--- title: "Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano" lang: en type: tour city: Florence country: Italy price: 195 currency: EUR price_unit: per_person availability: bookable rating: 4.79 reviews: 348 duration_minutes: 540 languages: [en] free_cancellation: "true" rank_in_category: 24 of 39 (Day Trips) schedule_checked: 2026-10-03 data_updated: 2026-10-12 canonical: https://guidekin.com/italy/florence/tours/florence-day-trip-chianti-wine-tasting-siena-san-gimignano/ --- # Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano **Guidekin's take:** A small group day capped at fourteen: Piazzale Michelangelo, free time in San Gimignano and Siena, and a seasonal lunch with wine tasting at a family farm in Chianti, in minivans that reach the town centres. Lunch and tastings are in the €195 per person for 9h; hotel pickup and Siena Cathedral tickets are not. Rated 4.79 by 348 travellers. In our comparison: #24 of 39 in Day Trips, by rating weighted by review volume (table below). ## Overview When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, wander the storybook streets of the UNESCO-listed village San Gimignano. Indulge your taste buds with a seasonal lunch and wine tastings at a family-run farm in the Chianti region, and visit the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race. Group size is limited to 14 for a more personalized experience. ## Before you book - Meeting point: Please arrive 15 minutes prior to the… - Group size varies by option: small group from €195 · private from €675 - Starts 08:30, 09:00: 2 departures a day - Food included: see what is included - Strollers OK: infants accepted - Children from €185: ages 2 to 14 **Pickup:** No hotel pickup: everyone meets at the start point ## Key facts - Price: from €195 per person for the Small Group Tour option; other options up to €675 - Duration: 9h - Rating: 4.79/5 from 348 reviews (collected from Guidekin & Viator & Tripadvisor) - Free cancellation (see policy below) - Operator: Walks - Italy & Spain - Group: Group size varies by option: small group from €195 · private from €675 - Guide languages: English - Start times: 08:30, 09:00 - Booking: Instant confirmation, mobile ticket - Price checked on Viator: 2026-10-03 ## Reviews 4.79 from 348 ratings on Guidekin, Viator & Tripadvisor. 96% of ratings with a star breakdown are 4 or 5 stars: 334 of 348. - 5 stars: 299 (86%) - 4 stars: 35 (10%) - 3 stars: 9 (3%) - 2 stars: 1 (0%) - 1 star: 4 (1%) ### What reviewers say Reviewers praise the guides and winery lunch; commentary can be hard to hear when travelling in a separate van from the guide. **Praised:** - Informative historical commentary and guides willing to answer questions - Winery lunches with food and wine pairings that reviewers enjoy - Comfortable vans with convenient drop points near town sights - Free time to explore Siena and San Gimignano independently - Small groups that make it easy to get to know fellow travellers **Complaints:** - Travellers in the van without the guide report losing or being unable to hear commentary - Some find town stops sufficient, while others want more time in Siena and San Gimignano Written by Guidekin from the 100 most recent English reviews on Viator & Tripadvisor (2025-09-13 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 | |---|---|---|---| | Small Group Tour | €195 / person | English | Group Tour | | Private Tuscany from Florence | €675 / person (for 2+ people) | English | Siena, San Gimignano & Chianti: Enjoy a Siena guided tour, a gourmet lunch at a vineyard in Chianti, and free time to explore San Gimignano at your own pace. | ## What's included - Expert English-speaking tour leader - Piazzale Michelangelo - Free time in San Gimignano and Siena - Designated professional driver - Siena Cathedral (exterior) - Gourmet lunch and wine tasting in Chianti - Chianti farmhouse & vineyard - Air-conditioned transport ## Not included - Gratuities - Hotel Pick-Up/Drop-Off ## Itinerary 1. **Tuscany** (1h 30m) - Your driver and tour leader will pick you up in a comfortable, air-conditioned transport in central Florence and drive you through the hills of Tuscany. You'll pass the best panoramic viewpoint of Florence and pause for pictures. 2. **San Gimignano** (1h 30m) - Indulge your imagination with a stop at San Gimignano, a town of such unique architectural beauty it has been designated a UNESCO World Heritage Site. You'll have free time to explore its winding streets on your own. Please note that the private option does not include a... 3. **Tuscany** (3h) - Walking the hills of Tuscan towns will make you hungry so your next stop is an authentic Italian family farm where some of our good friends will give you a behind-the-scenes tour of the vineyards, winery, and wine cellars before sitting you down for a sumptuous, all-inclusive... 4. **Siena** (2h) - is one of the best-preserved examples of medieval Italian architecture in the world. Spared German bombing in WWII, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world. 5. **Piazza del Campo** (pass by, no stop) - One of the highlights your tour leader will recommend during your free time. Pause amidst the square where fervent horses race to win the honor of bringing home the palio - a handpainted silk banner of the highest regard. 6. **Duomo di Siena** (pass by, no stop) - If time allows, a visit to the Siena Cathedral, a Tuscan gem, during your free time won't disappoint! 7. **Piazza Della Repubblica** (1h) - At the end of the day, hop aboard your comfortable private coach bus back to Florence. We've taken care of the logistics so all you have to do is enjoy the food, the sights, and the scenery. ## Schedule - Runs: daily - Departures: 08:30, 09:00 - Schedule last checked: 2026-10-03 - 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 Please arrive 15 minutes prior to the start of your tour, your guide will be holding a yellow WalksDevour sign. This tour meets by the Carousel in Piazza della Repubblica. Map: https://www.google.com/maps/place/?q=place_id:EjFQaWF6emEgZGVsbGEgUmVww7liYmxpY2EsIDUwMTIzIEZpcmVuemUgRkksIEl0YWx5Ii4qLAoUChIJdzanlQFUKhMRr81T0BYPoRISFAoSCa3W0oCmVioTEQMqx-8XedWT Ends: back at the meeting point ## Good to know - Public transportation options are available nearby - Specialized infant seats are available - Suitable for all physical fitness levels - Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollers. - This is a walking tour. Guests should be able to walk at a moderate pace without difficulty. - Those with dietary restrictions need to contact us after booking the tour so we can arrange your lunch. Unfortunately, we cannot accommodate vegans or those with celiacs. - Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your tour leader will assist you. The Cathedral is closed on Sundays and for certain holy days. - In order to get into the city center, we utilize small luxury minivans. This allows us to avoid the parking lots outside of the center requiring us to walk. Your guide may need to split time between vehicles on groups larger than 8. - Please note that this description is an example, and your experience may vary depending on the season, day of the week, and group size. Regardless of where your tour goes, you always have an excellent experience. - Please note: This tour offers multiple options. Take a moment to choose the one that best suits your interests. ## Compared with other Day Trips | Tour | Price | Duration | Rating | Group | |---|---|---|---|---| | **This tour · #24 of 39** | €195 | 9h | 4.79 (348) | varies by option | | [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 #24 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/florence-day-trip-chianti-wine-tasting-siena-san-gimignano/ Filters, the full catalogue and the URL contract for this city: https://guidekin.com/italy/florence/?format=md