Tuscany in 8 Days: A Day-by-Day Itinerary

Italy · 8 days

Three days where the Renaissance started: the cathedral, the Uffizi, bridges over the Arno and hills that look down on all of it.

Day by day

Day 1 · 7 placesLanding and a first evening above the Arno

airport → center, 20 minutes; pick up the car right away

Palazzo Vecchio
City hall since 1299, and still the mayor’s office. The Hall of the Five Hundred was the largest room in Italy of its day, and a lost Leonardo may sit behind Vasari’s frescoes. The tower is a separate climb.
Piazzale Michelangelo
A terrace on the hill where Florence appears whole — dome, bridges and the hills behind them. Half the city comes up here for the sunset.
Aeroporto di Firenze-Peretola (FLR)
This is where you land and where you pick up the car. Twenty minutes to the center — though you cannot drive into it.
Basilica di Santa Maria Novella
The first thing you see off the train: a marble facade in green and white stripes right across from the station. Inside are Ghirlandaio frescoes and Giotto’s crucifix, with a third of the crowd the cathedral gets.
Piazza della Signoria
The city’s outdoor living room: a copy of the David where the original stood, a loggia full of statues, and cafés where a coffee costs what dinner should.
Ponte Vecchio
The only bridge in Florence the war spared: goldsmiths have worked on it since the 1500s, and the Medici corridor runs across the top.

Day 2 · 5 placesFlorence: the dome, the David, the Uffizi

all day on foot, everything within fifteen minutes

Cattedrale di Santa Maria del Fiore
Brunelleschi’s dome, still not fully explained: laid without scaffolding, in two shells. It is 463 steps up and a separate timed ticket.
Galleria degli Uffizi
The Renaissance room by room: Botticelli, Leonardo, Caravaggio. You cannot do it all at once — pick two or three rooms and the corridor over the Arno.
Galleria dell’Accademia
People come for one thing: the real David, five meters of marble. On the way to him stand the unfinished Prisoners, figures climbing out of the block.
Battistero di San Giovanni
The thousand-year-old octagon facing the cathedral. Its east doors — Ghiberti’s “Gates of Paradise” — are where the Renaissance started; the square has the copy, the originals are in the cathedral museum.
Mercato Centrale
Butchers and cheese stalls downstairs since 1874, a food hall upstairs until midnight. This is where you eat lampredotto, the tripe sandwich Florence runs on.

Day 3 · 4 placesChianti by car: Greve and the Brolio castle

~50 miles of hills on the SR222, the “Chiantigiana”

Castello di Brolio
The Ricasoli castle, where the formula for Chianti wine was written in 1872. A garden above the vineyards, a cellar below, tastings by appointment.
Castellina in Chianti
A hill town with a fortress and Via delle Volte — a covered medieval street running inside the town wall, with the hills showing through its windows. Wine cellars open off it.
Panzano in Chianti
A village on a ridge that people drive to for one shop: the butcher Dario Cecchini recites Dante over the counter and serves lunch in the back. Vineyards drop away on both sides.
Greve in Chianti
The capital of Chianti, with an arcaded triangular square and a butcher shop that has been there two hundred years. The wine road starts here.

Day 4 · 3 placesDrive to Siena through San Gimignano

Florence → San Gimignano → Siena, ~70 miles

San Gimignano
A town with fourteen towers — a medieval Manhattan, where families competed on height until it was banned. The gelato on the square has twice won the world championship.
Piazza del Campo
A shell of red brick tilted toward the town hall, and people sitting straight on the stone. Twice a year horses run around its edge for the Palio.
Monteriggioni
A round fortress with fourteen towers, intact since the 1200s — Dante compared those towers to giants. Twenty minutes to walk the walls; inside there is one square and two streets.

Day 5 · 5 placesAll of Siena: the Campo and the striped cathedral

the whole day inside the walls

Torre del Mangia
The town hall tower, a hundred meters up: four hundred steps and all of Tuscany turning around you. They let thirty people up at a time.
Duomo di Siena
A black-and-white striped cathedral like nowhere else, with a floor of fifty-six marble pictures — uncovered in full only in autumn.
Facciatone · Museo dell’Opera
Siena started building a cathedral four times the size and never finished: a bare facade wall is all that stands. Stairs inside it go to the top, and that is the best view in town.
Santa Maria della Scala
The hospital across from the cathedral, in service for nine hundred years and now a museum four floors deep. In the Pilgrim’s Hall the frescoes show how they treated the sick and took in foundlings — secular 15th-century painting, which is rare.
Basilica di San Domenico
A stern brick church with no façade, holding the head of Saint Catherine of Siena. The best view of the cathedral is from here, across the ravine.

Day 6 · 4 placesInto the Val d’Orcia: Pienza, cypresses, a hot square

Siena → Pienza → Montalcino, ~45 miles of hills

Pienza
The town Pope Pius II rebuilt as an “ideal city” in three years. From the lane along the cliff the whole valley opens up, and the shops sell pecorino.
Podere Belvedere
The hill with the farmhouse and the cypress drive that people come to the Val d’Orcia for: waves of fields to the horizon. Shot from the road, best at dawn or the hour before sunset.
Cappella della Madonna di Vitaleta
The white chapel among cypresses that ends up on every postcard of Tuscany. You cannot walk to it — the field is private; people look and shoot from the road.
Bagno Vignoni
A village whose main square is a pool of steaming water, running since Roman times. You cannot swim in it, but you can in the free cascades below.

Day 7 · 3 placesMontalcino, the abbey, and Montepulciano

~40 miles, three stops across the hills

Montalcino
A fortress on a hill and Italy’s great red wine, Brunello. There is a wine bar inside the fortress itself: you drink your glass on the wall, looking at the hills.
Abbazia di Sant’Antimo
A 12th-century Romanesque abbey standing alone in a field of olives. Pale stone inside and not one unnecessary decoration.
Montepulciano
A town along a ridge, all Renaissance palaces with wine cellars underneath them. This is where Vino Nobile is made — and where they filmed New Moon.

Day 8 · 2 placesBack to Florence and the flight home

Val d’Orcia → Florence airport, ~90 miles, 2 hours

Basilica di Santa Croce
A church that became a pantheon: Michelangelo, Galileo and Machiavelli are buried here. In the courtyard stands the Pazzi Chapel, early Renaissance at its purest.
Museo Nazionale del Bargello
A former prison turned sculpture museum: Donatello’s David, the first freestanding nude since antiquity, and early Michelangelo. Half empty, because everyone is in line at the Accademia.