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10 days travel ideas Porto-Sintra-Obidos-Alentejo-Madrid no car

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I have booked a flight into Lisbon 23/3/16 from Asia. This will be the first time I am travelling alone and would like to have Sintra-Obidos-Porto-Dougo Valley-Alentejo (for walk), Madrid and thereabouts before joining friends in Lisbon on 2/4/16 for 4 nights. Can anyone assist which route I should take to travel on a budget? Are there any groups / forum where I can join other ppl travelling safely on the same route where I can share costs. I would like to do a bit of shopping in Madrid besides tapas. Thanks

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