Beyond Florence: exploring Tuscany's hilltop towns

Last summer, I spent three glorious, golden months in Florence. I appreciate the self-satisfied nature of that sentence – it was indeed a smug 12 weeks of swanning around palazzos, gorging on cacio e pepe pasta and delighting at the beauty of this ancient place. Like most Italian cities, Florence presents herself on a plate – she is not shy and retiring about her good looks, excellentrestaurants and magnificent art. However, while Michelangelo’s David is spectacular, viewing him through a forest of selfie sticks is less than desirable. Marrying time in Florence with a day or two in the countryside makes for a very happy long weekend and a much needed antidote to the crowds.

Without wanting to stereotype Italians, they approach driving with what can politely be described as vim. In high season, I would advise hiring a car from beyond the city walls. There is a Europcar on Via Enrico Forlanini to the north of the city, from where you can easily access the motorway.

San Gimignano – named after the bishop of Modena, who is said to have saved the city from Attila the Hun – is an hour and a half drive south of Florence. In midsummer, the medieval town swarms with day trippers, but earlier in the season, it is a joy to walk around. The hilltop town is known for its tower-houses, built by patrician families as symbols of their wealth and power. San Gimignano is also home to Gelateria Dondoli, an award-winning ice-cream parlour with some cracking flavours – saffron with pine nut and chestnut with rosemary are two particular favourites. Nip into the Duomo to see the fabulous frescoes by Domenico Ghirlandaio before a basic but delicious lunch at Osteria del Carcere. (Be warned: the service can be a little brusque.)

Borgo Pignano is some 40 minutes drive from San Gimignano and an excellent spot to spend the night. During April and May, poppies and Marguerite daisies spring into bloom along the winding roads, so ensure you make your journey during daylight hours. The hotel is set in a 750-acre estate with sweeping views across the valley. An infinity pool has been gouged from a quarry and the eighteenth-century villa boasts an unusually good art collection. All produce is from the land – there are free-range pigs, hens and bees, an on-site bakery and a picturesque kitchen garden bursting at the seams with herbs. We spent a happy night there, drinking cocktails on the terrace bar and eating wood-fired pizzas at the Al Fresco restaurant.

Monteriggioni, which is referenced in Dante Alighieri’s Divine Comedy, is 40 minutes east of Borgo Pignano. Built at the dawn of the thirteenth century, the town is surrounded by circular walls, which, for a few euros, you can walk along. It is a small but romantic place, heavy with the weight of history and definitely worth a quick pitstop. Still further south is Castello di Vicarello, a hotel with only eight rooms. As your car wends through Maremma and the roads begin to narrow, have faith that you are not lost. The twelfth-century castle, which is at the top of a cypress-covered hill, has been owned by Aurora and Carlo Baccheschi Berti since the Seventies. For the past 13 years, they have been running their house as a small yet exceedingly sophisticated hotel. Delicious local dishes are served under a vine-draped pergola in the cobbled courtyard. Vicarello produces its own wine and olive oil and much of the meat cooked in the kitchen is hunted on the castle grounds. There are endless secluded spots to disappear to and two pools to choose from. This really is a very special place.

Siena is roughly an hour and a half drive north from here. If a day is all you have, wandering the streets gives you a sense of the city but the Duomo is a must. Be sure to visit the Piccolomini Library, in which Pinturicchio illustrates 10 episodes from the life of Pope Pius II in a kaleidoscopic array of colours. Enoteca i Terzi on Via dei Termini serves excellent pasta and has a terrific wine list. It is a good place to refuel before hitting the road back to Florence. Once you are back in town, wrap up the day with a glass of wine and a couple of tiny anchovy sandwiches at Le Volpi e L’Uva.

Emily Tobin stayed as a guest of Borgo Pignano (borgopignano.com), which has rooms from €300, and Castello di Vicarello (castellodivicarello.com), which has rooms from €520, both B&B.