5 fabulous Tuscan trips from Florence

Florence can be a claustrophobic city and there may come a time when you need to escape. Fortunately, it is well placed for all sorts of expeditions; to other major art centres, to smaller towns, to the coast, or to the fabulous Chianti countryside for a gentle meander with stops for the odd wine-tasting and a lazy meal on a vine-clad terrace.
Streets of Volterra. Photo: Shutterstock
Streets of Volterra. Photo: Shutterstock

Streets of Volterra. Photo: Shutterstock 

Insight Guides can help with the planning, organising and booking of your trip to Italy. Simply contact our local expert with details of the length of your trip, budget and places you would like to visit and they will plan your personalised itinerary. For inspiration browse Insight Guides ready-made Italy trips, which are fully customisable. 


1. San Gimignano – 53km (33 miles) south of Florence

San Gimignano is a very popular excursion from Florence and with good reason. Famous for the sculptural quality of its skyline, Italy's best-preserved medieval city is a spectacular sight. It may be a cliche to call this hill town a 'medieval Manhattan', but the famous towers do resemble miniature skyscrapers. Seen from inside, it is the unspoilt townscape that bowls you over: almost nothing seems to have changed since the Middle Ages. In its heydey, the city had a total of 76 towers, only 14 of which remain. After San Gimignano fell under under Florentine control, it became an economic backwater, bypassed by the Renaissance - for which we are eternally grateful.

The towers are concentrated around the Piazza del Duomo and Piazza della Cisterna, which is teeming with tourists all year round. The towers alone make a visit here worthwhile, but the town abounds in quirky sights. The Romanesque Collegiata will detain you longest, as every inch of wall space is covered in frescoes. The Museo di San Gimignano seeks to show how the city was in its 13th century prime. 

You can reach San Gimignano from Florence by bus (1 hour 35 minutes, changing at Poggibonsi) and by train (1 hour 20 minutes, changing at Poggibonsi for the bus to San Gimignano). Let our local experts plan a tailor-made trip to Italy for you; click here to get the ball rolling.  


2. Lucca – 55km (34 miles) west of Florence

Perfectly proportioned Lucca is a city built on a human scale, designed to be savoured slowly, and on foot. Often bypassed by visitors intent on ticking off the Leaning Tower of Pisa, Lucca is Tuscany's self-deprecating star. In spite of this, it is the only Tuscan city to see tourism expand exponentially in recent years. Its perfectly preserved walled heart, quiet sophistication and peaceful pace of life are all credited with winning over visitors. And that's before talking about its pinky-gold palaces, pedestrian-friendly bastions, crowd-pleasing concerts, enchanting churches, and its renowned olive oil and wine estates. To jaded urbanites, Lucca represents life as it should be led. 

The Duomo di San Martino, the church of San Michele in Foro and the Casa Museo Puccini (where the composer was born) are all worth exploring, as are the many villas that surround Lucca, such as the Villa Reale and the Villa Garzoni. 

You can reach Lucca from Florence by bus (1 hour) and by train (1 hour 20 minutes). Browse our existing trips to Florence, all of which are fully customisable!


Piazza del Anfiteatro of Lucca. Photo: Shutterstock


3. Volterra – 75km (46 miles) south-west of Florence

Perched on a windy plateau overlooking the Sienese hills, Volterra remains the most Etruscan of cities. Walking around the ancient fortifications is an excellent way to view the medieval town, the Roman and Etruscan walls, and the wide sweep of countryside below. 

The Porta all'Arco is the best-preserved Etruscan gateway in Italy, dating from the 4th century BC. From the arch, a pretty road winds its way uphill to the Piazza dei Priori. The best of the city's ancient treasures are displayed in the Museo Etrusco Guarnacci. On the north side of town, just below the city walls, is the excavated Teatro Romano, the impressive remains of a complex built during the reign of Augustus.

Twilight fans will delight in the knowledge that Volterra was the inspiration for the fictional home of the Volturi, a coven of elite vampires.

You can reach Volterra from Florence by bus and train (2 hours, including a change at Colle di Val d'Elsa). Let our local experts plan a tailor-made trip to Italy for you; click here to get the ball rolling.


4. Siena – 76km (47 miles) south of Florence

From its striped marble Cathedral to its tunnelled alleys, brilliant Campo and black-and-white city emblem, Siena is a chiaroscuro city. In its surging towers it is truly Gothic. Where Florence is boldly horizontal, Siena is soaringly vertical; where Florence has large squares and masculine statues, Siena has hidden gardens and romantic wells. Florentine art is perspective and innovation, while Sienese art is sensitivity and conservatism. Siena is often considered the feminine foil to Florentine masculinity. Let our local experts plan a tailor-made trip to Siena for you; click here to get the ball rolling, and tell us how long you'd like to go for, and what you are interested in.  

All roads lead to Il Campo, the huge main central square, shaped like an amphitheatre. The city's famous Palio horse race, fiercely contested by the city's 17 contrade (medieval districts) takes place here. At the square's base is the Palazzo Pubblico, the dignified Town Hall with its crenellated facade and waving banners, surmounted by the tall and slender tower. Siena's Cathedral is a controversial monument - either a symphony in black-and-white marble, or a tasteless iced cake, depending on your point of view. 

You can reach Siena from Florence by bus (1 hour 15 minutes on the Rapida service) and by train (1 hour 30 minutes on the direct service, but bear in mind that Siena's train station is located 2km outside the city).

 Aerial view over the medieval city of Siena. Photo: Shutterstock


5. Pienza

117km (73 miles) south-east of Florence

Pienza is an exquisite Renaissance showpiece, slightly suffering from its over-popularity. Although created by a humanist pope, Pius II, Pienza is almost too perfect to be human and too precious to be spiritual. Every fountain, piazza and painting is harmonious. Model citizens walk through streets as romantic as their names - Via dell'Amore, Via del Bacio, Via della Fortuna - streets of 'love', 'kiss' and 'fortune'. Locals call it citta d'autore, a city inspired by one vision. After Pienza, other cities in Tuscany are liable to look chaotic. Browse all of our existing trips to Florence here, all of which are fully customisable!

Much of the symmetry lies in the cathedral square, Piazza Pio II, and the slightly listing Duomo adds to the charm. The Duomo's facade, the gracious arches, the well and the Palazzo Piccolomini, the pope's home, are just as Pius left them when he set off to fight the Crusades, never to return. 

And of course, Pienza has the best pecorino cheese in all of Italy!

The easiest way to reach Pienza from Florence is by car, but public transport is possible via Siena and Montepulciano. 


This blog was originally published on April 5, 2014. 


Planning a trip to Italy?

Insight Guides can help with the planning, organising and booking of your trip. Simply contact our local expert with details of the length of your trip, budget and places you would like to visit and they will plan your personalised itinerary. For inspiration browse Insight Guides ready-made Italy trips, which are fully customisable. 


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