Give me Ideas for an Oregon Vacation

Hopefully I can get all those days covered in 5 days. Where do you suggest I fly into and out? I’m open to fly into Seattle, Portland, Redmond (Bend) but plan to fly on Delta as I have a lot of priority with them through work travel

They're just suggestions, depending on your interest.

If you only have five free days, you can easily fill those just around Bend & Crater Lake. Lots of outdoor activities in those areas. I wouldn't fly to Seattle - too much of a drive. If you're not doing the coast or Willamette, just as well fly to Redmond if they meet your airline needs. I've never flown into there.

Not to be mean, but have you looked at a map?
It is 16 hours of driving from Sacramento to Bend
It is 16 hours of driving from Bend to Seattle while doing the coast and the Mts you have listed on the way
That is with no stops and no 2 yr old accounted for

I'm a big fan of driving and packing stuff into small windows, but that will not work. You can do it but everyone will be miserable and you will see nothing.

I did 6 days between Portland the Oregon coast last year and barely scratched the surface with Portland for 2.5 days driving out to coast and using Cannon Beach as home base for 3 more days.

You should cut out literally half of that.

Redwoods NP

Base near Bend. So much to see and do.

We loved staying at the Sun River Resort!

Definitely do a day trip to Crater Lake. One of the most amazing sites in the world.

Selected Photos From A Prior Trip

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cheapest travel days are Tuesday-Tuesday

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Something to keep in mind as I've done this plenty of times myself. It doesn't make any sense to spend $200/ night on a hotel plus likely multiple meals eating out and other expenses, to save $50 or $100 each on 2 flights.

At the same time, if you are in the south with a 2 year old and don't travel a ton for work you likely won't make it back to the Pacific Northwest for a long time. So adding an extra day to go somewhere you likely won't re visit for 20 years is well worth it.

People that are old and retired and have times on their hands love to say "you can always go back". But those of us with kids, careers, etc. its just not easy to go back to Italy, or Seattle, or Brazil, etc for many many years.

He would be young enough to be lap infant but quite a few people have advised since it’s a long flight day from New Orleans to buy his own seat

We decided we’re gonna make it easy. Land in Portland and drive out to the coast for 2-3 days. Then drive inland to bend and stay there the rest of the trip and go see various things with Bend as our base camp. And MAYBE catch Mt Hood our last day back driving to Portland before flying out the next morning