--- title: San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch lang: en type: tour city: Florence country: Italy price: 79 currency: EUR price_unit: per_person availability: bookable rating: 4.52 reviews: 5334 duration_minutes: 660 languages: [en, es] free_cancellation: "true" guidekin_pick: Farm lunch and Monteriggioni rank_in_category: 39 of 39 (Day Trips) schedule_checked: 2026-09-25 data_updated: 2026-10-12 canonical: https://guidekin.com/italy/florence/tours/san-gimignano-siena-monteriggioni-chianti-day-trip-with-lunch/ --- # San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch **Guidekin's take:** A coach loop with free time in San Gimignano, a stop inside the walls of Monteriggioni, three wines and a three course farm lunch in Chianti, then a guided walk of Siena with a cathedral entry tier. Monteriggioni drops out from November to March; knees and shoulders must be covered for the churches. 4.52 from 5334 reviews at €79 per person. In our comparison: #39 of 39 in Day Trips, by rating weighted by review volume (table below). ## Overview Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence. Please note that the order of the visits may change (*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier ## Before you book - Meeting point: Check in time: 07:45am - Montelungo… - Starts 08:00: one departure a day - Food included: see what is included - Strollers OK: infants accepted - Children from €40: ages 4 to 12 **Pickup:** No hotel pickup: everyone meets at the start point ## Key facts - Price: from €79 per person for the SPA Semi-Independent & Lunch option; other options up to €109 - Duration: 11h - Rating: 4.52/5 from 5334 reviews (collected from Guidekin & Viator & Tripadvisor) - Free cancellation (see policy below) - Operator: CAF Tour and Travel - Gray Line Florence - Group: Shared tour - Guide languages: English, Spanish - Start times: 08:00 - Booking: Instant confirmation, mobile ticket - Price checked on Viator: 2026-09-25 ## Reviews 4.52 from 5334 ratings on Guidekin, Viator & Tripadvisor. 89% of ratings with a star breakdown are 4 or 5 stars: 4758 of 5334. - 5 stars: 3707 (69%) - 4 stars: 1051 (20%) - 3 stars: 320 (6%) - 2 stars: 164 (3%) - 1 star: 92 (2%) ### What reviewers say Reviewers praise the guides and smooth organisation, though some find the groups too large. **Praised:** - Friendly, knowledgeable guides who share local history with humour - Clear meeting instructions and smooth organisation between stops - Careful driving through narrow roads and winding countryside - Historic towns and countryside scenery along the route - Enjoyable wine tastings at the winery **Complaints:** - Some enjoy the winery lunch, while others find the food basic or the setting like a cafeteria - Some find the large groups well managed, while others feel there are too many people - Some find the pace comfortable, while others want more time to explore Siena - The initial meeting point can be confusing or chaotic Written by Guidekin from the 100 most recent English reviews on Viator & Tripadvisor (2026-09-17 to 2026-10-02); last checked 2026-10-04. ## Tour options Prices are the operator's current list price for two travellers (whole euros); options sold only to bigger parties say so; pick the option on the booking page. | Option | Price | Guide languages | Details | |---|---|---|---| | SPA Semi-Independent & Lunch | €71 / person | Spanish | Spanish with Lunch & Wine: Round trip with tour Leader on board and Lunch with Wine Pairing. Not included: Siena Guided Visit & Cathedral admission | | ENG Semi-Independent & Lunch | €71 / person | English | English with Lunch & Wine: Round trip with tour Leader on board and Lunch with Wine Pairing. Not included: Siena Guided Visit & Cathedral admission | | SPA Guided Tour - no Cathedral | €97 / person | English, Spanish | Spanish without Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena. Not included: Cathedral admission. | | ENG Guided Tour - no Cathedral | €97 / person | English | English without Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena. Not included: Cathedral admission. | | ENG Guided Tour with Cathedral | €109 / person | English | Full English Tour & Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena with Cathedral admission. | | SPA Guided Tour with Cathedral | €109 / person | Spanish | Full Spanish Tour & Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena with Cathedral admission. | ## What's included - Siena Cathedral and Libreria Piccolomini entrance with guided visit (if option selected) - Comfortable G.T. Coach transport from Florence in a modern, air-conditioned bus - Immersive journey led by a Licensed Multilingual Tour Leader (English & Spanish) - If option selected: from November to March the visit in Siena can be bilingual (English and Spanish) - If option selected: April to October, visit in Siena is monolingual. Language selected while booking - Dedicated Caf Tour & Travel Staff Assistance at the meeting point - Chianti Winery experience: Guided Cellar visit plus 3-course Tuscan lunch & 3 Chianti Wines Tasting - Guided tour in Siena with Earphones provided (if option selected) ## Not included - From November to March, the itinerary does not include the stop at Monteriggioni - Hotel pick up and drop off ## Itinerary 1. **San Gimignano** (2h) - Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from... 2. **Piazza Della Cisterna** (pass by, no stop) - Piazza della Cisterna is a charming medieval square situated in the heart of San Gimignano. Surrounded by well-preserved medieval towers and historic buildings, the square takes its name from the ancient cistern located at its center. The triangular-shaped square is paved... 3. **Mura di San Gimignano** (pass by, no stop) - These well-preserved walls, dating back to the 13th century, served both defensive and symbolic purposes. The "Mura" offer a scenic stroll along their length, providing panoramic views of the charming town, its iconic towers, and the picturesque Tuscan countryside. 4. **Monteriggioni** (40m) - Step inside a storybook fortress village encircled by intact walls and ramparts, beloved by filmmakers and history fans alike. Enjoy free time to browse tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany. (*) From November to March, the itinerary does... 5. **Siena** (2h 30m) - Join a guided walking tour (if option selected) through contrade banners, artisan storefronts, and grand palazzi that reveal Siena’s golden age. Afterward, enjoy free time to sip an espresso, browse boutiques, or continue exploring this Gothic masterpiece at your own pace. 6. **Piazza del Campo** (15m) - is the main square of Siena, famous for its distinctive shell shape and elegant brick pavement. Surrounded by historic buildings, it is home to the Palazzo Pubblico and the Torre del Mangia. It is also the setting for the famous Palio di Siena, a historic horse race between... 7. **Duomo di Siena** (30m; admission included) - Cathedral Entrance and inside guided visit only if option selected - officially known as the Cathedral of Santa Maria Assunta, is a stunning medieval cathedral in Siena. Renowned for its distinctive Gothic architecture, the cathedral showcases a magnificent facade adorned... 8. **Biblioteca Piccolomini** (15m; admission included) - Only if cathedral entrance option is selected - The Piccolomini Library, housed within the Duomo di Siena, is a Renaissance gem adorned with vibrant frescoes by Pinturicchio. Commissioned by Pope Pius III, these artworks depict scenes from his life, creating a cultural and... ## Schedule - Runs: daily - Departures: 08:00 - Schedule last checked: 2026-09-25 - These are published departures, not a live seat count; availability is confirmed at checkout. ## Cancellation For a full refund, cancel at least 24 hours before the scheduled departure time. ## 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. Map: https://www.google.com/maps/place/?q=place_id:EixQaWF6emFsZSBNb250ZWx1bmdvLCA1MDEyOSBGaXJlbnplIEZJLCBJdGFseSIuKiwKFAoSCRNkVHqmVioTEarSbnbVqfdTEhQKEgmt1tKAplYqExEDKsfvF3nVkw Ends: back at the 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 - A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements. - 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. - From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier - It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay or no show it will not be possible to join the tour, 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. - Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation. ## Compared with other Day Trips | Tour | Price | Duration | Rating | Group | |---|---|---|---|---| | **This tour · #39 of 39** | €79 | 11h | 4.52 (5334) | shared | | [Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner](/italy/florence/tours/small-group-tuscan-wineries-olive-oil-gourmet-lunch-or-dinner/?format=md) | €149 | 8h | 4.96 (1592) | shared | | [Tuscany Vespa Tours Through the Hills of Chianti](/italy/florence/tours/tuscany-vespa-tours-through-the-hills-of-chianti/?format=md) | €160 | 6h | 4.99 (580) | shared | | [SMALL-GROUP Wine Safaris: Tuscany Wine Tasting Tour from Florence](/italy/florence/tours/small-group-wine-safaris-tuscany-wine-tasting-tour-from-florence/?format=md) | €130 | 6h | 4.94 (5805) | shared | Ranked #39 of 39 in Day Trips by Guidekin score (rating weighted by review volume). Prices here run from €39 to €275, median €106; typical length 8h. 2 of 39 are private. Figures are live from the tour cards; the rubric is our handpicked set, not the whole market. Full list: https://guidekin.com/italy/florence/day-trips-from-florence/?format=md ## More in Florence - All Florence tours: https://guidekin.com/italy/florence/?format=md - This page as HTML: https://guidekin.com/italy/florence/tours/san-gimignano-siena-monteriggioni-chianti-day-trip-with-lunch/ Filters, the full catalogue and the URL contract for this city: https://guidekin.com/italy/florence/?format=md