4 Days / 3 Nights
From your base in the charming medieval town of Siena, experience hilltop villages, rows of vineyards, and culinary specialties of Tuscany.
Enjoy a private guided walk of Siena and marvel at the many sites of the city including the Palazzo Comunale (Town Hall), the majestic gothic Basilica of San Domenico and the Piazza del Campo, where the horse race (Palio di Siena) is held twice a year.
Venture to the beautiful countryside of the Orcia Valley, recognized as a UNESCO World Heritage Site in 2004; visit the gorgeous medieval village of Montepulciano, known for its Vino Nobile red wine, and the Renaissance center of Pienza, celebrated for its production of Pecorino cheese.
Finally, take a traditional Tuscan cooking class in Siena and learn the secrets of this delicious cuisine!
This is a great Add-On Package for anyone visiting Tuscany, Rome, or any part of Italy.
Itinerary
Today, arrive in Siena on your own and check in to the hotel.
This afternoon, enjoy a private guided walk of Siena and marvel at the many sites of the city including the Palazzo Comunale (Town Hall), the majestic gothic Basilica of San Domenico and the Piazza del Campo, where the horse race (Palio di Siena) is held twice a year.
*The arrival transfer from Florence or Rome airport or train station is not included in the price of this package. We are happy to arrange it for you.
Venture to the beautiful countryside of the Val D'Orcia (Orcia Valley) to discover ancient, hilltop villages, rows of vineyards, and culinary specialties while surrounded by unique scents and amazing tastes. Crossed by the Orcia River, from which the Valley was named, this amazing region of Tuscany has been recognized as a UNESCO World Heritage Site in 2004, and it is considered to be a rustic treasure with breathtaking views and picturesque landscapes.
Your journey will take you to the Renaissance town of Pienza, celebrated as the 'ideal city' for its harmonious blend of stunning architectural treasures. You will also explore Montepulciano, famous for its medieval architecture and renowned Vino Nobile wine. The tour includes a visit to a charming local winery, where you will enjoy a delicious lunch and an exquisite wine tasting session, immersing you in the rich flavors of the region.
Enjoy a morning or afternoon cooking class at a cooking school in the center of Siena. Join a small group and take a traditional Tuscan cooking lesson to learn the secrets of this delicious cuisine! You will later enjoy eating what you prepared during your cooking class.
This morning you may wake at your leisure and enjoy breakfast in your hotel before it's time to check out.
The day is yours. You can either stay and explore Siena, or continue on your own travel itinerary.
*The departure transfer to Florence or Rome train station or another destination is not included in the price of this package. We are happy to arrange it for you.
Inclusions
- 3 nights in a 4-star hotel in Siena
- Breakfast daily at hotel
- Private half-day guided tour of Siena
- Private tour to Montepulciano and Pienza with lunch and wine tasting
- Group - Cooking class in Siena followed by lunch
- Transportation during the excursion
Hotel Info

Hotel Athena ★ ★ ★ ★ ☆
For a stay in Siena with easy access to its historic sites, Hotel Athena is is your ideal location just a few minutes walk away from the Duomo and Piazza del Campo. Situated in a quiet and easily accessible area in the heart of the old town center inside the ancient city walls.
Siena
Optional Tour Add-Ons
Duration: 8 hours
City: Siena
Take a journey to the two most historical villages in Tuscany: San Gimignano and Volterra.
Your tour begins with a visit to San Gimignano, often called the "Medieval Manhattan" for its iconic skyline of ancient towers. As you stroll through the UNESCO World Heritage-listed town, discover its charming piazzas, vibrant artisan shops, and breathtaking views of the Tuscan countryside.
Next, continue to Volterra, a hilltop town rich in history, known for its well-preserved Roman ruins, Etruscan walls, and stunning alabaster craftsmanship. Wander through its narrow streets and admire the medieval architecture that transports you back in time. Along the way, savor the region’s famous cuisine and perhaps sample some of its renowned wines. This full-day tour offers a perfect blend of history, culture, and the captivating beauty of Tuscany, making it a must for travelers seeking an authentic experience.
Exact time will be provided in final documents. Pick up at your hotel.
Duration: 9 hours
City: Siena
Traveling through the hills of Crete Senesi, just around an hour from Siena, you will discover the ancient cities of Arezzo and Cortona. On this full day tour, you will first stop in Arezzo, an ancient city with Etruscan roots, famous for its stunning works of art by Piero della Francesca and Cimabue. Visit the Basilica of San Francesco, Piazza Grande, and the medieval Church of San Domenico, home to Cimabue’s remarkable crucifix. Stroll through charming antique shops and boutiques, soaking in the city's rich artistic heritage.
Next, travel through the picturesque Val di Chiana to Cortona, a hilltop town offering sweeping views of the valley below. You may explore the Sanctuary of Santa Margherita, perched at the highest point of the village, and take in the panoramic scenery. Descend into the city center, where you can visit the tranquil Eremo delle Celle, a 13th-century convent founded by St. Francis. As you arrive in the main square, admire the historic Town Hall and Clock Tower. You’ll have time to shop, capture stunning photos, and soak in the timeless beauty of Cortona.
Exact time will be provided in final documents. Pick up at your hotel.
Duration: 9 hours
City: Siena
Travel through the stunning hills of Crete Senesi and along the northern shores of Lake Trasimeno with your private English-speaking driver, as you explore the ancient cities of Assisi and Perugia.
Upon reaching Assisi, you'll meet your private guide and immerse yourself in this charming town, with its 14th-century streets, squares, and churches. Take time to discover the magnificent Basilica of St. Francis, perched above the city and the entire valley. This architectural masterpiece, with its two churches stacked upon one another, houses incredible artworks by Cimabue, Simone Martini, Lorenzetti, and Giotto. You'll also have the opportunity to admire the Cathedral of San Rufino and the Church of Santa Chiara, both rich in history and beauty.
Continuing your journey, you'll arrive in Perugia, where you will explore the town on your own. Discover ancient archaeological sites and wander through the brick vaults of the Rocca Paolina, a fortress built in the mid-16th century. Ascend to the Carducci Gardens for panoramic views of the valley below. Explore the city's historic center, including Corso Vannucci, Piazza IV Novembre with the stunning Fontana Maggiore, Palazzo dei Priori, and the impressive San Lorenzo Cathedral.
Exact time will be provided in final documents. Pick up at your hotel.
Duration: 8 hours
City: Siena
In the rolling hills of Chianti, you’ll immerse yourself in the rich history of medieval villages, savor local delicacies, and taste the world-famous Chianti Classico wine. This enchanting region is celebrated for its picturesque towns, ancient castles and abbeys, and long-standing wine making traditions.
Your journey will take you through two of Chianti’s most captivating villages: Castellina in Chianti, known for its historic charm and panoramic views, and Radda in Chianti, a medieval treasure that captures the essence of Tuscany. Along the way, you’ll visit two renowned wineries, tour their wine cellars, indulge in exquisite wine tastings and enjoy a traditional Tuscan lunch.
Exact time will be provided in final documents. Pick up at your hotel.
Duration: 5 hours
City: Siena
Castles, unique landscapes, rolling hills, and winding roads are just a few of the magnificent views you will admire along the way to Montalcino from Siena. While crossing the heart of Crete Senesi you will have the chance to stop and take pictures of the dune-like hills which have the appearance of a “lunar” landscape due to the grey coloration of its soil.
Then you will stop at a winery that produces the famous Brunello wine and visit their cellars with a wine expert that will reveal the steps and techniques of the wine making process. You will have the chance to taste a selection of three Brunello wines, which are among the most famous and appreciated worldwide. On the way back to Siena, you will stop in the town of Montalcino for a walk on your own among the artisan shops and small cafes while discovering monumental building dating back to the fourteenth-century.
Exact time will be provided in final documents. Pick up at your hotel.