16 days in Oregon Itinerary

16 days in Oregon Itinerary

Created using Inspirock Oregon holiday planner

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Route & dates

16 days in Oregon Itinerary

Start: Queenstown
Fly:  22​h
1
Portland
— 3 nights
Drive:  1​h 30​min
2
Cannon Beach
— 3 nights
Drive:  3​h 15​min
3
Yachats
— 2 nights
Drive:  4​h
4
Redmond
— 2 nights
Drive:  2​h 45​min
5
Hood River
— 3 nights
Drive + Fly:  24​h
End: Queenstown

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.
Step out of Portland with an excursion to Multnomah Falls in Bridal Veil--about 38 minutes away. Dedicate the 27th (Mon) to wine at some of the top wineries in the area. The adventure continues: take in nature's colorful creations at Portland Japanese Garden, get to know the resident critters at Oregon Zoo, identify plant and animal life at Oaks Bottom Wildlife Refuge, and walk around Tom McCall Waterfront Park.

For ratings, maps, reviews, and more tourist information, read our Portland road trip planning tool .

Queenstown, New Zealand to Portland is an approximately 22-hour flight. You can also do a combination of bus and flight; or do a combination of flight and train. Due to the time zone difference, you'll gain 20 hours traveling from Queenstown to Portland. In May, daytime highs in Portland are 24°C, while nighttime lows are 12°C. Finish your sightseeing early on the 28th (Tue) to allow enough time to drive to Cannon Beach.

Things to do in Portland

Tours Parks Zoos & Aquariums

Side Trip

Multnomah Falls
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Powell's City of Books ©
Powell's City of Books
International Rose Test Garden ©
International Rose Test Garden

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Get out of town with these interesting Cannon Beach side-trips: Astoria (Astoria Column, Astoria-Megler Bridge, & more). The adventure continues: enjoy the sand and surf at Haystack Rock, immerse yourself in nature at Oswald West State Park, appreciate the history behind Seaside Beach Lewis and Clark Monument, and look for gifts at Seaside Candyman.

For maps, more things to do, where to stay, and tourist information, use the Cannon Beach trip itinerary maker site .

Drive from Portland to Cannon Beach in 1.5 hours. Alternatively, you can take a bus. Expect a bit cooler weather when traveling from Portland in May: highs in Cannon Beach hover around 19°C, while lows dip to 10°C. Wrap up your sightseeing on the 31st (Fri) early enough to drive to Yachats.

Things to do in Cannon Beach

Parks Nature Outdoors

Side Trips

Astoria, Seaside
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

2
nights
Yachats

Yachats ©
Yachats is a small coastal city in Lincoln County, Oregon, United States. Start off your visit on the 1st (Sat): take a leisurely stroll along Yachats coastline, cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, and then enjoy some diversion at Sand Master Park. Keep things going the next day: take in the dramatic natural features at Thor's Well, then enjoy the sea views from Heceta Head Lighthouse, then putt your heart out at Sandland Adventures, and finally admire all the interesting features of Oregon Coast Hwy.

For where to stay, more things to do, reviews, and tourist information, you can read our Yachats day trip planning tool .

You can drive from Cannon Beach to Yachats in 3.5 hours. Alternatively, you can do a combination of bus, flight, and car; or take a bus. In May, daily temperatures in Yachats can reach 17°C, while at night they dip to 9°C. Cap off your sightseeing on the 2nd (Sun) early enough to travel to Redmond.

Things to do in Yachats

Outdoors Scenic Drive Nature

Side Trips

Florence, Oregon Coast Hwy
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sand Master Park - Sandboarding ©
Sand Master Park - Sandboarding

2
nights
Redmond

Redmond ©
Redmond is a city in Deschutes County, Oregon, United States. Start off your visit on the 3rd (Mon): get a new perspective on nature at High Desert Museum and then immerse yourself in nature at Smith Rock State Park. Get ready for a full day of sightseeing on the 4th (Tue): take a peaceful walk through Deschutes National Forest, then take a peaceful walk through Shevlin Park, and then explore the activities along Deschutes River.

For other places to visit, photos, where to stay, and more tourist information, go to the Redmond trip planner .

Drive from Yachats to Redmond in 4.5 hours. While traveling from Yachats, expect a bit warmer days and little chillier nights in Redmond, ranging from highs of 30°C to lows of 7°C. Cap off your sightseeing on the 4th (Tue) early enough to travel to Hood River.

Things to do in Redmond

Parks Nature Wildlife

Side Trip

Bend
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
Deschutes National  Forest ©
Deschutes National Forest

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Explore the numerous day-trip ideas around Hood River: Timberline Lodge and Ski Area (in Timberline Lodge) and Bonneville Lock & Dam (in Cascade Locks). There's much more to do: identify plant and animal life at Columbia River Gorge National Scenic Area, admire the majestic nature at Starvation Creek State Park, hike along Historic Columbia River Highway State Trail, and brush up on your knowledge of spirits at Hood River Distillers Tasting Room.

To find other places to visit, reviews, traveler tips, and tourist information, you can read our Hood River trip maker .

Getting from Redmond to Hood River by car takes about 2.5 hours. While traveling from Redmond, expect little chillier days and a bit warmer nights in Hood River, ranging from highs of 26°C to lows of 15°C. Wrap up your sightseeing on the 7th (Fri) to allow time to travel back home.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

Oregon, Cascade Locks, Historic Columbia River Highway State Trail, Columbia Gorge Discovery Center & Museum, Timberline Lodge and Ski Area
Highlights from your plan

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