Florence Offbeat Day Trips: 6 Days
Six Days: Where Cinque Terre Finally Earns Its Spot
Six days is the point where the most day-trip-marginal destination on this whole list, Cinque Terre, becomes worth attempting. Florence to Cinque Terre runs 2.5 to 3 hours each way, so this only gets its own day once the trip is already long enough to absorb a genuinely long one without wrecking everything before it. This extends the 5-day itinerary by one final train day; nothing before it changes.
| 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 |
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 included for Day 6, since the train connections alone (a change at Pisa or Empoli) eat a real chunk of the day if you’re managing them yourself.
Day 1: Florence, Lightly
Base yourself near Santa Maria Novella; five of your six remaining mornings start there. Ponte Vecchio, the free sculptures in Piazza della Signoria, and a slow Oltrarno wander are enough for day one; a full Uffizi-and-Accademia day doesn’t fit six days already carrying five separate trips out of the city, and belongs instead on the Florence-only itineraries .
Day 2: Siena and San Gimignano
Fast trains reach Siena in about 1h27 (check Trenitalia for the day’s schedule); San Gimignano needs a train to Poggibonsi plus Autolinee Toscane bus 130, which is why pairing both on one organized day is the simpler call. Piazza del Campo and the striped Duomo first, then San Gimignano’s towers in the afternoon.
Day 3: Pisa and Lucca
An early train to Pisa, about an hour, covers Piazza dei Miracoli in two to three hours; skip the 20 EUR tower climb unless the tilted stairwell is genuinely the point. Continue to Lucca for its flat, 4.2-kilometer wall-top bike loop, the gentlest stop on this whole itinerary.
Day 4: The Chianti Wine Road
Pick up the rental car at Florence’s train station and drive the SR222 Via Chiantigiana to Greve in Chianti, then Castellina in Chianti, stopping in Panzano in Chianti between the two for Dario Cecchini’s Antica Macelleria, quieter than either official stop on the route.
Day 5: Val d’Orcia and Montepulciano
Keep the rental for the roughly 2 to 2.5 hour drive south to Montepulciano 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 chief among them, a 14th-century fortress turned barrel-vaulted cellar, are worth more time than a rushed itinerary usually gives them. Cover Montepulciano and Pienza, return the car in Florence that evening, and stop there.
Day 6: Cinque Terre, Honestly
This is a long day and there’s no point pretending otherwise: 2.5 to 3 hours out with a change at Pisa or Empoli, sometimes stretching to 3-4 hours depending on the connection, meaning a full day trip runs 5-6 hours of round-trip train time bookending 5-6 hours in the villages. That’s a 7am-out, 8pm-back day. Once there, the Cinque Terre Express regional train links all five villages every 10-15 minutes, and the national park’s own Cinque Terre Card covers train-hopping between them plus trail access. If your schedule genuinely has zero give, this is doable. If it has even one spare night, moving this day to an overnight in Levanto or La Spezia turns a rushed dash into an actual visit.
Getting Around and What to Book Ahead
Return the Chianti/Val d’Orcia rental in Florence before Day 6 starts; you won’t need a car again after that. Pisa’s tower-climb ticket needs booking through OPA Pisa up to 90 days ahead if you want it. Everything else on this itinerary runs on regional trains bought same-day or the rental you’ve already arranged.
If you’d rather close the trip with one more slow day in Florence instead of packing up right after Cinque Terre, the 7-day itinerary adds exactly that.