23 days in Oregon Itinerary

23 days in Oregon Itinerary

Created using Inspirock Oregon vacation planner

This plan was created by another user. Make it your plan

Route & dates

23 days in Oregon Itinerary

Start: San Juan, Puerto Rico
+2
Fly + Tram + Bus:  14​h 15​min
1
Cannon Beach
— 3 nights
Drive:  3​h 15​min
2
Yachats
— 3 nights
Drive:  1​h 45​min
3
Coos Bay
— 2 nights
Drive:  4​h 30​min
4
Klamath Falls
— 3 nights
Drive:  2​h 45​min
5
Redmond
— 3 nights
Drive:  2​h 30​min
6
Hood River
— 3 nights
Bus:  1​h 15​min
7
Portland
— 5 nights
Fly:  12​h 30​min
End: San Juan, Puerto Rico

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Change things up with these side-trips from Cannon Beach: Astoria (Columbia River Maritime Museum, Astoria Column, & more). There's lots more to do: kick back and relax at Haystack Rock, get up close and personal with brilliant marine life at Seaside Aquarium, admire the majestic nature at Oswald West State Park, and stroll through Cannon Beach.

To find where to stay, traveler tips, reviews, and tourist information, use the Cannon Beach trip planning website .

San Juan, Puerto Rico to Cannon Beach is an approximately 14.5-hour combination of flight and bus. You can also do a combination of car, flight, and bus; or do a combination of shuttle, flight, and bus. You'll gain 4 hours traveling from San Juan to Cannon Beach due to the time zone difference. Plan for cooler temperatures traveling from San Juan in October, with highs in Cannon Beach at 20°C and lows at 10°C. Wrap up your sightseeing on the 5th (Sat) 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

3
nights
Yachats

Yachats ©
Yachats is a small coastal city in Lincoln County, Oregon, United States. Explore the numerous day-trip ideas around Yachats: Lincoln City Glass Center (in Lincoln City), Whale Park (in Depoe Bay) and Newport (Oregon Coast Aquarium, Made in Oregon, & more). And it doesn't end there: take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, visit a coastal fixture at Heceta Head Lighthouse, take a leisurely stroll along Yachats coastline, and putt your heart out at Sandland Adventures.

Before you visit Yachats, use our trip planner to discover what you can do and see there.

Traveling by car from Cannon Beach to Yachats takes 3.5 hours. Alternatively, you can do a combination of bus, flight, and car; or take a bus. In October, daily temperatures in Yachats can reach 18°C, while at night they dip to 10°C. Wrap up your sightseeing on the 8th (Tue) early enough to drive to Coos Bay.

Things to do in Yachats

Parks Historic Sites Outdoors

Side Trips

Newport, Florence, Lincoln City Glass Center, Whale Park
Highlights from your plan
Yachats coastline ©
Yachats coastline
Oregon Coast Aquarium ©
Oregon Coast Aquarium

2
nights
Coos Bay

Coos Bay ©
Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. Start off your visit on the 9th (Wed): immerse yourself in nature at Cape Arago State Park, admire the majestic nature at Shore Acres State Park, and then contemplate the long history of Marshfield Pioneer Cemetery. Get ready for a full day of sightseeing on the next day: stop by Face Rock Creamery, admire the majestic nature at Face Rock State Scenic Viewpoint, and then play a few rounds at Bandon Dunes Golf Resort.

For maps, where to stay, other places to visit, and other tourist information, use the Coos Bay trip planner .

Traveling by car from Yachats to Coos Bay takes 2 hours. In October, plan for daily highs up to 20°C, and evening lows to 11°C. Wrap up your sightseeing on the 10th (Thu) early enough to travel to Klamath Falls.

Things to do in Coos Bay

Nature Parks Outdoors

Side Trip

Bandon
Highlights from your plan
Shore Acres State Park ©
Shore Acres State Park
Face Rock State Scenic Viewpoint ©
Face Rock State Scenic Viewpoint
Bandon Dunes Golf Resort ©
Bandon Dunes Golf Resort

3
nights
Klamath Falls

Klamath Falls is a city in and the county seat of Klamath County, Oregon, United States. Venture out of the city with trips to Crater Lake National Park (Pinnacles Trail & Crater Lake National Park) and Ashland (Oregon Shakespeare Festival, Lithia Park, & more).

To find more things to do, maps, photos, and more tourist information, go to the Klamath Falls trip itinerary planning site .

Traveling by car from Coos Bay to Klamath Falls takes 4.5 hours. Traveling from Coos Bay in October, expect a bit cooler with lows of 0°C in Klamath Falls. Cap off your sightseeing on the 13th (Sun) early enough to travel to Redmond.

Things to do in Klamath Falls

Parks Nature Outdoors

Side Trips

Ashland, Crater Lake National Park
Highlights from your plan
River Rafting & Tubing
Crater Lake National Park ©
Crater Lake National Park
Lithia Park ©
Lithia Park

3
nights
Redmond

Redmond ©
Redmond is a city in Deschutes County, Oregon, United States. Explore the numerous day-trip ideas around Redmond: Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls) and High Desert Museum (in Bend). And it doesn't end there: immerse yourself in nature at Smith Rock State Park, take a stroll through City of Sisters, stroll around Drake Park, and explore the wealth of natural beauty at Deschutes National Forest.

To find photos, traveler tips, ratings, and more tourist information, read Redmond itinerary planner .

Traveling by car from Klamath Falls to Redmond takes 3 hours. In October, plan for daily highs up to 20°C, and evening lows to 0°C. Finish your sightseeing early on the 16th (Wed) to allow enough time to travel to Hood River.

Things to do in Redmond

Parks Nature Wildlife

Side Trips

Bend, Sisters
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. You'll find plenty of places to visit near Hood River: Timberline Lodge and Ski Area (in Timberline Lodge) and The Dalles Murals (in The Dalles). Next up on the itinerary: contemplate the waterfront views at Columbia River Gorge National Scenic Area, see the interesting displays at Columbia Gorge Discovery Center & Museum, contemplate the geological forces at Mount Hood, and stroll through Historic Columbia River Highway State Trail.

To find photos, reviews, more things to do, and tourist information, use the Hood River day trip tool .

Traveling by car from Redmond to Hood River takes 2.5 hours. Traveling from Redmond in October, you can expect nighttime temperatures to be a bit warmer in Hood River, with lows of 8°C. Finish your sightseeing early on the 19th (Sat) so you can take a bus to Portland.

Things to do in Hood River

Nature Parks Winter Sports

Side Trips

The Dalles, Historic Columbia River Highway State Trail, Columbia River Gorge National Scenic Area, Bridge of the Gods, Timberline Lodge and Ski Area
Highlights from your plan

5
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.
Change things up with these side-trips from Portland: Multnomah Falls (in Bridal Veil), Multnomah Falls (in Troutdale) and Evergreen Aviation & Space Museum (in McMinnville). Next up on the itinerary: take in nature's colorful creations at Portland Japanese Garden, indulge your taste buds at Food & Drink, learn about wildlife with up-close encounters at Oregon Zoo, and hike along Forest Park.

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

Take a bus from Hood River to Portland in 1.5 hours. Alternatively, you can drive; or take a train. In October, daytime highs in Portland are 22°C, while nighttime lows are 11°C. Finish your sightseeing early on the 24th (Thu) so you can travel back home.

Things to do in Portland

Parks Tours Museums

Side Trips

Multnomah Falls, Evergreen Aviation & Space Museum
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

Similar Plans

8 days in Oregon BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, slow & easy, hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 22 days in West Coast BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, slow & easy, hidden gems PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Slow & easy 28 days in United States BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 12 days in Oregon BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, beaches, shopping, wildlife, popular & hidden gems PREFERENCES: July, teens, culture, outdoors, relaxing, beaches, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Oregon BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Oregon BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 26 days in Washington State, Oregon & California BY A USER FROM JAPAN April, museums, wildlife, hidden gems PREFERENCES: April, museums, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 13 days in Oregon BY A USER FROM UNITED STATES July, teens, outdoors, relaxing, beaches, shopping, wildlife, popular & hidden gems PREFERENCES: July, teens, outdoors, relaxing, beaches, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 47 days in United States BY A USER FROM UNITED STATES May, outdoors, relaxing, beaches, wildlife, slow & easy, popular sights PREFERENCES: May, outdoors, relaxing, beaches, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 16 days in Oregon BY A USER FROM UNITED STATES June, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems PREFERENCES: June, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Oregon BY A USER FROM UNITED STATES September, teens, culture, relaxing, museums, shopping, popular & hidden gems PREFERENCES: September, teens, culture, relaxing, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans