Why travelers love this tour
Highlights
Private Walking Tour of Siena
Relaxed walking tour of Siena with a private guide
Vineyard Lunch & Wine Tasting
Delicious authentic Tuscan farmhouse lunch and informal wine tasting at a vineyard
Free Time in San Gimignano
Explore the hilltop town of San Gimignano at your leisure
Scenic Drive Through Tuscany
Scenic drive through the iconic Tuscan landscape of rolling hills, vineyards and castles
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Tour at a Glance
Prices, times and meeting point — all in one place.
From€ 500,00
Free CancellationUp to 24 hours before departure
Duration10 hours
DeparturePick up at your accommodation
Meeting pointPick up and drop off at your accommodation.
Itinerary
Two Cities, One Valley, One Perfect Day
San Gimignano's medieval towers, a family organic winery in the Chianti hills, then Siena's Piazza del Campo — a full sweep of Tuscany's greatest medieval legacy in a single private tour.
Depart FlorenceOur fabulous private Tuscany tour taking in Siena and San Gimignano is a wonderful introduction to two of the most charming and picturesque cities in the region. Step back in time and make the memories of a lifetime! You’ll leave Florence and head to beautiful San Gimignano, passing through the iconic Tuscan landscape of rolling hills, vineyards and castles. As you go, your guide will give you an overview of the history of the town, throughout its most powerful period in the thirteenth and fourteenth centuries. You’ll learn all kinds of interesting facts about the culture and traditions of this place, which was set along the famous pilgrim’s route and became renowned as the Manhattan of Tuscany for the 72 towers that made up its centre. Today just 14 of these remain, but understanding the stories behind them will give you a valuable insight.
San GimignanoOnce you arrive in the walled hilltop city, you’ll be free to explore its ancient architecture and cobbled streets at your leisure. It’s up to you how you spend your time but you certainly won’t be short of choices, from climbing the tallest of the towers, tasting award winning gelato, and visiting the stunning cathedral with its priceless frescos, to wandering through the frescoed courtyard of the old city hall. To top off your visit you might want to stroll to the highest viewpoint and take in panoramic views over the landscape, then finish with a coffee or wine at one of the many delightful cafes.
Lunch at a Chianti wineryYou will not want to leave but the guide will entice you away with the promise of another beautiful place: an organic farmhouse and winery in Chianti boasting unbeatable views of the hilltop town and the surrounding countryside. Here you will have the unique opportunity to get a glimpse into the life of a family run organic Tuscan farm. You’ll take a tour of the farm, visit the wine cellar and then enjoy a walk through the vineyard. Then you’ll be ready to sit down and enjoy the beautiful surroundings, whilst doing a wine tasting and eating a traditional homemade Tuscan meal.
SienaThe final stop on this private Tuscany tour is the magnificent city of Siena, where your guide will regale you with stories and the history of the Palio horse race, for which it is so famous, and the 17 contradas (districts) that vie for the coveted prize every year. You’ll wander around the lovely Piazza del Campo and, if you’re up for it, climb the daunting Torre del Mangia for the ultimate views. Other highlights you’ll visit are the spectacular Duomo, with its jaw-dropping architecture and the priceless cache of artworks by Michelangelo, Donatello, Bernini, Nicola Pisano and other famous artists. Your guide will also point out features of interest in the interiors, including the frescos in the tiny library and the intricate marble inlaid floors. You’ll finish off this wonderful private Tuscany tour with some free time to explore further at your leisure, or simply relax in an outdoor cafe in the Piazza del Campo and watch the world go by with a coffee or vino.
Highlights
What's included
- Air-conditioned travel by luxury minivan
- Delicious winery lunch with gluten-free or vegetarian options available
- Four varieties of wine tasting
- Walking tour of Siena with your private guide, includes entrance to the cathedral
- Information and handy maps of places visited
Duration10 hours
DeparturePick up at your accommodation
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 ScalaIf your visit is at a time when the Duomo of Siena is closed for religious services, you will instead visit the wonderful Santa Maria della Scala museum
- Not Suitable for Limited MobilityBecause the tour includes uneven and steep surfaces we are not able to accept people with limited mobility or wheelchair users
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.
If you would like to change the day of your tour, you may do so (depending on availability) up to 24 hours before the start of the tour with no extra fees.
We always love to hear feedback about the tour! You can find us on TripAdvisor by searching for the Walkabout Florence Tours.
