--- title: Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence lang: en type: tour city: Florence country: Italy price: 710 currency: EUR price_unit: per_group availability: bookable rating: 4.85 reviews: 436 duration_minutes: 480 free_cancellation: "true" guidekin_pick: Private car, three to seven rank_in_category: 18 of 39 (Day Trips) schedule_checked: 2026-09-25 data_updated: 2026-10-04 canonical: https://guidekin.com/italy/florence/tours/private-tour-in-siena-san-gimignano-and-chianti-day-trip-from-florence/ --- # Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence **Guidekin's take:** A private driver day through Chianti to Siena, Monteriggioni and San Gimignano for parties of three to seven, with hotel pickup in Florence and a luxury car or minivan. Priced per group at €710 per group/vehicle for 8h; the driver is not a licensed guide inside Siena, and the winery lunch is paid on the spot. Rated 4.85 by 436 travellers. In our comparison: #18 of 39 in Day Trips, by rating weighted by review volume (table below). ## Overview *Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni (just if you won't need a stop for lunch) and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * Would you like to have a traditional Italian meal’s experience? We can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lovers. ## Before you book - Hotel pickup: from 39 pickup points - Starts 09:30: one departure a day - Food not included: Full lunch + wine tasting at winery (to be… - Strollers OK: infants accepted - Age rule: Specialized infant seats are available **Pickup:** Hotel pickup from 39 pickup points ## Key facts - Price: from €710 per group/vehicle - Duration: 8h - Rating: 4.85/5 from 436 reviews (collected from Guidekin & Viator & Tripadvisor) - Free cancellation (see policy below) - Operator: Chianti Drivers private tours - Group: Private tour, your party only - Start times: 09:30 - Booking: Instant confirmation, mobile ticket - Price checked on Viator: 2026-09-25 ## Reviews 4.85 from 436 ratings on Guidekin, Viator & Tripadvisor. 95% of ratings with a star breakdown are 4 or 5 stars: 415 of 436. - 5 stars: 402 (92%) - 4 stars: 13 (3%) - 3 stars: 13 (3%) - 2 stars: 5 (1%) - 1 star: 3 (1%) ### What reviewers say Reviewers praise helpful drivers and winery lunches, but some expected a guide to accompany them in the towns. **Praised:** - Friendly drivers who share local history and practical suggestions - Flexible itineraries with extra stops tailored to travellers' interests - Comfortable, clean vehicles and confident driving - Winery lunches, wine tastings and welcoming family hosts - Scenic countryside drives and exploring Siena and San Gimignano **Complaints:** - Some expected guided town visits and found the trip poor value for a driving service - Some wanted more time in the towns, while others felt they had ample time to explore Written by Guidekin from the 100 most recent English reviews on Viator & Tripadvisor (2024-11-25 to 2026-09-19); last checked 2026-10-04. ## What's included - expert english speaking driver - Bottled water - Onboard Wi-Fi (on request at reservation) - Air-conditioned vehicle - Private luxury car or minivan - Hotel pickup and drop-off in Florence ## Not included - Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult - mance - Licensed Guide in Siena ## Itinerary 1. **Siena** (2h) - is known throughout Italy for the quality of its medieval architecture. Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the outstanding 13th-century Siena Cathedral. Many local shops fill the historic streets of Siena that... 2. **San Gimignano** (2h) - *Option to organize lunch at a Farm/Winery for home made lunch with wine tasting (to be payed on site). We have several options about wineries. (This option will reduce the time in the cities of Siena and/or San Gimignano and exclude Monteriggioni). 3. **Strada Statale 222 Chiantigiana** (pass by, no stop) - We explore the country of Tuscany, we will drive through the chianti hills. Stop for picture!!!! 4. **Historic Centre of San Gimignano** (2h) - Here we are in the beautiful stronghold of San Gimignano. Freeze at the age 1300dc, San Gimignano a pearl of medieval architecture famous for its houses tower! This is our last spot of the day before returning to Florence ## Schedule - Runs: daily - Departures: 09:30 - 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. Pickup points listed by the operator: 39 ## Good to know - Specialized infant seats are available - Infants and small children can ride in a pram or stroller - Suitable for all physical fitness levels - A maximum of seven people per booking ## Cost for your party | People | Total | Per person | |---|---|---| | 2 | €710 | €355 | | 4 | €710 | €178 | | 6 | €710 | €118 | Cheapest option for that party size from the operator's current price tiers; the calendar shows the exact figure for your date. Shared tours in Day Trips start at €39 per person. ## Compared with other Day Trips | Tour | Price | Duration | Rating | Group | |---|---|---|---|---| | **This tour · #18 of 39** | €710 per group | 8h | 4.85 (436) | private | | [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 #18 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/private-tour-in-siena-san-gimignano-and-chianti-day-trip-from-florence/ Filters, the full catalogue and the URL contract for this city: https://guidekin.com/italy/florence/?format=md