5 Days in Siena: Smalltown Italian Charm Itinerary

Begin your day with a visit to the National Art Gallery of Siena (Pinacoteca Nazionale Siena). This gallery houses an impressive collection of Sienese paintings from the 12th to 16th centuries.

Next, explore the Siena Civic Museum (Museo Civico di Siena) located in the Palazzo Pubblico. The museum showcases important frescoes and artifacts from Siena's history. For lunch, dine at one of the charming local trattorias nearby.

In the evening, climb up the Mangia Tower (Torre del Mangia) for breathtaking views of Siena and its surroundings. Afterward, enjoy dinner at another highly-rated restaurant in town.

Kick off your day with an exciting culinary experience by joining the Tuscan Culinary Secrets Unveiled Cooking Class & Dinner. Learn how to prepare traditional Tuscan dishes from scratch.

After your cooking class, take part in a wine tasting session with the Siena Wine and Food Pairing Class with Tuscan Wine Tastings. You'll get to sample some of Tuscany's finest wines paired with delicious local foods.

For dinner, savor more Tuscan flavors at another top-rated restaurant in Siena.

Start your day with a serene horseback riding tour through the Tuscan countryside by joining the Siena 2 hour Horseback Riding Tour in the Siena Countryside. Enjoy picturesque landscapes as you ride through vineyards and olive groves.

Return to Siena for lunch at one of its cozy cafes or bistros. In the afternoon, unwind with a visit to an organic winery for a tour and tasting session such as Organic Winery Tour and Wine Tasting in Siena. Discover how local wines are made while enjoying some samples.

End your day back in town with dinner at another delightful Sienese restaurant.

Begin your final day in Siena with a visit to the Basilica of San Domenico (Basilica di San Domenico). This historic church is known for its stunning architecture and important relics, including the head of St. Catherine. Afterward, enjoy a coffee at a nearby café to soak in the morning atmosphere.

Spend your afternoon exploring the Santa Maria della Scala, one of Europe's oldest hospitals turned museum. The complex houses fascinating exhibits on art, archaeology, and history. For lunch, try a meal at one of Siena's charming trattorias.

Conclude your day with a visit to the Fonte Gaia (Gaia Fountain) in Piazza del Campo. This beautiful fountain is a perfect spot for evening relaxation. For dinner, choose another highly-rated restaurant in Siena to savor your last meal in this enchanting city.