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Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano

4.8 · 348 ratings on Guidekin, Viator & Tripadvisor 96% of star-rated reviews are 4★ or 5★ Florence Operated by Walks - Italy & Spain Free cancellation · up to 24 hours before
Duration
9h
Group
Group size varies by option: small group from €195 · private from €675
Guide languages
English
Start & pickup
08:30, 09:00 · No hotel pickup: everyone meets at the start point
Booking
Instant confirmation · mobile ticket
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 (see the comparison).

How we choose tours →Commissions never affect our verdicts.

Options and prices

2 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
Small Group TourThe page priceGroup Tour€195
Private Tuscany from FlorenceSiena, 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.€675 for 2+ people

Children from €185 (ages 2 to 14). Option texts and prices come from the operator's listing; prices checked on Viator on 3 October 2026.

Included and not 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
  • Gratuities
  • Hotel Pick-Up/Drop-Off

Reviews

4.8
348 ratings
Guidekin, Viator & Tripadvisor

96% of ratings with a star breakdown are 4★ or 5★: 334 of 348

Star breakdown of all 348 ratings

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 (13 September 2025 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
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. · Open in Google Maps
Departure
08:30, 09:00 daily; scheduled through September 2027 (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
Walks - Italy & Spain; booking and payment are completed on Viator

Itinerary

About this tour, from the operator

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.

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
  • This is a walking tour. Guests should be able to walk at a moderate pace without difficulty.
  • 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.

Children

  • Specialized infant seats are available

Accessibility

  • Strollers OK
  • Public transportation options are available nearby
  • Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollers.

Good to know

  • Food included see what is included
  • Children from €185 ages 2 to 14

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 · #24 of 39€1959h4.79 (348)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 #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. Compare all 39 Day Trips

From €195 per adult · Small Group Tour