Florence Offbeat Day Trips: 5 Days
Five Days: Keep the Rental Car One More Day
The fifth day is a one-word decision: keep the car. Chianti and Val d’Orcia are the only two stops in this family that need one, they’re both south of Florence in roughly the same direction, and returning the rental after a single day when a second UNESCO-listed landscape sits an hour further on is the kind of thing you regret on the flight home. This extends the 4-day itinerary by exactly one day, same spine, same car.
| Day | Focus | Distance / time |
|---|---|---|
| 1 | Florence, settling in | - |
| 2 | Siena + San Gimignano | ~1.5h train / ~1.5-2h train+bus |
| 3 | Pisa + Lucca | ~1h and ~1-1.5h by train |
| 4 | Chianti wine road (car) | ~40 min drive to Greve |
| 5 | Val d’Orcia + Montepulciano (car) | ~2-2.5h drive via the A1 |
Book these before you go: the Siena and San Gimignano tour , the rental car pickup at Florence’s train station for Days 4 and 5 together, and if you’d rather not drive Val d’Orcia yourself, a guided Val d’Orcia and Montepulciano tour instead.
Day 1: Florence, Lightly
Base yourself near Santa Maria Novella; four of your five remaining mornings run from there. An afternoon on Ponte Vecchio, the free sculptures in Piazza della Signoria, and a slower Oltrarno wander sets the tone: this trip is deliberately light on museum queues, since five days already covers four separate day trips. A dedicated Uffizi-and-Accademia day belongs on the Florence-only itineraries if a future trip has room to spare.
Day 2: Siena and San Gimignano
Regional train to Siena runs about 1h27 on the fast services (check Trenitalia , since off-peak trains can take closer to two hours); San Gimignano has no station of its own, so the standard independent route is train to Poggibonsi then Autolinee Toscane bus 130. Piazza del Campo and Siena’s striped Duomo first, then San Gimignano’s fourteen surviving towers in the afternoon light, best covered on a joint tour if you’d rather skip the transfer logistics yourself.
Day 3: Pisa and Lucca
Regional train to Pisa, about an hour. See the tower, cathedral, and Baptistery in Piazza dei Miracoli, skip the 20 EUR climb unless the tilted stairwell itself is the point, then continue to Lucca for its flat, tree-shaded wall-top bike loop, 4.2 kilometers, rentals around 3-4 EUR an hour near the city gates.
Day 4: The Chianti Wine Road
Pick up the rental at Florence’s train station, follow the SR222 Via Chiantigiana to Greve in Chianti (about 40 minutes) and Castellina in Chianti (20-25 minutes further), stopping between the two in Panzano in Chianti for Dario Cecchini’s Antica Macelleria, a quieter lunch stop than Greve’s tour-bus density. Budget 100-180 EUR for a small group and fix a non-drinking driver before the first tasting.
Day 5: Val d’Orcia and Montepulciano
This is the longest drive in the whole family, roughly 2 to 2.5 hours each way via the A1, which is exactly why it earns a full day rather than a rushed add-on. Val d’Orcia is a UNESCO World Heritage cultural landscape, cypress-lined roads and rolling hills, best seen on loop roads like the SP53 between Montepulciano and Monticchiello. Under Montepulciano’s palazzi, Cantina de’ Ricci , a wine cellar built into a 14th-century fortress, is worth more time than most visitors give it, barrel vaults and stone passageways that feel like a cathedral built for wine instead of worship. Cover Montepulciano plus Pienza and stop there; adding Montalcino on the same day turns a long day into an exhausting one, and returning the rental in Florence after dark on unfamiliar roads is its own kind of risk.
Getting Around and What to Book Ahead
Return the rental car in Florence before nightfall on Day 5; don’t drive it into the ZTL-restricted historic center at any point, camera-enforced fines run 80-335 EUR per sector and arrive by mail weeks later. Pisa’s tower-climb ticket needs booking through OPA Pisa up to 90 days ahead if you want the climb; everything else on this itinerary runs on walk-up regional trains or a rental you’ve already arranged.
If five days still leaves Cinque Terre on the list, the 6-day itinerary adds it as an honest, long final day.