Off-Topic

Luckily for you I've been obsessively researching a similar trip all day even though it will almost certainly be of no benefit to me. I found flights to/from Portland for under $500 RT. Comparable pricing for flying into/out of SFO or Seattle too.

What week? At less than 3 weeks out, fares are only going to get worse unless you do absolute last minute with 3 stops.

How's the weather out there in late August? Airfare gets a lot cheaper like the third/fourth week of August versus anything before then.

Toogs, might wanna move your trip up a couple weeks. Pretty formidable guest list at first glance.

I'm actually doing this trip, though booking it REALLY last minute. I have a flight and a car, and two days planned. They say to book Crater Lake like a year in advance, but I called and they had one room available one day, and a different room available the next day. I have to switch rooms - lol. Oh well.

Any hotel recs in Portland? I guess near the airport would be nice, but not totally necessary. Near stuff to do (restaurants, breweries) would be nice too.

7/14 - BWI to PDX, arrive 11:00pm
7/15 thru 7/17 - ???
7/18, 7/19 - Crater Lake. Hiking 7/18, booked a touristy boat trip for half the day on 7/19.
7/20 - Drive back to Portland, arrive by evening, probably a decent dinner (any recs <$200?) and bars
7/21 - fly home @ 11:00am

Does something like this look like a decent itinerary for two days? http://www.travelportland.com/things-to-see-and-do/activities/portland-oregon-day-trips-itineraries/oregon-coast

Also, I'm definitely doing breweries in the Portland area one day - probably 7/15. Will everything be open on a Sunday? Which places have the best tours?

GB can probably help w/ some hotel recommendations, but I always stayed in the HIX on 23rd & Vaughn in Portland. There are oodles of restaurants & shopping nearby on 23rd & 21st streets. That section reminded me a lot of downtown Frederick for reference. You're in Portland but it doesn't feel like the big city. Plus, Forest Park, the 2nd largest city park in the U.S., is nearby. I would go hiking or running there every night after work. Lots of great trails there -- it's like you're on the forest moon of Endor while still being in the city.

As for the coast, I did it in one day, starting and ending in Portland. I started at the crack of dawn and left at sunset, but it's light out pretty late out there right now. I drove down I-5 to Eugene, across to Florence, up US-101 to Astoria and then US-30 back to Portland. It's a long day, so I still had time to visit the sea lions caves, all the lighthouses, pretty much any interesting view I saw, Haystack Rock, Ecola Park, Three Capes, Yaquina Park, etc. What you probably should do is start in Astoria and then make your way down. Spend the night in either Eugene or Medford if you want to go that far south. Then you'll only be 2 hours or so from Crater Lake.

Hit me up if you need any specific recommendations.

You may want to consider staying in Eugene, Medford, OR or Grants Pass on the day you go to Crater Lake. Medford is closest to Crater Lake at ~85miles . Eugene is the furthest away from the lake at ~140 miles . The good thing about Portland -> Eugene -> Crater Lake is that it is least miles. The good thing about the Grants Pass / Medford route is you get to see them (and Eugene and Crater Lake). (If you stay in Euguene, be sure to pee on Nike.)

When I go to Crater Lake, I'm coming up from from NoCal so I usually time my trip to arrive in Medford in the evening. I like to eat at 38 Central and then get a good nights rest and leave to head into the park by 7:30AM. Grants Pass and Medford are neat towns but have a sprawling suburban side to them because of retirees and Californians.

Crater Lake is one of the most beautiful places in the world and top 5 National Park in USA for my money and I've been to most of the big ones.. You can do it in a day from Medford. Klamath Falls is very close and worth doing also. And lastly, you can do some great white water rafting if you are so inclined. Oregon is a great state. Porland, Bend, and Cannon Beach are also quite nice as others have correctly stated.

There are many options for the coast depending on how much you want to see and how much time you want to use up. You could see all kinds of great stuff if you just ran out to the coast and headed north when returning from Crater Lake, but that'd be a pretty big time commitment depending on how far up you go.

I've done the big loop from Portland up to Astoria (I-5 to 30) and down the coast to come back either from around Cannon Beach (26) or Tillamook (6). I like Astoria, but that is also a time commitment...a pretty full day, especially if you go all the way to Tillamook. Usually what I do when guests are out is run out 6 to Tillamook, get on the 101 and cruise up to Seaside/Cannon Beach and then head back to town on 26. This can be done in about a half day and there's a lot of great shit to see like Oswald State park, Hug Point, Ecola State Park, and lots of cool little towns.

Honestly, if you're looking to spend a good amount of time out there I'd probably recommend going south instead of all the way up to Astoria (unless you're a history buff or Goonies fanatic). I'm a big fan of the 3 capes scenic drive, which goes down to about Pacific City. You also pass some decent dunes (Sand Lake).

Does this sound reasonable?

Saturday 7/14 - arrive late in Portland
Sunday 7/15 - do Portland stuff, stay in Portland
Monday 7/16 - leave early, head towards Astoria, go south down the coast from Astoria (doing whatever we want along the way), stay somewhere on the coast (where's a good stopping point where we won't mind spending a night?)
Tuesday 7/17 - go from wherever we stayed the night before to Eugene, wineries on the way (what's a good route?), stay in Eugene
Wednesday 7/18 - leave early from Eugene, go to Crater Lake

Haystack Rock (Cannon Beach), Hug Point, Random spot.

Doesn't really matter as long as there's stuff to see/do along the way. I can't imagine we'll have more than 5 hours of straight driving at any point, right?

Yea like Bnyman said, there really won't be much dead driving. The only boring part will be when you're on I-5 on the way up to Astoria and then I guess heading back to Portland. You have a handful of options depending on how much civilization you need for the overnight. Remember a lot of the towns on the coast are little old fishing communities or cutsie B&B type towns, so there isn't goign to be a Holliday Inn across from a Best Western everywhere.

I would probably try to make it down to Lincoln City or Newport (both fairly big) to take the sting out of the next day's drive over to Crater Lake, but there are options before that. From PDX to Astoria then down to Newport is about 5 hrs driving, but it'll probably be double that since you'll be stopping to smell the roses along the way.