Florence 6 Day Itinerary (Tuscany Base)
Six days adds Val d’Orcia and Montepulciano, the second and last car day on this list, to the 5-day plan ’s Siena, Pisa and Lucca, San Gimignano, and Chianti. This is a long day trip by any honest measure, an overnight in Montepulciano or Pienza would improve it, but it fits if six days is what you have. Want the full week instead? Our 7-day version adds Cinque Terre, with a caveat.
Book these before you go
- Check rates on Discovercars and book the rental across both car days (Chianti and Val d’Orcia) in one reservation if the dates work, it is cheaper than two separate short rentals.
- Check rates on Booking.com for a hotel near Firenze SMN for the four transit days.
- A Siena and San Gimignano day tour on GetYourGuide if you would rather not manage those two transit days yourself.
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, keep day one to orientation and confirm your week’s train times and rental car pickup.
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 whole 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 (around 10 euros one way), a walled town for the ramparts walk. Both fit one day.
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 full day, two towns, one winery tasting, budget 100 to 180 euros for a small group and book the tasting weeks ahead in peak season.
Day 6: Val d’Orcia and Montepulciano
The drive is 2 to 2 hours 20 minutes each way via the A1 (135 km), which makes this a genuinely long day, four-plus hours of driving for realistically one or two towns. Val d’Orcia is a UNESCO cultural landscape inscribed in 2004, cypress-lined roads and rolling hills, best seen along loop roads like the SP53 between Montepulciano and Pienza. The Medici Villas and Gardens UNESCO listing covers the wider region’s protected estate landscape, if that context interests you before you drive out. If your schedule has any flexibility at all, staying the night in Montepulciano beats doing this round trip in one day.
| 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 |
Fill the tank before you leave Montepulciano. Rural Val d’Orcia stations keep shorter hours than you expect, and running low on a dark countryside road at 9pm is not how you want to end a six-day trip.