50 days in Portland & Bend Itinerary

50 days in Portland & Bend Itinerary

Created using Inspirock United States vacation planner

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Plan created by another user. Make it yours
1
Portland
— 24 nights
2
Bend
— 24 nights

24
nights
Portland

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Explore Portland's surroundings by going to Dolphin & Whale Watching (in Gloucester), Rockport Breakwater (in Rockport) and Boston (Otis House, Freedom Trail, &more). Next up on the itinerary: get to know the fascinating history of Marginal Way Walkway, enjoy the sea views from Nubble Lighthouse, explore the galleries of The House of the Seven Gables, and take in nature's colorful creations at Coastal Maine Botanical Gardens.

To find ratings, where to stay, and tourist information, you can read our Portland planner.

Redmond to Portland is an approximately 11.5-hour flight. You can also drive. The time zone difference when traveling from Redmond to Portland is 3 hours. When traveling from Redmond in July, plan for slightly colder days and a bit warmer nights in Portland: temperatures range from 79°F by day to 61°F at night. Wrap up your sightseeing on the 25th (Sat) early enough to travel to Bend.

Things to do in Portland

Parks · Outdoors · Historic Sites

Side Trips

Boston, Salem, North Conway, Ogunquit, Boothbay Harbor
Highlights from your plan
Dolphin & Whale Watching
Marginal Way Walkway ©
Marginal Way Walkway
Duck Tours

24
nights
Bend

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.
You'll find plenty of places to visit near Bend: East Lake (in La Pine), Redmond (Tumalo Mountain & Smith Rock State Park) and Dee Wright Observatory (in Blue River). The adventure continues: let the river carry you with a rafting and tubing tour, trek along Pilot Butte State Scenic Viewpoint, explore the activities along Deschutes River, and examine the collection at High Desert Museum.

To find more things to do, other places to visit, reviews, and other tourist information, you can read our Bend travel itinerary planner.

Getting from Portland to Bend by flight takes about 14 hours. Other options: drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 3 hours traveling from Portland to Bend. Traveling from Portland in July, you will find days in Bend are somewhat warmer (85°F), and nights are little chillier (52°F). Finish up your sightseeing early on the 19th (Wed) so you can go by car back home.

Things to do in Bend

Parks · Outdoors · Nature

Side Trips

Sisters, Redmond, Sunriver, Oakridge, Prineville
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
River Rafting & Tubing
Deschutes River ©
Deschutes River

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