Would it be more cost effective to stay in Madrid for the 1st portion of my trip (September 2nd - September 7th)vs. staying 3 days in Madrid and 2 days in Barcelona? If so, what day trips would be available (ie Barcelona and Valencia) and associated transportation costs? (i.e., Europass or purchasing train pass in Madrid, etc.) I feel we are firm on going to Naples, Italy for the 2nd portion of our trip.
It would be cheaper to stay in one place due to transportation cost, but then you would miss out on Barcelona. I would recommend 3 nights in Madrid and 2 in Barcelona if that is you available time. You can day-trip from Madrid to Toledo or Segovia, but I would recommend only one at most. There is a lot to see in Madrid. Taking the train is the simplest way to get between the two cities. although airfare is competitive price-wise. For your flight between Barcelona and Naples, try this link: www.skyscanner.net