Fly into Florence Peretola (FLR) or Pisa Galileo Galilei (PSA) — both are 60–80 minutes from central Tuscany. Pick up your rental car on Day 2; on arrival day take the train or a taxi into Florence and stay in the Oltrarno — the "other side of the Arno," the craftsmen's quarter that tourists underestimate.

The Oltrarno contains the Palazzo Pitti and Boboli Gardens, the Brancacci Chapel (Masaccio's frescoes that influenced Michelangelo), and some of Florence's best independent wine bars and restaurants. Begin your Tuscan wine education tonight at Il Santino (the wine bar sibling of the Michelin-starred Il Santo Bevitore) or Buca Mario — Florence's oldest restaurant, in continuous operation since 1886. Order the bistecca fiorentina with a glass of Chianti Classico Riserva. This is what dinner in Florence is supposed to feel like.

Collect your car and drive south from Florence on the Via Chiantigiana (SS222) — the original Chianti wine road, winding through olive groves and vineyards with the occasional appearance of a medieval stone tower above the treeline. Stop first in Greve in Chianti (25 km from Florence) — a small market town whose central triangular piazza is lined with wine shops. The Enoteca Falorni here has been selling Chianti Classico since 1806 and offers an excellent self-guided tasting at their wine wall.

Book a morning tour at Antinori nel Chianti Classico — a breathtaking contemporary underground winery built inside the hillside at Bargino, designed by architect Marco Casamonti. The cellar descends four floors into the hill; the tasting room is suspended over the vineyards behind glass walls. Tour and tasting: approximately €40–60. Afternoon: Badia a Coltibuono — an 11th-century Benedictine monastery converted to a wine estate with a restaurant serving estate wines with produce from the monastery gardens.

Morning in Siena — arguably the most perfect medieval city in Italy, still contained within its original 13th-century walls. The Piazza del Campo, where the Palio horse race has been run since 1644, is one of Italy's great civic spaces. The Duomo di Siena — striped black and white marble in the Sienese Gothic style — contains Pinturicchio frescoes, Michelangelo's Piccolomini statues, and a Pisano pulpit that Michelangelo considered among the finest sculpture in existence.

Afternoon at Castello di Brolio — the ancestral seat of the Barone Ricasoli family since 1141 and the estate where Bettino Ricasoli (Italy's second Prime Minister after unification) refined the Chianti formula in 1872. The castle gardens overlook an enormous amphitheatre of vineyards. The winery tour includes the original cellars, the family chapel, and a tasting of the estate's full range including the flagship Colledilà Chianti Classico Gran Selezione.

Drive south from Siena 40 minutes to Montalcino — a hilltop fortress town above the Val d'Orcia with views stretching to Monte Amiata. The medieval fortress at the top of the town contains the most important enoteca in Montalcino: a barrel-vaulted room offering tastings of over 100 Brunello producers, some of which cannot be visited by appointment. Buy here what you cannot otherwise access.

The most important estate visit in all of Italian wine: Biondi-Santi at Il Greppo. The Biondi-Santi family created Brunello di Montalcino in the 1870s when Ferruccio Biondi-Santi isolated the Sangiovese Grosso clone (locally called Brunello) and aged it in large Slavonian oak barrels to create the first modern Brunello. Bottles from 1888 and 1891 have been recorked and retasted in recent decades and found to still be alive. Visits require advance booking and involve tasting current releases alongside older library vintages — a genuinely rare opportunity. Reserve 2–3 months ahead.

Afternoon visit: Il Poggione — one of Montalcino's most consistent and visitor-friendly estates. The estate has been in the Franceschi family for four generations, the tours are conducted in excellent English, and the tasting of Rosso di Montalcino alongside Brunello illustrates the quality difference that five additional years of ageing produces in the same grape from the same soil.

Drive through the Val d'Orcia — the UNESCO landscape of sinuous clay hills, isolated farmhouses, and perfectly aligned cypresses that appears on every Tuscany postcard. Stop at the famous cypress avenue at Monticchiello for the photograph everyone takes; the light is best in the morning. The landscape is more photogenic in reality than in any reproduction.

Pienza — the ideal Renaissance city commissioned by Pope Pius II in 1459 — is a 45-minute walk end to end and contains the finest Pecorino di Pienza (sheep's milk cheese) shops in Italy. Buy aged Pecorino stagionato, honey, and truffle products to accompany your wine purchases. Lunch at a table outside facing the Val d'Orcia view.

Afternoon in Montepulciano — the main street of this hilltop town is lined with cantine (wine cellars) belonging to local producers. Descend into the Contucci cellars, dug into the volcanic tufa beneath the Palazzo Contucci, where thousands of bottles of Vino Nobile age in the cool darkness beneath the town. Tasting and estate visit: Avignonesi — reserve the Vin Santo tasting, which includes the extraordinary Occhio di Pernice.

Drive north to San Gimignano — the walled hilltop town whose 14 medieval towers made it the most distinctive skyline in Tuscany when they were built as status symbols by rival noble families in the 13th century. Arrive before 9am to walk the streets without the daytime tour groups; the towers against a morning sky with nobody else around is one of Tuscany's most remarkable urban views.

Visit Panizzi estate outside the town walls for the best Vernaccia tasting in the zone — a guided tour and tasting showing the full range from the entry-level Vernaccia to the single-vineyard Vigna Santa Margherita, which demonstrates what Italy's first DOCG white can achieve with old vines and precision winemaking.

Afternoon: a Tuscan cooking class — several excellent operators run half-day sessions in farmhouses near San Gimignano including Toscana Mia and In Tavola. Learn to make fresh pici pasta (the thick, hand-rolled Sienese pasta), ribollita (the thick bread-and-kale soup of Florence), and cantucci. Everything is eaten with the wines you have been tasting all week.

Return to Florence for the final day. Book your Uffizi Gallery timed entry weeks in advance — the most important collection of Italian Renaissance painting in the world, including Botticelli's Birth of Venus and Spring, Leonardo's Annunciation, Raphael's portraits, and Titian's Venus of Urbino. Allow 3–4 hours minimum. The queues for walk-up entry in peak season are extraordinary — do not make the same mistake twice.

Lunch at Mercato Centrale — Florence's covered food market, renovated to a two-floor food hall that combines produce market at ground level with restaurant stalls above. Affordable, excellent, and full of Florentines rather than tourists at the early lunch service.

Final dinner: book Buca Mario or Trattoria Sostanza (founded 1869) — the original burro pasta (butter pasta) and the legendary fritto misto with a half-bottle of whatever Chianti Classico Riserva the proprietor suggests. This is the correct way to end a Tuscan wine trip.