A Taste of Tuscany

Welcome! Please be prepared to meet in the lobby at 6:30pm to gather together with your fellow travelers for dinner. The dinner reservation time will be finalized closer to your trip date. If you plan on arriving today, we recommend flying into Florence Airport (FLR).

After breakfast, embark on a guided walking tour of Florence’s historic center. See the magnificent Duomo with its stunning dome, the Baptistery’s renowned Gates of Paradise, and the elegant Campanile. Walk through Piazza della Signoria, home to Palazzo Vecchio and remarkable sculptures. Cross the picturesque Ponte Vecchio and explore the lively Piazza della Republica. Enjoy some free time in Florence for lunch on your own, then in the afternoon, leave Florence to your hotel in the Tuscan Countryside. Along the way discover the World Heritage Site of San Gimignano, a hilltop town with a praised skyline. At the end of the visit, transfer to your hotel in the Tuscan Countryside. Today you’ll want to wear comfortable walking shoes and bring a small bag for personal items like a hat, sunglasses, and a water bottle.

• Florence guided walking tour

  With a local guide, begin your exploration of Florence with a fascinating private walking tour. Step into the historical center of Florence, a true cradle of Italian Renaissance art and culture, where you'll enjoy an intimate journey through the city, discovering its most enchanting and authentic corners. Stroll through Piazza della Repubblica and explore Florence’s incredible churches including the breathtaking Cathedral of Santa Maria del Fiore (entrance not included), crowned by Brunelleschi’s dome and accompanied by Giotto’s Bell Tower (climb to the dome and the bell tower not included). Your guide will provide you with a unique and immersive journey through the city's rich tapestry of art and history. Expect to walk approximately 2 miles on paved and cobblestone streets.

  09:00· 150 min· Florence
• Free time in San Gimignano

  Your first stop in Tuscany is San Gimignano, a charming medieval hilltop town in the province of Siena, often referred to as the "Town of Fine Towers." Renowned for its stunning preservation, the town is home to around a dozen towers that rise gracefully against the backdrop of the Tuscan countryside, creating a remarkable medieval skyline that is truly unique. Encircled by well-preserved walls, San Gimignano offers a rare glimpse into the past, where both Romanesque and Gothic architectural styles are beautifully represented in its buildings. Here you’re free to explore this Tuscan hill town on your own with your guide making recommendations of landmarks to visit along the way.

  15:30· 90 min· San Gimignano

This morning, enjoy breakfast and a leisurely morning. Late in the morning you will leave your hotel and travel towards the idyllic landscapes of the Val d’Orcia, with scenic stops along the way. Your first stop is Pienza, a charming town renowned for its renaissance architecture and panoramic views. Explore the town with some time at leisure for lunch on your own. Often called the “Ideal City,” Pienza is also famous for its Pecorino di Pienza, a rare and delicious cheese. In the afternoon visit a local creamery for a tasting of different varieties before continuing your journey. Next, stop in Montepulciano, a beautiful hilltop village offering breathtaking views over the Tuscan countryside. Explore Montepulciano and enjoy time for dinner on your own before heading back to your hotel. Today you’ll want to wear comfortable walking shoes and bring a small bag for personal items like a hat, sunglasses, and a waterbottle.

• Visit of Pienza

  Pienza, a true treasure that perfectly embodies the charm of the region. The historic center of Pienza is a UNESCO World Heritage site, celebrated for its Renaissance urban planning and stunning architecture. The town was famously redesigned by Pope Pius II in the 15th century, transforming it into an ideal example of Renaissance ideals. Perched high on a hill, Pienza offers panoramic views that stretch across the lush, rolling hills of the Orcia Valley, an area renowned for its picturesque landscapes, olive groves, and vineyards. The stunning vistas are just one of the many reasons why this village is often called the "ideal town." Wander through Pienza’s narrow streets on your own with your guide making recommendations of landmarks to visit along the way. Enjoy lunch on your own before continuing onward.

  12:30· 90 min· Pienza
• Creamery visit and Pecorino cheese tasting

  On a trip to Pienza, culinary delights are not to be missed as the region abounds in amazing products, including pecorino cheese. From Pienza, you’ll take a 15 minute transfer to a local creamery to learn more about pecorino cheese. The origins of Tuscan pecorino go back to Etruscan times: Pecorino toscano DOP (Protected Designation of Origin) is made from two different types of whole sheep's milk, to which calf rennet is added. The mass is boiled until curdled into flakes the size of corn kernels of semi-solid to soft textures. It is then pressed and salted before the maturing phase begins which varies according to the type of cheese required. During your visit at a local creamery, you’ll learn more about all that goes into making authentic Pecorino cheese. Then, you’ll have the opportunity to taste at least three types of cheeses.

  14:30· 45 min· Pienza
• Montepulciano Visit

  After a 15 minute transfer to Montepulciano, you’re free to explore this Tuscan hill town on your own with your guide making recommendations of landmarks to visit along the way. Reach the highest point of the town, in the middle of Piazza Grande, to soak up a 360-degree architectural panorama. On the west side of the square, the Palazzo Comunale was built in the late 1300s then revamped in 1424 by one of the Medici’s favourite architects, Michelozzo, in homage to Florence’s Palazzo Vecchio. Just outside the town gates, a stiff downhill walk from Piazza Grande, is Sangallo the Elder’s masterpiece, and one of the most photographed churches in Tuscany. Fronted entirely in travertine, San Biagio is designed on a perfect Greek cross pattern, and dedicated to St. Blaise, an Armenian doctor martyred in the 4th century. After exploring, you’ll have time at leisure for dinner before being transferred to your accommodation.

  16:00· 270 min· Montepulciano

Today you will spend a whole day exploring the Chianti wine region. After breakfast you will depart to visit a local olive mill, but first, you’ll stop in Castellina, a charming medieval Tuscan village. Explore its cobblestone streets and soak in the views from the hilltop, then continue to the olive mill. Here, you will get extensive information on why tuscan olive oil is considered among the finest in the world. A tasting of olive oil with bruschetta is a must. After your olive mill tour, you’ll continue to Radda, a classic Chianti town. You’ll have some time to explore and have lunch on your own before transferring to a local winery. Tour the vineyards and learn more about the wine making process behind the infamous Chianti wines; then indulge in a tasting straight from the source. After the winery visit, you’ll make one last stop at Monteriggioni, a walled castle-village. Steeped in rich medieval history, you’ll have some time to explore this unique town and learn more about its rich history. Finally, you’ll transfer back to your hotel where you’ll enjoy dinner after a long day. Today you’ll want to wear comfortable walking shoes, and pack a hat, sunglasses, and a water bottle.

• Visit of Castellina in Chianti

  After a 30 minute transfer from your hotel, arrive at your first stop of the day: Castellina, a hilltop village nestled among rolling vineyards and cypress-lined hills. This charming town captures the essence of Tuscany’s Chianti region with its medieval streets, scenic overlooks, and laid-back atmosphere. Accompanied by your guide, stroll along ancient stone walls and take in sweeping views of the countryside. From its historic fortress to peaceful piazzas, Castellina offers a genuine taste of Tuscan life, far from the bustle of the beaten path.

  09:30· 60 min· Castellina in Chianti
• Olive oil mill visit and tasting

  Transfer 30 minutes and step into the heart of Tuscany’s olive-growing tradition with a visit to an authentic olive oil mill. Nestled amidst rolling hills blanketed with ancient olive groves, this experience offers a glimpse into the time-honored craftsmanship that has made Tuscany a beacon of quality in the olive oil world. Your visit begins with a tour of the mill, where expert producers guide you through the fascinating process of turning freshly harvested olives into liquid gold. Learn about traditional and modern pressing techniques, the importance of selecting the finest olives, and the care that goes into every step to ensure a superior product. The highlight of your visit is a guided tasting of three types of olive oil, where you’ll discover the nuances of extra virgin olive oil. Savor its rich, fruity flavors and peppery finish, and learn how to distinguish its quality and pair it perfectly with food.

  11:00· 60 min· Tuscany
• Visit of Radda in Chianti

  After your visit to the Olive Oil Mill, enjoy a scenic 20 minute transfer to Radda, a hilltop village nestled in the Chianti hills. With its ivy-draped walls and winding cobblestone lanes, Radda exudes timeless Tuscan charm. Join your guide for a stroll through the town’s stone archways and historic streets, then enjoy free time to wander at your own pace and choose a local spot for lunch. Don’t miss the opportunity to sample Chianti Classico—bold and full of character—paired with regional cheeses and cured meats. Intimate in scale and rich in atmosphere, Radda offers a tranquil window into the heart of Tuscany’s wine country.

  12:30· 90 min· Radda in Chianti
• Chianti winery visit

  After lunch and your visit to Radda, you’ll transfer 30 minutes to a local winery to learn more about the iconic Chianti Classico wine. One of the most known wines of the world with its unmistakable logo of the Black Rooster, it shines as an authentic taste of Tuscan wine. At a local winery, you’ll explore the vineyards that produce some of the best wines in the world using a blend of a variety of grapes including the Sangiovese, Canaiolo varietals. During your visit you will learn the different characteristics of the wines from this region, and learn to distinguish the acidity, the taste, and flavor. Your visit will include a tasting of at least 3 different wines.

  14:30· 90 min· Chianti
• Visit of Monteriggioni

  Departing the winery, begin your journey back to the hotel—but not before making a stop after 15 minutes at Monteriggioni, a hilltop village frozen in time. Surrounded by remarkably intact medieval walls, this small town offers peaceful stone streets, sweeping views of the Tuscan countryside, and a lively central piazza. With your guide, ascend the ancient ramparts for a dramatic look over the vineyards and olive groves that stretch beyond the walls. With its rich history and fairytale charm, Monteriggioni offers a brief yet memorable glimpse into the heart of medieval Tuscany. After your visit, you will transfer 15 minutes back to your hotel.

  16:00· 60 min· Monteriggioni

This morning, enjoy breakfast with the morning at your leisure at the hotel. In the afternoon head to Siena, a medieval gem known for its warm, earthy tones and rich history. Enjoy a guided tour of Siena with some free time after to continue your exploration of the town and to grab dinner on your own. Then in the evening, transfer back to the hotel. Today you’ll want to wear comfortable walking shoes.

• Guided walking tour of Siena

  From your hotel, you’ll take a 30 minute transfer to Siena. Then, with a private guide, explore the city's historic neighborhoods and visit the stunning Duomo. Conclude your tour at the iconic Piazza del Campo, home to the legendary Palio horse race, a tradition dating back to 1656. During the tour, you can expect to walk 1.5 miles.

  15:00· 120 min· Siena
• Free time in Siena

  After the guided tour, enjoy time at leisure to explore Siena and have dinner on your own before returning to your accommodation. After dinner, you’ll take a 30 minute transfer back to your hotel.

  17:00· 240 min· Siena

Say goodbye to the Tuscan countryside and return to Florence. You’ll have the day at your leisure to explore on your own or stroll the elegant shopping streets like Via Tornabuoni. It is also highly recommended that you explore the Oltrarno neighborhood, literally "the other side of the Arno River", a vibrant area where you can truly soak in the authentic Florentine spirit, far from the crowds of tourists. Here, you can admire a variety of hand-crafted treasures from the rich artisan heritage of the city: the delicate art of bookbinding and marbled paper, intricately designed mosaics, custom-made ladies’ shoes and handbags, and beautifully crafted jewelry. In the evening, reconvene with your group to put together the flavors of Tuscany you experienced during the week in a cooking class situated in a stunning location in Florence.

• Tuscan cooking class and dinner

  In the evening you will attend an amazing Tuscan cooking class. Departing on foot from your hotel, you’ll enjoy a 20 minute leisurely walk to the cooking school. Your private chef will be glad to share the secrets of Florentine cuisine with you. During the class you will learn how to select the highest quality ingredients and taste local foods. Create your own three course meal (starters, home made fresh pasta and a main course) under the expert supervision of the Chef. The cooking class will end with a delicious dinner.

  17:00· 240 min· Florence

All good things must come to an end, but only until your next adventure! Enjoy a final breakfast and then make your own way onward. If departing directly from the hotel, we recommend flying out of Florence Airport (FLR).