Here's a detailed itinerary for exploring Siena and its surroundings in Italy for 7 days from 06:00 to 22:00, including historical monuments, gardens, nature, shopping, and gastronomy, with recommendations for nearly free accommodation and dining options.

 

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### Day 1: Discovering Siena

- **06:00 - 08:00**: Breakfast at **Caffè Fiorella**, enjoying local pastries.
- **08:30 - 10:30**: Visit **Piazza del Campo**, the heart of Siena, and explore the **Palazzo Pubblico** and **Torre del Mangia**.
- **11:00 - 13:00**: Tour the **Siena Cathedral** (Duomo di Siena) and the **Museum of the Cathedral** (Museo dell'Opera).
- **13:00 - 14:30**: Lunch at **Ristorante Da Roberto**, known for its traditional dishes.
- **15:00 - 17:00**: Stroll through the city's **gardens** like the **Orto dei Tolomei**.
- **17:30 - 19:00**: Free time to explore the small shops in the **Via Banchi di Sopra** area.
- **19:30 - 21:00**: Dinner at **Osteria Il Vinaio**, offering local cuisine at reasonable prices.
- **21:30 - 22:00**: Enjoy a coffee or aperitif at **Caffè Nannini**, an iconic spot.

#### Accommodation in Siena:
- **Hotel Alma Domus** or **B&B Il Casato** - budget-friendly and well-located options.

### Day 2: Excursion to Monteriggioni and San Gimignano
- **06:00 - 08:00**: Breakfast at **Bar Pasticceria Romana**.
- **08:30 - 10:00**: Drive to **Monteriggioni**, a medieval village with impressive walls.
- **10:30 - 13:00**: Visit the **Monteriggioni Castle** and walk through its picturesque streets.
- **13:00 - 14:30**: Lunch at **Osteria Alla Storia** in Monteriggioni.
- **15:00 - 17:00**: Drive to **San Gimignano**, explore its medieval towers and **Piazza della Cisterna**.
- **17:30 - 19:00**: Visit the **Collegiate Church of San Gimignano**.
- **19:30 - 21:00**: Dinner at **Ristorante Perucà**, known for its excellent Tuscan cuisine.
- **21:30 - 22:00**: Return to Siena and relax at **Caffè Scudieri**.

### Day 3: Chianti Wine Region Exploration
- **06:00 - 08:00**: Breakfast at **Pasticceria Rinaldini**.
- **08:30 - 10:30**: Excursion to the **Chianti region**. Visit a **winery** (like **Castello di Verrazzano**) for a wine tasting.
- **11:00 - 13:00**: Walk through the **Chianti hills** and visit local **vineyards**.
- **13:00 - 14:30**: Lunch at a local **osteria** in Greve in Chianti.
- **15:00 - 17:00**: Visit the medieval town of **Greve in Chianti** and **Piazza Matteotti**.
- **17:30 - 19:00**: Return to Siena with a stop in **Radda in Chianti** for a brief visit.
- **19:30 - 21:00**: Dinner at **Trattoria La Torre** in Siena, with local dishes.
- **21:30 - 22:00**: Coffee or dessert at **Caffè del Corso**.

### Day 4: Day Trip to Pisa

- **06:00 - 08:00**: Breakfast at **Caffè del Teatro**.
- **08:30 - 10:00**: Drive to **Pisa**.
- **10:30 - 13:00**: Visit the **Piazza dei Miracoli** and see the **Leaning Tower of Pisa**.
- **13:00 - 14:30**: Lunch at **Osteria dei Cavalieri**, near Piazza dei Miracoli.
- **15:00 - 17:00**: Explore the **Borgo Stretto** area and visit the **Pisa Cathedral**.
- **17:30 - 19:00**: Return to Siena with a stop in **Lucca** to explore the historic center.
- **19:30 - 21:00**: Dinner at **Ristorante L'Antica Torre** in Lucca or back in Siena.
- **21:30 - 22:00**: Coffee or aperitif at **Bar Gallo** in Siena.

### Day 5: Val d'Orcia Region

- **06:00 - 08:00**: Breakfast at **Caffè Il Nido**.
- **08:30 - 10:30**: Drive to the **Val d'Orcia** region.
- **11:00 - 13:00**: Visit the towns of **Pienza** and **Montalcino**, exploring their historic sites.
- **13:00 - 14:30**: Lunch at **Ristorante Le Logge** in Pienza.
- **15:00 - 17:00**: Wine tasting at a **winery** in Montalcino, such as **Castello Banfi**.
- **17:30 - 19:00**: Enjoy the picturesque landscapes of **Val d'Orcia**.
- **19:30 - 21:00**: Dinner at **Osteria La Porta** in Monticchiello.
- **21:30 - 22:00**: Return to Siena and relax at **Caffè Buon Governo**.

 ### Day 6: Culture and Relaxation in Siena
- **06:00 - 08:00**: Breakfast at **Caffè Malti**.
- **08:30 - 11:00**: Visit the **Siena Archaeological Museum**.
- **11:30 - 13:00**: Discover the **Baptistery of Siena** and the **Fonte Gaia** (Fountain of the Virgin).
- **13:00 - 14:30**: Lunch at **Osteria Da Cice**, offering delicious local dishes.
- **15:00 - 17:00**: Free time for shopping in **Via Montanini** and **Via di Città**.
- **17:30 - 19:00**: Enjoy views from the **Piazza Salimbeni**.
- **19:30 - 21:00**: Dinner at **Trattoria della Storia**.
- **21:30 - 22:00**: Coffee or dessert at **Caffè Il Duomo**.

### Day 7: Surrounding Areas Exploration
- **06:00 - 08:00**: Breakfast at **Caffè Vecchio**.
- **08:30 - 10:00**: Excursion to **San Galgano** to visit the **Abbey of San Galgano** and the famous **Sword in the Stone**.
- **10:30 - 13:00**: Visit the **Monastery of Monte Oliveto Maggiore**.
- **13:00 - 14:30**: Lunch at **Ristorante Il Monastero** in Asciano.
- **15:00 - 17:00**: Return to Siena and enjoy some final sightseeing or shopping.
- **17:30 - 19:00**: Relax at the **Piazza Salimbeni**.
- **19:30 - 21:00**: Farewell dinner at **Ristorante La Chiocciola**.
- **21:30 - 22:00**: Final evening at **Caffè Gilli**.

### Accommodation and Dining

- **Accommodation**: Look for options like **Hotel Duomo** or **B&B La Piccola** for budget-friendly stays.
- **Dining**: Choose local restaurants and trattorias for affordable meals.

Enjoy your stay in Siena with a perfect blend of culture, gastronomy, and beautiful landscapes!

 

 

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