We're planning a 3-week trip in Oct. 2015 -- Heart of Italy in 9 days plus Siena and Assisi plus about 7-9 days in south (Pompeii, Sorrento, Capri). If we start in south, should we fly into Naples? If we end up in Florence (end of the RS tour) which airport would we use to fly back to Boston?
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San Francisco Bay Area (USA)
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You can land in Naples (NAP) and return from Florence (FLR).
However neither NAP in the south nor FLR in Tuscany (or nearby airports, such as Pisa and Bologna) have direct non stop from/to BOS.
Whichever solution you want, you will have to go through some other EU hub.
Rome (FCO) is in between (about 2hrs from either Florence or Naples area by train) and being the largest hub in Italy, and one of the largest in EU, might have more options at better prices. Check prices with Air Lingus from BOS to FCO via DUB. They often have the best prices from BOS to Italy. Then compare it with the open jaw to NAP with return from FLR. The latter will save you the train fare from/to Rome, but flying to Rome is usually cheaper.