9-Day Siena Adventure Itinerary

Begin your second day with a visit to the National Art Gallery of Siena (Pinacoteca Nazionale Siena). This gallery houses an impressive collection of Sienese art from the 12th to 16th centuries. For breakfast, stop by Pasticceria Nannini, known for its delicious pastries and coffee.

In the afternoon, explore more of Siena's artistic heritage with a tour of Siena: Medieval Families Quest Experience. This interactive experience will take you through historical sites while engaging you in fun activities related to medieval family life. For lunch, dine at Trattoria Papei, offering traditional Sienese cuisine.

Conclude your day with a visit to the stunning Basilica of San Domenico (Basilica di San Domenico), known for its Gothic architecture and beautiful frescoes. Enjoy dinner at Osteria Le Logge, followed by drinks at Libreria Piccolomini Bar.

Kick off your third day with a trip to the impressive Mangia Tower (Torre del Mangia). Climb to the top for breathtaking views over Siena. Have breakfast at Bar Il Palio, located nearby.

Afterward, visit the historic Pubblico Palace (Palazzo Pubblico) and explore its grand halls filled with frescoes. Participate in the tour titled Siena: Palazzo Pubblico Entry Ticket for an in-depth understanding of this significant landmark. Lunch can be enjoyed at Ristorante Guido which offers delicious local dishes.

End your day by exploring more local flavors on a unique culinary adventure: join the tour titled From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards. This experience will take you out into Tuscany's beautiful countryside for an unforgettable evening.

Start your fourth day with a visit to the Siena Civic Museum (Museo Civico di Siena). Located within the Palazzo Pubblico, this museum houses stunning frescoes and offers a deep dive into Siena's rich history. Enjoy breakfast at Caffè Fonte Gaia, known for its delightful pastries and coffee.

In the afternoon, take part in the tour titled Siena: Small Group Cooking Class in Chianti Farmhouse. This hands-on experience will teach you how to prepare traditional Tuscan dishes, providing a unique insight into local culinary traditions. For lunch, savor your own creations during the class.

As evening approaches, head to Siena Piazza del Mercato, a lesser-known but charming square where you can enjoy a relaxed atmosphere. Dine at Osteria Babazuf, which offers delicious local cuisine. After dinner, unwind with a drink at Enoteca I Terzi, known for its excellent wine selection.

Baptistery of San Giovanni (Battistero di San Giovanni) is your first stop today. This beautiful baptistery is renowned for its intricate Gothic architecture and stunning frescoes. Enjoy breakfast at Pasticceria Buti, famous for its delectable pastries.

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch awaits you in the afternoon. This tour will take you to the picturesque town of Montalcino, where you'll visit renowned wineries and enjoy tastings of Brunello wines accompanied by a delicious lunch.

Ristorante Grotta Santa Caterina da Bagoga is an excellent choice for dinner upon your return to Siena. Afterward, take an evening stroll around the beautifully lit streets of Siena or relax with a drink at Bar Il Palio.

Piccolomini Library (Libreria Piccolomini) within the Siena Cathedral is your first destination today. This library is famed for its exquisite frescoes by Pinturicchio. Start your day with breakfast at Caffè del Corso, located nearby.

From Siena: Pienza and Montepulciano Small-Group Tour will fill your afternoon with scenic beauty and cultural exploration. Visit these charming towns known for their Renaissance architecture and world-class wines.

For dinner, return to Siena and dine at Ristorante Mugolone, offering traditional Tuscan dishes in an elegant setting. End your day with drinks at Libreria Piccolomini Bar, enjoying its cozy ambiance.

Begin your seventh day with a visit to the Siena Cathedral Museum (Museo dell’Opera Metropolitana). This museum houses a remarkable collection of artworks and artifacts from the cathedral. Enjoy breakfast at Caffè Fiorella, known for its excellent coffee and pastries.

In the afternoon, join the tour titled Siena: 3h Private City Walking Tour with Optional Cathedral. This personalized tour will provide you with an in-depth understanding of Siena's history, culture, and architecture. For lunch, dine at Trattoria La Torre, offering traditional Sienese dishes.

Conclude your day with a visit to the stunning Siena Cathedral and Piccolomini Library Entry Ticket. Afterward, enjoy dinner at Ristorante La Taverna di San Giuseppe, followed by drinks at Enoteca I Terzi.

Start your eighth day with a relaxing horseback ride through the Tuscan countryside on the tour titled Siena: 2 hour Horseback Riding Tour in the Siena Countryside. Have breakfast at Bar Il Palio before heading out.

In the afternoon, explore more of Tuscany's scenic beauty with the tour titled From Siena: Chianti and Castles Tour with Wine Tastings. This tour will take you through picturesque vineyards and historic castles while offering delightful wine tastings. Enjoy lunch during the tour.

Return to Siena for dinner at Osteria Le Logge, known for its elegant ambiance and delicious cuisine. End your evening with a drink at Libreria Piccolomini Bar.

On your final day, visit the famous Mangia Tower (Torre del Mangia) once more to capture any missed views or photos. Have breakfast at Pasticceria Nannini, renowned for its pastries.

Spend your afternoon on a unique culinary adventure by joining the tour titled Siena: Small Group Pasta and Tiramisu Class. Learn how to make these Italian favorites from scratch. Enjoy lunch as part of this cooking class experience.

For your last evening in Siena, dine at Ristorante Guido, savoring traditional Tuscan dishes one last time. Conclude your trip with drinks at Bar Il Palio, reflecting on your wonderful journey through this historic city.