• Siena - Siena is a true medieval treasure and is renowned as one of Tuscany’s most stunning hilltop towns. Upon arrival, join a one-hour guided walking tour with a local guide through Siena’s most charming streets and landmarks, including entry to the Cathedral, a trove of artworks. Afterwards, enjoy Siena at your leisure with time for shopping or relaxing in an open-air café.
• Piazza Salimbeni - The first stop on the Siena walking tour is a bank headquartered in this square - the oldest surviving bank in the world. Known as Monte dei Paschi di Siena, it has been operating continuously since 1472. Your guide will explain how Siena’s wealth over the centuries stemmed from its location on the pilgrim route, Via Francigena, which connected Rome and Northern Europe. Siena thrived as a banking town by lending and exchanging money for merchants using the pilgrim route as a safe passage. The Sienese remain prosperous from their banking heritage and are still renowned for their banks today!
• Contrada della Torre - Your local guide will then lead you through some of Siena’s most picturesque back streets, sharing insights about the 17 districts that form the historical center. These ancient divisions are called ‘contrade’. Each contrada has its own symbol, often an animal like a snail, rhino, or giraffe. You will visit the church and museum of one of the contrade. The sense of identity and belonging to one’s ‘contrada’ is extremely significant. They are self-contained communities with their own church, where newborns are baptized, and a public fountain for a second baptism! Needless to say, there are strong rivalries between these districts, which culminate during the Palio horse race held twice a year in Piazza del Campo.
• Piazza del Campo - Piazza del Campo is one of the most beautiful squares you will ever see and serves as the city’s gathering place, where locals meet for coffee, conversation, and of course, gossip. The unique square (not actually a square, but shell-shaped and sloping!) is the site of the famous Palio horse race, a 600-year-old tradition in Siena. The piazza transforms into a racetrack twice a year, and the contrade, or city neighborhoods, compete for the highest honor – winning the Palio. You’ll learn more about this on the tour, as your local guide sets the scene to help you experience the vibrant atmosphere of this incredible race.
• Duomo di Siena - The walking tour concludes inside the Duomo of Siena – undoubtedly the city’s crown jewel. If you’ve seen the interior of Florence’s Duomo, it pales in comparison to Siena’s. The most unique feature of this cathedral is its floor, an artwork in itself, crafted from the world’s most precious marbles. It’s a combined masterpiece of over 50 images created over two centuries by some of Italy’s most important artists. Then, enjoy strolling through the city center on your own before meeting your guide again to proceed to your next destination!
• Fattoria Poggio Alloro - After exploring Siena in the morning, a 45-minute drive will take you to 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 a stunning location overlooking breathtaking views of the surrounding countryside. Take the opportunity to savor fresh organic farm food, including homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad, and Tuscan biscotti. There is also the chance to purchase local products from the winery before heading to San Gimignano.
• San Gimignano - After lunch, a 15-minute drive will take you to San Gimignano, an even smaller, walled Tuscan hill town than Siena - about six times smaller - and a UNESCO World Heritage Site. San Gimignano is most famous for its towers, of which there were originally 72, though only 14 remain today. This gives the city its nickname, the “Little Manhattan of Tuscany.” Your guide will provide a map and highlight the best landmarks, allowing you to explore the picturesque streets and squares of this enchanting hilltop town independently.
• Piazza della Cisterna - Your guide will lead you to the city gate entrance, where the main boulevard, Via San Giovanni, begins. This street leads to Piazza della Cisterna, the heart of San Gimignano and the setting for several films. This square hosted festivals and tournaments, while Piazza Duomo served as the religious and political center. Here, you’ll find the best gelato in the world – Gelateria della Piazza ‘Dondoli’. It’s won numerous awards as the best gelato, so you can try it and see what you think!
• Piazza del Duomo - From Piazza della Cisterna, the next piazza is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but well worth visiting! The cathedral’s beautiful interior is adorned with colorful 14th-century frescoes in every available space. You can also climb one of the medieval towers here in this piazza, next to the Duomo (the Torre Grossa), to enjoy an incredible ‘bird’s eye’ view over San Gimignano.
• Rocca of Montestaffoli - Another stunning view over the towers of San Gimignano is from La Rocca. It is easily accessible behind the Duomo and offers a peaceful setting with olive trees and a wall surrounding the garden, part of the 14th-century fortress built by the Medici of Florence 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.
• Pisa - After visiting San Gimignano, a 1.5-hour scenic drive through iconic Tuscan countryside will take you to your final stop, Pisa.
• 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!
• 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. Part of the fun is also climbing the stairs inside the Leaning Tower, which may leave you feeling a bit dizzy at the end!
• Florence - After leaving Pisa, it will take about an hour to return to Florence. You will be dropped off at the starting point with a camera full of pictures and a stomach full of hearty Tuscan food.

• 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
• Professional English speaking tour guide with you for the whole day
• Guided walking tour of Siena with entrance fee to the cathedral
• 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

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!

For a full refund, cancel at least 24 hours before the scheduled departure time.