Tuscany Hill Towns and Vineyards: Florence, Siena, Pisa and San Gimignano
A deeply immersive 5-day exploration of Tuscany using public buses and regional trains. Base in Florence to tour the Renaissance masterpieces, visit the Leaning Tower of Pisa, and base in Siena to explore medieval towers and rolling cypress hills.
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Intercity route legs
Day-by-day itinerary
Florence Historic Core and Oltrarno
FlorenceArrive in Florence. Visit the Duomo complex, walk through Piazza della Repubblica, and cross to the Oltrarno quarter for artisan leather shops and ribollita soup.
Uffizi and Piazzale Michelangelo Sunset
FlorenceTour the Uffizi Gallery. Wander the Boboli Gardens and climb to San Miniato al Monte church for evening Gregorian chants and panoramic views.
Day Excursion to Pisa
PisaTake the 50-minute regional train to Pisa Centrale (€9.30). Walk through the pedestrian town to Piazza dei Miracoli. Enter the Cathedral and photograph the Leaning Tower.
Express Bus to Medieval Siena
SienaTake the 1h15 Autolinee Toscane Rapida bus directly to Piazza Gramsci in Siena. Settle on the brick pavement of Piazza del Campo and tour the zebra-striped Gothic Duomo.
San Gimignano Towers and Tuscan Wine
SienaTake the local bus to San Gimignano to admire the 14 surviving stone towers. Sample Vernaccia white wine and return to Florence or Rome by rail.
✂️ What I Would Cut If Short on Time
Skip Pisa and focus entirely on Florence and Siena for a 3-day Renaissance and medieval focus.
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