Florence 5 Day Itinerary (Tuscany Base)
Five days adds the first day trip on this list that actually needs a rental car: the Chianti wine road. The first four days stay identical to the 4-day plan , transit-only trips to Siena, Pisa and Lucca, and San Gimignano, and day five swaps the train for a car. Need six days instead? Our 6-day version adds Val d’Orcia next.
Book these before you go
- Check rates on Discovercars for the Chianti day, and book it as soon as your dates are fixed, good rental stock (and good winery slots) both thin out in peak season.
- 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. Keep the day light on sightseeing, our full Florence guide covers the Uffizi, the Duomo dome, and the Accademia properly, and confirm your Siena train and Chianti car pickup for later in the week.
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, the striped Duomo, and the medieval core the whole day rather than a rushed half of one. 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 , bookable up to 90 days out. See our honest verdict on the tower before deciding whether the climb is worth it. Lucca is another hour to 90 minutes beyond (around 10 euros one way), a walled town for walking or biking the ramparts. 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, 13.60 return. The stone towers are worth the transit friction once, and this is the trip most worth trading for a guided tour if you would rather not manage the train-plus-bus connection twice.
Day 5: Chianti, the first car day
Pick up a rental car in Florence and follow the SR222, the Via Chiantigiana, to Greve in Chianti (about 30 km, 40 minutes), then on to Castellina in Chianti (20 to 25 minutes further). A full day covers two towns plus one winery tasting; budget 100 to 180 euros for a small group across rental, fuel, tolls, tastings, and lunch, and book the tasting itself weeks ahead in peak season. Designate a non-drinking driver before you leave Florence, not after the first pour. Note that this is the only day in this itinerary where a car actually helps, Florence’s centro storico and every hill town above run camera-enforced ZTL zones that fine a rented car 80 to 335 euros per camera crossed.
| 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 |
Return the rental car the same evening if you can. Keeping a car parked overnight inside Florence’s ZTL sectors is how a relaxing wine day turns into a mailed fine three weeks after you have gone home.