Travel agendas from Spain to Portugal or visa versa for approx two weeks?

Sam, we prefer to rent a car when we visit/explore the two Countries. That way we can go to obsure locations. But, it can be very expensive trying to use a rental car in two different countries. To get around that problem we just hop a flight on one of the lo-cost inter-EU airlines. Find these airlines on Whichbudget.com. Be careful and read all of their restrictions (luggage size and rates). When we did Portugal we flew in and out on Ryan Air. Last year we used Vueling in Spain; my Cousin used another airline.

I agree, you can fly easily and cheaply between Madrid and Lisbon. Make sure you get an open-jaw flight to-from the US to avoid backtracking. Renting a car in one and dropping it off in the other has been reported to be very high cost for the foreign drop-off fees. More than a flight cost. As far as I know, there is no daytime train linking Madrid and Lisbon. You could get close to the border visiting small towns/cities in Spain and then maybe take the bus into Lisbon. But I'm not sure of the timing or logistics of that.

Thanks for the great ideas. I am thinking about travel via train in Portugal first. Then I would like to possibly take a train from Portugal into southern Spain, depending on available schedules, and then on to Madrid and Barcelona. The issue is which cities in southern Spain first from Portugal. Any further ideas?

The rail networks of the two countries do not connect in the south. Frankly - what time do you want to spend on these destinations on your wish list and what little do you have? I suggest you do some real research.

Thanks again for the posts. As I do the research, you are right: we need more time to do what I posted earlier. If I keep to my two week time frame, then I must limit what I can do in both countries. I have been in Madrid & Barcelona before. I would skip Barcelona this time around and use Madrid/Lisbon as an entrance point into the region and finish up at the other city . My big issue then is how to do the cross border change to/from the two countries with minimal transportation constraints and greater flexibility to travel to other smaller cities. I want to avoid the midnight train between the Madrid/Lisbon if at all costs. Research I am doing.....

I'm not sure there is a train from southern Portugal into southern Spain. But for sure there are bus connections. If you're going into southern Spain, Sevilla is a must. Plus maybe some of the white hill towns, or the southern coast. A ferry to Morocco is an option too. But your first post stated you had 10-14 days to travel. Now you say you want to travel Portugal, then southern Spain, then Madrid and finally Barcelona. That's too much in less than 2 weeks.

As has been said, consider flight Madrid to Lisbon. As I said there is no connectivity for train in the south. This is the bus company which can link you from Lisboa to city destinations in Spain - http://www.alsa.es/en#capa_internacionalto destinations This may be of use - http://www.algarvebus.info/001.htm#seville