Sample Itinerary
Classic Tuscany in 7 Days
7 days — Tuscany's greatest hits: Florence, Siena, and the hill towns, with a wine detour.
The route
The classic first-timer's loop. Do the art in Florence, the medieval in Siena and San Gimignano, and slow down in the Val d'Orcia hill towns. Rent a car only for the rural stretch — the cities are train-friendly.
7 stops
Town · Toscana
Florence
Florence is worth two full days minimum and handles three well. It is small enough to walk end to end, which means it is also small enough to feel crowded — book the Uffizi and the Accademia ahead or you will waste half a day in line.
Town · Toscana
Siena
Siena is worth a night, or a long day trip from Florence. It is the best Tuscan base if you want a real city rather than a village. The Piazza del Campo alone justifies the visit.
Town · Toscana
San Gimignano
San Gimignano is worth a half-day. It is beautiful and very crowded — go early or late, and don't stay overnight unless you want the town empty. The towers are the point; the souvenir shops are not.
Basilica · Lazio
St. Peter's Basilica
Essential. Go early, climb the dome if your knees allow, and accept that it is a pilgrimage site as much as an artwork. Bernini's baldacchino and the Pietà define it.
Castle · Puglia
Castel del Monte
Worth a detour. The interior is empty; the octagon is the point. Go for the geometry and the view, not for furnishings.
Piazza · Toscana
Piazza dei Miracoli
Essential as a first sight; the tower gets the crowds but the Baptistery acoustics and the Camposanto fresco fragments are the real draw.
Garden · Toscana
Boboli Gardens
Recommended. Pair with Palazzo Pitti. It is large and shaded; budget two hours and a hat.
Ready to make it yours?
Build a custom itinerary at Travel Itinerary Co
This is a sample route to spark ideas. When you're ready for a real, day-by-day itinerary — paced to your dates, transport, and budget — take it (and your saved places) to Travel Itinerary Co.
Start a custom itinerary