The only glitch that I can see is that the boat tours at Crater Lake end around mid September, so check on that and see if you need to juggle your schedule a bit or if you will need to just nix that altogether.

For the coast, you could do either as far as where to stay. Both are good locales.

What fog are you thinking of?

We typically have fantastic weather in September.

You may want to check out Bend as it fits with your requests of beautiful scenery, great shops and great food.

The hardest thing about your trip is that there is so much to see here and a week doesn't even scratch the surface. So just be prepared and do what you can and realize you will want to return

You have done a good job aloting your time.

If you don't mind moving frequently, you might find it fun to stay in Cannon Beach, Newport, and Yachats--three very different places.

Just north of Florence, there are interesting sea lion caves: http://sealioncaves.com/home/

When we pass through Bend we like to drive to the top of a cinder cone.

The High Desert Museum is one of several attractions in Bend: http://sealioncaves.com/home/

Spectacular Smith Rock State Park is located about 25 miles north of Bend.

HTTY

As mms said check on whether the boat to Wizard Island is still operating when you will be at Crater Lake. The hike down the Cleetwood Trail is easy going down but not so easy climbing back up after your boat trip.
Bend is just about 2 hours from the north entrance of Crater Lake NP via Rt. 138 East and US 97 north.
From Bend take US 97 N to Madras and US 26 to the turnoff onto Rt. 35 north which will take you past Timberline Lodge down to Hood River. Be sure to see Multnomah Falls even if you don't see the others on the way back to PDX.

Thanks for the info! I will check on the boat schedule.
I read in some earlier posts that it can get foggy in Sept. Not so?? Good!
I have no doubt that we'll want to return!!

I've tweaked our itinerary a bit...here's the new one:

Day 1-Arrive PDX, see a couple of sights in PORTLAND.
2-Spend a.m. in Portland and then tour the Columbia River Gorge via US-30. (Stay in Portland)
3-CANNON BEACH via Astoria
4-NEWPORT via Tillamook, 3 Capes Loop, other scenic areas
5-FLORENCE via aquarium, Yachats, Heceta Head Lighthouse, sea lions
6-PROSPECT via OR-38/138, Steamboat, hopefully driving down one side of Crater Lake
7-BEND via Crater Lake (trolley tour & up other side from previous day
8-PORTLAND via Mt. Hood (Timberline Lodge) and more of river gorge or Portland.

Questions--
On 2nd day, should we do the entire Mt. Hood Scenic Loop or make a u-turn at Hood River (or beyond?) We can return to Portland from Timberline via US-35 or US-26.
If we drive south, down one side of Crater Lake, which side would be best (late in the day)?
Have I missed anything??
FYI, our trip is less than 2 weeks away!

See all that you can of Portland on day 1. Day 2 make the entire Mt. Hood loop. You can see whatever you missed of Portland at the end (day 8).
The Oregon Coast Aquarium is just south of the bridge from Newport. The Sea Lion Caves (tourist trap) is just north of Florence. About 5 miles east of Reedsport on OR Rt 38 is the Deans Creek Elk viewing area. Rt. 138 turns off at the east end of Elkton. If you stay on 138 through Roseburg you will go past Steamboat and Diamond Lake and end up at the north entrance of Crater Lake. There is no need to visit the small town of Prospect. Spend your time in Crater Lake NP. In the late afternoon you should go down the west side of the lake so that the sun will be behind you. Wizard Island is also in the western third of the lake.
You will turn off US 97 (stay straight) onto US 26 in Madras.
The highway (with construction) on the east side of Mt. Hood past Timberline is OR Rt. 35.
If you can't get lodging at Timberline I would suggest a place in Hood River instead of going all the way back to Portland.
FYI the TriMet lightrail red line starts right outside baggage claim at PDX if you didn't want to rent the car at the airport as soon as you got off the plane.

Definitely do the whole Gorge/Hood River/Mt. Hood loop on your 2nd day (going out 84 and back 26) - - and you might have lunch at the Timberline Lodge - bar on the 3rd floor - looking up the glacier.

Also check out the beautiful stained glass windows at the Paul Bunyan/Blue Ox bar http://www.paulbunyanfineart.com/oregon/timberline_lodge.html - and the pool/hot tub (which also looks up at the glacier) - and you might just be tempted to check on reservations - and spend your last night there, as from the Lodge to the Portland airport is only a little over an hour usually.

Thanks Tom. I booked a room in Prospect, as I could not get one at the CLNP lodge. I will check again before we leave.
Day 9 we fly out of PDX fairly early, which is why I booked a room in Portland (at the Kennedy School).
Sounds like we should skip the sea lions!

The other lodging options near Crater Lake are cabins and rooms at Diamond Lake Resort and some cabins at Union Creek.
I was lucky enough last year to win a 2 night stay in a cabin at Diamond Lake plus a 4 hour fishing trip out on the lake.
The listed value on my prize was a bit over $500.

There are rooms available at Diamond Lake, so may switch from Prospect (although I read that the food at the Prospect Hotel is very good). Also, if we have time, we will drive along the west rim that day, so maybe it makes more sense to go on to Prospect, instead of turning around to go back to Diamond Lake??

If we can get a decent rate, we may spend the 2nd night at the Timberline instead of returning to Portland. We will definitely stop there for a meal or snack or coffee.

Is it worth the extra drive to see Astoria, or should we go directly to Cannon Beach?

Thank you BOTH Toms!

I can't tell you about the food at the Prospect Inn.
My DW and I with the friends we invited on the fishing trip had a Sunday morning breakfast at the small restaurant at Diamond Lake Lodge. It was OK. Our Saturday evening meal was trout we baked in the oven in the cabin. I don't remember what we had as a side dish but the trout we caught was fantastic.

The food at the Prospect is great! Fabulous breakfast and dinner has always been excellent as well- I believe better than what you would find at Diamond Lake Resort.

I have stayed at the Prospect several times- no complaints. The back rooms at the Prospect are rather Motel 6 like- but clean. The rooms in the actual Inn are nicer and decorated with antiques.

However, there is more to do at Diamond Lake- nice trail around the lake- you can rent bikes for an easy ride, boats to rent, fishing to be done-
Good luck on the trip

As TomF says - nothing better than fresh trout from Diamond Lake and I caught a string/limit of big beautiful Rainbow (all 20" or longer) when I was last there. Think you can also get fresh trout at the lodge which will be tasty for sure.

And nothing against Prospect - but being on a blue blue lake is much better than being in a small town. And while I grew up in a "small" town - we had beautiful 40 mile long Klamath Lake right next to Klamath Falls.

Thanks for all the info and suggestions. Still undecided about Prospect vs. Diamond Lake...may need to draw a name out of a hat! One more week!

I think your trip is doable, but you'll be traveling on the highways for most of the trip. I would recommend picking one or two areas including Portland which would give you the opportunity to spend more time enjoying the area and less time traveling.