Florence and Tuscany Day Trip Guide

Florence is magnificent, but some of the best experiences in Tuscany lie outside the city. The rolling hills, medieval towns, and vineyards that surround Florence are the stuff of postcards and daydreams. A day trip (or two) into the countryside is essential for any visit to this part of Italy.

Chianti Wine Region

The Chianti region between Florence and Siena is Tuscany at its most stereotypical, and that is meant as a compliment. Cypress-lined roads wind through vineyards, olive groves, and hilltop villages. A wine tour typically visits 2 to 3 estates, with tastings of Chianti Classico paired with local pecorino cheese, salami, bruschetta, and olive oil.

The village of Greve in Chianti is a charming base with an atmospheric triangular piazza, a wine-tasting shop, and excellent restaurants. Castellina in Chianti and Radda in Chianti are equally beautiful alternatives.

Browse Chianti wine tours from Florence →

Siena

Siena is Florence's historic rival and one of Italy's most beautiful cities. The shell-shaped Piazza del Campo is one of Europe's great public spaces, famous as the venue for the Palio horse race (held twice annually in July and August). The Gothic Siena Cathedral has an interior so ornate it almost overwhelms the senses, with marble floors depicting Biblical scenes.

Siena is about 75 minutes from Florence by bus. A half-day is enough for the highlights, but combining it with a wine tour or San Gimignano visit makes a full and rewarding day.

San Gimignano

Known as the "Medieval Manhattan" for its 14 surviving towers (originally there were 72), San Gimignano is a tiny hilltop town that punches well above its weight. The towers were built by rival families as status symbols, and the town's skyline is unforgettable. Visit Gelateria Dondoli on the main piazza, which has won multiple World Gelato Championship titles.

Pisa

The Leaning Tower of Pisa is more impressive in person than you might expect. The entire Piazza dei Miracoli (Square of Miracles) is a UNESCO World Heritage Site, including the tower, the cathedral, and the baptistery. You can climb the tower (294 steps, timed entry) for views across the Tuscan plains.

Pisa is about an hour from Florence by train. You can see the main sights in 2 to 3 hours, making it easy to combine with another destination.

Browse Florence day trips to Tuscany →

Val d'Orcia

The Val d'Orcia is the Tuscany of your imagination: endless rolling hills, lonely cypress trees, golden wheat fields, and picture-perfect hilltop towns. Pienza (famous for pecorino cheese) and Montepulciano (known for Vino Nobile wine) are the standout villages. The drive itself through this UNESCO-listed landscape is one of the most scenic in Italy.

Lucca

Lucca is a walled city with tree-lined ramparts you can walk or cycle along. It is less touristy than many Tuscan destinations, with an atmospheric old town, excellent restaurants, and the oval-shaped Piazza dell'Anfiteatro built on the ruins of a Roman amphitheatre. About 1.5 hours from Florence by train.

Cinque Terre

Technically in Liguria rather than Tuscany, the Cinque Terre (five colourful fishing villages clinging to sea cliffs) is accessible as a long day trip from Florence (about 2.5 hours by train to La Spezia, then local trains between villages). It is a full day but one of Italy's most spectacular experiences.

Practical Tips for Tuscan Day Trips

• Organised tours are the easiest option for wine regions and multi-stop trips, since public transport to small towns is limited.
• If you are comfortable driving, car hire gives maximum flexibility. Italian roads are good, but hill-town parking can be challenging.
• Trains connect Florence to Pisa, Lucca, and Siena directly. Buses serve smaller towns.
• Most Tuscan towns are small. 2 to 3 hours per town is usually sufficient.
• Summer is hot and busy. Spring (April to June) and early autumn (September to October) are ideal for Tuscan day trips.

Browse all Florence tours and experiences →