7 Days Exploring Tuscany's Vineyards and Historic Towns Itinerary

Begin your second day with an early morning drive to Val d'Orcia, a UNESCO World Heritage site renowned for its stunning landscapes. Kick off your day with Val d'Orcia: Private Photography Safari Tour with Aperitif. Capture breathtaking views of rolling hills, cypress trees, and charming farmhouses while learning photography tips from an expert guide. Enjoy a refreshing aperitif amidst this picturesque setting.

After your photography tour, indulge in a delightful lunch at La Bottega del Trenta, located in the heart of Val d'Orcia. This restaurant is celebrated for its traditional Tuscan cuisine prepared with fresh local ingredients. Post-lunch, embark on another adventure with Val d'Orcia: Horse Trekking Trip and Picnic under the Oak. Ride through scenic trails on horseback, ending with a relaxing picnic under an ancient oak tree.

As evening falls, treat yourself to an unforgettable dining experience with Val d'Orcia: Magical 3-Course Dinner under the Oak Tree. Savor three courses of gourmet Tuscan dishes paired perfectly with local wines while enjoying the serene ambiance of dining outdoors under twinkling stars. Conclude your day by returning to your accommodation in Val d'Orcia.

On your third day, travel to Pienza, often referred to as "the ideal city" due to its Renaissance architecture planned by Pope Pius II. Start your exploration at Pienza: Palazzo Piccolomini & Palazzo Borgia Entrance Ticket. These historic palaces offer insight into Pienza's rich cultural heritage and provide stunning views over Val d'Orcia from their gardens.

For lunch, dine at Trattoria Latte di Luna, known for its hearty Tuscan fare including handmade pastas and succulent meats. Afterward, join Pienza: Scenic hiking on the Gladiator's movie location. This guided hike takes you through iconic landscapes featured in Ridley Scott’s film "Gladiator," offering both natural beauty and cinematic history.

In the evening, participate in a hands-on culinary experience with Pienza: Tuscan Cooking Class of Homemade Pastas and Cantucci. Learn how to make traditional pasta dishes and cantucci (Tuscan almond biscuits) from scratch under the guidance of a local chef. End your day by enjoying the fruits of your labor paired with fine local wines at dinner time.

Start your day in the historic city of Siena, known for its medieval brick buildings and the famous Piazza del Campo. Begin with a visit to the stunning Siena Cathedral, an architectural masterpiece with intricate marble floors and stunning frescoes. After exploring the cathedral, take a leisurely stroll through the narrow streets of Siena's old town, soaking in the atmosphere and stopping by local shops. For breakfast, enjoy a cappuccino and pastry at Caffè Nannini, a beloved local café.

In the afternoon, embark on Siena: Guide Bike Tour of Val d’Orcia. This guided bike tour will take you through some of the most picturesque landscapes in Tuscany, offering breathtaking views of rolling hills and vineyards. The tour includes stops at charming villages where you can interact with locals and learn about their way of life. For lunch, stop at Osteria Le Logge, known for its delicious Tuscan cuisine and warm hospitality.

As evening approaches, return to Siena for a relaxing dinner at Ristorante La Taverna di San Giuseppe. This restaurant is renowned for its traditional Tuscan dishes made from locally sourced ingredients. After dinner, take a leisurely walk around Piazza del Campo to experience its magical ambiance under the evening lights.

Begin your day with an exciting truffle hunting adventure in Trequanda. Join Trequanda: Tuscan Truffle Hunting Experience with Lunch, where you'll be guided by an expert truffle hunter and his trained dogs through the woods in search of these prized delicacies. Learn about the history and techniques of truffle hunting while enjoying the beautiful Tuscan countryside.

After your truffle hunt, enjoy a sumptuous lunch featuring freshly found truffles at Ristorante Conte Matto. This restaurant specializes in dishes that highlight local ingredients, including truffles. In the afternoon, explore Trequanda's charming village center with its medieval architecture and picturesque streets. Visit local artisan shops to find unique souvenirs or simply relax at a quaint café like Bar Il Barrino for an espresso or gelato.

In the evening, treat yourself to another culinary delight with Val D'Orcia: Private Olive Oil Tasting and Tuscan Dinner. This experience offers an exclusive olive oil tasting session followed by a gourmet dinner featuring traditional Tuscan dishes paired perfectly with local wines. End your day savoring these flavors while enjoying views over Val d'Orcia.

Travel to Montepulciano for a day dedicated to wine tasting and exploration. Start your morning with Montepulciano: Winery and Perfume Laboratory Sensory Tour. This unique tour combines wine tasting with a sensory experience involving perfumes made from local ingredients. Learn about winemaking processes while indulging your senses.

For lunch, dine at Osteria Acquacheta, famous for its bistecca alla fiorentina (Florentine steak) cooked to perfection over an open flame. Afterward, continue your wine journey with Wine Tasting in Toscana with Priority Access. Visit some of Montepulciano's top wineries where you'll have priority access to tastings of their finest wines along with insights into their production methods.

Conclude your day with an elegant dinner at La Grotta, located near San Biagio Church offering both exquisite cuisine and stunning views over Montepulciano’s countryside.

On your final day in Tuscany, return to the charming town of Pienza. Begin your morning with a visit to Pienza: Dairy Farm Tour with Pecorino Cheese Tasting. This tour offers a unique opportunity to learn about the production of Pecorino cheese, one of Tuscany's most famous culinary delights. You'll get to see the entire process from milking the sheep to aging the cheese, and of course, enjoy a tasting session featuring various types of Pecorino.

For lunch, head to La Bandita Townhouse Caffe, known for its modern take on traditional Tuscan dishes. After lunch, continue your exploration with Pienza: Guided E-bike Tour through the Val d'Orcia. This guided e-bike tour will take you through some of the most scenic parts of Val d'Orcia, offering stunning views and plenty of photo opportunities. The electric bikes make it easy to navigate the rolling hills and enjoy the ride without too much effort.

In the evening, cap off your Tuscan adventure with Pienza: Dining Experience at a Local's Home. This unique dining experience allows you to enjoy a home-cooked meal prepared by a local chef in their own home. Savor traditional Tuscan dishes made from fresh, local ingredients while enjoying warm hospitality and engaging conversation. It's the perfect way to end your journey through Tuscany.