Best day trips from Florence for your Tuscany Holidays

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Planning your dream getaway in Florence or nearby? Get ready to explore the fascinating destinations just a stone’s throw away with exciting day trips around Tuscany. Among the top places to see near Florence, you can dive into the medieval charm of San Gimignano, experience the lively atmosphere of Siena with its famous Palio, or unwind in the romantic Chianti region, renowned for its exceptional wines.


Siena is renowned for its historical charm, stunning architecture, rich artistic heritage, and vibrant events, making it a must-visit destination among the best day trips from Florence. The Tuscan city is like an open-air museum, showcasing strong local traditions highlighted by the Palio di Siena, a spectacular horse race held twice each summer.

Begin your visit with the majestic Duomo, a remarkable example of Romanesque-Gothic architecture. Inside, discover works by renowned artists such as Donatello and Michelangelo, and don’t miss the exquisite mosaic floor panels, revealed only a few months each year. In 2024, the Duomo’s floor is open for visits from June 27th to July 31st and from August 18th to October 16th.

Descend to Piazza del Campo, acclaimed as Italy’s most beautiful square. Its distinctive shell shape and brick pavement, flanked by grand buildings, create a captivating atmosphere, and bear witness to the renowned Palio di Siena every July 2nd and August 16th.

Afterward, wander through the town’s charming streets and alleys and sample its gastronomic delights at one of the many “botteghe” offering savory specialties, paired with fine wine for a truly delightful experience.


The Chianti region in Tuscany is one of the most beautiful and renowned areas of Italy, celebrated worldwide for its exceptional wines and picturesque landscapes. Stretching between Florence and Siena, Chianti is characterized by rolling hills covered with vineyards and ancient olive groves, medieval hamlets, stunning castles, winding country roads, and scenic cypress trees.

Wine tasting is a must during your trip to Chianti, the perfect destination for experiencing traditional Tuscan food and wine. The region produces a variety of wines, each with its own unique taste and flavor, including Chianti Classico, Chianti Rufina, and Chianti Colli Fiorentini. Exploring Chianti means discovering must-see villages like Castellina and Greve in Chianti, making it one of the top places to see near Florence.

Castellina in Chianti is a charming medieval village in Tuscany, surrounded by ancient walls and dominated by a 15th-century fortress housing an Etruscan Museum. The village is renowned for its wine, with numerous wine shops and excellent restaurants in the historic center.

Greve in Chianti is a fascinating village known for its annual Chianti Wine Festival in September. The main square, Piazza Matteotti, features arcades and a statue of explorer Giovanni da Verrazzano. With its wine shops, restaurants, and a lively Saturday market, Greve retains its historic charm as a key trading post between Florence and Siena.


If you’re looking for the best day trips from Florence, consider exploring the charming hill towns of Volterra and San Gimignano.

Volterra will enchant you with its rich history and stunning views. With its museums, archaeological sites, restaurants, and shops, it offers a full day of exploration. Wander the scenic streets, especially around Piazza dei Priori, the main square lined with important buildings like Palazzo dei Priori, the oldest town hall in Tuscany, and Palazzo Pretorio. For a breathtaking view, climb the tower of Palazzo dei Priori and take in the panorama of this beautiful Tuscan gem.

San Gimignano is a must-see medieval hill town, renowned for its iconic medieval towers, of which 14 remain from over 70 during its peak in the 1300s. Known as the “Manhattan of the Middle Ages,” its historic center is visually striking and perfectly preserved. Explore Piazza Duomo with the Renaissance frescoes exposed in the Duomo, and the enchanting Piazza della Cisterna. Don’t miss tasting the local white wine, Vernaccia di San Gimignano, made from grapes grown on the surrounding hills.

Dimora Ghirlandaio is the perfect base to discover Tuscany’s most beautiful places, offering day-trip journeys through the region’s rich history, culture, and events. With our tailored tours, you can witness Tuscany’s timeless traditions and vibrant history firsthand. Whether you’re eager to uncover hidden gems on a day trip or indulge in a culinary adventure with our food and wine tasting tours, Dimora Ghirlandaio ensures unique experiences crafted to meet your every need.

Contact us to discover the exclusive experiences that Dimora Ghirlandaio can arrange for you during your stay.

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