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Florence: Siena & San Gimignano with Dinner in a Boutique Winery

4.7 · 356 ratings on Guidekin, Viator & Tripadvisor 93% of star-rated reviews are 4★ or 5★ Florence Operated by Towns of Italy Free cancellation · up to 24 hours before
Duration
9h–12h
Group
Group size varies by option: max 20 from €110 · max 8 from €172 · private from €615
Guide languages
English
Start & pickup
08:00, 13:00, 14:00 · No hotel pickup: everyone meets at the start point
Tickets
Admission not included, pay on site
Booking
Instant confirmation · mobile ticket
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 (see the comparison).

How we choose tours →Commissions never affect our verdicts.

Options and prices

4 options from the operator, described in its own words. Prices are the operator's from-prices per adult for a party of two. Click an option to book it on Viator. Guide languages on every option: English.

OptionWhat the operator saysFrom, per adult
Essential Coach Tour & DinnerThe page priceAfternoon with Dinner : Siena & San Gimignano by coach - top Tuscan sights and a typical dinner at a winery—great experience, budget-friendly price!€106
Small Group: Siena & DinnerAfternoon with dinner: Siena & San Gimignano in a premium small group (max 20) by Mercedes minivan—top-tier tour with winery dinner included!€110
Semiprivate Tuscany Grand TourUpgrade to the Grand Tour:: Full-day (12h) with 8 AM departure: Siena, San Gimignano, Chianti, Pisa & Tuscan lunch—semiprivate journey (max 8) in style!€172
Private Siena and San Gimignano tour with dinnerPrivate Group: Siena & Dinner: Private Afternoon in Siena & San Gimignano with Traditional Winery Dinner€615 for 2+ people

Children from €91 (ages 4 to 12). Option texts and prices come from the operator's listing; prices checked on Viator on 3 October 2026.

Included and not 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
  • 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)

Reviews

4.7
356 ratings
Guidekin, Viator & Tripadvisor

93% of ratings with a star breakdown are 4★ or 5★: 332 of 356

Star breakdown of all 356 ratings

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 (26 May 2026 to 2 October 2026). Refreshed as new reviews arrive; last checked 4 October 2026.

Latest reviews

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Ratings collected from Guidekin, Viator & Tripadvisor.

Meeting point and route

Meeting point

Where
Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River) · Open in Google Maps
Departure
08:00, 13:00, 14:00 daily; scheduled year-round (operator schedule, seats confirmed at checkout)
Return
This activity ends back at the meeting point
Pickup
No hotel pickup: everyone meets at the start point
Operator
Towns of Italy; booking and payment are completed on Viator

Itinerary

About this tour, from the operator

Walking, children and accessibility

The operator's own notes, grouped by topic. Nothing here is added by Guidekin.

Walking and health

  • Suitable for all physical fitness levels
  • 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.

Children

  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available

Accessibility

  • Strollers OK
  • Public transportation options are available nearby

Good to know

  • Food included Visit of a winery with wine tasting,…
  • Children from €91 ages 4 to 12

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

  • 1+ days: Full refund
  • 0-1 days: No refund

Compared with other Day Trips

TourPriceDurationRatingGroup
This tour · #27 of 39€1069h–12h4.72 (356)varies by option
Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner€1498h4.96 (1592)shared
Tuscany Vespa Tours Through the Hills of Chianti€1606h4.99 (580)shared
SMALL-GROUP Wine Safaris: Tuscany Wine Tasting Tour from Florence€1306h4.94 (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. Compare all 39 Day Trips

From €106 per adult · Essential Coach Tour & Dinner