13 days in Oregon Itinerary

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 to go to Bridal Veil and see Multnomah Falls, which is approximately 38 minutes away. Dedicate the 26th (Sun) to wine at some of the top wineries in the area. There's much more to do: admire the natural beauty at Portland Japanese Garden, stop by Powell's City of Books, hunt for treasures at Portland Saturday Market, and walk around Tom McCall Waterfront Park.

To find ratings and other tourist information, refer to the Portland online trip planner.

New York City to Portland is an approximately 9.5-hour flight. You can also drive; or take a train. Traveling from New York City to Portland, you'll gain 3 hours due to the time zone difference. In May, plan for daily highs up to 70°F, and evening lows to 51°F. Cap off your sightseeing on the 26th (Sun) early enough to go by car to Hood River.

The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 27th (Mon): hike along Historic Columbia River Highway State Trail and then identify plant and animal life at Columbia River Gorge National Scenic Area.

For other places to visit, maps, ratings, and other tourist information, read our Hood River tour itinerary planning tool.

Traveling by car from Portland to Hood River takes 1.5 hours. Alternatively, you can take a bus; or take a train. In May, daily temperatures in Hood River can reach 67°F, while at night they dip to 49°F. Wrap up your sightseeing on the 27th (Mon) early enough to drive to Cannon Beach.

Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 28th (Tue): pause for some photo ops at Astoria Column, then take in the dramatic natural features at Haystack Rock, and then admire the majestic nature at Oswald West State Park. On the 29th (Wed), you'll have a packed day of sightseeing: admire the majestic nature at Ecola State Park, then view the masterpieces at Bronze Coast Gallery, and then kick back and relax at Cannon Beach.

To see other places to visit, maps, traveler tips, and other tourist information, you can read our Cannon Beach trip planning app.

Traveling by car from Hood River to Cannon Beach takes 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. When traveling from Hood River in May, plan for little chillier days and about the same nights in Cannon Beach: temperatures range from 62°F by day to 48°F at night. Finish your sightseeing early on the 29th (Wed) so you can drive to Florence.

Florence is a coastal city in Lane County, in the U.S. Kick off your visit on the 30th (Thu): explore and take pictures at Cape Perpetua Visitor Center - Siuslaw National Forest, take a leisurely stroll along Yachats coastline, and then enjoy the sea views from Heceta Head Lighthouse. On the 31st (Fri), you'll have a packed day of sightseeing: experience the excitement of Sandland Adventures, enjoy the sand and surf at Heceta Beach, and then get outside with Sand Master Park - Sandboarding.

To find more things to do, reviews, maps, and other tourist information, go to the Florence sightseeing planner.

You can drive from Cannon Beach to Florence in 4 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 62°F in May, and nighttime lows around 49°F. Finish up your sightseeing early on the 31st (Fri) so you can go by car to Crater Lake National Park.

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.

Kick off your visit on the 1st (Sat): explore the wealth of natural beauty at Crater Lake National Park.

To see maps, where to stay, ratings, and tourist information, read Crater Lake National Park trip planner.

Getting from Florence to Crater Lake National Park by car takes about 5 hours. Other options: do a combination of bus, train, and taxi. Traveling from Florence in May, expect nights in Crater Lake National Park to be about the same, around 49°F, while days are somewhat warmer, around 77°F. Wrap up your sightseeing on the 1st (Sat) to allow time to drive to Bend.

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.

Start off your visit on the 2nd (Sun): cruise along McKenzie Pass-Santiam Pass loop and then admire the majestic nature at Smith Rock State Park. On your second day here, contemplate the waterfront views at Deschutes River and then examine the collection at High Desert Museum.

For maps, traveler tips, where to stay, and other tourist information, read our Bend trip planner.

Drive from Crater Lake National Park to Bend in 2.5 hours. Alternatively, you can do a combination of taxi and bus. Traveling from Crater Lake National Park in June, things will get little chillier in Bend: highs are around 75°F and lows about 45°F. Wrap up your sightseeing on the 3rd (Mon) early enough to travel back home.