5 Days in Florence: Tuscany Day Trips
Five days covers the same Siena, Pisa, Lucca and Chianti days as the shorter versions of this plan, then pushes further out on day five to Val d’Orcia and Montepulciano, a UNESCO landscape that is genuinely a 2 to 2h20 drive each way. Want San Gimignano too? The 6 day version adds one more town to this same spine.
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, booked ahead for both winery tastings and better rates
Day 1: Base yourself in Florence
Check into your base near Santa Maria Novella station. Instead of rushing the Uffizi and the Duomo into one afternoon, use today 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 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. Climbing is optional, our Pisa places guide breaks down whether it earns the ticket price. 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, not after.
Day 5: Val d’Orcia and Montepulciano, the long car day
Start early, this is genuinely a 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 and rolling hills; the SP53 loop between Montepulciano and Monticchiello cuts straight through the classic scenery. A day trip realistically covers Montepulciano plus one more stop like Pienza, and that is a long day for two towns. If your dates have any flexibility, this is the one day on the whole itinerary worth turning into an overnight instead.
| 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 |
Keep the rental car through days 4 and 5 rather than returning and re-renting, it is the only way both car days pencil out without paying for two separate pickups.