10 days in Oregon Itinerary
Created using Inspirock Oregon planner
Start: Playa del Carmen
Ferry to Cozumel, Fly to Portland
1
Portland
— 3 nights
Drive
2
Cannon Beach
— 2 nights
Fly
3
Crater Lake National Park
— 1 night
Drive
4
Bend
— 3 nights
Fly
End: Playa del Carmen
Fri, Sep 1 - Sun, Sep 10
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Portland — 3 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.Escape the urban bustle at Columbia River Gorge National Scenic Area and Multnomah Falls. You'll visit kid-friendly attractions like Powell's City of Books and Portland Japanese Garden. Next up on the itinerary: admire the natural beauty at International Rose Test Garden, don't miss a visit to Pittock Mansion, browse the eclectic array of goods at Portland Saturday Market, and get to know the resident critters at Oregon Zoo.
For other places to visit, where to stay, photos, and tourist information, refer to the Portland trip maker tool.
Playa del Carmen, Mexico to Portland is an approximately 11.5-hour combination of ferry and flight. You can also drive; or take a bus. The time zone difference when traveling from Playa del Carmen to Portland is minus 3 hours. Expect slightly colder temperatures when traveling from Playa del Carmen in September; daily highs in Portland reach 28°C and lows reach 15°C. Finish your sightseeing early on the 4th (Mon) so you can drive to Cannon Beach.
Side Trips
Highlights from your trip
Cannon Beach — 2 nights

Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 5th (Tue): look for gifts at Cloud and Leaf Bookstore, then kick back and relax at Cannon Beach, then take in the dramatic natural features at Haystack Rock, and finally immerse yourself in nature at Ecola State Park. Get ready for a full day of sightseeing on the 6th (Wed): admire the majestic nature at Hug Point State Park, then immerse yourself in nature at Oswald West State Park, and then admire the majestic nature at Tolovana Beach State Recreation Site.
To find traveler tips, photos, other places to visit, and tourist information, read Cannon Beach attractions website.
You can drive from Portland to Cannon Beach in 1.5 hours. Alternatively, you can take a bus. When traveling from Portland in September, plan for a bit cooler days and about the same nights in Cannon Beach: temperatures range from 24°C by day to 13°C at night. Wrap up your sightseeing on the 6th (Wed) early enough to fly to Crater Lake National Park.
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To find traveler tips, photos, other places to visit, and tourist information, read Cannon Beach attractions website.
You can drive from Portland to Cannon Beach in 1.5 hours. Alternatively, you can take a bus. When traveling from Portland in September, plan for a bit cooler days and about the same nights in Cannon Beach: temperatures range from 24°C by day to 13°C at night. Wrap up your sightseeing on the 6th (Wed) early enough to fly to Crater Lake National Park.
Side Trip
Highlights from your trip
Crater Lake National Park — 1 night

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.Start off your visit on the 7th (Thu): explore the wealth of natural beauty at Crater Lake National Park.
To find where to stay, traveler tips, maps, and other tourist information, refer to the Crater Lake National Park travel website.
Fly from Cannon Beach to Crater Lake National Park in 2.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Traveling from Cannon Beach in September, you will find days in Crater Lake National Park are a bit warmer (33°C), and nights are about the same (13°C). Wrap up your sightseeing on the 7th (Thu) to allow time to drive to Bend.
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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.Kick off your visit on the 8th (Fri): relax and float downstream with a rafting and tubing tour, then see Off-Road Tours, and then take in the dramatic scenery at Tumalo Falls. Get ready for a full day of sightseeing on the next day: take a peaceful walk through Deschutes National Forest, then immerse yourself in nature at Smith Rock State Park, and then trek along Pilot Butte State Scenic Viewpoint.
To see maps, ratings, and more tourist information, refer to the Bend itinerary maker app.
Getting from Crater Lake National Park to Bend by car takes about 2.5 hours. Other options: do a combination of taxi and bus. Prepare for little chillier weather when traveling from Crater Lake National Park in September: high temperatures in Bend hover around 26°C and lows are around 7°C. Cap off your sightseeing on the 10th (Sun) early enough to catch the flight back home.
Side Trip
Highlights from your trip
Oregon travel guide
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.