A half-day minivan tour from San Gimignano that pairs two Chianti winery visits with walks through Castellina in Chianti and the medieval walls of Monteriggioni. Expect cellar tastings, short cobbled walks, and panoramic hill views.
More ways to explore the area's outdoor wonders
You step out at Porta San Giovanni and the minivan eases onto a ribbon of road framed by cypresses; the hills ahead roll in bands of vineyards that seem to push the sky back. That first winding descent into Chianti smells of sun-warmed grapes and crushed herbs, an olfactory invitation to the region’s long relationship with wine.
Difficulty
easy
Duration
6 hours
Fitness Level
Suitable for most fitness levels; involves short periods of standing and walking on uneven streets.
Wildlife
History
Monteriggioni was constructed in the early 1200s by the Republic of Siena as a defensive ring against Florence; many towers still stand along the circular wall.
Conservation
Support small producers, avoid leaving litter in vineyards, and stick to marked areas—productive slopes are working agricultural land that benefits from low-impact tourism.
Reserve your spot on the Chianti and Castles Tour from San Gimignano Small Group today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Bring Photo ID
Alcohol tastings are restricted to guests 18+; carry a valid passport or ID to avoid being turned away from pours.
Wear Sturdy Shoes
Streets in Castellina and Monteriggioni are cobbled; choose supportive shoes for short climbs and uneven surfaces.
Hydrate and Pace Tastings
Sip water between samples and eat small bites during tastings to gauge alcohol intake and enjoy flavors.
Carry Small Cash
Many family-run wineries and town shops prefer cash for bottles or souvenirs, even if cards are accepted at larger estates.
Comfortable walking shoes
Provides traction on cobbles and comfort during village strolls.
Valid photo ID
Required for alcohol tastings (18+ in Italy).
Light layers
Mornings can be cool and afternoons warm; layers adapt to changing conditions.
spring
Sun protection (hat, sunscreen)
Open vineyard sections offer little shade under midday sun.
summer