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Long Weekend Fly to Pisa for 1 day and spend the remaining time (2-3 days) in Florence.
One Week Dedicate 1 day to Pisa, 3 days to Florence, and 2 days to San Gimignano. Set aside 2 days to drive or cycle through the beautiful Tuscan countryside.
Two Weeks Start with 3 days in Siena. After a day trip to a Chianti vineyard, head to Florence for 3-4 days; then to San Gimignano for 2 days. After 2 days in Cortona, end your trip by driving or cycling through the countryside.