15 days in Oregon Itinerary

15 days in Oregon Itinerary

Created using Inspirock Oregon visit planner

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Route & dates

15 days in Oregon Itinerary

Start: Miami
Fly:  10​h 45​min
1
Redmond
— 2 nights
Drive:  2​h 30​min
2
Hood River
— 3 nights
bus:  1​h 15​min
3
Portland
— 3 nights
Drive:  1​h 30​min
4
Cannon Beach
— 2 nights
Drive:  3​h 15​min
5
Yachats
— 2 nights
Drive:  4​h 45​min
6
Ashland
— 2 nights
bus + Fly:  12​h 15​min
End: Miami

2
nights
Redmond

Redmond ©
Redmond is a city in Deschutes County, Oregon, United States. On your second day here, see the sky in a new way at Oregon Observatory, then let the river carry you with a rafting and tubing tour, and then contemplate the waterfront views at Deschutes River.

For more things to do, reviews, where to stay, and other tourist information, read Redmond travel route site .

Miami to Redmond is an approximately 11-hour flight. You can also drive. Due to the time zone difference, you'll gain 3 hours traveling from Miami to Redmond. When traveling from Miami in May, plan for little chillier days and colder nights in Redmond: temperatures range from 70°F by day to 37°F at night. Cap off your sightseeing on the 14th (Thu) early enough to travel to Hood River.

Things to do in Redmond

Parks Museums Nature

Side Trips

Bend, Oregon Observatory
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
River Rafting & Tubing
High Desert Museum ©
High Desert Museum

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Change things up with these side-trips from Hood River: Timberline Lodge and Ski Area (in Timberline Lodge) and Bonneville Lock & Dam (in Cascade Locks). There's much more to do: look for all kinds of wild species at Columbia River Gorge National Scenic Area, admire the sheer force of Starvation Creek State Park, brush up on your knowledge of spirits at Hood River Distillers Tasting Room, and stroll around Port Marina Park.

For other places to visit, where to stay, photos, and more tourist information, refer to the Hood River trip planner .

You can drive from Redmond to Hood River in 2.5 hours. Traveling from Redmond in May, expect somewhat warmer with lows of 49°F in Hood River. Cap off your sightseeing on the 17th (Sun) early enough to catcht the bus to Portland.

Things to do in Hood River

Parks Nature Wildlife

Side Trips

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

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.
Venture out of the city with trips to Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). There's much more to do: admire the natural beauty at Portland Japanese Garden, walk around Laurelhurst Park, admire the striking features of Pittock Mansion, and sample some tasty brews at a beer tour and tasting.

Plan trip to Portland with our itinerary maker to find out where to go and what to do.

You can take a bus from Hood River to Portland in 1.5 hours. Other options are to drive; or take a train. In May, plan for daily highs up to 70°F, and evening lows to 51°F. Finish up your sightseeing early on the 20th (Wed) so you can go by car to Cannon Beach.

Things to do in Portland

Parks Tours Museums

Side Trips

Evergreen Aviation & Space Museum, 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

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 21st (Thu), kick back and relax at Cannon Beach, then tour the pleasant surroundings at Haystack Rock, then admire the majestic nature at Ecola State Park, and finally stop by Cloud and Leaf Bookstore. On your second day here, admire the majestic nature at Oswald West State Park, admire the majestic nature at Fort Stevens State Park, then look for all kinds of wild species at Astoria Column, and finally admire the sheer force of Young River Falls.

For maps, reviews, photos, and more tourist information, read Cannon Beach route builder .

Traveling by car from Portland to Cannon Beach takes 1.5 hours. Alternatively, you can take a bus. When traveling from Portland in May, plan for a bit cooler days in Cannon Beach, with highs around 62°F, while nights are about the same with lows around 48°F. Wrap up your sightseeing on the 22nd (Fri) early enough to drive to Yachats.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Cloud and Leaf Bookstore
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. On the 23rd (Sat), cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, take in the waterfront at Yachats coastline, and then look for all kinds of wild species at Yaquina Head Outstanding Natural Area. Keep things going the next day: try for a hole-in-one at Sandland Adventures, observe the fascinating underwater world at Oregon Coast Aquarium, and then admire the majestic nature at Yachats State Park.

To find reviews, other places to visit, where to stay, and more tourist information, read Yachats holiday planner.

Getting from Cannon Beach to Yachats by car takes about 3.5 hours. Other options: do a combination of bus, flight, and car; or take a bus. May in Yachats sees daily highs of 58°F and lows of 46°F at night. Wrap up your sightseeing on the 24th (Sun) early enough to drive to Ashland.

Things to do in Yachats

Parks Nature Zoos & Aquariums

Side Trips

Newport, Sandland Adventures
Highlights from your plan
Yachats coastline ©
Yachats coastline
Yaquina Head Outstanding Natural Area ©

2
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 25th (Mon): look for gifts at Rogue Creamery, then stroll around Lithia Park, then catch a live performance at Oregon Shakespeare Festival, and finally let the river carry you with a rafting and tubing tour.

For photos, where to stay, ratings, and more tourist information, go to the Ashland trip itinerary maker site .

Traveling by car from Yachats to Ashland takes 5 hours. Alternatively, you can do a combination of car and flight; or take a bus. When traveling from Yachats in May, plan for somewhat warmer days and about the same nights in Ashland: temperatures range from 77°F by day to 49°F at night. Finish your sightseeing early on the 26th (Tue) so you can travel back home.

Things to do in Ashland

Nightlife Adventure Outdoors

Side Trip

Rogue Creamery
Highlights from your plan
River Rafting & Tubing
Lithia Park ©
Lithia Park
Oregon Shakespeare Festival ©
Oregon Shakespeare Festival

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