MFNYC, we are planning the same sort of trip as you do, at the end of September. We arrive Porto and drive straight to Coimbra for 2 nights. Then Sintra for 3 nights from where we will visit Lisbon, probably 2 full days. Will visit Obidos on our way from Coimbra to Sintra. Then again up north, via Evora, to Porto for the remaining 4 days. From Porto we will drive the Douro Valley (grape harvest time at the end of September!) and further north to Guimaraes and probably Braga, if time allows. We plan on doing a different port wine tasting every day while in Porto!

Loved Obidos: stayed last time in the Pousada, a walled fortress/castle that has been converted..It is always 'booked' well in advance, as it is very popular, and has only 6 units, I believe. The restaurant is spectacular, and if you get there early, request the window seat that looks out over the town, then get somebody to go out and take a photo of you sitting in it...what a souvenier..The town is interesting, lots of cobblestone streets..take good walking shoes, and maybe a stick, if you are in any way impaired..of course, lots of little junky shops, but also some fair walks starting in the town. We loved it.

I always recomment Karen Brown as a source, and suggested itineries.

Ok, I bought a map and Karen Brown's book to get started. We will be arriving in Lisbon very early in the morning. I'm thinking we'll spend the first night there, then leave the next day for Porto.

Does it make sense to take a train to Porto and then rent a car there for the rest of the trip, or should we just get the car in Lisbon, and drive to Porto.

I'm thinking 2 nights in Porto at Guest House Duoro. It looks like a great little place to stay. Thoughts??

From Porto, I'm thinking we'll work our way back down to Lisbon, and end up spending the last 2 night in Lisbon. That give us 3 nights on the road. Where should we spend those 3 nights?

Does this beginning of an itinerary make sense?

On second thought, I'm thinking of, upon arrival in Lisbon, taking the train straight to Porto. Then something like this:
2-3 nights Porto, rent car, possibly Guest House Duoro
1 night - Coimbra area
1 night - Obidos area
1-2 nights - Sintra area
2 nights - Lisbon

Does this make sense? Any hotel recs (thinking in the $150-250 range).

Hi MFNYC; You mentioned 'optimizing you time'. Going ftom Lisbon to Porto and back does not accomplish that. If it were 'open jaw' that would work. You will lose half a day for just eight days. I agree with 'bobthe navigator', only in reverse. We have been in Portugal just twice, boh driving tours. For us, what I would do, is land in Lisbon and drive to Evora. If you like small medevial towns there are many in this area. Beja, Monsaraz, Estremoz, Villa Vicosa and others. Two or three days. Then drive north , visiting Marvao, Tomar on the way to Obidos. [two or three days]. Many sites already mentioned to visit in this area. Then drive south to drop off the car and visit Lisbon for three days. Richard http://en.wikipedia.org/wiki/beja http://en.wikipedia.org/wiki/monsaraz http:en.wikipedia.org/wiki/marvao http://.wikipedia.org/wiki/tomar http://en.wikipedia.org/wiki/evora http://en.wikipedia.org/wiki/obidos

Unfortunately the open jaw option wasn't available with our frequent flyer miles so we had to book RT Lisbon. Our flight is scheduled to arrive in Lisbon at 6:15am which is too early to do anything, so my thought was, we'd take the train to Porto, and at least we can sleep for a few hours (it's about a 2.5 - 3 hr ride depending on the train). I think we'll be too exhausted to drive anywhere when we first arrive in Lisbon (I don't sleep well on planes).

I see on the map that fitting in both Evora and Porto doesn't make any sense at all so that's not an option. They are too far apart with no good direct route in between, so we either have to focus on the coastal thing, or the inland medieval town thing, maybe going a little north.

I guess the bottom line is I have to narrow down to a specific area to focus on. When I look on the map, the recommended places to visit are literally "all over the map", so it's confusing.

I went for Porto, just because it sounded like both an interesting and beautiful area. I like medieval towns as well (been to a few in Italy).

It's much easier to plan a 1 city trip! Luckily I have several months to get my act toegther, although I'd like to start researching accommodations, but unitl I know where I'm going, it makes no sense.

"1-2 nights - Sintra area
2 nights - Lisbon"

Sintra is a very easy day trip from Lisbon, I'd reduce the number of times I had to move between hotels and change that to 3-4 nights in Lisbon.

Thursday, That thought occurred to me when I relooked at the map and realized how close they all are. I'm thinking similar for 2 nights on the road between Porto and Lisbon, that possibly I could stay in 1 place for 2 nights instead of 1 night in 2 different places.

So maybe
3 nights Porto
2 nights somewhere accessible to Coimbra and Obidos areas
3 nights Lisbon (visit Sintra)

Are you driving from Porto to Lisbon? Because if so (or maybe even if going by train), I'd stay in Coimbra (don't miss Conimbriga while there) and visit Obidos on the way to Lisbon. I visited Obidos by bus from a place near Caldas da Rainha, and I think two-three hours would be enough.

BTW, my Lisbon TR is here: http://www.fodors.com/community/euro...ing-lisbon.cfm and my north Portugal TR is here: http://wilhelmswords.com/rtw2004/index.html

Yes, I'm thinking we'll rent a car to travel from Porto back to Lisbon.

thursday, your TRs are wonderful!

Why thanks, MFNYC! So is Portugal - easy to write about good places.

I'd consider staying in Coimbra two nights, and on the drive to Lisbon spend part of the day in Obidos.

There were other little towns near Obidos that looked appealing that I wasn't able to reach - I think Nazare was one of them?

Have a seafood lunch overlooking the sea in Nazare.

I started a new, more speecific thread so no need to add ot this one.
http://www.fodors.com/community/euro...october-10.cfm

Thanks all.