--- title: Florence: Siena & San Gimignano with Dinner in a Boutique Winery lang: en type: tour city: Florence country: Italy price: 107 currency: EUR price_unit: per_person availability: bookable rating: 4.71 reviews: 340 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: 2026-09-18 data_updated: 2026-09-18 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 €107 per person with dinner included; a semiprivate full day upgrade adds Pisa and swaps dinner for lunch, and hotel pickup is not included. Rated 4.71 by 340 travellers. ## 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. ## Key facts - Price: from €107 per person - Duration: 9h–12h - Rating: 4.71/5 from 340 reviews (collected from Guidekin & Viator & Tripadvisor) - Free cancellation (see policy below) - Operator: Towns of Italy ## 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 | €107 / 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 | €149 / 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: 2026-09-18 - 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) ## 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. ## How it compares in Day Trips Ranked **#27 of 39** by Guidekin's weighted score (rating weighted by review volume). Alternatives worth comparing: 1. [small-group-tuscan-wineries-olive-oil-gourmet-lunch-or-dinner](https://guidekin.com/italy/florence/tours/small-group-tuscan-wineries-olive-oil-gourmet-lunch-or-dinner/?format=md) — 4.96 (1542) 2. [tuscany-vespa-tours-through-the-hills-of-chianti](https://guidekin.com/italy/florence/tours/tuscany-vespa-tours-through-the-hills-of-chianti/?format=md) — 4.99 (577) 3. [SMALL-GROUP Wine Safaris: Tuscany Wine Tasting Tour from Florence](https://guidekin.com/italy/florence/tours/small-group-wine-safaris-tuscany-wine-tasting-tour-from-florence/?format=md) — €130 per person, 4.94 (5675) 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/ ## Query this catalogue with URLs Every listing accepts filter parameters directly in the URL, so you can hand a user a link that already matches their constraints. 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