Booking Wolf
Private 8-Hour Tuscany Day Trip in Siena, San Gimignano and Chianti from Florence
food_culinary

Private 8-Hour Tuscany Day Trip in Siena, San Gimignano and Chianti from Florence

by Chianti Drivers

8 hours
Florence
€639€710 on ViatorSave 10% total for 2 guests
From
€639€710 on ViatorSave 10%total for 2 guests

Choose from 1 available option

8 hours
Starting time
Friday 11 September 2026
Free cancellation until 10 Sept 2026.
€639€710Save 10%
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.€710

Overview

The tour begins with a hotel pickup in Florence by a private luxury car or minivan equipped with air conditioning and bottled water. An English-speaking driver familiar with Tuscany drives the group through the Chianti wine region, offering historical details and local insights along the way. Travelers can request onboard Wi-Fi when booking. The first major stop is Siena, where visitors spend about two hours visiting key sites such as the Piazza del Campo, known for its shell shape and the Palio horse race, and the 13th-century Siena Cathedral. The historic streets offer shops with local products for tasting or purchase. After Siena, the journey continues through the Chianti hills along the Strada Statale 222 Chiantigiana, with stops for photos of the surrounding countryside. The tour then reaches San Gimignano, where there are about two hours to explore the medieval hilltop town famous for its towers dating back to the 1300s. This is the final sightseeing stop before returning to Florence. There is an option to include lunch with wine tasting at a farm or winery, which must be paid on site. Choosing this option reduces time in Siena and San Gimignano and excludes the stop at the Monteriggioni fortress. The driver is available throughout for questions and assistance during the full eight-hour private tour.

Highlights

Private tour with English-speaking driver
Visit Siena’s Piazza del Campo and Cathedral
Explore San Gimignano’s medieval towers
Drive through Chianti hills with photo stops
Option for lunch and wine tasting at winery
Hotel pickup and drop-off in Florence

What's included

Services of an expert English-speaking driver
Bottled water provided during the tour
Onboard Wi-Fi available if requested at booking
Air conditioning in the vehicle
Private luxury car or minivan use
Hotel pickup and drop-off in Florence

What's not included

Full lunch and wine tasting at winery to be paid on site from 50/70 euros per adult
Licensed guide service in Siena is not included
Other personal expenses not listed

Itinerary

1

Siena

Siena is noted for its medieval architecture. Visitors spend about two hours seeing key landmarks including the Conch-shaped Piazza del Campo and the 13th-century Siena Cathedral. The town’s historic streets have local shops offering food tastings and souvenirs.

120 min

2

San Gimignano

The stop in San Gimignano offers about two hours to explore the medieval town known for its historic towers. There is an option to arrange lunch and wine tasting at a local farm or winery, payable on site. Selecting this reduces time in Siena and San Gimignano and excludes the Monteriggioni fortress.

120 min

3

Strada Statale 222 Chiantigiana

The drive passes through the Chianti hills along the Strada Statale 222 Chiantigiana with a stop for photographs of the countryside.

4

Historic Centre of San Gimignano

San Gimignano’s historic centre, dating back to the 1300s, is known for its medieval towers. This is the last sightseeing stop before returning to Florence.

120 min

Cancellation policy

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

Additional info

1–15 travelers per booking
Mobile ticket
Infant seats are available
Pushchair and stroller friendly
Suitable for all fitness levels
Tours accommodate a maximum of seven people per booking
Total
€639Save 10% vs Viator