--- title: "Florence: Siena & San Gimignano with Dinner in a Boutique Winery" lang: en type: tour city: Florence country: Italy price: 106 currency: EUR price_unit: per_person availability: bookable rating: 4.72 reviews: 356 duration_minutes: 540 duration_max_minutes: 720 languages: [en] free_cancellation: "true" guidekin_pick: Afternoon start, dinner rank_in_category: 27 of 39 (Day Trips) schedule_checked: 2026-10-03 data_updated: 2026-10-12 canonical: https://guidekin.com/italy/florence/tours/florence-siena-san-gimignano-with-dinner-in-a-boutique-winery/ --- # Florence: Siena & San Gimignano with Dinner in a Boutique Winery **Guidekin's take:** An afternoon into evening run through the Chianti hills: a guided walk in Siena, free time in San Gimignano, then dinner with wine at a countryside winery, by minibus. The base option is €106 per person with dinner included; a semiprivate full day upgrade adds Pisa and swaps dinner for lunch, and hotel pickup is not included. Rated 4.72 by 356 travellers. In our comparison: #27 of 39 in Day Trips, by rating weighted by review volume (table below). ## Overview Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo, and stunning Gothic landmarks. Taste local specialties before heading to San Gimignano, the medieval town of towers, where you’ll have time to wander its enchanting streets. As the sun sets, continue to a scenic winery in the Chianti countryside for a typical Tuscan dinner and wine tasting in an unforgettable location. Looking for the full Tuscan experience? Upgrade to our Tuscany Grand Tour: a full-day adventure that also includes a visit to Pisa and its iconic Leaning Tower, plus a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and embrace the art, history, and flavors of Tuscany from dawn to dusk. ## Before you book - Meeting point: Via dei Vagellai 22R, - Entry ticket not included: buy it separately - Group size varies by option: max 20 from €110 · max 8 from €172 · private from €615 - Starts 08:00, 13:00, 14:00: 3 departures a day - Food included: Visit of a winery with wine tasting,… - Strollers OK: infants accepted - Children from €91: ages 4 to 12 **Pickup:** No hotel pickup: everyone meets at the start point ## Key facts - Price: from €106 per person for the Essential Coach Tour & Dinner option; other options up to €615 - Duration: 9h–12h - Rating: 4.72/5 from 356 reviews (collected from Guidekin & Viator & Tripadvisor) - Free cancellation (see policy below) - Operator: Towns of Italy - Group: Group size varies by option: max 20 from €110 · max 8 from €172 · private from €615 - Guide languages: English - Tickets: Admission not included, pay on site - Start times: 08:00, 13:00, 14:00 - Booking: Instant confirmation, mobile ticket - Price checked on Viator: 2026-10-03 ## Reviews 4.72 from 356 ratings on Guidekin, Viator & Tripadvisor. 93% of ratings with a star breakdown are 4 or 5 stars: 332 of 356. - 5 stars: 298 (84%) - 4 stars: 34 (10%) - 3 stars: 12 (3%) - 2 stars: 8 (2%) - 1 star: 4 (1%) ### What reviewers say Reviewers praise the guides and winery dinner; some want more time to explore Siena and San Gimignano. **Praised:** - Knowledgeable guides explain local history and offer practical tips - Winery dinners and wine pairings frequently described as the highlight - Welcoming winery hosts share their knowledge of wine and family traditions - Visits to historic towns with countryside and vineyard views **Complaints:** - Some find Siena and San Gimignano rushed, while others are happy with the time allowed - Substantial uphill and downhill walking in Siena - Wine tasting pours smaller than some travellers expected Written by Guidekin from the 100 most recent English reviews on Viator & Tripadvisor (2026-05-26 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 | |---|---|---|---| | Essential Coach Tour & Dinner | €106 / person | English | Afternoon with Dinner : Siena & San Gimignano by coach - top Tuscan sights and a typical dinner at a winery—great experience, budget-friendly price! | | Small Group: Siena & Dinner | €110 / person | English | Afternoon with dinner: Siena & San Gimignano in a premium small group (max 20) by Mercedes minivan—top-tier tour with winery dinner included! | | Semiprivate Tuscany Grand Tour | €172 / person | English | Upgrade to the Grand Tour:: Full-day (12h) with 8 AM departure: Siena, San Gimignano, Chianti, Pisa & Tuscan lunch—semiprivate journey (max 8) in style! | | Private Siena and San Gimignano tour with dinner | €615 / person (for 2+ people) | English | Private Group: Siena & Dinner: Private Afternoon in Siena & San Gimignano with Traditional Winery Dinner | ## What's included - Free WiFi on board - English speaking driver/tour leader - Typical Tuscan dinner or Lunch for the Tuscany Grand Tour Option - Transportation IN/OUT Florence by luxury Mercedes Minibus or Minivan - Guided walking tour of Siena - Tuscany Grand Tour Option: Visit to Pisa and Miracle Square (Leaning Tower entrance not included) - Visit of a winery with wine tasting - Surprise tasting in Siena - San Gimignano visit with free time - Free Time in San Gimignano ## Not included - Gratuities - Hotel pickup and drop-off - We are sorry to inform you that pets are not permitted on our tours - Tuscany Grand Tour Option: Entrance ticket to the Tower of Pisa (purchase on-site if time allows) ## Itinerary 1. **Florence** (pass by, no stop) - Towns of Italy indicated meeting point 2. **Siena** (2h) - Arrival in Siena for a guided tour 3. **Historic Centre of San Gimignano** (1h) - Free time in San Gimignano, UNESCO Heritage Site 4. **Diadema Wine & Evo** (1h; admission included) - Gourmet Dinner in a Boutique Winery in Chianti 5. **Florence** (pass by, no stop) - Return to Florence and end of the tour at the initial meeting point ## Schedule - Runs: daily - Departures: 08:00, 13:00, 14:00 - 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 Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River) Map: https://www.google.com/maps/place/?q=place_id:ChIJG616UwdUKhMRlG53ckMTZBA 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 - Suitable for all physical fitness levels - The tour operates regardless of weather conditions - Semiprivate Tuscany Grand Tour Option: Choose the Grand Tour upgrade for a full-day experience starting at 8:00 AM. Discover the highlights of Tuscany in one unforgettable journey: visit Siena with a guided walking tour and a surprise tasting, enjoy free time in the medieval town of San Gimignano, savor a traditional Tuscan lunch, then continue to Pisa to admire the stunning Piazza dei Miracoli and the iconic Leaning Tower (tower tickets not included). The experience includes round-trip transportation from Florence in a luxury Mercedes minivan with free Wi-Fi, an English-speaking driver/tour leader, and all the charm, history, and flavor of Tuscany in one complete itinerary. ## Compared with other Day Trips | Tour | Price | Duration | Rating | Group | |---|---|---|---|---| | **This tour · #27 of 39** | €106 | 9h–12h | 4.72 (356) | 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 #27 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-siena-san-gimignano-with-dinner-in-a-boutique-winery/ Filters, the full catalogue and the URL contract for this city: https://guidekin.com/italy/florence/?format=md