Why travelers love this tour
Three Cities, One Epic Day
Siena's Gothic streets, a farmhouse lunch in Chianti, San Gimignano's medieval towers and the Leaning Tower of Pisa — the ultimate private Tuscany day trip
Guided Tour of Medieval Siena
Guided walking tour through the medieval city of Siena
Vineyard Lunch & Wine Tasting
Traditional Tuscan lunch and informal wine tasting at a Chianti vineyard
Free Time in San Gimignano
Free time in the hilltop town of San Gimignano
Pisa & the Leaning Tower
Scenic drive to historic Pisa to explore its hidden corners and iconic tower
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Tour at a Glance
Prices, times and meeting point — all in one place.
From€ 580,00
Free CancellationUp to 24 hours before departure
Duration12 hours
Departure8.30 am
Meeting pointPick up and drop off at your accommodation.
Itinerary
The Grand Tuscany Loop
Nine hours, three UNESCO cities, a Chianti lunch and one unforgettable private drive through the heart of Tuscany.
Depart FlorenceOne of our experienced guides will meet at your accommodation for the start of your private Tuscany tour. We will depart at 9am in a comfortable, air conditioned vehicle for a whirlwind itinerary.
Visit SienaYour guide will introduce you to Siena through the eyes of a local as you explore the city streets lined with medieval and Renaissance buildings. You’ll discover the world’s first bank, learn about the city’s illustrious heritage and tour the sumptuously decorated Duomo. Your guide will help you visualise the 600-year-old Palio race as you stand in the Piazza del Campo, the site of this renowned and ancient competition. There will also be time for you to absorb the city over a coffee in an open-air cafe or to pick up some local souvenirs.
A Chianti Farmhouse LunchYour next stop is considered by many of our guests to be the climax of this private Tuscany tour. We’ll take you to the vineyards of a family-owned Chianti estate for a relaxed wine tasting class where you can sample a range of the wines that they produce: Chianti, Vernaccia and Vin Santo (the regional dessert wine). Once we’ve whet your appetite with Tuscan wines you’ll be ready for the regional culinary experience that awaits you. You and your party will dine on the farmhouse terrace where you can feast on the stunning landscape and the delicious dishes, washed down by the sublime wine. You’ll be offered homemade pasta, cured meats, local cheeses, salads and Tuscan biscotti.
You’ll want to have your camera ready, too - the views are delectable!
San GimignanoAfter you’ve had your fill of the lunchtime delicacies, we’ll take you to San Gimignano, one of the region's finest gems, and one of our favourite stops on this private Tuscany tour. Perched on a hill overlooking the countryside, the compact town is a wonderful place to do some shopping, wander the charming streets, indulge in the region’s most famous gelato or explore the renowned medieval towers.
Scenic Country Drive & PisaFrom San Gimignano you’ll set out on a trip through the rolling hills of Tuscany to Pisa, which is the final destination on the day’s itinerary. Your guide will give you a personal tour around the historic parts of the city and you’ll have the opportunity to learn more about the Leaning Tower, the Cathedral and the Baptistery. If you want to enjoy the amazing views from the Tower we will arrange a skip-the-line ticket - all you’ll need to bring is the stamina to climb all those steps!
Return to FlorenceAt the end of your private Tuscany tour, our guide will bring you back to Florence with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new experiences.
Highlights
What's included
- Travel by air-conditioned luxury van
- A guided walk around Siena
- A Tuscan meal prepared in a regional farmhouse
- Wine tasting session
- Maps of and information about all the towns visited
Duration12 hours
Departure8.30 am
Free cancellationUp to 24 hours before departure
Know before you go
Helpful details before booking
A few practical notes to help you choose the right Tuscany day trip and arrive prepared.
- Duomo May Be Replaced by Santa Maria della ScalaWhen the Duomo of Siena is closed for religious services, Santa Maria della Scala museum will be visited instead.
Plan your Tuscany trip
Travel guides before you go
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Frequently Asked Questions
Once you have made your reservation and made the payment by credit card through our secure website, you will be able to print the information or save it to your mobile device to bring with you to the check-in.
We offer a full refund to any cancellation up to 24 hours before the departure time of the tour.
We always love to hear feedback about the tour! You can find us on TripAdvisor by searching for the Walkabout Florence Tours.
