Booking Wolf
Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano
food_culinary

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

by Walks Italy Spain

9 hours
Assisi
€175.50€195 on ViatorSave 10%/person
From
€175.50€195 on ViatorSave 10%per person

Choose from 2 available options

9 hours
Starting time
Friday 11 September 2026
Language
English
Free cancellation until 10 Sept 2026.
€351€390Save 10%
2 adults × €175.50
All taxes and fees included

How do you want to book?

Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.

Book on Viator Confirmed right away, but you pay full price.€390
9 hours
€351€390Save 10%
2 adults × €175.50
All taxes and fees included

Overview

This nine-hour small-group tour departs from central Florence in an air-conditioned vehicle with a maximum of 14 participants. The tour begins with a drive through the hills of Tuscany, including a stop at a panoramic viewpoint overlooking Florence for photos. The first destination is the medieval town of San Gimignano, a UNESCO World Heritage Site known for its towers and historic streets. Guests have about one and a half hours of free time to explore San Gimignano independently. Next, the tour continues to a family-run farm in the Chianti region. Visitors receive a guided tour of the vineyards, winery, and wine cellars, followed by a lunch featuring local seasonal ingredients paired with Chianti wines selected to complement the meal. The lunch includes a wine tasting of several Chianti wines. After lunch, the tour proceeds to Siena, a well-preserved medieval town famous for its architecture and the Palio horse race. Guests have two hours of free time to walk around the town and visit landmarks such as the Piazza del Campo. Time permitting, guests may also visit the Duomo di Siena; entrance tickets are not included but the tour leader will provide assistance. The day ends with a comfortable coach ride back to Florence.

Highlights

Small-group tour limited to 14 people
Free time in San Gimignano and Siena
Lunch and wine tasting at family farm in Chianti
Air-conditioned transport through Tuscan countryside
Visit Siena Cathedral with guide assistance

What's included

English-speaking expert tour leader
Free time for independent exploration in San Gimignano and Siena
Professional driver for all transport
Gourmet lunch and wine tasting at Chianti farm
Air-conditioned vehicle throughout the tour

What's not included

Tips and gratuities
Hotel pick-up and drop-off

Itinerary

1

Tuscany

Pickup occurs in central Florence by an expert driver and tour leader in an air-conditioned vehicle. The route goes through the Tuscan hills with a stop at a panoramic viewpoint of Florence for photographs.

90 min

2

San Gimignano

Guests have about one and a half hours of free time to explore the UNESCO-listed town known for its medieval towers and architecture. The private tour option does not include a guided walk here, allowing more time for independent exploration.

90 min

3

Tuscany

The tour continues to a family-run farm in the Chianti region where guests receive a guided tour of vineyards, the winery, and wine cellars. Following the tour, a lunch featuring local and seasonal ingredients is served with Chianti wines chosen to pair well with each dish. This stop lasts about three hours.

180 min

4

Siena

Guests have two hours of free time in the medieval town of Siena, noted for its well-preserved architecture. The town is famous for the Palio horse race held in the Piazza del Campo. Visitors can explore on their own and optionally visit the Siena Cathedral.

120 min

5

Piazza del Campo

During free time in Siena, the tour leader recommends visiting the Piazza del Campo, the square where the Palio horse race takes place and where the winning team receives a hand-painted silk banner.

6

Duomo di Siena

If time allows, guests can visit the Siena Cathedral, a notable example of Tuscan architecture, during their free time. Entrance tickets are not included, but the tour leader can assist with arrangements.

7

Piazza Della Repubblica

At the end of the day, guests board the private coach for the return trip to Florence. The transport is comfortable and air-conditioned, allowing guests to relax after the day's activities.

60 min

Meeting point

Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets by the Carousel in Piazza della Repubblica.

End point

Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets by the Carousel in Piazza della Repubblica.

Languages

English (guide)

Cancellation policy

  • Cancel at least 24 hours before start for a full refund.

Additional info

1–15 travelers per booking
Mobile ticket
Reachable by public transport
Infant seats are available
Suitable for all fitness levels
The tour is not suitable for guests with mobility impairments, wheelchairs, or strollers due to its nature.
Guests should be able to walk at a moderate pace as the tour involves walking.
Guests with dietary restrictions must contact the operator after booking to arrange lunch; vegans and those with celiac disease cannot be accommodated.
Tickets for the Siena Cathedral are not included; the tour leader can assist with purchasing them. The cathedral is closed on Sundays and some holy days.
Small luxury minivans are used to access city centers to avoid parking outside, requiring walking. For groups larger than eight, guides may split time between vehicles.
The itinerary and experience may vary depending on season, day, and group size.
Multiple tour options are available; guests should select the one that fits their preferences.
Total
€351Save 10% vs Viator