Hello. My wife and I are flying to Portland from Chicago this fall around Columbus Day. We'll arrive around noon Thursday 10/9 and leave around noon Monday 10/13.

We love checking out different cities, interesting neighborhoods, and just hanging around... nothing too touristy. However, we do want to hit a couple of places outside the city, so here's my thoughts... let me know if this is realistic.

Thursday: Arrive and just check out Portland for the rest of the day.

Friday: Leave early and head to the coast. I'd like to see Cannon Beach and nearby for a few hours. Then head south and east for some wine tastings and dinner in the Willamette Valley. Back to Portland that sometime that night. Is this too much for one day?

Saturday: Explore the city.

Sunday: Columbia River Gorge, Multnomah Falls, and surroundings. Back to city in afternoon.

Monday: Not much time before heading back to Chicago.

Any help would be appreciated!

Driving out to the Coast is a good day, (90 min from downtown Portland by Rt 26) a drive back through wine country is possible and so is dinner. It will be a very full day, I would have dinner in town instead..but the "wine country" never held that much appeal for us .
Sat and Sun sound great !
The Falls is about 30-4- min from downtown- take the Historic Highway, stop at the Womens Forum Lookout, photo ops! stop at Vista House , photo ops!! and drive slowly along, stopping at ALL of the waterfalls!
If you walk across the scary bridge at Multnomah Falls, be sure to have someone take a picture of it...lol.

Enjoy Portland..
* small pleasant surprise-PDX is a fabulous airport *

Friday would be a long day but it you like to drive it's very beautiful. I agree with scarlett, you'd be better off to have dinner in Portland. When we were in the wine country last year we couldn't find a really good restaurant. Two good winery stops were Domain Serene and Sokol Blosser.

Yeah, like Scarlett says, Friday will be tight. Given that wineries close 4:00-5:00pm, and most are a 2 hour drive from Cannon Beach, you'll have limited time in both areas. And once you see it, you won't want to short-change the coast, especially if the weather's nice. So consider planning the wine tasting on Saturday after the Columbia River Gorge. I'd also agree with Scarlett; of the major things you've planned, wine tasting should be the optional. If it fits, okay....

As the others have said, you have too much on tap for Friday. Also keep in mind that you start to lose daylight, so doing just the coast that day makes more sense.

If you want to taste, there are places in downtown you can do that without having to leave the city.

jnjfraz--Sorry you missed the good places down here. Next time you visit, let us know. There are some excellent places all around the wineries for meals.

Yes, Friday is too much for one day (just my opinion). It could be done for sure but would be a lot of driving for not much time in each place. Maybe that's OK with you.

Thanks for the replies. So maybe we could spend a little more time on the coast Friday and maybe check out some wineries on Saturday or Sunday afternoon. We've done the Napa/Sonoma thing, so we don't want to get too involved in tours and such... just check out the area and taste a few wines.

Since we may spend a full day driving between Portland and the coast, what recommendations do you have other than Cannon Beach? Restaurants? Sights? Scenic routes?

Thanks again.

On the north edge of Cannon Beach is Ecola State Park. A must see! And then at CB is Haystack Rock. A good restaurant in town is the Wayfarer, which looks right out to Haystack Rock. The tidepools at the base of Haystack Rock are fantastic at low tide.

A really nice trip is the three capes scenic loop. From Tillamook down to Cape Kiwanda the drive is stunning with some great places to stop off, such as Cape Lookout and Cape Meares. At Cape Kiwanda there is a big dune there that if you walk to the top, the far edge has some great scenery.