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Help with Tuscany Itinerary

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We are two couples with 8 nights in Tuscany, arriving and departing from Pisa Airport. We arrive mid-afternoon from Brussels on April 21 and we want to spend a few days in Florence and the rest of our time exploring the hill towns and Val d'Orcia. We have accommodation near Chianciano Terme for as many nights as we like but I'm looking for advice on how to divide our time. Also, where should we rent our vehicle for the week? Right from the Pisa Airport or should we train to Florence, spend two nights there and rent a car in Florence and continue on? Our return flight is at 10:30 a.m. on April 29th from Pisa. Would it be advisable to spend our last night in Florence and train to Pisa on the morning of our return flight? Appreciate your advice.

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