Tuscany's Medieval Hill Towns — Montepulciano and San Gimignano
Tuscany, Italy
About This Activity
Rent a car and spend the day looping between two of Tuscany's most atmospheric hill towns. Montepulciano sits 605 metres above sea level, its main street Corso lined with wine shops pouring Vino Nobile (try Poliziano or Contucci, tasting rooms often free). Drive 45 minutes north to San Gimignano — its 14 medieval towers are UNESCO-listed and the gelato at Gelateria Dondoli on Piazza della Cisterna has won multiple world championships. Walking the town costs nothing; gelato runs €3-4.
Seasonal note: Summer is busy but evenings are magical; autumn harvest season adds colour and activity
See This in an Itinerary
This activity appears in 152 of our curated itineraries.
Best 10 Days in Italy
Rome → Florence → Venice → Sorrento → Capri → Positano → Milan → Cinque Terre → Tuscany
Best 10 Days in Italy — Food & Wine
Rome → Florence → Venice → Sorrento → Capri → Positano → Milan → Cinque Terre → Tuscany
Best 10 Days in Italy — Walking Tours
Rome → Florence → Venice → Sorrento → Capri → Positano → Milan → Cinque Terre → Tuscany
Best 10 Days in Italy — History
Rome → Florence → Venice → Sorrento → Capri → Positano → Milan → Cinque Terre → Tuscany
Best 10 Days in Italy — Temples & Shrines
Rome → Florence → Venice → Sorrento → Capri → Positano → Milan → Cinque Terre → Tuscany
Best 10 Days in Italy — Family Friendly
Rome → Florence → Venice → Sorrento → Capri → Positano → Milan → Cinque Terre → Tuscany
More Activities in Tuscany
Cascate del Mulino — Saturnia Natural Hot Springs
Soak in free 37°C thermal cascades at Saturnia's Cascate del Mulino, open 24/7 in the heart of the Maremma
Bagno Vignoni — Medieval Village with Thermal Pool Piazza
Visit Val d'Orcia's extraordinary village whose main piazza is a Renaissance thermal pool, then soak in the free Parco dei Mulini cascades below
Val d'Orcia Scenic Drive — Brunello Vineyards and Medieval Villages
Drive through UNESCO-listed Val d'Orcia, stopping at cypress-lined roads, Pienza village, and a Brunello di Montalcino tasting
Cinque Terre Day Trip from Tuscany — Five Pastel Fishing Villages
Take the train to the Ligurian coast and hike the coastal Blue Trail between Monterosso, Vernazza, and Corniglia
Siena Day Trip — Piazza del Campo and Gothic Duomo
Climb the Torre del Mangia for panoramic views, then tour Siena Cathedral's Piccolomini Library and marble-striped interior
Lucca Day Trip — Renaissance Walls and Medieval Towers
Rent a bike and ride the top of Lucca's intact 16th-century city walls, then climb the Guinigi Tower for rooftop views
Pisa Day Trip — Leaning Tower and Piazza dei Miracoli
Climb the 294 steps of the Leaning Tower of Pisa and photograph the marble ensemble of cathedral, baptistery, and campanile
Perugia Day Trip from Tuscany — Umbria's Hill Town Capital
Take the train to Perugia and walk the medieval escalators up to Piazza IV Novembre and the Perugina chocolate factory