Florence is a dream destination in itself — with its Renaissance art, stunning architecture, and mouthwatering cuisine. But what makes Florence even more special is its location in the heart of Tuscany, one of Italy’s most picturesque regions. Just a short train ride or drive away, you’ll find rolling hills, medieval villages, vineyards, and towns that feel straight out of a fairytale.
If you’re planning a trip, don’t just stay in Florence — take some time to discover the best day trips from Florence and explore Tuscany’s hidden gems. Each of these destinations offers a unique glimpse into the region’s rich culture, history, and natural beauty.
1. Siena: A Medieval Jewel
Just over an hour from Florence, Siena is one of Tuscany’s most enchanting towns. Known for its fan-shaped Piazza del Campo, this city feels like stepping back in time. Wander through narrow cobblestone streets, admire the Gothic-style Siena Cathedral, and climb the Torre del Mangia for sweeping views of the countryside.
If you visit in July or August, you might even catch the Palio di Siena, a world-famous horse race that brings the whole town to life.
2. San Gimignano: The Town of Towers
Nicknamed the “Medieval Manhattan,” San Gimignano is famous for its impressive skyline of ancient towers. A UNESCO World Heritage Site, this hilltop town is filled with charming squares, artisan shops, and breathtaking views of the Tuscan countryside.
Don’t miss a scoop (or two!) of gelato from Gelateria Dondoli, often ranked among the best in the world.
3. Pisa: Beyond the Leaning Tower
Most travelers know Pisa for its iconic Leaning Tower, but there’s so much more to see here. The Piazza dei Miracoli is home not only to the tower but also to the Cathedral, Baptistery, and Camposanto Monumentale — all architectural masterpieces.
After snapping your classic tower photo, stroll along the Arno River and discover Pisa’s lively local atmosphere, far from the tourist crowds.
4. Chianti Wine Region: Vineyards and Rolling Hills
If you’re a wine lover, a trip to the Chianti region is a must. Just a short drive from Florence, Chianti is filled with vineyards, olive groves, and postcard-perfect villages.
Take a wine tour and sample the famous Chianti Classico, paired with local cheeses, cured meats, and fresh olive oil. Even if you’re not a wine connoisseur, the scenery alone makes this day trip unforgettable.
5. Lucca: The Walled City
Often overlooked compared to its famous neighbors, Lucca is a true hidden gem. Surrounded by perfectly preserved Renaissance walls, this charming city is best explored by bike. Pedal along the tree-lined paths on top of the walls, admire Romanesque churches, and wander through quiet piazzas.
Lucca’s relaxed vibe makes it the perfect escape from Florence’s busy streets.
6. Arezzo: Art and Antiques
Less touristy than other Tuscan towns, Arezzo is rich in art and history. The city boasts works by Piero della Francesca and Vasari, and its historic center is filled with medieval architecture.
If you visit on the first weekend of the month, don’t miss the Arezzo Antique Fair, one of the largest in Italy — a treasure trove for collectors and curious travelers alike.
7. Cortona: Under the Tuscan Sun
Made famous by the book and film Under the Tuscan Sun, Cortona is a quintessential hilltop town. Its narrow alleys, charming piazzas, and panoramic views over the Valdichiana valley make it a must-visit.
Enjoy a leisurely lunch at a trattoria, sip local wine, and simply soak in the beauty of authentic Tuscan life.