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lodging near Florence, way to get there from New England, US

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We have lodging in the Tuscany area between Florence and Siena and are wondering the best way to get there from New England. We could fly out of Boston and go direct to Rome and drive to our lodging or fly to Florence which we know would mean a connecting flight somewhere (Rome being one option). So the question is: would it be wiser to fly to Florence with a connecting flight (Munich, Paris, Amsterdam are showing up on some flight plans) and drive to our destination or would it be better to fly direct to Rome and get ourselves to our destination? When I say "better", I mean easier, faster, least amount of stress, etc.
Any ideas would be helpful. Thanks!

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