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Spain and Portugal Travel

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Hello, myself and 3 other roommates are studying this fall in Rome. We are traveling early to Rome and plan to travel in Spain and Portugal. We plan to leave for Spain on August 6th and return to Rome on the 18th or 19th. We were wondering if we should get a Eurail pass or what the best way to travel and where we should go we are really interested in Barcelona and Madrid Lisbon and Algarve. We want to be able to enjoy the culture and really take everything in. We are interested in sight seeing the scenery some museums and partying at night. If we traveled by train we planned to go from Rome to Barcelona to Madrid then into Portugal. Do you gave any suggestion on how long we should stay at each place and would a train from Portugal to Rome be complete unbearable?

Thank you very much!

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