Booking Wolf
San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch and Wine Tasting from Florence
food_culinary

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch and Wine Tasting from Florence

by Caf Tour Travel

11 hours
Florence
€71.10€79 on ViatorSave 10%/person
From
€71.10€79 on ViatorSave 10%per person

Choose from 6 available options

11 hours
Starting time
Friday 11 September 2026
Language
Free cancellation until 10 Sept 2026.
€142.20€158Save 10%
2 adults × €71.10
All taxes and fees included

How do you want to book?

Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.

Book on Viator Confirmed right away, but you pay full price.€158
11 hours
€142.20€158Save 10%
2 adults × €71.10
All taxes and fees included
11 hours
€142.20€158Save 10%
2 adults × €71.10
All taxes and fees included
11 hours
€142.20€158Save 10%
2 adults × €71.10
All taxes and fees included
11 hours
€142.20€158Save 10%
2 adults × €71.10
All taxes and fees included
11 hours
€142.20€158Save 10%
2 adults × €71.10
All taxes and fees included

Overview

This full-day bus tour starts in Florence and heads to San Gimignano, a medieval hilltop town famous for its towers. You will have about two hours of free time to walk the narrow streets, visit artisan shops, and take photos of the skyline. After San Gimignano, there is a brief stop at its main piazza to learn about the town’s merchant history. Next, the tour passes by the 14th-century walls of Monteriggioni, where your guide will explain the village’s historic defenses as you view the town from outside the walls. From April to October, you will have about 40 minutes to walk inside the intact walls of Monteriggioni and browse shops; note that this stop is not included from November to March. The group then crosses the Chianti countryside by coach, arriving at a winery where you will enjoy a guided cellar and vineyard visit. This includes tasting three Chianti wines and vin santo, accompanied by a three-course farm-to-table Tuscan lunch. In the afternoon, you arrive in Siena for a guided walking tour (if selected). The guide will show you the contrade banners, artisan shops, and main sights such as Piazza del Campo and Palazzo Pubblico. The tour includes a stop to admire Renaissance architecture and the Palio horse race square. If the cathedral visit option is chosen, you will enter Siena Cathedral and the Piccolomini Library, seeing the polychrome floors and frescoes. After the guided portion, you have free time to explore or relax before the return coach ride to Florence. The entire trip uses a comfortable, air-conditioned coach, includes a licensed tour escort, and offers bilingual guides in certain months. The itinerary may change depending on the season, and the return time is about 30 minutes earlier when Monteriggioni is not visited. Hotel pickup is not included.

Highlights

Two hours free time in San Gimignano
Visit Monteriggioni walled village from April to October
Three-wine tasting and three-course lunch at Chianti winery
Guided walking tour of Siena with optional cathedral visit
Round-trip air-conditioned coach transport from Florence
Licensed tour escort and optional bilingual guide

What's included

Licensed tour escort providing information and coordination on board
Skip-the-line entry to Siena Cathedral and Piccolomini Library if option selected
Tasting of three Chianti wines plus traditional vin santo
Departure and return transport from Florence by coach
Bilingual guided tour of Siena from November to March if option selected
Guided walking tour of Siena with local professional guide if option selected
Monolingual Siena visit from April to October with language chosen at booking if option selected
Guided cellar and vineyard visit at Chianti winery plus three-course Tuscan lunch
Assistance from Caf Tour Team at the meeting point
Round-trip transportation by air-conditioned coach

What's not included

Siena guided visit and cathedral admission not included with shared round transport option
Monteriggioni stop excluded from November to March
Hotel pickup and drop-off service not available

Itinerary

1

San Gimignano

Spend about two hours in the UNESCO-listed town known as the “town of towers.” Walk through well-preserved medieval streets with panoramic views, artisan shops, and photo opportunities of the skyline.

120 min

2

San Gimignano Piazza

Stop for around 10 minutes in the main square to view the medieval stone well and tower-houses. A brief photo stop with historical commentary about the town’s merchant past.

10 min

3

Monteriggioni Drive-by

Pass by the 14th-century fortified walls and main gate of Monteriggioni while the guide explains the village’s medieval defenses and historical significance.

4

Monteriggioni Visit

From April to October, spend about 40 minutes walking inside Monteriggioni’s intact walls. Browse small craft shops and stroll through the piazza in this medieval village. From November to March, this stop is not included and the return to Florence is approximately 30 minutes earlier.

40 min

5

Chianti Winery

Travel through the Chianti hills and vineyards to a winery for a guided cellar and vineyard tour. Enjoy tasting three Chianti wines and vin santo along with a three-course farm-to-table Tuscan lunch.

90 min

6

Siena Guided Walking Tour

Join a guided walking tour lasting about two and a half hours (if selected). See contrade banners, artisan shops, and grand palaces that reflect Siena’s history. After the tour, enjoy free time to explore independently.

150 min

7

Siena Renaissance Architecture

Stop for about 15 minutes to view Renaissance buildings and learn about Siena’s banking history. This brief stop includes photo opportunities of elegant façades.

15 min

8

Piazza del Campo

Spend 15 minutes at Siena’s famous shell-shaped square, home to the Palio horse race. View Palazzo Pubblico and Torre del Mangia with guided explanations of the square’s traditions.

15 min

9

Siena Cathedral Exterior and Interior

Admire the striped marble Gothic exterior of Siena Cathedral. If the option is selected, enter the cathedral to see polychrome floors and important artworks during a 15-minute visit.

15 min

10

Piccolomini Library

Take a 10-minute look inside the Piccolomini Library to see Renaissance frescoes and illuminated manuscripts if the cathedral visit option is chosen.

10 min

11

Return to Florence

Travel back to Florence through vineyards and countryside, providing a relaxed conclusion to the day trip.

Meeting point

Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.

End point

Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.

Languages

English (guide)Spanish (guide)

Cancellation policy

  • Cancel at least 24 hours before start for a full refund.

Additional info

1–8 travelers per booking
Mobile ticket
Pushchair and stroller friendly
Reachable by public transport
Infant seats are available
A moderate level of fitness is needed
A strict dress code applies for places of worship and some museums: knees and shoulders must be covered for all, no shorts or sleeveless tops allowed.
For groups up to 8 people, the tour escort may be replaced by an English-speaking driver-guide without changing the itinerary.
Comfortable walking shoes are recommended.
From November to March, the tour does not visit Monteriggioni and returns to Florence about 30 minutes earlier.
Arriving on time at the meeting point is mandatory; late arrivals or no-shows cannot join or receive refunds.
Bringing an original ID during the tour is required.
Audio guides given before the guided tour become the customer’s responsibility; a lost device incurs an €80 fee.
Vegetarian and gluten-free meals are available at wineries but cross-contamination cannot be fully ruled out.
Participants with motor disabilities or wheelchair users must notify the organizer in advance and consult a doctor. The tour and transport are not suitable for such guests, and staff may refuse participation without compensation for safety reasons.
Total
€142.20Save 10% vs Viator