Private Tuscany Tour Pisa, Siena, San Gimignano and Winery Lunch

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Recommended by 100% of reviewers

| Florence, Italy

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11 hours (approx.)

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Overview

With this personalized tour of Tuscany, you and your friends may see all the area's hidden treasures in a single day. An experience made even better with an extravagant lunch and wine sampling in Tuscany.

We're going to leave in a cozy, air-conditioned minivan in the morning for a fast-paced tour.

In Siena, as you stroll through the alleyways adorned with Renaissance and medieval architecture, your guide will give you an insider's view of the first bank in history, the exquisitely designed Duomo, and the famous Piazza del Campo.

We'll take you to a family-run Chianti estate's vineyards for a laid-back wine-tasting experience and a superlative regional culinary experience while taking in the breathtaking scenery.

Then we'll drive you to San Gimignano, one of the area's greatest treasures and one of our favorite stops on this private tour.

The final stop will be Pisa, where you will have the chance to discover the Baptistery, the Cathedral, and the world-famous Leaning Tower!

What's Included

Scenic drive to historic Pisa to explore its hidden corners and iconic tower
Winery tour and wine tasting of four varieties
Hearty farmhouse lunch – veggie and gluten-free options available
Visit the church and the museum of one of the contrade in Siena
Travel by air-conditioned luxury van
Free time to explore San Gimignano at your own pace
Guided walking tour of Siena with entrance fee to the cathedral
Professional English speaking tour guide with you for the whole day

Meeting and Pickup

Pickup point

Pickup details

Pick up at your accommodation

What To Expect

Siena

Siena is a real medieval gem and in fact one of Tuscany's most famous and beautiful hill top towns. When you arrive you will join a 1 hour guided walking tour with a local city guide through Siena's most beautiful streets and sites, including the entrance to the Cathedral, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.

3 hours • Admission Ticket Free

Piazza Salimbeni

The first stop on the walking tour of Siena is a bank that has its headquarters in this square - the oldest surviving bank in the world. It's called Monte dei Paschi di Siena and it has been running continuously since 1472. Your guide will explain how Siena's wealth through the centuries came from being on the pilgrim route known as the Via Francigena, a route that led pilgrims between Rome and Northern Europe. Siena prospered as a banking town by lending money and exchanging money for the merchants who were using the pilgrim route as a safe travel route. The Sienese are still wealthy from their banking past and are still famous for their banks today!

15 minutes • Admission Ticket Free

Contrada della Torre

Your local guide will then walk through some of the most picturesque back streets of Siena, while telling about something very unique to Siena are the 17 districts which make up the historical centre.The name for these ancient divisions is 'contrade'. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. You will visit the church and museum of one of the contrade. The sense of identity and belonging to ones 'contrada' is extremely important. They are self-contained little worlds with their own church, where newborns are baptised, and a public fountain where the newborns are baptised a second time! Needless to say there are strong rivalries between these districts, that explodes during the Palio horserace held twice a year in Piazza del Campo.

15 minutes • Admission Ticket Free

Piazza del Campo

Piazza del Campo is one of the most beautiful squares you will ever see and it is also the city's gathering place, where the locals meet for a coffee and to chat and of course gossip. The unusual square (actually not a square, it's in the shape of a sea-shell, and sloping!) is the site of the famous Palio horse-race. A 600 year old tradition of Siena. The piazza gets transformed into a racing track twice a year and the contrade, or neighbourhoods of the city battle out for the highest honour possible – winning the palio. You'll hear more about this on the tour, your local guide will set the scene so that you can somehow live for a moment the vibrant atmosphere of this incredible race.

15 minutes • Admission Ticket Free

Duomo di Siena

Our walking tour then ends inside the Duomo of Siena – undoubtedly the jewel of the city. If you've seen the interior of Florence's Duomo, it is nowhere near as spectacular as Siena's. The most unique part of this city's cathedral is its floor. It's an artwork on its own, made out of the world's most precious marbles – in fact, it's a combined masterpiece of over 50 images created over 2 centuries by some of Italy's most important artists. Then, enjoy walking through the city center on your own before meeting your guide again to head to your next stop!

15 minutes • Admission Ticket Included

Fattoria Poggio Alloro

After the morning exploration of Siena, a 45-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Enjoy an informal wine tasting lesson and a traditional Tuscan lunch with plenty of wine, in the most gorgeous location overlooking stunning views of the surrounding countryside. Take the opportunity to try fresh organic farm food of homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad, and Tuscan biscotti. There is also the opportunity to buy the local products of the winery before heading to San Gimignano.

1 hour 30 minutes • Admission Ticket Free

San Gimignano

After lunch, a 15-minute drive will take you to San Gimignano, that is an even smaller, walled Tuscan hill town than Siena - about 6 times smaller - and a UNESCO World Heritage Site. San Gimignano is most famous for its towers of which there were 72 though there are just 14 remaining today. From this the city gets its nickname of the little Manhattan of Tuscany. Your guide will give you a map and point out the best landmarks, so that you can roam independently the picturesque streets and squares of this enchanting hilltop town.

1 hour 30 minutes • Admission Ticket Free

Piazza Della Cisterna

Your guide will lead you to the entrance city gate and that is where the main boulevard starts from, Via San Giovanni. This street will take you to Piazza della Cisterna, the heart of San Gimignano and also the setting for several films. This was the square where festivals and tournaments took place while the Piazza Duomo was the religious and political centre. This is also where the best gelato in the world is – Gelateria della Piazza 'Dondoli'. It's won many awards as the best gelato, you could try it and see what you'll think!

20 minutes • Admission Ticket Free

Piazza del Duomo

From Piazza della Cisterna, the next piazza along is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but is well worth visiting! The beautiful interior of the cathedral walls is filled with colorful 14th century frescoes in every space available. You could also climb up one of the medieval towers here in this piazza, next to the Duomo (the Torre Grossa) to appreciate the incredible 'BIRD'S EYE' view over San Gimignano.

20 minutes • Admission Ticket Free

Rocca of Montestaffoli

Another stunning view over the towers of San Gimignano is from La Rocca. It is easily accessible behind the Duomo and It is a peaceful setting with olive trees and the wall surrounding the garden that formed part of the 14th-century fortress Medici of Florence built to protect this town from Siena. if you walk to the back of the garden and climb the steps to the top, the views over San Gimignano's skyline are absolutely breathtaking.

20 minutes • Admission Ticket Free

Pisa

After the visit of San Gimignano, a 1 hour and an half scenic drive through iconic Tuscan countryside will take you to your final stop, Pisa.

1 hour • Admission Ticket Free

Piazza dei Miracoli

Upon arrival, your guide will lead you straight to the famous Square of Miracles. At first sight, it is truly breathtaking - the white marble buildings glow in contrast to the perfect, green lawns. You will have about an hour to explore the Cathedral, Baptistry, Monumental Cemetery, and of course - The Leaning Tower!

15 minutes • Admission Ticket Free

Leaning Tower of Pisa

During your time in Pisa, you can climb the Leaning Tower to admire the incredible views of the Square of Miracles from above. The views from the top of the Tower are truly breathtaking - from the monuments below, to the city surrounding the square, the Arno River, and the countryside in the distance... and part of the fun is also climbing the stairs inside the Leaning Tower that we will make you feel a bit dizzy at the end!

30 minutes • Admission Ticket Included

Florence

After leaving Pisa, it will take about an hour to return to Florence. You will dropped off at the start point with a camera full of pictures and a stomach full of hearty Tuscan food.

1 hour • Admission Ticket Free

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Additional Info

Confirmation is instant and will be received at time of booking
Public transportation options are available nearby
Not recommended for travelers with spinal injuries
Not recommended for travelers with poor cardiovascular health

Travelers should have at least a moderate level of physical fitness
Infants and small children can ride in a pram or stroller
Infants are required to sit on an adult’s lap

Frequently Asked Questions

(7)

Q: What is the cancellation policy for the Private Tuscany Tour Pisa, Siena, San Gimignano and Winery Lunch?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CEST).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025