---
title: Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano
lang: en
type: tour
city: Florence
country: Italy
price: 195
currency: EUR
price_unit: per_person
availability: bookable
rating: 4.79
reviews: 336
duration_minutes: 540
languages: [en]
free_cancellation: true
rank_in_category: 24 of 39 (Day Trips)
schedule_checked: 2026-09-18
data_updated: 2026-09-18
canonical: https://guidekin.com/italy/florence/tours/florence-day-trip-chianti-wine-tasting-siena-san-gimignano/
---

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

**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 336 travellers.

## Overview

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.

## Key facts

- Price: from €195 per person
- Duration: 9h
- Rating: 4.79/5 from 336 reviews (collected from Guidekin & Viator & Tripadvisor)
- Free cancellation (see policy below)
- Operator: Walks - Italy & Spain

## 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 |
|---|---|---|---|
| Small Group Tour | €195 / person | English | Group Tour |
| Private Tuscany from Florence | €675 / person (for 2+ people) | English | Siena, 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. |

## What's 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

## Not included

- Gratuities
- Hotel Pick-Up/Drop-Off

## Itinerary

1. **Tuscany** (1h 30m) - Your driver and tour leader will pick you up in a comfortable, air-conditioned transport in central Florence and drive you through the hills of Tuscany. You'll pass the best panoramic viewpoint of Florence and pause for pictures.
2. **San Gimignano** (1h 30m) - Indulge your imagination with a stop at San Gimignano, a town of such unique architectural beauty it has been designated a UNESCO World Heritage Site. You'll have free time to explore its winding streets on your own. Please note that the private option does not include a...
3. **Tuscany** (3h) - Walking the hills of Tuscan towns will make you hungry so your next stop is an authentic Italian family farm where some of our good friends will give you a behind-the-scenes tour of the vineyards, winery, and wine cellars before sitting you down for a sumptuous, all-inclusive...
4. **Siena** (2h) - is one of the best-preserved examples of medieval Italian architecture in the world. Spared German bombing in WWII, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world.
5. **Piazza del Campo** (pass by, no stop) - One of the highlights your tour leader will recommend during your free time. Pause amidst the square where fervent horses race to win the honor of bringing home the palio - a handpainted silk banner of the highest regard.
6. **Duomo di Siena** (pass by, no stop) - If time allows, a visit to the Siena Cathedral, a Tuscan gem, during your free time won't disappoint!
7. **Piazza Della Repubblica** (1h) - At the end of the day, hop aboard your comfortable private coach bus back to Florence. We've taken care of the logistics so all you have to do is enjoy the food, the sights, and the scenery.

## Schedule

- Runs: daily
- Departures: 08:30, 09:00
- 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

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.

## Good to know

- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollers.
- This is a walking tour. Guests should be able to walk at a moderate pace without difficulty.
- Those with dietary restrictions need to contact us after booking the tour so we can arrange your lunch. Unfortunately, we cannot accommodate vegans or those with celiacs.
- Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your tour leader will assist you. The Cathedral is closed on Sundays and for certain holy days.
- 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.
- Please note that this description is an example, and your experience may vary depending on the season, day of the week, and group size. Regardless of where your tour goes, you always have an excellent experience.
- Please note: This tour offers multiple options. Take a moment to choose the one that best suits your interests.

## How it compares in Day Trips

Ranked **#24 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

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