San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

At a glance

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting is a 11h guided experience in Florence, Italy, operated by CAF Tour and Travel - Gray Line Florence. Travellers rate it 4.5 out of 5 across 196 reviews on Viator and Tripadvisor. Prices start from $90.48 per person, and free cancellation is available. Included: Caf Tour staff assistance at the meeting point for smooth check-in, Licensed English-speaking tour escort throughout the day, Chianti winery experience: guided visit of cellars and vineyards & 3-course traditional Tuscan lunch.

Quick facts

Duration

11h

Group

Small group, up to 60 travellers

Languages

English

Pickup

Meet at the start point

Confirmation

Instant confirmation

Ticket

Mobile or paper ticket accepted

Cancellation

Free cancellation (see policy)

Overview

Itinerary

1. Stop 1 · 2h

   Explore a perfectly preserved walled hilltown famed for its soaring medieval towers and fresco-filled churches. Stroll the UNESCO-listed historic center at your own pace, browsing artisan shops and quiet lanes. Enjoy panoramic viewpoints over the Val d’Elsa and time for gelato or souvenirs.

2. Stop 2 · 40m

   Step inside a storybook fortress village encircled by intact 13th-century walls. Wander the tiny piazza and gates, soaking up its authentic medieval atmosphere. Quick, easy visit with great photo spots from the ramparts.
   
   (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

3. Stop 3 · 1h 30m

   Cruise one of Tuscany’s most scenic roads, rolling past vineyards, olive groves, and stone farmhouses. Settle into a cozy winery for a guided tasting of three Chianti wines paired with a zero-mile, three-course lunch. Finish sweetly with traditional cantucci and vin santo.

4. Stop 4 · 2h

   Enjoy generous free time to feel Siena’s Gothic soul—narrow lanes, noble palaces, and lively enotecas. Browse artisan boutiques, sample local specialties, and capture the city’s warm, terracotta hues. Ideal for independent discovery and relaxed photos.

5. Stop 5 · 15m

   Pause for an exterior and brief interior look at Siena’s striking striped-marble cathedral. Admire its ornate façade, sculptures, and masterworks that hint at the city’s artistic power. A swift but unforgettable highlight.

6. Stop 6 · 30m

   Descend into one of Italy’s most beautiful squares, famed for the Palio horse race. Take a moment to sit at a café, admire the shell-shaped slope, and view the Torre del Mangia and Palazzo Pubblico. A perfect finale for people-watching and photos.

Meeting point

Good to know

• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Specialized infant seats are available
• Travelers should have at least a moderate level of physical fitness
• For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.
• Comfortable walking shoes are recommended
• Please note that the order of the visits may change
• It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the excursion, nor to have a refund or reschedule the tour.
• Please be advised that it is required to bring your original ID with you during the tour
• Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
• Vegetarian and gluten-intolerant options are available at the wineries; however, cross- contamination cannot be fully excluded.

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Frequently asked questions