Despite the scale of the Torre di Bellosguardo (2 Via Roti Michelozzi; 39-055/229-8145, fax 39-055/229-008; doubles from $244)—the sprawling lobby was once a ballroom—the 16th-century villa turned hotel feels intimate, not intimidating. The 16 guest rooms, with their heavily carved wardrobes and, in some cases, canopy beds, are almost painfully nostalgic, a sentiment underscored by the views. As Massimo says, "There is no better vantage point for surveying Florence than the Bellosguardo." Santa Maria Novella, San Lorenzo, the Palazzo Vecchio, Santo Spirito, the Pitti Palace—all are at your feet. Tucked in the hills just outside the city's periphery, the hotel is a five-minute taxi ride or a beautiful 15-minute walk from town (time spent peeking over garden walls and inhaling the jasmine not included).
A former monastery across the city from the Bellosguardo, the Villa San Michele (4 Via Doccia, Fiesole; 800/237-1236 or 39-055/59451, fax 39-055/567-8250; doubles from $706, including breakfast and one additional meal for two) dates to the same era and has a similar setting, though the resemblance ends there. With a façade attributed to Michelangelo, a chapel (complete with altar) for a lobby, and a spectacular living and dining loggia pitched above a verdant ravine, the San Michele is one of the world's most celebrated hotels. Unfortunately, attitude problems among the staff have also made it notorious, though Maurizio Ammazzini gets gold stars for finding me what no other concierge in Florence could: a tailor to replace the shredded lining of a treasured sports coat. The 38-room, four-suite hotel has the chic to leave its public spaces empty, or nearly so. On the other hand, accommodations in the main building are so tight they could ruin your stay; cut your losses and book into the slicker, costlier annex. "The San Michele," says Giovanna, "is for people who want a very special holiday—and don't mind paying for it."
"Florentine food is Tuscan food is simple food," says Ferruccio. "It's healthful, wastes nothing, and makes a direct appeal to the palate. It's the very best Italian cooking."
Though the Venetians and Neapolitans might disagree, and though eating in Florence is not quite as austere as Ferruccio says, it is nevertheless an earthy adventure. Beans, unsalted bread, and olive oil are ingredients that turn up again and again. Wide pasta, grilled meats, and game—wild boar, rabbit, pheasant—crowd the menus. Fresh and aged pecorino, Tuscany's great contribution to the national cheese platter, makes an appearance between the secondo and dolce.
Folded into a 13th-century palazzo with lacy wrought-iron chandeliers, Osteria del Caffè Italiano (11-13R Via Isola delle Stinche; 39-055/289-368; dinner for two $65) has a young vibe unmatched by any restaurant in town. Ferruccio's weakness is for the soups: porcini; potato and artichoke; and ribollita—a bread-thickened bean dish anointed at the table with olive oil to taste. Caffè Italiano also has one of the most extensive and carefully composed wine lists in Florence. Order that super-Tuscan you can never find at home.
The list at Cantinetta Antinori (3R Piazza degli Antinori; 39-055/292-234; dinner for two $80) is made up exclusively of bottles from the Tuscan estates where the Antinoris have been making wine since the 14th century. Even the rarest, most expensive vintages are available by the glass. Of special interest is the Tenuta Belvedere from the new Bolgheri appellation, a red made with Cabernet Sauvignon, Sangiovese, and Merlot grapes. "The Cantinetta is a bit more refined than most Florentine restaurants, but not overwhelmingly so," says Leonardo, director of Ferragamo's European and Asian arms, who always has the pappa al pomodoro, another bread-and-olive-oil-bolstered soup, this one with a tomato base. Like the wines, the oil is the Antinoris' own, as are the pecorino and caprino cheeses.
To escape one's fellow tourists (there are easier things to do in Florence), slip into Giacosa (83R Via Tornabuoni; 39-055/239-6226; lunch for two $27), a genteel café-cum-tearoom jammed with well-born locals digging into midday plates of ziti and risotto. "This is where I go on Saturdays when I'm out doing errands with my granddaughters and I want something good but quick," says Giovanna, who oversees women's ready-to-wear. "My little girls love it." Habitués order at the counter and eat standing up, elbow to elbow, after sipping a Negroni, the legendary gin, Campari, and sweet vermouth cocktail that was invented at Giacosa. Vitrines magnificently arranged with fruit tarts, candied chestnuts, and bottles of lemon liqueur are as much of a draw as the crustless sandwiches. Giacosa's sister institution is the Rivoire (5R Piazza della Signoria; 39-055/211-302), where, tomorrow if not today, everyone who is anyone in Florence (including lots of Ferragamos) stops by for an aperitivo or a pudding-rich hot chocolate.
When you just can't face another bowl of pasta, Procacci (64R Via Tornabuoni; 39-055/211-656; lunch for two $25), a wonderfully old-fashioned specialty foods shop and bar with a small menu, is a good, light alternative. No point in starting with anything less than three panini tartufati, the house sandwich, a dainty glazed roll the size and shape of an egg, filled with white-truffle paste. Nurse a spumante while deciding whether to take home a bottle of the best-quality balsamic vinegar or a jar of Sicilian marmalade. With sheaves of lilies scenting the shop, a mosaic floor, and marble tables, Procacci has set the standard for civility in Florence since 1885. Even the paper napkins are luxurious.
Coco Lezzone (26R Via del Parioncino; 39-055/287-178; dinner for two $75) isn't concerned with niceties. If it were not for the tempting bowl of sliced peaches in white wine sitting in the entrance, the scowls of the three hostesses would be enough to send you running. And yet, and yet. "Coco Lezzone has the best bistecca alla fiorentina in the city," says Ferruccio. "And its yellow and white wall tiles make you feel as if you're eating in a kitchen." Everyone from Prince Charles to Pavarotti sits on hard wooden benches at communal tables for the privilege of paying 35,000 lire ($19) for truffles shaved over buttered bow-tie pasta. The thing is, it is a privilege, even as a sign admonishes customers to silence their cell phones. Seems the ringing disturbs the simmering ribollita. (They ring anyway.)
Le Cave di Maiano (16 Via delle Cave, Fiesole; 39-055/59133; lunch for two $65) restores your faith in the guileless, open-armed trattoria—the kind that puts bones aside for your dog, which is what this restaurant does for Ferruccio's Labrador. Fifteen minutes from town among hills swathed in parasol pines and olive trees, Le Cave goes beyond familiar Florentine fare to offer roast pork alla casentino (with fennel, rosemary, and garlic), "chimney-sweep" risotto (with black cabbage and beans), and pollastro al mattone (a small herb-stuffed chicken, grilled under a brick). In warm weather, linden trees form a canopy over tables on a terrace with humbling vistas of Florence.