Ultimate 8-Day Siena and Tuscany Exploration Itinerary

Indulge in a hearty breakfast at Antica Trattoria Papei, a local favorite. Then, embark on a memorable Siena 2 hour Horseback Riding Tour in the Siena Countryside.

After working up an appetite, enjoy a picnic lunch in the vineyards. In the afternoon, visit an Organic Winery for a tour and wine tasting.

For a rustic and authentic dinner, head to La Taverna di San Giuseppe, known for its traditional Tuscan dishes.

Start your day with a cappuccino and pastry at Il Pomodorino. Then, take a Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets to learn about the city's history and art.

For lunch, enjoy a variety of local flavors on a Siena Walking Food Tour with Tastings. In the afternoon, visit the Siena Civic Museum (Museo Civico di Siena).

Dine at Enoteca I Terzi, a top choice for wine lovers, and sample a selection of Tuscan wines with your meal.

Enjoy a leisurely breakfast at Trattoria La Torre before heading to Montalcino for a Montalcino Brunello Wine Tasting Experience.

Have a gourmet lunch at a Tuscan castle as part of the Montalcino Brunello Wine Tasting & Lunch in a Tuscan Castle experience. After lunch, explore the Montalcino Fortress (Fortezza di Montalcino).

Return to Siena for dinner at Antica Trattoria Papei, where you can enjoy classic Tuscan dishes in a cozy setting.

Start your day with a delicious breakfast at La Taverna di San Giuseppe. Then, take a Private Guided Tour in San Gimignano to explore the medieval architecture and famous towers.

Enjoy a traditional Tuscan lunch at a winery in San Gimignano, followed by a Chianti visita la più piccola cantina del Chianti Classico.

Conclude the day with a romantic vineyard dinner at San Gimignano Romantic Vineyard Dinner [170682], overlooking the rolling hills of Chianti.

Begin your day with a leisurely breakfast at Enoteca I Terzi. Then, visit the National Art Gallery of Siena (Pinacoteca Nazionale Siena).

Enjoy a wine and oil tasting with Tuscan appetizers at Wine and Oil Tasting with Tuscan Appetizers. In the afternoon, explore the Siena Cathedral Museum (Museo dell’Opera Metropolitana).

Dine at Ristorante Guidoriccio, a fine dining establishment known for its creative dishes and extensive wine list.

Take a peaceful hot air balloon flight over Tuscany with a glass of wine, a truly magical experience.

After the flight, enjoy a leisurely lunch at a local trattoria. Spend the afternoon wandering the streets of Siena at your own pace, perhaps visiting any sites you want to see again or doing some last-minute shopping.

For your final evening in Siena, have a memorable dinner at Osteria Le Logge, savoring the flavors of Tuscany one last time.

On your last morning in Siena, enjoy a relaxed breakfast at a local cafe. Take a final stroll through the city to soak in the atmosphere before heading to your next destination.

Depending on your departure time, you may have a few hours to visit any last-minute spots or pick up some souvenirs. Alternatively, you can simply relax in a cafe and savor your remaining time in this beautiful city.

Departure from Siena, taking with you the memories of a wonderful week in the heart of Tuscany.