We have just booked a flight to Lisbon for next March! Quite excited, we have never been to Portugal.

Not counting travel days we will have 2 weeks. I'm thinking we would like to spend one week in Lisbon, and use public transport for any day trips.

Sintra has been mentioned, it looks pretty amazing!

We love historical towns and sites, small villages, beautiful countryside. I'm not sure Cascais looks interesting to me, we're not into yachts and nightlife, casinos etc.

Obidos? Batalha Monastery? Wineries at Azeitão?

And for the second week, is a week in Madeira too long? Would we rent a car here?

Obidos would be near the top of my list, after fabulous Sintra and its two fairy-tale castles. Obidos appears to be an untouched medieval city from afar - a walled ancient town out in the middle of nothing. Great place to stay - a Parador-type hotel built into the town walls.

Cabo de Rabo is the most western tip of continental Europe - with a light house and waves usually crashing hard into rocks - next stop - the New World! can go by bus from Cascais or Sintra - Cascais itself is a nice old watering hole of the rich and famous - nice beach.

Evora is a longer day trip - better overnight but a really neat old city with many old churches, etc.

Fatima is a day trip for special interests - religious folks into the Fatima thing - one of Europe's most thriving pilgrimage meccas.

Seven days would be a little long - about 4 days too long for me - why not stay in Obidos a day or Evora a day or two - en route to Evora you pass thru many cork plantations.

I've only visited the Portuguese mainland once, so am not qualified to comment on the first part of your questions. Madeira though - I've been over ten times and it's one of the few places in the world I visit multiple times. It's amazing!

Yes definitely rent a car provided you are not fazed by some twisty mountainous roads - the scenery is some of the most dramatic and beautiful anywhere in Europe. A week is fine for a first visit - you won't get bored or run out of things to see and do, particularly if you have a car. Come back to me if you have any more questions about Madeira.

Sintra can be visited easily by train. Then Obidos, a little over touristed but still worth a visit, Evora for sure. You mentioned Batalha; we much preferred Alcobaça. Portugal is a very welcoming and lovely country.

Batalha is a long day trip from Lisbon but a really neat old monatery - a ***-site for sure but not much else around it of interest - rather than staying in Lisbon 7 days why not base in say Coimbra, a lovely university town or Porto, to me one of Europe's most old-looking cities with several neat day trips beside Batalha - Braga and Guimares being really sweet ones.

A week in Madeira is long. We spent a week there but part of that was relaxing. In Portugal consider in different parts of the country Evora, Sintra, Amarante, Braga, Viana do Castelo, Coimbra, and Oporto.

OK, so how difficult is driving in Portugal? I have driven in England, Scotland, Italy, Ireland, Germany, Switzerland, Austria and we have done OK. Anything I need to know about Portugal?

If I take some time off Lisbon and/or Madeira, and we stay somewhere else, I looked at Obidos, Coimbra, Braga, Guimaraes, Amarante, Porto, and Viana do Castello, they are all in the same direction, Evora is not.

So, if we took any time off Lisbon and/or Madeira, it looks like we could base around Porto, (3 hrs from Lisbon?) and have lots to do?

Lots and lots to do from a Porto base besides take the famous Port Wine tours at prestigious Port Houses right smack in the heart of Porto - but Guimares, a national patrimony for Portugeuse, Braga and drives up the neat Duoro River Valley would be tops IMO for starters.

Hit Obidos and Coimbra (be sure to see the classical-built upper town with stately university buildings).

If you've survived driving in Italy, you'll be fine in Portugal.

I completely agree with Gordon on driving.

A week is certainly not too long for Lisbon!

See: http://www.fodors.com/community/euro...ing-lisbon.cfm

I've been back for another visit about the same length since I wrote that, and am thinking of going back again this year.