Florence

Santa Maria Novella station puts you in the historic center immediately — a five-minute walk to any hotel in the medieval city. Drop your bags and head to Piazzale Michelangelo before sunset, the hilltop terrace south of the Arno that offers the definitive view of Florence: the terracotta dome of the Duomo, the slender tower of the Palazzo Vecchio, and the entire Renaissance cityscape laid out before you while the Tuscan light turns golden. Walk back down through the Boboli Gardens and into the Oltrarno neighborhood for dinner — the south bank of the Arno is more authentic and more affordable than the tourist center. Buca Mario (Florence's oldest restaurant, open since 1886) or the more modern Buca dell'Orafo for a first Florentine meal: bistecca alla fiorentina, ribollita, and a bottle of Chianti Classico. This is where the week begins.

Book the Uffizi at 9am and plan to spend three to four hours — the gallery's greatest works include Botticelli's Birth of Venus and Primavera (room 10-14), Leonardo's Annunciation, Titian's Venus of Urbino, and Caravaggio's Medusa. Don't rush; the Uffizi rewards lingering. Lunch at a wine bar near Piazza della Signoria, then walk to the Cathedral complex in the afternoon. The Duomo itself is free to enter; climb Giotto's Campanile (414 steps, the best view in Florence) or the Dome itself (463 steps, Brunelleschi's greatest engineering miracle, with a view through the lantern to the nave floor far below). The Baptistery's bronze doors — Ghiberti's Gates of Paradise — face the Duomo and are one of the Renaissance's founding masterpieces. End the day with a Negroni at Rivoire on Piazza della Signoria, the cocktail Florence invented.

Rent a car or hire a driver for a day in the Chianti Classico wine zone — the rolling hills between Florence and Siena that produce some of Italy's greatest red wine and constitute one of the world's most beautiful agricultural landscapes. The route through Greve in Chianti, Panzano, and Castellina passes through a landscape of olive groves, cypress avenues, medieval hilltop castles, and vineyards climbing impossibly steep slopes. Book a morning tour and tasting at Antinori nel Chianti Classico — the state-of-the-art winery designed to disappear into the hillside — or the historic Castello di Brolio, the ancestral seat of the Ricasoli family who created the Chianti wine blend in the 1870s. Lunch at a winery restaurant before the drive back via Greve for a stop at Falorni, the legendary butcher and salumi producer who has been curing meats in the Chianti hills since 1806.

Drive 75km south to Siena — a perfectly preserved medieval city that has changed almost nothing since the 14th century, built in dark brick (called Siena brown, the color named after it) on three hills above the Tuscan plain. The Piazza del Campo, the scallop-shaped central square where the Palio horse race is held twice yearly, is one of the great public spaces of the world. The Siena Duomo has a façade of white, green, and pink marble and an interior inlaid floor of 56 marble panels depicting scenes from the Old Testament — extraordinary. Lunch in Siena before driving 40km to San Gimignano, the medieval city of towers, where 14 surviving medieval towers still pierce the Tuscan skyline (there were once 72). The town's small scale makes it walkable in an hour, but the views from the towers and the famous white Vernaccia wine make it deeply worthwhile. Return to Florence by evening.

Today is about Florence's food culture. Start at the Mercato Centrale on Via dell'Ariento — the city's main covered food market, open since 1874, where the ground floor vendors sell the finest Tuscan ingredients: white truffles, porcini mushrooms, aged Pecorino, Chianina beef, handmade pasta, and every variety of olive oil. Pick up breakfast on the upper floor food hall, which has excellent coffee and pastries. The morning is given over to a hands-on cooking class — several excellent schools operate in the Oltrarno, including Giulio Divini's cooking school in a medieval palazzo — where you'll make fresh pasta from scratch, a classic ribollita, and a tiramisu. Eat what you've cooked for lunch. Afternoon free in the Oltrarno: browse the artisan leather workshops on Via del Parione, the gold jewelers on the Ponte Vecchio, and the design boutiques of Via de' Tornabuoni.

The Galleria dell'Accademia holds Michelangelo's David — the most famous statue in the world, and one of those rare famous things that exceeds its reputation in person. The David stands 17 feet tall in white Carrara marble, surrounded by four of Michelangelo's unfinished Prigioni (prisoners) struggling to emerge from the stone. Book the first entry slot of the day and take time with each piece. Afternoon: drive or take the bus to Fiesole, the Etruscan and Roman hilltop town directly above Florence, for lunch with views of the entire city spread below and a very different, very quiet atmosphere from the urban center. Visit the Roman amphitheater (still used for summer concerts), walk the archaeological museum grounds, and have a slow lunch at one of the restaurants on the main piazza before returning to Florence for a final long dinner at Il Latini or Buca dell'Orafo.

A final morning in Florence is best spent at the Sant' Ambrogio market — smaller and more local than the Mercato Centrale, in the eastern part of the city, with excellent coffee bars nearby. The Basilica of Santa Croce (the great Franciscan church with tombs of Michelangelo, Machiavelli, Galileo, and Rossini) is worth a final visit if your flight allows time. Florence's Amerigo Vespucci Airport (FLR) is just 10 minutes from the city center — one of Italy's most convenient major airports — or trains run frequently to Pisa's international airport (1 hour) and Bologna (35 minutes by high-speed). A final scoop of gelato at Vivoli or Gelateria dei Neri, and the slow realization that you've eaten, drunk, and looked at art better than anywhere else on earth.