Medieval Marvels of Tuscany: A 5-Day Exploration from Siena Itinerary

Enjoy a relaxed morning with breakfast at Il Pomodorino, known for its fresh and simple dishes. Then, explore the masterpieces at the Siena Cathedral Museum (Museo dell’Opera Metropolitana) and the National Art Gallery of Siena (Pinacoteca Nazionale Siena).

For lunch, head to Trattoria La Torre and taste the flavors of Tuscany. Spend the afternoon visiting the Baptistery of San Giovanni (Battistero di San Giovanni) and the Santa Maria della Scala, a former hospital with a rich history.

Dine at Ristorante Guidoriccio, a family-run restaurant known for its warm hospitality and traditional dishes.

Take a scenic drive to the medieval town of San Gimignano. Start with a coffee at Enoteca I Terzi and then explore the San Gimignano Historic Centre, known for its well-preserved tower houses.

Enjoy a leisurely lunch at La Vecchie Mura and take a stroll through the town's charming streets. Don't miss a visit to the Duomo di San Gimignano.

Return to Siena and dine at Antica Trattoria Papei, where you can share stories of your day trip.

Indulge in a hearty breakfast at Osteria Le Logge before setting off to the town of Montalcino. Visit the Montalcino Fortress (Fortezza di Montalcino) and enjoy the panoramic views.

For a true Tuscan experience, have lunch and a wine tasting at Enoteca La Fortezza. Explore the charming streets of Montalcino and visit a local winery for a more in-depth tasting.

Return to Siena and dine at Il Pomodorino, reminiscing about the flavors of the day.

For your last day, enjoy a special breakfast at Trattoria La Torre, known for its traditional Tuscan dishes. Take a guided food tour of Siena, visiting local markets and tasting regional specialties.

Conclude your trip with a memorable farewell lunch at La Taverna di San Giuseppe, savoring the best of Tuscan cuisine. Spend the afternoon at leisure, perhaps shopping for local souvenirs.

As the sun sets on your Tuscany adventure, have a relaxed dinner at Ristorante Guidoriccio, sharing your favorite moments of the trip with your travel companions.