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First Oregon Trip in July

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Hello, my wife and I have never been to Oregon and wanted to take a trip there rather than our normal trip to the San Francisco area. We are coming from Florida and flying into Portland for four and a half days. We like to go wine tasting and also see some outdoor attractions that we can't see in Florida.

I have spent a lot of time on this forum looking at the various discussions of Oregon so I'm not asking to rehash what's already available. This is actually the only site I've looked at to plan this trip. However, I was hoping to get some information to fill in the blanks. Here's what I intend to do based on what people have mentioned on this site.

I plan to spend two days wine tasting and two days seeing some sites and/or Portland. For the non-wine tasting days, i was going to go to the Colombia Gorge area and/or Cannon Beach. As for the wine tasting days, I have a list of wineries recommended here and we were just going to go to as many of those as practical.

Here are my questions.

Is this a viable plan?

Can we just get one hotel in Portland and drive out to these places during the days? I don't know that we like the outdoor places enough to spend more than a day at a time there. That may not be true of the wineries though.

If so, can you recommend a decent hotel in Portland for our needs? It doesn't need to be too nice since we won't be there mush, but if we can walk to a couple of good places or restaurants, that would be a bonus.

Based on what i mentioned, is there any thing specific I would need to know about these areas, specific wineries, this time of year?

Thank you.

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