After having an aimless wander around the ancient streets, head to the city’s renowned Piazza del Campo, the center of the town. Here you’ll find the Torre del Mangia bell tower, which you can climb for remarkable views, as long as you’re not afraid of heights.

Siena is a UNESCO World Heritage Site, mostly because of the architectural mastery of such buildings as the Duomo (+39 0577 283 048), a Romanesque cathedral with a striped, marble dome and remarkable mosaic floors. Try to go early or be prepared to fight your way through the other tourists. Inside you’ll find the Museo dell’Opera del Duomo, which houses artwork removed from the cathedral, including Duccio’s "Maestra." Head up to the top for an amazing 360-degree view of the city.

Football fans should head to the Stadio Artemio Franchi (+39 0577 281084, Via Peruzzi). Not to be confused with the stadium of the same name in nearby Florence, this is home to AC Siena. Or if you prefer men on horses to men in shorts, Il Palio, Siena’s famous bareback horse race around the Piazza del Campo, occurs on July 2 and August 16, although the festivals last for a few days. Speaking of festivals, there’s jazz festival in late July/early August, and a film festival in late September/early October.

If your sport is shopping, Siena will deliver just as much. Big Italian names such as Versace or Dolce and Gabbana can be found at Cortecci (+39 0577 280096; Via Banchi di Sopra 27), whilst Ginger offers a more boutique range (Via dei Pellegrini). For authentic home woven wares, visit Fioretta Baci and her looms at Tessuti a Mano (+39 0577 282200; Via San Pietro 7).

When it’s time for lunch, head to La Taverna di Cecco (+39 0577 288518, Via Cecco Angiolieri 19). It has an eclectic decor and great food, but you end up getting to know you’re neighbours very well as the tables are pretty close together. Be sure to book ahead for a leisurely lunch or dinner at Osteria Le Logge (+39 0577 747424; 31 Via del Porrione), arguably the best restaurant in Siena, serving Tuscan cuisine and superb regional wines. The memorable food combined with the charming owner and waitstaff keeps bringing back regulars, including Sting, who has a house in the area. For an afternoon treat, stop by Nannini (+39 0577 236009, 23 Via Banchi di Sopra) to sample excellent pastries; try the local cake, panforte, or ricciarelli, a macaroon-like almond cookie which, when done properly, is as light as air. These can be accompanied by an espresso, or something a little stronger …

The key wine of the area is Brunello, and you can taste this, along with several others at Enoteca Sapordivino in the medieval wine cellar at the Grand Hotel Continental (+39 0577 56 011, Via Banchi di Sopra 85), or Avignonesi Winery (+39 0578 724304; Valiano di Montepulciano). Another good spot for a sophisticated dinner is in the vaulted basement of Compagna del Vinattieri (+39 0577 236568; Via delle Terme 79, Via dei Pittori 1).

After a full day of climbing bell towers and sipping Brunello, you’ll be in need of somewhere very comfortable to rest your head. In the heart of town, just a short stroll from the Piazza del Campo, is the aforementioned Grand Hotel Continental (+39 0577 56 011) an aptly named grand, elegant hotel with 51 rooms and suites in a 17th-century palazzo. If you have a car and would prefer to stay outside of town in the countryside, two lovely and more intimate options, both with outdoor pools, are the Hotel Certosa di Maggiano (+ 39 0577 28 81 80), a 17-room hotel in a converted Carthusian monastery, very close to town; a bit further away in Chiusdino, about a half-hour’s drive, is Borgo Santo Pietro (+39 0577 751 222), a 13th-century villa with 7 rooms and magnificent cypress trees and gardens.