Worth getting out of bed for
The area between Montalcino and Montepulciano is renowned for its wine, and only the most philistine palate should miss out on a visit to one of the many vineyards. Poggio Antico in Montalcino runs tasting sessions in English and also boasts a great formal restaurant – book a sampling session in the morning and follow it with a lingering lunch (+39 057 784 8044). Valdipiatta, in Montepulciano, is set on a beautiful hillside and produces some delicious Vino Nobile di Montepulciano (+39 057 875 7930).
If your tastes lean more towards shops than grapes, there are plenty designer outlets dotted around the region. Prada in Montevarchi offers discounts of up to 70 per cent (+39 055 91901) – go early in the day to snare the best bargains. The Mall in Regello is home to most designers, including McQueen, Balenciaga, Armani, Yohji Yamamoto and Stella McCartney. Call ahead for opening hours (+39 055 865 7775).
Admire the magnificent San Antimo abbey in Montalcino, a still-functioning 12th-century Cistercian monastry, and listen to the soothing sounds of the monks singing at vespers (7pm). The Bagno Vignoni is home to natural hot springs and historic Roman baths – you can book treatments at Hotel Adler Thermae in Siena (+39 057 788 9000).
Authentic Tuscan eateries abound in this region. The best of the bunch is Latte di Luna (+39 057 874 8606), a trattoria on the main street in Pienza that serves pici al Ragu (spaghetti in wild boar sauce) worth making pilgrimages for – check out the photos of celebs who've done just that. Il Rosellino is an elegant couple-run eaterie with a great wine selection (+39 057 874 9064). Humbler, but no less flavoursome, is the fare at Buca delle Fate, where locals come in droves to savour the steak (+39 057 874 8272). Further afield, built into the village walls of Monticello, you'll find a warm welcome and a delightful menu at La Porta – the view from the terrace encompasses the entire valley (+39 057 875 5163). In Montepulciano, La Logge delle Vignole is modern and intimate and promises excellent service (+39 057 8717 7290), and La Grotta, in front of the towering San Biagio Church, boasts the most formal dining in the region (+39 057 875 7479).
A two-minute walk down the Via Ricci from Montepulciano's main town square, Locanda San Francesco is a sweet little hostelry that opens late and offers a huge range of wines (+39 057 875 8725).
Sette di Vino in Pienza is well worth a lunch stop, as it serves a delectable selection of salads and soups, as well as a wide choice of the regional specialty, Pecorino cheese (+39 057 874 095).