Savvy shoppers snap up last season's lines at discounts of 35 to 70 percent off Italian retail prices (which can be 15 to 30 percent lower than U.S. prices). Non-European Union residents can also claim a tax refund on outlet purchases; ask at the checkout for details.
ONE-STOP SHOPPING: Those who have limited time should make it to The Mall (8 Via Europa, Leccio Reggello; 39-055/865-7775; call for details about the twice-daily shuttle bus from Florence), a low brick building divided into branded stores. In May, the first arcade (Gucci, Yves Saint Laurent, Giorgio Armani, Sergio Rossi, and Loro Piana) was joined by a second strip (Ferragamo, Ungaro, Zegna, Bottega Veneta, Valentino, and Agnona). Heavily discounted Gucci bags and shoes, woven leather bags by Bottega Veneta, and Collezioni Armani suits (from $290, for a suit with slight imperfections) are among the main draws.
PRADA'S LITTLE SECRET: Ever wonder how ordinary Italians can afford to look so smart?Local label-lovers pack the aisles at I Pellettieri d'Italia (Località Levanella, SS69, Montevarchi; 39-055/91901) for 40 to 50 percent off last season's Prada collections. Avoid weekends, when you have to pick up a numbered ticket and stand in line for a couple of hours just to get inside.
LABELS FOR LESS: Despite their addresses, Fendi (66/33 Via Pian dell'Isola, Rignano sull'Arno; 39-055/834-981) and Dolce & Gabbana (49 Via S. Maria Maddalena, Località Pian dell'Isola, Incisa in Val d'Arno; 39-055/833-1300) are just around the corner from each other. Recently, Celine and Loewe—both, like Fendi, part of LVMH—have opened in the same hangar-like building as the Roman fashion houses. The best buys are bags at Fendi and shoes at Dolce & Gabbana, where discounts hover at about 50 percent.
BETTER THAN DUTY-FREE: On your way to the airport, stop by the Roberto Cavalli Outlet (3/3 Via Volturno, Osmannoro, Sesto Fiorentino; 39-055/317-754), in Florence's northern, industrial zone. A burly bodyguard is all that marks the second-floor entrance of the outlet, in a nondescript white building. Can't see yourself in a pair of zebra-printed, rhinestone-studded jeans?The simple suede jackets and well-cut white shirts will suit even the most moderate tastes.
1 FLORENCE AND IMPRUNETA
Three or four days; for all categories. Allow two or three days to explore Florence's shops, and an extra day or two to check out terra-cotta workshops in Impruneta, ceramics in Montelupo Fiorentino, outlets in Valdarno, and fabrics in Casentino. WHERE TO STAY Try this new design hotel: J.K. Place (7 Piazza Santa Maria Novella, Florence; 39-055/264-5181; www.jkplace.com; doubles from $364). Alternatively, opt for a B&B such as the affordable Castello di Cafaggio (58 Via del Ferrone, Impruneta; 39-055/201-2085; www.cafaggio.com; doubles from $92), which also sells wine and award-winning olive oil. WHERE TO EAT Go to Beccofino (1R Piazza degli Scarlatti, Florence; 39-055/290-076; dinner for two $95) for nouvelle Tuscan food and Conran-style furnishings. HINT Finding the outlets can be tricky, so it's best to hire a driver. Luca Grazi of Auto Centrale (39-055/973-8815; www.auto-centrale.it) organizes shopping tours.
2 THE AREZZO REGION
Three or four days; for jewelry, fashion and tailoring, fabrics and linens, housewares, antiques markets, and outlets. Schedule day trips to Arezzo (plan an extra two days if your vacation coincides with the antiques fair) and Anghiari. The designer outlets in Valdarno are also within easy reach (one day). WHERE TO STAY It's 20 miles from Arezzo, but the antiques-filled Castelletto di Montebenichi (Località Montebenichi, Bucine; 39-055/991-0110; www.castelletto.it; doubles from $260) is one of the province's best hotels.
3 CHIANTI AND SIENA
Four days; mostly for food, wine, and crystalware. Take the S222 Chianti wine route from Florence to Siena (43 miles), stopping at Greve and Panzano in Chianti. Make a detour to Radda in Chianti and take a day to explore Siena. Follow the wine route through Montalcino, Pienza, and Montepulciano. Head back to Florence via Colle di Val d'Elsa and Certaldo Alto. WHERE TO STAY The Grand Hotel Continental (85 Banchi di Sopra, Siena; 39-0577/44204; www.ghcs.it; doubles from $540), is in a frescoed palazzo. Or choose the Castelletto di Montebenichi (see Itinerary 2). The Chianti and Siena portions can also be easily done from Castello di Cafaggio (see Itinerary 1). WHERE TO EAT Arnolfo (50/52 Via XX Settembre, Colle di Val d'Elsa; 39-0577/920-549; dinner for two $185) combines refined food and service with fabulous views.
VALERIE WATERHOUSE is the Italy correspondent for Travel + Leisure.