Six Day Trips from Florence: Chianti, Val d’Orcia, Siena, Lucca, Pisa and Emilia-Romagna

Florence sits at the centre of a region where good day trips are unusually easy to arrange. Chianti is 30 minutes south by car; Pisa and Lucca are an hour by train; Siena and Montalcino take a little longer. And in the other direction, just north of Tuscany, the high-speed train puts Bologna and the food producers of Emilia-Romagna within 40 minutes. Below are six excursions worth planning around a stay in Florence.

Destination	Travel time from Florence	Best way to get there
Chianti	30–45 min	Car
Siena	1h15	Car or express bus
Lucca	1h–1h20	Train (direct)
Pisa	1h–1h15	Train (direct)
Montepulciano / Montalcino	1h30–1h45	Car
Val d’Orcia	~2h	Car
Bologna / Emilia-Romagna	35–40 min	High-speed train

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1. Chianti

The Chianti wine region starts about 30 minutes south of Florence by car — close enough for a half-day trip. The vineyards around Panzano and San Casciano are among the most visited, partly because of the quality of the wine and partly because the area is genuinely beautiful. Tastings at individual estates can be booked in advance; most welcome walk-ins outside peak summer.

The most useful single stop in Chianti for wine is Greve in Chianti — a small town with a triangular central piazza lined with arcades and a well-stocked enoteca. For food, the butcher Dario Cecchini in Panzano is worth building a stop around; his lardo and bistecca are serious. Chianti gets busy at weekends — a weekday visit is more relaxed and the roads are clearer.

2. Val d’Orcia

The Val d’Orcia is a UNESCO World Cultural Landscape about two hours south of Florence by car — there is no practical train connection, so a hire car or driver is the realistic option. The valley is quieter than Chianti and less visited. Pienza, a small Renaissance town built to a single plan by Pope Pius II in 1459, is the main stop; it is also the centre of production for Pecorino di Pienza, the sheep’s milk cheese aged in walnut leaves or grape marc.

The landscape — cypress avenues, rolling clay hills, medieval farmhouses — is the most photographed version of Tuscany. Bagno Vignoni, a village built around a thermal pool used since Roman times, is a quieter alternative stop. The drive itself, particularly the gravel roads between Monticchiello and San Quirico d’Orcia, is part of the experience.

3. Montepulciano and Montalcino

Both towns are in the Sienese hills and reachable by car in around 1h45 from Florence. Montalcino produces Brunello di Montalcino, one of Italy’s most respected red wines — made exclusively from Sangiovese Grosso and aged for a minimum of five years before release. The town is compact and walkable; the fortress at the top has a wine bar selling by the glass with views over the Val d’Orcia.

Montepulciano is a few kilometres east and produces Vino Nobile di Montepulciano — a slightly lighter style with a longer history. The main street climbs steeply from gate to gate, lined with cantina entrances. The two towns are 15 km apart and easy to combine in a single day; allow at least two to three hours in each.

4. Siena

Siena is about 1h15 by car from Florence, or by bus via the direct Siena–Florence express service (around 1h20, no train connection). The Campo — the sloping fan-shaped piazza at the heart of the city — is one of the finest public spaces in Italy. The Palazzo Pubblico and Torre del Mangia on its edge are the civic heart of the medieval republic; the tower is climbable and worth it for the view.

The Duomo is remarkable in several ways: the marble inlaid floor — 56 panels depicting biblical scenes and allegories, created over two centuries — is one of the most detailed in the world and only fully uncovered for a few weeks each autumn. For food, Siena is the home of panforte (the dense spiced fruit cake), ricciarelli (soft almond biscuits), and cantucci. It is possible to combine Siena with a Chianti wine stop on the same day since the wine region lies roughly along the same route south from Florence. See the Siena guide for more.

5. Lucca and Pisa

Both are reachable by direct train from Florence in under an hour and work well as a combined day. Lucca has intact Renaissance city walls wide enough to walk or cycle along the top — hire a bike at any of the rental points near the gates. The historic centre inside the walls is almost entirely traffic-free. The food market and local trattorie around Via San Paolino are the best places to eat; the local specialities are tordelli lucchesi (fresh pasta stuffed with meat and ricotta), cecina (chickpea flatbread), and buccellato (the sweet ring-shaped bread sold in every bakery).

Pisa is primarily Piazza dei Miracoli — the Leaning Tower, Cathedral, Baptistery, and Camposanto. Book Tower entry online well in advance; walk-up availability is unreliable in peak season. The Cathedral and Baptistery contain some of the finest medieval sculpture in Italy and are visited by far fewer people than the Tower — allow time for both. Beyond the square, Piazza delle Vettovaglie (the daily food market) and the arcade of Borgo Stretto are the parts of the city most visitors miss. Visit Pisa in the morning and Lucca in the afternoon for the most comfortable timing.

6. Parmigiano Reggiano and Balsamic Vinegar — Emilia-Romagna

This is the excursion most visitors don’t think of, and often the one they remember most. Emilia-Romagna — the region directly north of Tuscany — is where Parmigiano Reggiano, traditional balsamic vinegar, and Prosciutto di Parma are produced. The high-speed train from Florence reaches Bologna in under 40 minutes, making it a genuine day trip. A dedicated Parmigiano Reggiano and balsamic vinegar tour from Florence takes you inside working dairies at dawn, visits an acetaia where balsamic ages in small wooden barrels for 12 to 25 years, and includes tastings throughout.

Bologna itself is worth the trip independently: the arcaded streets, the food market at Quadrilatero, the oldest university in the world, and a food culture that is arguably the most serious in Italy. It is a different category of day trip from anything available within Tuscany — and the speed of the train makes the logistics easier than any of the car-dependent destinations above.

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See also: Pisa in September — events, food, and what to do beyond the tower — Pisa Cathedral and Baptistery: what to see inside — Day trips from Lucca