The quality of Tuscan leather has been renowned since medieval times (fashion houses Gucci, Prada, and Ferragamo all have their roots here). A clutch of artisans—both old and new—keep the handmade tradition alive. Note these names:
• The best assistant that bespoke shoemaker Stefano Bemer (143R Borgo San Frediano, Florence; 39-055/211-356; www.stefanobemer.com) ever had was actor Daniel Day-Lewis, who spent 10 months in this lilac-and-mahogany workshop learning the craft in 2001. Bemer makes men's and women's shoes out of 180 different leathers, including hippopotamus and sharkskin. His shoes are built to last 15 years, and every detail is a work of art: even the waxed, flat cotton laces are specially woven on an antique machine.
• Wooden footwear forms hang like bunches of grapes above the head of shoemaker Alessandro Stella at Arti Minori (53 Via Camollia; 39-0577/43861), a cluttered workshop in Siena's center. Made-to-measure men's oxfords, loafers, and derbies are his signature, but Stella also fashions women's handbags. In-demand designs include shoes made of reindeer skin salvaged from a ship that sank in 1786.
• Even Southern belles order their elbow-length, white debutante's gloves from Madova (1R Via Guicciardini, Florence; 39-055/239-6526; www.madova.com), one of only a few companies that keeps the dying art of glove-making afloat. The tiny store overflows with piles of silk- and cashmere-lined kidskin gloves in jewel-like colors. My favorites: black, silk-lined styles with cuffs in turquoise, burgundy, or brown; driving gloves with contrasting stitching and tiny buttons.
Most of the 230 tons of gold that passes though Arezzo each year is processed industrially, so handcrafted jewelry boutiques are surprisingly hard to find. Below, jewelers you shouldn't miss:
• Arezzo's newest jeweler, Eclét (19 Via Cavour; 39-0575/351-854), offers bold designs (big, uncut stone rings; updated medieval necklaces), many of which are commissioned from area designer-craftsmen. The clean-cut pieces by Arezzo-based jeweler Pitti & Sisi—especially their DNA double-helix earrings in white or yellow gold—are a hit with just about anyone who enters the store.
• If you've always suspected that diamonds could become your best friend, head to the Unoaerre Outlet (550 Via Fiorentina; 39-0575/9251), Arezzo's oldest industrial jeweler, for 18-karat-gold-set diamond pieces at more than 20 percent off retail prices. Also look for ice-blue tourmaline rings, smoked citrine and gold-bead necklaces, and diamond and gold-mesh bracelets. Book a tour of the adjoining jewelry museum and factory (by appointment only).
Even the most demanding gourmands can satisfy their cravings at these stores:
• Le Cantine di Greve in Chianti (2 Galleria delle Cantine, Greve in Chianti; 39-055/854-6404; www.lecantine.it) is the Virgin Megastore of Tuscan wine-tasting cellars. Buy a prepaid wine card, insert it into any of the seven wine-tasting "machines," and press one of 140 buttons for a thumb's-width swig of your chosen wine or olive oil. Linger in the cellars to find your preferred producers (the reds of Chianti, Brunello di Montalcino, Montepulciano, and Sassicaia from Bolgheri are all good starting points); then set off on the Chianti trail.
• You're as likely to catch Dario Cecchini, the flamboyant owner of Antica Macelleria Cecchini (11 Via XX Luglio, Panzano in Chianti; 39-055/852-020)—more a theater than a butcher's shop—spouting Dante or humming along to an opera as sprinkling salt and herbs on a side of pork. But clients such as Prada's Patrizio Bertelli and Tod's Diego della Valle say his bistecca panzanese (cut from the thigh) is the best for miles around. Stock up on condiments, including spicy red-pepper jam and Tuscan herbs with salt.
• The Renaissance village of Pienza is the Tuscan capital of pecorino cheese (made from sheep's milk), honey, and red wine (Montepulciano and Montalcino are nearby). Among the best of the countless food stores is La Cornucopia (2 Piazza Martiri della Libertà; 39-0578/748-150; www.emporiofattorie.com), where you'll find everything from spicy stuffed peppers to Tuscan chocolates.
• Florence's food and fashion set swears by Olio & Convivium (4 Via Santo Spirito; 39-055/265-8198; www.conviviumfirenze.it), which recently opened in the frescoed Palazzo Capponi and offers 60 types of olive oil and 250 Tuscan wines. Stop in for lunch or an oil-tasting session (by appointment only).
• The best viands store in Siena is Gastronomia Morbidi (27 Banchi di Sotto; 39-0577/280-541). This small, quaint branch has everything you need for a picnic, from bottled eggplant to fig spread.