Florence 7 Day Itinerary (Tuscany Base)
Seven days completes the list with Cinque Terre, and it comes with a warning attached: this is a genuine stretch as a day trip. Days one through six repeat the 6-day plan exactly, Siena, Pisa and Lucca, San Gimignano, Chianti, and Val d’Orcia with Montepulciano, so day seven is the only new ground. Prefer to skip Cinque Terre entirely and use day seven as a rest day instead? That is a defensible call, and this itinerary tells you honestly why.
Book these before you go
- Check rates on Discovercars for the Chianti and Val d’Orcia car days, one reservation covering both is cheaper than two.
- Check rates on Booking.com for a hotel near Firenze SMN.
- A Cinque Terre day tour on Viator if you decide day seven is worth the long train ride, it at least handles the connections for you.
Day 1: Settle into Florence
Arrive and check into a hotel near Firenze SMN. Our full Florence guide covers the Uffizi, the Duomo dome, and the Accademia in depth, so day one here stays light: confirm the week’s train times and your two rental car pickups.
Day 2: Siena
Regional train on Trenitalia , 1 hour 20 to 1 hour 30 minutes each way, around 30 departures a day from SMN. Give Piazza del Campo and the striped Duomo the full day. Check Terre di Siena’s official tourism site for current Palio dates if your visit lands in July or August.
Day 3: Pisa and Lucca, one train day
Pisa (about an hour, 8 to 13.50 euros) for the Leaning Tower, a separate 20-euro climb ticket via the official opapisa.it site . Our honest verdict on the tower leans skip-the-climb, keep-the-photo. Lucca is another hour to 90 minutes beyond, a walled town for the ramparts walk.
Day 4: San Gimignano
Regional train to Poggibonsi (about an hour) plus local bus 130 (20 to 30 minutes), roughly 6.80 euros one way. The stone towers are worth the transit friction once.
Day 5: Chianti wine road
Rental car, the SR222 (Via Chiantigiana) to Greve in Chianti (about 30 km, 40 minutes) and on to Castellina in Chianti (20 to 25 minutes further). One winery tasting, booked weeks ahead in peak season, plus lunch.
Day 6: Val d’Orcia and Montepulciano
The drive is 2 to 2 hours 20 minutes each way via the A1 (135 km). Val d’Orcia is a UNESCO cultural landscape inscribed in 2004, best seen slowly along loop roads like the SP53 between Montepulciano and Pienza, see the Medici Villas and Gardens UNESCO listing for the wider region’s protected estates.
Day 7: Cinque Terre, or a rest day
The honest transit time to Cinque Terre is 2.5 to 3 hours each way, with a change at Pisa or Empoli, and connections often stretch that to 3 to 4 hours. A day trip means 5 to 6 hours of round-trip train time bookending 5 to 6 hours in the villages themselves, a 7am-out, 8pm-back day that works but shortchanges both ends. If you go, the Cinque Terre Express regional train links all five villages every 10 to 15 minutes once you arrive, so the time on the ground is at least efficient. If you would rather not spend a third of your last day in transit, use day seven to revisit Florence itself (our Florence itineraries cover that ground) or simply do nothing, which is also a legitimate way to end a week of early trains.
| Day | Focus | Transit from Florence SMN |
|---|---|---|
| 1 | Florence orientation | None, already in the city |
| 2 | Siena day trip | Regional train, 1h20-1h30 each way |
| 3 | Pisa plus Lucca | Regional train, about 1h each way |
| 4 | San Gimignano | Train to Poggibonsi plus bus 130, 1.5-2h each way |
| 5 | Chianti wine road | Rental car, SR222, about 40min to Greve |
| 6 | Val d’Orcia plus Montepulciano | Rental car, A1, 2h-2h20 each way |
| 7 | Cinque Terre (optional) | Regional train, 2.5-3h each way, often longer |
If Cinque Terre makes the final cut, book the earliest reasonable outbound train, not the earliest possible one. A 5am departure after six days of early starts costs more in exhaustion than the extra hour in the villages is worth.