Hotel Certosa di Maggiano
Just a kilometre from the centro storico, this refined four-star hotel is set on parkland in a restored 14th-century Carthusian monastery. Its 17 rooms and suites are all converted monks' cells and its stylish restaurant, Il Canto, is one of Italy's finest. A heated pool, tennis court, spa and a jogging track are among the many amenities available. Rooms from $522 per night. Hotel Certosa di Maggiano, Strada di Certosa 82, +39 0577 288 180
At the foot of the 100-metre-tall Torre del Mangia on the vast, scallop-shaped Piazza del Campo, which doubles as a racetrack for Il Palio, the 13th-century Palazzo Pubblico is a lovely building. Inside, it's an embarras de richesses for art lovers. Not to be missed are two Renaissance masterpieces: Il Buon Governo by Ambrogio Lorenzetti and Guidoriccio da Fogliano by Simone Martini. You'll have seen them on postcards but the genuine articles are something else. Palazzo Pubblico, Piazza del Campo 1, +39 0577 292 111
Lined in Renaissance times with banks, patrician palazzi and guild workshops, Via Banchi di Sotto and Via Banchi di Sopra, now locals and tourists flock there to shop for everything from food to fashion. At Morbidi (Via Banchi di Sopra 75) you'll find Tuscan charcuterie and cheese, while Liberty (Via Banchi di Sopra 28) offers designer clothes and shoes. For the best panforte and cantucci in town, head to Bar Nannini Conca d'Oro pâtisserie (Via Banchi di Sopra 24), run by the Nannini family, famous thanks to the exploits of whizz-kid scions rock star Gianna and her brother, ex-Formula One racing driver Alessandro.
Housed in the 15th-century palace of the same name, a stone's throw from Piazza del Campo, Enoteca Palazzo Piccolomini (Via del Paradiso 56) stocks a staggering assortment of wines and spirits, while close by, Enoteca I Terzi (Via dei Termini 7) has about 1800 labels in its 13th-century cellar, a number of which are always available by the glass and for group tastings. The popular Compagnia dei Vinattieri (Via delle Terme 79), in a basement opposite the house where Saint Catherine, the city's patron saint, was born, is the place to go for apéritifs of an evening.
Osteria Le Logge
This centrally situated modern restaurant is run by Brunello di Montalcino producer Gianni Brunelli. It's housed in a former pharmacy and the original display cabinets are still part of the décor in the ground-floor dining room where classic Tuscan cuisine is served, revisited with contemporary tweaks. Via del Porrione 33
Antica Osteria da Divo
The magical dining spaces here are hewn out of the tufa rock of ancient Etruscan tombs. The menu, which alternates traditional with creative, is unabashedly carnivore-leaning, but occasionally features seafood, too. The wine list is excellent. Via Franciosa 25-29
Hosteria Il Carroccio
A typical osteria with outside tables, this is a great place to enjoy hearty, unfussy Tuscan fare: hence tripe in tomato and chilli sauce, ribollita, pappardelle with wild boar ragù, and more besides on a menu that changes monthly. Via Casato di Sotto 32