Distance from Pisa airport: 82 km (1 hour and 10 minutes)
Historic landmarks.
Day 2: Pis
Distance from Florence: 96 km (1 hour and 20 minutes)
Roman amphitheater.
Day 3: Siena
Distance from Pisa: 94 km (1 hour and 30 minutes)
Medieval architecture.
Day 4: San Gimignano
Distance from Siena: 41.4 km (50 minutes)
Tuscan hilltop town.
Day 5: Montalcino
Distance from San Gimignano: 77.5 km (1 hour and 40 minutes)
Wine tasting.
Day 6: Pienza
Distance from Montalcino: 29.7 km (40 minutes)
Unesco Heritage.
Day 7: Montepulciano
Distance from Pienza: 15.9 km (25 minutes)
Medieval architecture.
Day 8: Lucca
Distance from Montepulciano: 164 km (2 hours)
Medieval wall.
Day 9: Livorno
Distance from Lucca: 28 km (40 minutes)
Seafood lunch.
Day 10: Volterra
Distance from Livorno: 80 km (1 hour and 30 minutes)
Hilltop town.
Day 11: Arezzo
Distance from Volterra: 121 km (1 hour and 50 minutes)
Artistic treasures.
Day 12: Carrara Marble Caves
Distance from Arezzo: 238 km (3 hours)
Natural wonder.
Day 13: Cinque Terre
Distance from Carrara: 50.5 km (1 hour and 10 minutes)
Scenic hike.
Day 14: Pisa
Distance from Cinque Terre: 88 km (1 hour and 30 minutes)
Leaning Tower.
Time and Costs Estimates
Florence (1 full day, $50)
Pisa (1 full day, $40)
Siena (1 full day, $60)
San Gimignano (1 full day, $20)
Montalcino (1 full day, $80)
Pienza (1 full day, $30)
Montepulciano (1 full day, $20)
Lucca (1 full day, $40)
Livorno (1 full day, $60)
Volterra (1 full day, $20)
Arezzo (1 full day, $50)
Carrara Marble Caves (1 full day, $40)
Cinque Terre (1 full day, $30)
Pisa (1/2 day, $20)
Total Estimated Costs: $550
Useful Tips
If you have more time, add a visit to thermal baths in Bagno Vignoni. For a shorter trip, skip Carrara Marble Caves and/or Cinque Terre. Don't forget to try the local cuisine, such as Tuscan bread, ribollita, and T-bone steak.