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Cities, regions, hilltop towns & driving distances — printable travel guide


| Region | Landscape | Best For | Anchor Town | Villa Note |
|---|---|---|---|---|
| Chianti | Vine terraces, olive groves, stone farmhouses | Wine touring, Florence & Siena day trips, first visits | Greve in Chianti | Highest villa density; best all-round base |
| Val d'Orcia | Rolling clay hills, cypress avenues, UNESCO landscape | Photography, Brunello & Vino Nobile, seclusion | Pienza / Montalcino | More remote; strade bianche access; 2 hrs from Florence |
| Maremma & Tuscan Coast | Pine forests, wetlands, sandy beaches, Etruscan hilltops | Beach + countryside, Etruscan history, hot springs | Grosseto / Castiglione della Pescaia | Only region combining countryside with beach access |
| Lucca & Northwest | Flat plain, walled city, Apuan Alps, Garfagnana forest | Lucca city, Garfagnana mountains, Cinque Terre day trip | Lucca | 30 min from Pisa airport; cooler in summer |
| Umbria (over the border) | Green hill towns, truffles, quieter than Tuscany | Assisi, Orvieto, Spoleto; ideal extension to Tuscany | Perugia / Orvieto | Natural extension from Val d'Orcia or Valdichiana base |
Chianti
Val d'Orcia
Maremma & Tuscan Coast
Lucca & Northwest
Umbria (over the border)
| From | To | km | Drive | Notes |
|---|---|---|---|---|
| Florence | Siena | 75 | 1 h 15 m | Via A1 / SS2 Cassia |
| Florence | Greve in Chianti | 30 | 45 m | Heart of Chianti Classico |
| Florence | San Gimignano | 55 | 1 h | The tower town |
| Florence | Pisa | 80 | 1 h | Leaning Tower, airport hub |
| Florence | Lucca | 80 | 1 h | Walled Renaissance city |
| Florence | Arezzo | 80 | 1 h | East Tuscany, antiques |
| Florence | Montalcino | 105 | 1 h 30 m | Brunello wine |
| Florence | Pienza | 120 | 1 h 45 m | Val d'Orcia, UNESCO |
| Florence | Montepulciano | 115 | 1 h 45 m | Vino Nobile, hilltop |
| Florence | Cortona | 110 | 1 h 30 m | Hilltop above Valdichiana |
| Florence | Volterra | 75 | 1 h 20 m | Etruscan city, alabaster |
| Florence | Pitigliano | 180 | 2 h 15 m | Deep Maremma, tufa cliff |
| Siena | Pienza | 52 | 55 m | Via SS2 through Buonconvento |
| Siena | Montalcino | 40 | 45 m | South via Torrenieri |
| Siena | Montepulciano | 65 | 1 h | Via A1 exit Chiusi-Chianciano |
Times are approximate by motorway. Scenic routes (SS222 Chiantigiana, SS2 Cassia) add 20–40 minutes and are generally preferable for villa guests.

Planning your villa?
tuscanyholidays.co.uk — hand-curated villas in Chianti, Val d'Orcia, Maremma and Umbria, sleeping 6–14 guests.
ZTL Zones (Zona Traffico Limitato)
All historic town centres — Florence, Siena, Lucca, Arezzo — operate restricted traffic zones. Park at designated car parks outside the walls and walk in. Entering a ZTL without a permit issues an automatic fine.
Strade Bianche (White Gravel Roads)
Many villas — particularly in the Val d'Orcia and deeper Chianti — are accessed via unpaved gravel roads. A standard hire car handles these at slow speed. Check access conditions with your villa team before arrival. GPS signal is often unreliable on strade bianche.
Motorway Key Routes
A1 (Autostrada del Sole): Florence ↔ Siena ↔ Rome. A11: Florence ↔ Pisa ↔ Lucca. A12: Pisa ↔ Livorno ↔ coast. Toll roads — bring cash or a compatible card.
Airports
Pisa Galileo Galilei (PSA): main UK/low-cost hub. Florence Peretola (FLR): smaller, closer to central Tuscany. Rome Fiumicino (FCO) and Bologna (BLQ) are viable for southern Tuscany with a 2–3 hour drive.
Return to the full interactive guide with driving distance calculator and region details.