of Roses

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.
Explore Portland's surroundings by going to Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). Dedicate the 20th (Tue) to wine at some of the top wineries in the area. And it doesn't end there: look for gifts at Powell's City of Books, learn the secrets of beer at a beer tour and tasting, admire the landmark architecture of Pittock Mansion, and examine the collection at Portland Art Museum.

To find reviews and tourist information, refer to the Portland day trip planner.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. In December, plan for daily highs up to 45°F, and evening lows to 35°F. Wrap up your sightseeing on the 21st (Wed) early enough to travel back home.
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Tours · Parks · Wineries · Museums
Side Trips

Oregon travel guide

4.5
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.
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