Afternoon start, dinner in our Siena & San Gimignano Day Trips comparison.
Trade-off: Grand Tour tier swaps dinner for lunch.
Last checked: September 18, 2026. Commissions never affect our verdicts.
An afternoon into evening run through the Chianti hills: a guided walk in Siena, free time in San Gimignano, then dinner with wine at a countryside winery, by minibus. The base option is €107 per person with dinner included; a semiprivate full day upgrade adds Pisa and swaps dinner for lunch, and hotel pickup is not included. Rated 4.71 by 340 travellers.
Discover the best of Tuscany in one magical afternoon!
Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo, and stunning Gothic landmarks. Taste local specialties before heading to San Gimignano, the medieval town of towers, where you’ll have time to wander its enchanting streets. As the sun sets, continue to a scenic winery in the Chianti countryside for a typical Tuscan dinner and wine tasting in an unforgettable location.
Looking for the full Tuscan experience?
Upgrade to our Tuscany Grand Tour: a full-day adventure that also includes a visit to Pisa and its iconic Leaning Tower, plus a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and embrace the art, history, and flavors of Tuscany from dawn to dusk.
This tour runs daily, departing at 08:00, 13:00, 14:00. It runs year-round. These are the operator’s scheduled departures, not a live seat count: availability is confirmed at checkout. Schedule last checked September 18, 2026.
Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River)
Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River)
For a full refund, cancel at least 24 hours before the scheduled departure time.
| 1+ days | Full refund |
| 0-1 days | No refund |