A Week Around Florence, Off the Beaten Path
Seven Days: All Six Day Trips, Then a Day That Isn’t One
By day seven, this itinerary has already done every genuine day trip this family has to offer: Siena, San Gimignano, Pisa, Lucca, the Chianti wine road, Val d’Orcia. There’s nothing left to add except more of the same, so day seven does something different instead, a second, unhurried day back in Florence, the one this itinerary deliberately skipped on day one. This is the 6-day itinerary with a closing day bolted on, not a new structure.
| 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 |
| 6 | Cinque Terre | ~2.5-3h each way by train |
| 7 | Florence, the second time | - |
Book these before you go: the Siena and San Gimignano tour , the rental car pickup at Florence’s train station for Days 4-5, and a Cinque Terre day trip with transport for Day 6, since all three are the genuine sell-out or logistics risks on a week this packed.
Day 1: Florence, Lightly
Base yourself near Santa Maria Novella. Ponte Vecchio, the free open-air sculptures in Piazza della Signoria, and a slow first pass through the Oltrarno are enough; save the deeper Florence time for day seven, once six day trips have made the case for what this city is actually worth returning to.
Day 2: Siena and San Gimignano
Fast trains to Siena run about 1h27 (check Trenitalia ); San Gimignano needs a train to Poggibonsi plus Autolinee Toscane bus 130, so pairing both on one organized day is simpler than managing the transfer yourself. Piazza del Campo and the striped Duomo first, San Gimignano’s towers in the afternoon light.
Day 3: Pisa and Lucca
An hour by train to Pisa covers Piazza dei Miracoli in two to three hours; skip the 20 EUR tower climb unless the stairwell itself is the draw. Continue to Lucca for its flat, 4.2-kilometer wall-top bike loop, the calmest stop on the whole week.
Day 4: The Chianti Wine Road
Pick up the rental at Florence’s train station and follow the SR222 Via Chiantigiana to Greve in Chianti, then Castellina in Chianti, stopping at Panzano in Chianti in between for Dario Cecchini’s Antica Macelleria, quieter than either official stop.
Day 5: Val d’Orcia and Montepulciano
Keep the rental for the roughly 2 to 2.5 hour drive south via the A1. Val d’Orcia’s UNESCO-listed cypress hills reward the SP53 loop toward Monticchiello, and Montepulciano’s underground wine cellars , Cantina de’ Ricci especially, a 14th-century fortress turned barrel-vaulted cellar, deserve more time than a rushed day usually allows. Cover Montepulciano and Pienza, then return the car in Florence that evening.
Day 6: Cinque Terre, Honestly
A long day and worth planning as one: 2.5 to 3 hours out with a change at Pisa or Empoli, occasionally stretching to 3-4 hours, meaning 5-6 hours of round-trip train time bookending 5-6 hours in the villages themselves. The national park’s Cinque Terre Card covers the regional train hopping between all five villages plus trail access once you’re there. This is the one day on the whole week where an earlier start pays off directly in extra time on the ground.
Day 7: Florence, the Second Time
This is the day this itinerary owes Florence after six days of leaving it. Cross into the Oltrarno properly this time, slower than day one allowed, and wander streets most week-long trips never circle back for. Skip trying to cram in the Uffizi or Accademia at the last minute; both need booking weeks ahead in peak season, and a same-week walk-up attempt usually fails anyway. If deep museum time genuinely matters for a future trip, the Florence-only guide is built for exactly that, unrushed.
Getting Around and What to Book Ahead
Return the Chianti/Val d’Orcia rental in Florence before Day 6; Pisa’s tower-climb ticket needs booking through OPA Pisa up to 90 days out if the climb matters to you. Everything else across the week runs on same-day regional trains or the car you’ve already arranged.
For the full logic behind why these six trips, in this order, and what a shorter version of this same week looks like, see the Florence, Italy day-trip guide .