Siena, San Gimignano & Chianti Day Trip from Florence

Explore Tuscany on a shared day trip from Florence, balancing independent wandering through medieval towns with a winery visit in the Chianti hills. Explore Siena at your own pace or take an option with a guided walking tour through its historic center.

• Explore the winery’s cellars and vineyards for a closer look at Chianti’s wine-growing setting
• Discover Siena Cathedral and the Piccolomini Library with skip-the-line tickets on cathedral-admission options

Itinerary

1. Depart at 08:00 from Piazzale Montelungo. Meet the assistant wearing light blue clothing with Caf Tour - Gray Line logos at the end of the ramp connecting to the railway station.
2. Explore San Gimignano independently for 2 hours. Discover the medieval hilltop town’s towers, artisan shops, and scenic alleys, with free time for gelato and skyline views.
3. Explore Monteriggioni independently for 40 minutes. Wander past medieval walls and craft shops, or relax in the piazza.
4. Visit a Chianti winery for a 1-hour 30-minute lunch stop with vineyard views, 3 wine tastings, and a farm-to-table 3-course lunch finished with traditional cantucci biscuits and vin santo wine. The menu may change with the season and ingredient availability.
5. Explore Siena’s artisan shops and grand palaces independently for 3 hours with the Round Trip Transportation with Lunch option. With the Full Guided Tour with Lunch and Wine tasting option, join a guided walk through historic neighborhoods and enjoy free time afterward; the Spanish-language option lists 3 hours in Siena.
6. With the Full Guided Tour with Lunch and Wine tasting + Admission to Siena Cathedral option, your 3-hour Siena stop includes the guided walking tour and a cathedral visit to see its marble floors and artworks.
7. Return to Piazzale Montelungo at 19:00.

What's Included

• Round-trip transportation by air-conditioned bus or minivan, depending on the option and group size
• Three-course Tuscan lunch and three wine tastings
• Cellar and vineyard visit
• WiFi on board
• English- or Spanish-speaking staff, depending on the option
• Guided Siena walking tour on full guided options
• Skip-the-line Siena Cathedral and Piccolomini Library tickets on cathedral-admission options

Important details

• Children aged 0–3 join free; child tickets cover ages 4–12, and adult rates apply from age 13
• Alcohol consumption is restricted to ages 18+
• Bring your original valid ID for the tour and proof of drinking age
• This activity is not wheelchair- or stroller-accessible
• Pets are not allowed
• Do not wear flip-flops, shorts, tank tops, or sleeveless shirts for entry to places of worship
• For groups of fewer than 9 on minivan options, no tour escort is provided
• From November to March, English-language and full guided options omit Monteriggioni and return to Florence approximately 30 minutes earlier
• Arrive 15 minutes before departure