Embark on a Tuscany tour and explore the charming towns of Siena and San Gimignano. Indulge in a winery lunch and discover the rich history and beauty of the region.
Embark on a Tuscany tour and explore the charming towns of Siena and San Gimignano. Indulge in a winery lunch and discover the rich history and beauty of the region.
- Florence - Upon meeting the expert guide, an air-conditioned minivan will transport you to the first destination of the day, Siena. The journey to Siena takes approximately 1 hour and 15 minutes. During the drive, the guide will outline the day’s itinerary and share fascinating insights about Siena and Tuscany.
- Siena - Following lunch, a…
- Florence - Upon meeting the expert guide, an air-conditioned minivan will transport you to the first destination of the day, Siena. The journey to Siena takes approximately 1 hour and 15 minutes. During the drive, the guide will outline the day’s itinerary and share fascinating insights about Siena and Tuscany.
- Siena - Following lunch, a 45-minute drive will bring you to Siena, a true medieval treasure and one of Tuscany’s most renowned and picturesque hilltop towns. Upon arrival, join a 1-hour guided walking tour with a local city guide through Siena’s most stunning streets and landmarks, including entry to the Cathedral, a trove of artworks. Afterwards, enjoy free time to explore Siena at your leisure, whether shopping or relaxing in an open-air café.
- Piazza Salimbeni - The walking tour of Siena begins at a bank headquartered in this square - the oldest surviving bank in the world, Monte dei Paschi di Siena, operational since 1472. The guide will explain how Siena’s historical wealth stemmed from its location on the Via Francigena pilgrim route, connecting Rome and Northern Europe. Siena thrived as a banking hub by lending and exchanging money for merchants traveling this safe route. The Sienese remain prosperous from their banking heritage and are still renowned for their banks today.
- Oca - The local guide will lead you through some of Siena’s most charming back streets, discussing the unique 17 districts that form the historical center, known as ‘contrade’. Visit a church and museum of one contrada. Each contrada has its own symbol, often an animal like a snail, rhino, or giraffe. The sense of identity and belonging to one’s ‘contrada’ is vital. They are self-contained communities with their own church, where newborns are baptized, and a public fountain for a second baptism! Intense rivalries exist between these districts, culminating in 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 encounter and serves as the city’s social hub, where locals gather for coffee and conversation. The uniquely shaped square (resembling a sea-shell and sloping) hosts the famous Palio horse race, a 600-year-old Siena tradition. The piazza transforms into a racetrack twice a year, with the city’s contrade competing for the highest honor – winning the Palio. The guide will vividly describe this event, allowing you to 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 cathedral’s most distinctive feature is its floor, an artwork in itself, crafted from the world’s most precious marbles. It’s a collaborative masterpiece of over 50 images created over two centuries by some of Italy’s most esteemed artists. Afterward, enjoy exploring the city center independently before reuniting with your guide.
- Fattoria Poggio Alloro - After the morning in Siena, a 15-minute drive will take you to the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the day’s highlight! Tour the farm, partake in an informal wine tasting lesson, and savor a traditional Tuscan lunch with ample wine, set in a breathtaking location overlooking the stunning countryside. Meet fellow travelers while enjoying fresh organic farm food, including homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a garden-fresh salad, and Tuscan biscotti. There’s also an opportunity to purchase local winery products before heading to San Gimignano.
- San Gimignano - San Gimignano is a small, walled Tuscan hill town and a UNESCO World Heritage Site, renowned for its towers, of which 14 remain from the original 72. This gives the city its nickname, the “Little Manhattan of Tuscany.” The guide will provide a map and highlight the best landmarks, allowing you to explore the charming streets and squares of this enchanting hilltop town independently.
- Piazza della Cisterna - The 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 world’s best gelato at Gelateria della Piazza ‘Dondoli’, which has won numerous awards. Try it and see what you think!
- Piazza del Duomo - From Piazza della Cisterna, the next square is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but worth visiting! The cathedral’s interior is adorned with vibrant 14th-century frescoes in every available space. You can also climb one of the medieval towers here, next to the Duomo (the Torre Grossa), to enjoy an incredible bird’s-eye view over San Gimignano.
- Rocca of Montestaffoli - Another breathtaking view over San Gimignano’s towers is from La Rocca. Easily accessible behind the Duomo, it offers a tranquil setting with olive trees and a garden wall that was part of the 14th-century fortress built by the Medici of Florence to protect the town from Siena. Climb the steps at the back of the garden for stunning views of San Gimignano’s skyline.
- Florence - After visiting San Gimignano, a 1-hour drive will return you to Florence. You’ll be dropped off at the starting point with a camera full of photos, a stomach full of delicious Tuscan food, and a host of new friends.

- Professional English speaking tour guide available all day
- Winery tour and tasting of four wine varieties (adults 18+ only)
- Comprehensive maps and information on every town visited
- Hearty farmhouse lunch with vegetarian and gluten-free options
- Guided walking tour of Siena, including cathedral entrance
- Comfortable travel with air-conditioned…
- Professional English speaking tour guide available all day
- Winery tour and tasting of four wine varieties (adults 18+ only)
- Comprehensive maps and information on every town visited
- Hearty farmhouse lunch with vegetarian and gluten-free options
- Guided walking tour of Siena, including cathedral entrance
- Comfortable travel with air-conditioned vehicles
- Free time to independently explore San Gimignano
- Gratuities
- Gratuities
Post departing from Florence, your journey continues toward San Gimignano. On the way, you’ll admire the scenery consisting of vineyards and undulating landscapes while acquiring captivating knowledge about this town’s past.
Upon reaching, your guide will lead you to the entrance, post which you are free to explore the enchanting lanes and plazas. You…
Post departing from Florence, your journey continues toward San Gimignano. On the way, you’ll admire the scenery consisting of vineyards and undulating landscapes while acquiring captivating knowledge about this town’s past.
Upon reaching, your guide will lead you to the entrance, post which you are free to explore the enchanting lanes and plazas. You have all the time to check out the local shops, taste an award-winning gelato, or stroll around the renowned medieval towers scattered around town.
Next, we take a break at a family-owned organic vineyard. Here, you’ll relish a traditional local meal accompanied with an array of wines, all while basking in the beautiful surroundings offering magnificent vistas of the neighboring countryside.
Post lunch, get ready to see Siena in the same way a local would during a guided stroll around the medieval city. Discover facts about the world’s most ancient bank, view the Piazza del Campo - the venue of the six-century-old Palio horse race - and marvel at the artwork-filled interior of the Duomo. Following that, immerse yourself in the Siena experience at your leisure with enough time set aside for shopping or unwinding at an alfresco cafe.
- Disclaimer: Only 18 years old and above are allowed for wine tasting
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.