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Vineyards on the Chianti hills

Beyond the city

The best day trips from Florence

Updated 2 November 2026 · 3 min read

Florence sits at the heart of Tuscany: within an hour or so you can reach vineyard-covered hills, medieval towns and cities of art. Here are the trips we recommend, with a rough idea of travel times to help you plan.

01The Chianti

Between Florence and Siena lies the Chianti: hills of vines and olive groves, castles, country churches and small villages such as Greve, Panzano, Castellina and Radda. The first villages are less than an hour's drive away. It is the perfect trip for wine lovers: many estates offer cellar visits and tastings, which should be booked ahead.

If you plan to taste, leave the driving to someone else: the roads are narrow and winding. For a private driver or a tour with tastings, we can put you in touch with trusted partners, so you can simply enjoy the day.

02Siena

Siena is about an hour and a half from Florence by car, coach or train. Its heart is the shell-shaped Piazza del Campo, with the Palazzo Pubblico and the Torre del Mangia; the Palio horse race is run here in summer. A few steps away stands the cathedral, striped in white and black marble, with its decorated floor. Allow time to wander the steep lanes.

Siena, Piazza del Campo and the Torre del Mangia
Siena, Piazza del Campo and the Torre del Mangia

03San Gimignano

San Gimignano, on the hills of the Val d'Elsa, is known for its medieval towers, visible from far away. It is about an hour from Florence and easiest to reach by car or on a tour; it pairs well with Siena or the Chianti on the same day. Try Vernaccia, the local white wine.

The towers of San Gimignano among the hills
The towers of San Gimignano among the hills

04Pisa and Lucca

Pisa is the easiest trip by train, taking about an hour. In the Piazza dei Miracoli, set on a wide lawn, the cathedral, the baptistery and the Leaning Tower stand side by side. If you want to climb the tower, book ahead. Then take a stroll along the river, which is quieter than you might expect.

Lucca, about an hour and a half by train, is enclosed by walls that survive intact, with a tree-lined path on top to walk or cycle. Inside are Romanesque churches, towers and the Piazza dell'Anfiteatro, an oval square built on the remains of a Roman amphitheatre. Pisa and Lucca can be combined in one day.

The Leaning Tower of Pisa
The Leaning Tower of Pisa

05Fiesole, the closest

The closest trip is Fiesole, on the hills above Florence: around twenty minutes by bus or taxi take you up to a small town of Etruscan origin, with a Roman theatre and a sweeping view over the city. It is ideal for an afternoon, perhaps staying on until sunset.

06The Val d'Orcia, for a longer day

For a longer day, head to the Val d'Orcia, south of Siena and about two hours' drive away: gentle hills, rows of cypresses and lone farmhouses, in a landscape listed by UNESCO. Set off early, or consider staying overnight to see it without rushing.

  1. PienzaThe Renaissance town created by Pope Pius II, with terraces over the valley and its famous pecorino.
  2. MontalcinoA hilltop town among the vineyards, home of Brunello.
  3. MontepulcianoA little further east, a town of palazzi and wine cellars, known for its Vino Nobile.

Frequently asked questions

What is the easiest day trip from Florence?
The closest is Fiesole, around twenty minutes away. Among the cities of art, Pisa is the simplest: about an hour by train.
Can I visit the Chianti without a car?
Yes, on an organised tour or with a private driver. It is also the safest choice if you plan to taste wine.
Can Siena and San Gimignano be seen in one day?
Yes, by car or on a tour it is a classic combination. It makes for a full day, so set off early.

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