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From Chile to the Aegean via Madrid - Suggestions and Help appreciated!

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Hi folks! I'm a woman from Chile traveling to Greece & Italy for the first time, 2 weeks each. I'm going with 6 other friends. For our greek journey we're interested in sightseeing and beaches! I've thought about devoting the first week to the islands (Santorini and Mykonos with a side trip to Delos) and the second week to the mainland, mostly Athenas, Delphi and Olympia. Any suggestions about other must-see town in the mainland would be appreciated. I haven't really started planing the Italy part yet.

We're flying from Santiago de Chile to Madrid, arriving at 06:20 on June 3rd. From there I would like to book a flight to Santorini, hopefully arriving there at night.

Thru Vueling.Com I can make the following routes by plane:

(Madrid-Santorini: 242 EUR)
Madrid 09:30
Barcelona 10:45

Barcelona 14:30
Roma 16:15

Roma 17:55
Santorini 21:00

First doubt: Is there enough time between connections? I'm mainly concerned by the Barcelona-Rome bit, because of customs and stuff.

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