Tuscany Day Trip Ideas: Chianti, Siena, and San Gimignano

Tuscany is an enchanting region that effortlessly blends natural beauty, historical landmarks, and some of the best wine in the world. While Florence is a hub of art and culture, the Tuscan countryside offers an entirely different allure that’s well worth exploring. If you’re visiting Florence and have a day to spare, taking a day trip through Tuscany is an experience that you’ll never forget. From scenic vineyards to medieval hilltop towns, these day trips offer a perfect mix of relaxation, exploration, and, of course, incredible food and wine.

Below are the top Tuscany day trips you must take from Florence:

1. Chianti Region: A Wine Lover’s Paradise

If you’re a fan of wine, then a day trip to the Chianti wine region is a must. Located between Florence and Siena, Chianti is famous for its rolling hills, vineyards, and charming villages.

Start your day in Greve in Chianti, the region’s main town. Stroll around its charming central piazza, where you can find artisan shops and local food markets. Then, make your way to one of the many family-run wineries in the area. Castello di Verrazzano is one of our favorite wineries in Chianti, and it offers guided tours of its historic wine cellars and a tasting of some of the region’s finest Chianti Classico wines.

For an authentic experience, consider booking a wine tour with a local guide, who can introduce you to smaller boutique vineyards. Pair the wine tastings with a rustic Tuscan lunch at a winery, where you’ll sample local cheeses, cured meats, and olive oils—all fresh from the region. Below are some of the most highly-rated winery tours you can book during your time in Chianti:

Private Full Day Winery Tour of Chianti: Discover Greve in Chianti, Castello di Montefioralle, Azienda Agricola Mauricio Brogioni Winery, Panzano in Chianti, and a farm-to-table lunch and wine pairing

The Chianti Safari: Discover the Chianti region and its Tuscan villas, enjoy a Tuscan lunch at one of the wineries, and explore the region onboard a 4×4 for an off-road adventure

Private Day Trip of Chianti and Siena from Florence: During this tour, you’ll be chauffeured through the most picturesque roads in Chianti, stopping along the way to discover its local wineries and villages.

2. Siena: A Step Back in Time

About an hour away Florence, Siena is a must-see city that feels like a step back in time. The medieval streets and dramatic architecture are nothing short of magical. Begin your visit at the Piazza del Campo, one of Italy’s greatest medieval squares.

Take some time to explore the Siena Cathedral, one of the most stunning examples of Italian Gothic architecture, and don’t miss the opportunity to climb the Torre del Mangia for panoramic views of the city and surrounding hills.

For lunch, head to Osteria Le Logge, a charming restaurant known for its traditional Tuscan dishes. Afterward, you can wander through the narrow streets and stumble upon hidden squares and quaint boutiques.

Siena’s beauty and rich history make it a top choice for a Tuscany day trip from Florence.

3. San Gimignano: The Medieval Manhattan

Known as the “Medieval Manhattan” because of its impressive skyline of medieval towers, San Gimignano is one of Tuscany’s most picturesque towns. This hilltop village, just one hour from Florence, is famous for its well-preserved medieval architecture and charming atmosphere.

Start your day at the Piazza del Duomo, the heart of San Gimignano, and visit the Duomo di Santa Maria Assunta, home to beautiful frescoes. The town is also known for its gelato, so make sure to stop by Gelateria Dondoli, an award-winning gelateria where you can try unique flavors like saffron and pear or Vernaccia wine-flavored gelato.

When it comes to wine, San Gimignano is famous for its Vernaccia di San Gimignano, a white wine that has been produced in the region for centuries. Visit the Fattoria San Donato for a wine tasting experience and a tour of their vineyards. Here, you can sample the region’s signature Vernaccia wine, paired with local cheeses and homemade olive oil.

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