4 Days in Florence: Tuscany Day Trips
Four days covers three train-only towns, Siena, Pisa and Lucca, then hands you the keys for a fourth day on the Chianti wine road, the first point on this trip where a rental car actually earns its cost. Want the full spread? The 5 day and 6 day versions extend this same spine with Val d’Orcia and San Gimignano.
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 on opapisa.it go within hours of release
- A rental car for the Chianti day , booked ahead since good pickup slots and winery tastings both fill in peak season
Day 1: Base yourself in Florence
Check into your base near Santa Maria Novella station. Rather than rushing the Uffizi and the Duomo into one afternoon, use today for orientation: walk to Ponte Vecchio, cross Piazza della Signoria, and see the Duomo’s facade from outside. The museums deserve a dedicated visit, our in-city itinerary handles that properly.
Eat dinner 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, both prices and crowds improve fast once you step away from the Campo itself. 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, EUR 8 to 13.50 one way. The Piazza dei Miracoli holds the cathedral, the Baptistery and the Leaning Tower itself. Climbing is optional, the view from the top is not dramatically different from ground level, our Pisa places guide has the full breakdown on whether it is worth booking.
Midday, take the short hop from Pisa Centrale to Lucca, 25 to 30 minutes. Spend the afternoon on Lucca’s Renaissance ramparts, a gentler pace than Pisa or Siena. Evening train back to Florence.
Day 4: Chianti wine road, your one car day
Pick up a rental car in the morning and take the SR222, the Via Chiantigiana, straight into the hills. Greve in Chianti sits 30 to 40 minutes out, and Castellina in Chianti another 20 to 25 minutes past that. A full day realistically covers those two towns plus one winery tasting, book the tasting ahead since good estates fill weeks out in peak season.
Designate a non-drinking driver before you leave Florence, not after the first pour. Return the car by evening, since none of the earlier three days need it and holding onto it longer just risks a ZTL fine back in the city center.
| 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 |
Rent the car for day 4 only. A car works against you every other day on this itinerary, Siena, Pisa and Lucca all have their own restricted zones or no useful center parking, and Florence’s ZTL cameras fine an unregistered plate by mail weeks after the fact.