6 Days in Florence: Tuscany Day Trips
Six days is enough to run every real Tuscany day trip from a single Florence base: Siena, Pisa, Lucca, the Chianti wine road, Val d’Orcia and Montepulciano, then a closing day in San Gimignano’s medieval towers. This is the longest version of this itinerary, if you only have a couple of days, start with the 2 day or 3 day plan instead.
Book these before you go:
- Hotel near Santa Maria Novella station , the starting point for every train day on this plan
- A Pisa Leaning Tower skip-the-line ticket , since peak summer slots go within hours of release
- A rental car for Chianti and Val d’Orcia , the two car days on this itinerary
- A Siena, San Gimignano and Chianti day tour as a fallback if the Poggibonsi bus transfer on day 6 sounds like too much
Day 1: Base yourself in Florence
Check into your base near Santa Maria Novella station. Skip rushing the Uffizi and the Duomo into one afternoon, today is for orientation: Ponte Vecchio, Piazza della Signoria, and the Duomo’s facade from outside. The museums deserve a dedicated visit of their own, our in-city itinerary covers that ground properly.
Eat away from the tourist-priced Duomo blocks, the Mercato Centrale area does better food for less. Confirm tomorrow’s Siena train before bed, regional departures from SMN run roughly hourly from around 7:30am.
Day 2: Siena, the single best day trip from Florence
Early regional train to Siena, 1h20 to 1h30, no reservation needed but validate your paper ticket first. Morning in Piazza del Campo, then the striped Duomo di Siena. Lunch a block off the main piazza. Wander the contrade in the afternoon, evening train back to Florence.
Day 3: Pisa and Lucca, one ticket to two towns
Morning regional train to Pisa, under an hour. The Piazza dei Miracoli holds the cathedral, the Baptistery and the Leaning Tower. Our Pisa places guide breaks down whether the climb is worth booking. Midday, the short hop from Pisa Centrale to Lucca, 25 to 30 minutes, then an afternoon on Lucca’s ramparts and an evening train back.
Day 4: Chianti wine road, your first car day
Pick up a rental car and take the SR222, the Via Chiantigiana, into the hills. Greve in Chianti sits 30 to 40 minutes out, Castellina in Chianti another 20 to 25 minutes past that. A full day covers those two towns plus one winery tasting, booked ahead. Designate a driver before the first pour.
Day 5: Val d’Orcia and Montepulciano, the long car day
Start early, this is a genuine 2 to 2h20 drive each way via the A1, keep the same rental from day four. Val d’Orcia is a UNESCO cultural landscape of cypress lined roads; the SP53 loop between Montepulciano and Monticchiello cuts through the classic scenery. Montepulciano plus Pienza is a realistic day, and a long one, an overnight would improve it if your schedule allows.
Day 6: San Gimignano, the medieval skyline
Return the rental car and go back to trains for the last day trip. Regional train to Poggibonsi runs about an hour, then local bus 130 covers the last 20 to 30 minutes into San Gimignano, a combined fare around EUR 6.80 one way. The town’s stone towers give it the nickname “the medieval Manhattan,” and a few hours covers the walkable center comfortably.
This is the most transit-heavy day trip on the whole itinerary, so build in slack for the bus connection. If the Poggibonsi transfer does not appeal, a guided Siena, San Gimignano and Chianti day tour covers this town without the DIY routing, though you would then skip repeating Siena from day two.
| Day | Focus | Time from Florence |
|---|---|---|
| 1 | Settle into Florence, orientation walk | (base) |
| 2 | Siena | 1h20 to 1h30, regional train |
| 3 | Pisa, then Lucca | Pisa under 1h; Lucca +25 to 30min from Pisa |
| 4 | Chianti wine road | 30 to 40min drive to Greve |
| 5 | Val d’Orcia and Montepulciano | 2 to 2h20 drive |
| 6 | San Gimignano | ~1.5 to 2h via Poggibonsi + bus 130 |
Six days, four towns by train and two by car, and every one of them a genuine day trip rather than a rushed dash. That is the real ceiling for a Florence-based Tuscany trip before you start needing overnights elsewhere.